Annapolis MD Homes with Pools MLS Search

Browse All Annapolis MD Properties with Pool for Sale

$745,000
4 Beds ⋅ 3 Baths
There are homes that impress you. Then there are homes that make you imagine a completely different way of living. Imagine ending your workday with a walk to the beach to watch the sun set over the Chesapeake Bay. Weekend mornings begin with coffee on your deck surrounded by mature trees, afternoons are spent boating on the South River, swimming at the community pool, or exploring Quiet Waters Park, and evenings end with neighbors gathering for concerts, celebrations, and waterfront sunsets. This is the lifestyle that has made Hillsmere one of Annapolis' most cherished waterfront communities for generations—and it's waiting for you at 104 Groh Lane. Beautifully updated from top to bottom, this home offers the perfect balance of modern style and everyday comfort. Every room reflects a fresh, timeless aesthetic with thoughtful finishes, abundant natural light, and a warm, welcoming feel that allows you to simply move in and begin enjoying life from day one. The beautifully renovated kitchen is designed for those who love to cook. Whether you're preparing fresh Maryland crab cakes after a day on the water, perfecting your favorite family recipes, baking holiday desserts, or creating an elegant dinner for friends, this is a space where great meals become lasting memories. The adjoining dining and living areas flow effortlessly together, making entertaining feel natural while allowing everyone to stay connected long after dessert has been served. Step outside and discover one of this property's greatest assets—a lush, private, level backyard that's becoming increasingly difficult to find in Annapolis. This exceptional homesite offers endless possibilities, with room for the custom pool you've always envisioned, vibrant gardens, an outdoor kitchen, a fire pit, or simply a wide expanse of green lawn where children and pets can run freely. Host summer barbecues on the spacious deck, celebrate birthdays beneath the stars, enjoy quiet mornings listening to the birds, or spend peaceful evenings surrounded by the beauty of your own backyard sanctuary. The finished lower level provides the flexibility today's lifestyles demand, offering the perfect space for a recreation room, media lounge, fitness studio, home office, guest accommodations, or a combination of all four. Whether you're working from home, hosting overnight guests, or creating a place for everyone to spread out, this home easily adapts to the way you live. But what truly sets this property apart is what lies beyond your front door. Hillsmere is far more than a neighborhood—it's a true waterfront community where neighbors know one another and every season brings new opportunities to enjoy the outdoors. Residents have access to a private sandy beach overlooking the Chesapeake Bay, a private marina with boat slips and direct access to the South River, boat ramps, a community swimming pool, waterfront pavilions, playgrounds, volleyball courts, picnic areas, and an active calendar of events that creates a genuine sense of community. Quiet Waters Park, Hillsmere Elementary School, the library, shopping, restaurants, Eastport, Historic Downtown Annapolis, and City Dock are all just minutes away, giving you the perfect blend of convenience, recreation, and coastal charm. Finding a beautifully updated home is easy. Finding one on a lush, level lot in one of Annapolis' most beloved waterfront communities is not. 104 Groh Lane offers more than beautiful spaces and thoughtful updates. It offers morning walks to the water, evenings filled with laughter on the deck, lifelong friendships, unforgettable gatherings, and the simple joy of coming home to a place that feels exactly where you're meant to be.

104 Groh Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$965,750
5 Beds ⋅ 3 Baths
Perfectly positioned on a beautifully landscaped corner lot in the heart of Anchorage, one of Annapolis' most coveted waterfront communities, 3115 Starboard Drive offers the rare opportunity to enjoy a home that has been thoughtfully and extensively updated throughout while embracing the exceptional lifestyle that makes this neighborhood so beloved. Just steps from the community marina, waterfront park, swimming pool, tennis and basketball courts, playground, and walking paths, you'll quickly discover why so many families choose to call Anchorage home. Here, children ride bikes until sunset, neighbors wave from their front porches, friends gather at the marina, dogs are walked along quiet tree-lined streets, and every season brings community events and lasting friendships. Beautifully finished living space blends timeless style with everyday comfort. Rich hardwood floors, elegant finishes, updated baths, designer lighting, and beautifully renovated living spaces create a fresh, move-in ready home where every room reflects quality and care. The stunning gourmet inspired kitchen serves as the heart of the home, opening effortlessly to a sunny breakfast nook where mornings begin over coffee and family breakfasts before school. For larger celebrations, the spacious formal dining room easily accommodates holiday dinners, Thanksgiving feasts, birthday celebrations, and gatherings that become treasured family traditions. Designed for the way families truly live, the spacious living areas offer room to spread out, entertain, or simply relax together beside one of two cozy gas fireplaces. Five generously sized bedrooms and three full baths provide exceptional flexibility for growing families, guests, home offices, or multigenerational living, while the oversized two-car garage offers abundant storage for vehicles, bicycles, paddleboards, kayaks, tools, and everything needed to enjoy life on the Chesapeake Bay. Outdoor living is equally inviting. The expansive deck becomes a favorite place to unwind after a long day, whether enjoying dinner under the open sky, hosting summer barbecues, watching the kids and dogs play in the yard, or ending the evening beneath the stars with family and friends. The screened porch offers the perfect retreat to enjoy fresh Chesapeake breezes from spring through fall, making every season feel just a little more special. Living in Anchorage is about far more than owning a beautiful home—it's about becoming part of one of Annapolis' most welcoming waterfront communities, where neighbors know one another, children grow up together, evening walks are a daily tradition, and the marina, pool, parks, and waterfront become an extension of your own backyard. Just minutes from Historic Annapolis, Eastport, Quiet Waters Park, premier shopping, dining, and major commuter routes, 3115 Starboard Drive offers the perfect balance of updated luxury, community connection, and the Chesapeake Bay lifestyle so many dream of but few ever experience.

3115 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$475,000
1 Beds ⋅ 1 Baths
Discover the perfect blend of comfort and convenience in this charming 1-bedroom, 1-bathroom condo, ideally situated in the vibrant Park Place community. Built in 2007, this unit features an entry-level bedroom and elevators in the building for easy access. Faces West for sunset views. Enjoy modern living with a fully equipped kitchen boasting a built-in microwave, gas oven/range, dishwasher, and refrigerator, making meal prep a delight. Upgraded Bosch HVAC,The bathroom walk-in shower has been renovated for comfort. Hardwood floors, new carpet in bedroom. Living area is currently blue, bedroom neutral. Photos at end depict if painted off-white for perspective. Step outside to a community oasis, with a refreshing pool and BBQ grill, back patio, perfect for summer gatherings. Park Place has a Social Committee that organizes speaker series and social events. Safety is paramount with 24-hour security, lobby desk service, and monitored exterior cameras. Located in a thriving neighborhood, you'll appreciate the proximity to restaurants, in-town parks, shopping, and in-town events just blocks away, enhancing your lifestyle. Embrace the community spirit with local events and activities that foster connections. This condo is not just a home; it's a gateway to a fulfilling lifestyle. Luxury living in Historic Annapolis. Don't miss your chance to make it yours!

5 Park Pl Unit #431, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$579,500
4 Beds ⋅ 2 Baths
Nestled in the charming community of Cape St. Claire, this delightful raised ranch home offers a perfect blend of comfort and convenience, making it an ideal retreat for those seeking a vibrant neighborhood lifestyle. With 4 spacious bedrooms and 2 full bathrooms, this residence boasts a generous 2,327 square feet of living space, perfect for gatherings or quiet evenings at home. The main floor laundry adds to the ease of living, ensuring that daily tasks are a breeze. Step outside onto the expansive screened in porch where you can enjoy morning coffee or evening cocktails while taking in the serene surroundings. Cape St. Claire is renowned for its community spirit and access to the beautiful Magothy River. Residents can enjoy a community pool, perfect for those hot summer days, and the nearby parks offer ample opportunities for outdoor activities, picnics, and leisurely strolls. The neighborhood is designed for an active lifestyle, with walking trails and green spaces that encourage exploration and connection with nature. The community is also well-served by public services, making daily life convenient and stress-free. Living in Cape St. Claire means embracing a lifestyle enriched by water features and community amenities. Whether you're kayaking on the river, enjoying a swim at the community pool, or simply relaxing in your backyard, this home offers a unique opportunity to create lasting memories in a welcoming environment. With its prime location, spacious layout, and community-focused amenities, this property is more than just a house; it's a place to call home. Experience the warmth and charm of Cape St. Claire, where every day feels like a getaway. The home is wired for a generator, however, a generator is not included. Existing VA loan may be assumable for qualified buyers subject to lender approval. Contact listing agent for current interest rate, loan balance, assumption requirements and timeline.

1045 Skyview Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 4439757555
$1,375,000
3 Beds ⋅ 3 Baths
Welcome to this impeccably maintained and extensively updated ranch-style residence, offering an exceptional blend of luxury, comfort, and resort-inspired living just minutes from historic Annapolis. From the moment you arrive, the quality craftsmanship and meticulous attention to detail are evident throughout. At the heart of the home is a beautifully appointed gourmet kitchen featuring premium Wolf appliances, abundant custom cabinetry, quartz countertops, a beverage and wine refrigerator, and generous space for both everyday living and entertaining. Two double-sided gas fireplaces—one shared by the living room and the other featured in the primary suite—offer both warmth and architectural elegance, adding a distinctive touch to this exceptional home. Recent renovations have enhanced the home's appeal, highlighted by a spectacular oversized primary suite designed as a private retreat. The suite features a spacious walk-in closet and a spa-inspired ensuite bath complete with heated floors, instant hot water, and integrated Bluetooth speakers/exhaust fan. The fully finished lower level offers remarkable flexibility with luxury vinyl plank flooring, a custom wet bar with a full-size refrigerator/freezer with ice maker, a full bath, and a private exterior entrance—ideal for entertaining, hosting guests, multigenerational living, or a home-based business. Outdoor living is equally impressive. The fully fenced backyard is surrounded by mature landscaping, creating a private setting that rivals a boutique resort. Enjoy the heated in-ground pool, newly replastered in 2024, relax in the 15-foot swim spa, or entertain with ease at the custom-built tiki bar and outdoor kitchen. Thoughtfully designed, the tiki bar features a built-in grill, refrigerator, stainless steel storage, accent lighting, television, and bar seating. A stamped concrete pool deck and expansive composite deck with cable railings provide multiple spaces for gathering, dining, and unwinding. Adding even greater versatility is the detached pool house, complete with electricity and air conditioning. Whether used as a home office, fitness studio, creative workspace, or private retreat, this space offers endless possibilities. Additional highlights include a brand-new stamped concrete driveway with parking for up to five vehicles. Combining sophisticated interior finishes with extraordinary outdoor amenities, this turnkey property delivers a lifestyle rarely found in such a convenient Annapolis location.

1501 Ritchie St, Annapolis

Listing courtesy of Samson Properties. Contact: 7033493900
$499,000
2 Beds ⋅ 2 Baths
JUST HIT THE MARKET! Don't miss this rare opportunity to own a beautifully maintained one-level, brick villa in the highly sought-after 55+ community of Heritage Harbour! Offering the perfect blend of comfort, convenience, and low-maintenance living, this 2-bedroom, 2-bath home features an attached one-car garage and a peaceful setting surrounded by mature trees. Inside, you'll appreciate the ease of single-level living and the confidence of knowing the home's major systems have already been updated, allowing you to move in and simply enjoy your new lifestyle. Step outside and discover why Heritage Harbour is one of Annapolis' most desirable active adult communities. Residents enjoy an incredible array of amenities including a championship golf course, fitness center, clubhouse, indoor and outdoor pools, tennis and pickleball courts, walking trails, boating opportunities with water access, and a vibrant calendar filled with clubs, classes, social events, concerts, and activities designed to keep you as active and engaged as you choose. Whether you're looking to relax in a tranquil setting, spend your days on the golf course or the water, or connect with friends and neighbors through an unmatched social lifestyle, this home offers it all. Opportunities like this don't come along often—schedule your showing today before this just-listed gem is gone!

2608 Quiet Water Cv Unit #26, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200
$319,900
2 Beds ⋅ 1 Baths
Welcome to 1231 Gemini Dr Unit L, a beautifully updated top-floor home featuring a rare and highly desirable lofted floor plan. Offering 2 bedrooms and 1 bathroom across 1,133 square feet, this unit is one of the largest layouts in the building and has been fully renovated to deliver a clean, modern aesthetic throughout. Soaring ceilings and recessed lighting create an open, airy feel the moment you step inside. The main living area is anchored by a stylish spiral staircase leading to the spacious loft—a versatile upper-level space ideal for a second bedroom, home office, or additional lounge area. Skylights and two ceiling fans enhance the loft with abundant natural light and year-round comfort, while the top-floor location provides added privacy with no neighbors above. The kitchen has been completely updated with modern wood cabinetry, stainless steel appliances—all less than one year old—and ample storage space. Just off the kitchen and family room, a private balcony offers a comfortable outdoor retreat. Multiple ceiling fans, including one in the main living room, one in the primary bedroom, and two in the loft, provide added comfort throughout the home. Additional updates include a new central air conditioning system, offering peace of mind and energy-efficient comfort. The bathroom has been refreshed with modern finishes, contributing to the home's cohesive, upscale feel. Ideally located in Annapolis, the home is just minutes from downtown, offering easy access to waterfront dining, restaurants, shopping, and local entertainment. Conveniently located near Route 50 and the Bay Bridge for an easy commute. Community amenities include trash removal, a swimming pool, and tennis courts. The condo association is FHA approved; buyers should verify eligibility with their lender.

1231 Gemini Dr Unit #L, Annapolis

Listing courtesy of Redfin Corp. Contact: 3016586186
$738,000
3 Beds ⋅ 3 Baths
** This stunning 3-bedroom, 3-full-bath detached home in Heritage Harbor is a true GEM!** Main Level laminated wood flooring throughout the living room- dinning room and Kitchen. The Kitchen features Elegant gold-and-white granite countertops. A cozy matching granite table that seats three. Brand new white cabinets adorned with gold knobs and pull handles. Complete with modern stainless steel appliances, offering a Z line brand hood above a new 4-burner stove. The Interior home has been freshly painted and re-carpeted, giving it a modern feel. On the main level The Master bathroom is a standout feature: Gold-and-white granite sinks. Spacious shower area. Well-designed closet spaces with flooring that matches the elegant theme. Two walk-in closets for ample storage. The 2nd bedroom has plenty of natural light and plenty of room. The 3rd quest room is located on the second level with a loft looking onto the newly renovated large closed-in sunroom and below a lovely family room...The "Florida "Sunroom equally has new flooring with plenty of sliding glass doors, offering natural light, with a separate heating & air conditioning system, looking out to plenty of greenery- perfect for relaxation. This home is not only beautifully designed with many upgrades for comfort and style, but also a must-see. If you’re considering moving or looking for a beautiful home in a desirable neighborhood. This property won’t last long in today’s market.

708 Sydney Ter, Annapolis

Listing courtesy of Taylor Properties. Contact:

$525,000
2 Beds ⋅ 2 Baths
Exceptional Properties. Exceptional Clients. Welcome to 1915 Towne Centre Blvd, Unit #707 — a stunning two-bedroom, two-bath luxury condominium offering breathtaking views of Annapolis Towne Centre and the Chesapeake Bay Bridge. Located on the 7th floor, this beautifully appointed residence combines upscale finishes, modern convenience, and an unbeatable lifestyle in the heart of one of Annapolis’ most vibrant communities. Step inside this gorgeous open-concept floor plan featuring soaring 10-foot ceilings, elegant hardwood floors, and an abundance of natural light. The gourmet kitchen is designed for both everyday living and entertaining with granite countertops, stainless steel appliances, and high-end finishes throughout. The spacious living area opens to a large private balcony where you can enjoy spectacular views of Towne Centre and the surrounding Annapolis skyline. This exceptional unit offers loads of upgrades. The thoughtfully designed layout provides comfortable living with two generously sized bedrooms and two full bathrooms, creating the perfect blend of privacy and functionality. Enjoy the convenience of two garage parking spaces, a private storage unit, and exclusive access to resort-style amenities. Residents can take advantage of the rooftop terrace, rooftop pool, outdoor kitchen, and lounge area featuring panoramic views — the perfect setting for entertaining or relaxing. Additional amenities include a state-of-the-art fitness center with modern equipment, elegant club rooms, concierge services, and more. Live steps away from everything Annapolis Towne Centre has to offer, including Whole Foods, Target, boutique shopping, fine dining, coffee shops, and seasonal entertainment. With easy access to major highways, commuting to Washington, DC or Baltimore is effortless. This remarkable condo offers the perfect combination of luxury, convenience, and urban living — a serene retreat with all the excitement of Annapolis right outside your door. Don’t miss the opportunity to experience the best of Towne Centre living!

1915 Towne Centre Blvd Unit #707, Annapolis

Listing courtesy of AB & Co Realtors, Inc.. Contact: (443) 275-7188
$250,000
2 Beds ⋅ 1 Baths
Very Nice move in ready condo with a nice deck and nice view in the back. Ask about 100 percent loans Hurry while this great home lasts. Buyers loan fell through hurry and make this home yours.

2572 Riva Rd Unit #19B, Annapolis

Listing courtesy of Samson Properties. Contact: 3049305621
$778,900
4 Beds ⋅ 3 Baths
Located in the sought-after, water-privileged community of Admiral Heights, this beautifully maintained 4-bedroom, 3-bath home offers a rare main-level primary suite, spacious light-filled living areas, and a large, private backyard surrounded by mature trees. Hardwood flooring extends throughout the main and upper levels, while the inviting living room features a wood-burning fireplace. The finished walkout lower level with a bedroom, full bath, and patio access provides flexible space for guests, recreation, a home office, or a gym, with abundant storage throughout. Outside, enjoy professional stonework in the front yard, a paver driveway, and a large maintenance-free deck overlooking the private backyard—perfect for entertaining or relaxing. Leave the car behind and enjoy an exceptional walkable lifestyle, just minutes to West Annapolis shops and restaurants, Navy-Marine Corps Memorial Stadium, parks, and the community dock/pier, pool, and kayak launch. Downtown Annapolis is just over a mile away, with easy access to Route 50 for commuting. Residents may also join the voluntary Admiral Heights Improvement Association, providing access to neighborhood amenities including the pool, community dock/pier, parks, and kayak/canoe storage.

509 Schley Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,475,000
5 Beds ⋅ 4 Baths
Annapolis New Stunning Luxury Renovation: Just Completed! Experience the perfect blend of timeless elegance and modern sophistication in this stunning luxury renovation in Annapolis. Thoughtfully redesigned with impeccable craftsmanship and upscale finishes throughout, this exceptional 5-bedroom / 3.5-Bathroom residence offers refined living at its finest. A bright, open-concept floor plan showcases a designer chef’s kitchen, premium appliances, custom cabinetry, and beautifully appointed living spaces ideal for both everyday living and entertaining. Luxurious baths, spacious bedrooms, and carefully curated details create a move-in-ready retreat. Situated in one of Annapolis’ most desirable locations, Anchorage waterfront community, this remarkable home delivers the best of coastal living with convenient access to downtown Annapolis, the Chesapeake Bay, marinas, shopping, and dining. A rare opportunity to own a brand-new luxury home in the heart of Annapolis. This extraordinary residential real estate transformation is the creation of a partnership between a contractor and an interior and space designer firm. Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien and partner Rachael Houser from Intuitive Design, joined forces and underwent on 3134 Starboard Drive a complete, down-to-the-studs renovation and expansion. They purchased this over .36-acre property from its original owner, and they turned a 2,000 square foot home into a 3,360 square foot of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedrooms, three-bathrooms, one-powder room, family room, recreation room, backyard, double garage residence was meticulously rebuilt—walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design, offering an open and elegant floor plan flooded with natural light. Situated in one of Annapolis’ premier waterfront enclaves, residents enjoy exclusive access to community amenities including a private marina with 49-boat slips, a boat ramp, pools, and scenic waterfront green spaces. If you’re seeking a truly move-in-ready home that is brand new in an established, amenity-rich community, this is your opportunity to own a masterpiece in Anchorage.

3134 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,175,000
5 Beds ⋅ 3 Baths
Seller has set an offer deadline of 4:00pm on Monday July 27th. Previous Buyers move from California fell through. Home is back on the market and ready for you! Wake up to panoramic views of the Magothy River from this beautifully updated home in the sought-after waterfront community of Cape St. Claire. Expansive windows fill the home with natural light while showcasing breathtaking water views from many of the primary living spaces. The stunning remodeled kitchen features quartz countertops, stainless steel appliances, custom cabinetry, a dry bar, and an open layout that flows seamlessly into the dining and living areas. Hardwood flooring, beautifully renovated bathrooms, updated stair railings, fresh paint, and designer finishes create a home that is both elegant and inviting. Offering a highly desirable layout with two main-level bedrooms and a private upper-level primary suite, the home provides exceptional flexibility for guests, multigenerational living, or a dedicated home office. The spacious primary retreat features a sitting area, custom walk-in closet, spa-inspired bath, and private balcony overlooking the Magothy River. The finished lower level provides additional flexible living space, abundant storage, and walk-out access to the backyard. Outdoor living shines with an expansive Ipe wood deck with glass railings, a hot tub, beautifully landscaped grounds, and stairs leading toward the shoreline—perfect for entertaining or simply enjoying the ever-changing waterfront scenery. With more than $250,000 invested in improvements over the past four years, this home combines timeless design with modern efficiency. Major updates include a complete kitchen renovation, three remodeled bathrooms, hardwood flooring, dual high-efficiency Carrier HVAC systems, updated electrical service with a Level 2 EV charger, reverse osmosis and whole-house water filtration systems, well pump replacement, waterproofing improvements, custom primary closet, backyard fencing, and much more. Conveniently located just minutes from downtown Annapolis, Broadneck schools, shopping, dining, commuter routes, and the Chesapeake Bay Bridge, this is a rare opportunity to own an extensively updated home with spectacular water views in one of Anne Arundel County's most beloved waterfront communities.

844 Harbor View Ter, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$709,999
4 Beds ⋅ 3 Baths
Stunning remodeled home in Hillsmere! Situated on a lovely street and a large flat lot, this breathtaking home has been fully remodeled and offers some of the nicest finishes in the community! Entering through a charming 3 season room, youll be greeted by brand new lvp flooring throughout the home, a spacious family room that opens into your brand new kitchen. Kitchen features include brand new cream shaker cabinets around the kitchen, a brand new shaker island featuring oak finish, quartz counters, and brand new SS appliances. Behind the kitchen is a charming addition with lots of natural light. The main level boast 2 bedrooms, 2 fully renovated and stunning full bathrooms, including an owners suite with 2 closets and a dual vanity. Downstairs youll find 2 more bedrooms, a fully remodeled full bathroom, and an extra and open family room. The home boasts lots of attic storage as well as generous closet space. Outside, youll notice a brand new patio, lovely landscaping, and a large firepit area. The community boasts beaches, pool, pavilion areas, and more. This is a must see and wont last long! Roof replaced in 2022 and HWH in 2025.

117 Pinecrest Dr, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$349,900
2 Beds ⋅ 2 Baths
Welcome to this bright and sunny 2 BR | 2 BA condominium in desirable Tidewater Colony of Annapolis. Superb location near hospital, Navy stadium and Mall and just off 50/97 for easy commuting. Located on top level, this inviting residence features soaring vaulted ceilings that create an open, airy feel throughout. Freshly painted with newer flooring, this home is move-in ready and filled with natural light. The updated Kitchen offers stainless appliances, granite countertops and ample cabinet space, opening seamlessly to the Living and Dining areas. Slider to your balcony and storage closet. The spacious Primary BR includes a private Bath and generous closet space, while the 2nd BR utilizes Hall Bath. Laundry Room included in list price. Residents of Tidewater Colony enjoy and exceptional array of amenities including community pool, tennis court, fitness center, and beautifully maintained grounds, all just minutes from Downtown Annapolis, shopping & dining. West Annapolis Elementary School. Bright, updated and perfectly located - this is Annapolis condo living at its best and move in ready!

2011 Gov Thomas Bladen Unit #303, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$320,000
3 Beds ⋅ 2 Baths
Welcome to 8 Georgetown Court! This charming end of group town home offers 3 bedrooms, 1.5 bath on a quiet culdesac in the heart of Annapolis. Offering a functional layout with spacious living areas and abundant natural light, this home is perfect for both everyday living and entertaining. Enjoy generously sized bedrooms, a welcoming outdoor space, and the convenience of being just minutes from downtown Annapolis, shopping, dining, parks, and major commuter routes.Step outside to enjoy the private fenced patio, complete with a privacy fence, creating the perfect space for relaxing, entertaining, gardening, or enjoying your morning coffee. Whether you're a first time homebuyer, looking to downsize, or searching for your next investment opportunity, this home offers comfort, convenience, and value in a desirable location. Don't miss your chance to make this Annapolis gem your own!

8 Georgetown Ct Unit #1-8, Annapolis

Listing courtesy of Keller Williams Gateway LLC. Contact: (443) 318-8800
$845,000
4 Beds ⋅ 3 Baths
Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. Enjoy Hillsmere’s community amenities including private sandy beaches on the South River, a private marina with boat slips and direct access to the South River, boat ramps, waterfront pavilions, a community swimming pool, playgrounds, volleyball courts, and picnic areas. Whether you're boating, kayaking, fishing, or simply taking in the waterfront scenery, this community offers an unmatched coastal lifestyle. Conveniently located just minutes from historic downtown Annapolis, Quiet Waters Park, shopping, and dining, this exceptional home combines extensive recent updates with one of the area's most desirable waterfront communities. Don't miss the opportunity to make this beautifully renovated home your own.

100 Oak Dr, Annapolis

Listing courtesy of Innovative Properties, Inc.. Contact:

$985,000
5 Beds ⋅ 5 Baths
Rare opportunity to buy into Annapolis Cove. Enjoy full water privileges and option for membership in the Bay Ridge Pool Club located in the adjacent Bay Ridge community. This extra-roomy 5 bedroom colonial is situated on the large corner lot of a quiet cul-de-sac. A newly renovated basement with a separate entrance can be used for a nanny or as a mother-in-law suite. The first floor features a two-story family room, informal dining area, formal dining room, formal living room, half bathroom, and a sunroom. The family room leads directly to a large screened porch adjacent to a brick patio which overlooks a generous fenced-in yard. Upstairs features a spacious loft, a large primary suite, and three additional bedrooms and bathrooms. Hardwood floors throughout the first and second floors. Portable generator and garage refrigerator convey. Kitchen includes all new appliances and reverse osmosis water system. This is a rare availability in the community of Annapolis Cove, which boasts piers, a dinghy dock, a picnic area on Lake Ogleton, and many community events/activities.

1205 Britania Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,025,000
3 Beds ⋅ 2 Baths
Experience a hassle-free waterfront lifestyle at The Point on Spa Creek, where this stunning condo offers exceptionally easy living with picturesque views overlooking Historic Annapolis and Spa Creek. This spacious 2 bedroom 2 bath condo with flexible loft space features beautifully appointed rooms and is just steps away from the clubhouse, pool, dock, and scenic walking paths. The expansive Living room with fireplace is the perfect setting to relax and take in the views. The 2 sided fireplace also provides ambiance for the adjacent cozy nook that is ideal for a desk or reading chair. The gourmet kitchen with peninsula is sure to please any chef and the gorgeous water views makes everyday feel like a vacation. Enjoy the covered deck overlooking the waterfront; perfect for entertaining or relaxing while taking in the tranquil surroundings. The primary bedroom features a spacious closet, ensuite bath and covered balcony. With an additional light-filled bedroom, hall bath and loft space, there is plenty of room for family and guests. This vibrant community offers a wealth of amenities and residents enjoy direct access to Spa Creek, including deep-water boat slips and two water-taxi locations for easy trips to Downtown Annapolis. The waterfront pool and deck, complete with a hot tub, are ideal for relaxation, while the clubhouse can be rented for private events. Other community features include tennis and pickleball courts, EV auto chargers, and a kayak/canoe launch with a convenient rack. Social gatherings and a monthly newsletter keep residents connected, while pet-friendly policies ensure all family members are welcome. A dedicated property maintenance supervisor and ample parking make life here seamless and enjoyable. Welcome Home!

6 President Point Dr Unit #B3, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$845,000
4 Beds ⋅ 3 Baths
Location, location, location! Your new home is waiting! Looks can be deceiving, must see inside to appreciate the open, airy, light filled space. This home is located in the highly desirable Hillsmere Shores community, offering a private beach, community pool, marina, and multiple launch areas for boats, kayaks, canoes, and paddleboards — the perfect setting for anyone who loves life on the water. The home features four spacious bedrooms and three full baths, all set within an open, airy floor plan designed to capture natural light and create an inviting sense of space. A generously sized kitchen serves as the heart of the home, offering abundant prep areas, modern appliances, and effortless flow into the main living spaces. The living room is anchored by a refined propane fireplace, adding warmth and ambiance throughout the seasons. The lower-level functions as an extension of the home, complete with a private bedroom and full bath—ideal for guests or multigenerational living. A sprawling great room provides endless possibilities for entertaining or relaxation, while a dedicated laundry space and two additional flex rooms offer versatility for a home gym, office, studio, or hobby space. Bring your vision and ideas to make this space your own. Sitting on a generous lot, the property backs directly to Quiet Waters Park and includes a private path for easy access and all the park has to offer...hiking trails, a playground, dog park, outdoor summer concerts and several other fun events throughout the year. The fully fenced backyard is designed for entertaining, complete with a bar area and firepit for evenings outdoors. The detached garage/barn provides endless possibilities — workshop, studio, storage, or more. A massive, fully covered deck spans the back of the home, creating an ideal space for crab feasts, cookouts, or simply relaxing and enjoying the peaceful surroundings. This home is truly a must‑see. Looks can be deceiving — it is far more spacious than it appears from the outside, offering room to spread out and enjoy every part of the property and its incredible location.

278 Hillsmere Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$649,900
3 Beds ⋅ 3 Baths
New price! Welcome to 108 Maple Drive, a beautifully updated rancher in the sought-after waterfront community of Hillsmere Shores. Renovated throughout in 2016, this move-in ready home offers 3 bedrooms, 3 full baths, and the convenience of single-level living in one of Annapolis' most beloved neighborhoods. Inside, you'll find updated finishes, an inviting floor plan, and comfortable living spaces designed for everyday living and entertaining alike. Step outside to enjoy the screened porch overlooking a fully fenced backyard, complete with a large storage shed and plenty of room for pets, play, gardening, or gatherings with family and friends. A spacious driveway provides abundant off-street parking for multiple vehicles, boats, or trailers. Living in Hillsmere Shores means much more than owning a home—it’s a lifestyle. Residents enjoy access to a private marina with South River access, a community pool (additional membership), sandy beach, waterfront pavilions, playgrounds, kayak launches, and boat ramps. The neighborhood is also adjacent to Quiet Waters Park and just minutes from downtown Annapolis, shopping, dining, and commuter routes. Whether you're looking for your first home, your forever home, or the perfect place to enjoy Annapolis waterfront living, 108 Maple Drive offers an incredible opportunity at $699,900.

108 Maple Dr, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200
$1,750,000
4 Beds ⋅ 5 Baths
Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining, with the current living room serving as a billiards room. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

3403 Hidden River View Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,895,000
8 Beds ⋅ 6 Baths
Set on nearly two serene acres, this stately brick-front colonial commands attention with timeless curb appeal. Inside, a formal living room and a separate office or study offer refined spaces for quiet pursuits, while the expansive great room and adjoining den are connected by a dramatic double-sided fireplace, one of four throughout the home. The partially open layout flows with intention, suited to entertaining on a grand scale or gathering in comfort. A grand formal dining room is framed by a wall of windows overlooking the side garden, and the renovated cook's kitchen impresses with stainless appliances, dual wall ovens, a 36" professional series gas cooktop, and an oversized island. A separate breakfast area and a large rear deck extend the living space outdoors, overlooking the grounds and swimming pool. Upstairs, five bedrooms include an extraordinary owner's suite with a gas fireplace, walk-in closet, and a beautifully renovated bath with soaking tub. The lower level offers exceptional versatility with three additional bedrooms, a large living area or recreation room, two full baths, a renovated kitchen, and separate access, ideal for guests or extended family. A three-car garage completes the residence. Brice Manor resides within the Meadows Community, known for its oversized lots, lush lawns, and heritage trees. Tree-canopied streets and award-winning Blue-Ribbon schools define this secluded enclave, moments from the Severn River with easy access to West Annapolis, Eastport, and historic Annapolis.

234 Meadowgate Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$349,900
2 Beds ⋅ 2 Baths
Welcome to a beautifully maintained home with so many amazing features! This 2 bedroom 2 bathroom 3rd floor top level unit with over 1,080 sq ft offers a spacious, open concept layout. If you are looking for a move-in-ready property that you can be proud of, then search no further! When you walk in the front door, you will first notice the open-concept living area. The living area has so much room for entertaining. A beautiful fireplace that accents the entire space. The kitchen is beautiful with a modern style, including beautiful cabinets, countertops and matching appliances. It flows into a nice extra space for an office or eat in kitchen. This open concept has a rear porch area and a peaceful wooded scenery to enjoy nature and the outdoors. Nature is offered all around this property and many ways to enjoy it. Either walking on the wooded paths, enjoying the playgrounds, working out in the fitness center or relaxing by the pool. Both bedrooms are a good size with quality closet space and space for large furniture. The main entrance to the building has an intercom system directly to each unit for gaining access. As part of the condominium fees, it covers for common area maintenance, exterior building maintenance, lawn maintenance, snow removal, trash services, water/sewer bill and more. To top it off and ensure you move in worry-free, the home has a new gas hot water heater (2026) and a washer/dryer in the unit. This home will have you beyond excited and stress-free! Do not miss your chance to own this unique property! You will have peace of mind knowing your new home was meticulously maintained and cared for. Not to mention move-in-ready! The location is ideal for commuting, as well as being in proximity to local shops, restaurants and walking distance to many amenities! It's time for you to call it HOME!

501 Mathias Hammond Way Unit #301, Annapolis

Listing courtesy of Showcase Real Estate, LLC.. Contact: (301) 648-6000
$865,000
5 Beds ⋅ 5 Baths
TIMELESS ARCHITECTURE & RESORT-STYLE LIVING IN KINGSPORT of ANNAPOLIS Nestled within the highly sought-after community of Kingsport of Annapolis, this exceptional Neo-Traditional residence offers timeless architecture, thoughtfully curated designer updates, and an idyllic setting backing to mature trees. With five bedrooms, FOUR full and one half baths, a finished walk-up lower level, and a side-entry two-car garage, the home blends elegant formal spaces with comfortable everyday living. A classic brick front, Hardi-Plank siding, covered front porch, manicured landscaping, custom Hardi-Plank storage shed, fenced rear yard, pergola entry, raised stone garden bed, and expansive stone patio create outstanding curb appeal and inviting outdoor living spaces. Inside, the entry foyer introduces beautifully proportioned living spaces filled with natural light and clad in hardwood floors. The formal living room is framed by architectural columns, multiple windows, and transoms, while the elegant dining room showcases a distinctive octagonal turret wrapped in plantation-shuttered windows. Privately tucked between the living room and great room, the study features French glass doors and tranquil views of the wooded rear landscape. The wrap-around kitchen is designed for both entertaining and everyday living, featuring crisp white cabinetry, brushed gold hardware, contrasting quartz on the center island with breakfast bar seating, gas cooktop, and designer nautical pendant lighting. The spacious breakfast area, highlighted by a striking Sputnik chandelier, flows effortlessly into the spectacular two-story great room where soaring windows and stacked clerestory windows frame peaceful tree views and flood the home with natural light. A cozy gas fireplace anchors the space, while an atrium door opens directly to the stone patio, gardens, and fenced backyard, seamlessly blending indoor and outdoor living. An upgraded main-level laundry room adds everyday convenience. Upstairs, an open loft provides the perfect work-from-home space overlooking the dramatic great room below. French doors welcome you into the luxurious primary suite featuring a tray ceiling, designer chandelier, sitting room, private balcony, and two spacious walk-in dressing closets. The renovated spa-inspired bath offers dual designer quartz vanities, custom feature walls, elegant sconces, a frameless glass shower, soaking tub, and plantation-shuttered windows. A generous ensuite bedroom with private bath and walk-in closet, plus two additional spacious bedrooms, complete the upper level. The finished walk-up lower level offers exceptional flexibility with a spacious recreation room opening directly to the backyard, an oversized guest suite with luxury vinyl plank flooring, walk-in closet and adjacent full bath, a versatile flex room ideal as a home office, gym or overflow guest space, plus abundant storage. Life in Kingsport is equally exceptional. Nestled along the scenic shores of Spa Creek and Back Creek, this award-winning planned community is known for its distinctive architecture, mature trees, village greens, pocket parks, sidewalks, tot lots, and beautifully landscaped common areas. Residents enjoy a resort-style pool and elegant brick pool house, signature stone monument entrance with fountain, walking and jogging trails, fishing dock, kayak launch, and water access. All this is located just minutes from Historic Downtown Annapolis, the U.S. Naval Academy, waterfront dining, shopping, marinas, and convenient commuter routes to Washington, D.C. and Baltimore. Come home to a coastal inspired lifestyle with a vibrant neighborhood feel.

704 Brannock Ter, Annapolis

Listing courtesy of Northrop Realty. Contact: 4105310321
$6,995,000
4 Beds ⋅ 6 Baths
Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

3728 Ramsgate Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$655,900
4 Beds ⋅ 3 Baths
Wonderful opportunity to live in this NON AGE RESTRICTED section of Heritage Harbor and enjoy all the amenities Heritage Harbour has to offer. No initial recreational fee and lower voluntary HOA fee. Tucked away on a cut-de-sac, this spacious home is in a quiet area just minutes from shopping. This home offers a first floor bedroom with walk in closet, office, full bath with large shower and granite countertops, dining room and kitchen open to family room with gas fireplace and lovely hardwood floors. Kitchen has granite counters, stainless appliances and porcelain tile floors. Upstairs is a master bedroom with en-suite bath, 2 additional bedrooms and another full bath. There are ceiling fans in all the bedrooms Step out of the kitchen to a screened porch and brick patio. The back yard is fenced with gardens and a small area with a fountain. The roof has been replaced in the last 5 years and there are pull down stairs for the attic. Attached 2 car garage. The seller is offering a 1 year home warranty. This home has been well maintained and is waiting for it's new owner!

2656 Shadow Cv, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$385,000
2 Beds ⋅ 2 Baths
Welcome home to this beautifully maintained 2-bedroom, 2-bathroom second-floor condo offering stylish updates and comfortable living! Step inside to find gleaming engineered hardwood flooring, and a stunning stone accent fireplace. The kitchen features quartz countertops, white cabinetry, a stone backsplash, stainless steel appliances (2024-2025), and an island with additional storage. The spacious primary suite boasts three closets and a private en-suite bath with dual sinks. Enjoy the convenience of a new washer and dryer (2024), as well as a private balcony with additional storage space. Additional updates include siding replaced in 2020. Residents can take advantage of community amenities including a swimming pool and fitness center. Meticulously maintained and move-in ready, this charming condo is ready to welcome its next owner!

1140 Lake Heron Unit #2A, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

$280,000
2 Beds ⋅ 2 Baths
FHA - APPROVED !! Welcome to 302-H Hilltop Lane, a beautifully maintained home that offers a perfect blend of comfort, convenience, and low-maintenance living , close to water, boating activities, concert venues.and more. Freshly painted 2BR/2BA condo in sought-after North Green Condominiums! Features a spacious living room filled with natural light, an inviting kitchen complete with stainless steel appliances, ample cabinetry, hardwood floors throughout, tile foyer/kitchen/enclosed balcony, newer microwave, Whirlpool washer/dryer, new sliding glass door. The fully enclosed glass balcony provides additional year-round living space for relaxing, entertaining, or enjoying morning coffee. This bright, open floor plan offers a separate dining area and spacious bedrooms. Community pool, lawn maintenance included, and convenient access to downtown Annapolis, shopping, dining, major highways, and BWI Airport. Move-in ready and maintenance-free living at its best!

302 Hilltop Ln Unit #H, Annapolis

Listing courtesy of RESCOM, REALTORS. Contact: (301) 332-3606
$520,000
5 Beds ⋅ 3 Baths
Motivated seller! New price reflects home and pool "as is." This spacious split-level home offers an exceptional combination of comfort and functionality. The main level features an updated kitchen with adjoining dining area, creating a welcoming space for meals and gatherings. A stunning 400-square-foot sunroom addition provides year-round enjoyment and opens directly to an expansive 400-square-foot composite deck, perfect for entertaining or relaxing outdoors. The primary suite includes a private ensuite bathroom, while two additional bedrooms and a full hall bath complete the upper level. The walk-out lower level offers incredible flexibility with a spacious family room, a separate living room featuring a wood-burning fireplace, two additional bedrooms, and a convenient half bath—ideal for guests, a home office, or multi-generational living. Outside, you'll find driveways on both sides of the house, with parking for up to four vehicles. There are two storage sheds for all your tools and equipment, and a portable generator that conveys with the property and is capable of powering approximately three-quarters of the home. Pool, pool equipment and home convey "as is." Mortgage savings may be available for buyers of this listing.

1115 Skyway Dr, Annapolis

Listing courtesy of Redfin Corp. Contact: 4102028454
$12,950,000
6 Beds ⋅ 9 Baths
Imagine arriving home each day to a place where the pace slows, the views stretch for miles, and every amenity for recreation, relaxation, and entertaining is right outside your door. Tucked away along the Chesapeake Bay, this extraordinary waterfront retreat offers a lifestyle that few properties can match, a private oasis where luxury and nature exist in perfect balance. Originally constructed by the renowned Pyramid Builders and later transformed through an extraordinary $7 million top-to-bottom renovation, also completed by Pyramid Builders, the estate has been reimagined to an uncompromising standard. Every space, finish, and amenity was thoughtfully designed and curated to create a residence that is as functional as it is beautiful, blending timeless craftsmanship with modern luxury. State of the art features include the Crestron Home Automation and integrated Lutron lighting systems while the modern luxuries entail top of the line Miele appliances including a built-in coffee maker, microwave and convection oven, BlueStar range, radiant heated floors in all bedroom bathrooms and much more. Here, days can begin with coffee overlooking the pond and its abundant wildlife, followed by a swim in the heated saltwater pool, a match on the tennis or pickleball court, a workout in the gym, or a stroll down to the sandy beach. Evenings are spent gathered with family and friends around the pool and hot tub, watching the game on the hydraulic television that rises from the landscape, enjoying a glass of wine from the tasting room, or simply taking in the stars above the Bay. The ever-changing waterfront scenery, southern exposure, and remarkable sense of privacy create a backdrop that feels more like a luxury resort than a private residence. Designed for those who believe home should be a destination, the property offers an incredible collection of indoor and outdoor amenities rarely found in a single estate. Tennis, pickleball, basketball, a climbing wall, playground, in-ground trampoline, expansive lawns, sandy beach, pond with fountain, indoor racquetball court with basketball and volleyball capabilities, golf simulator, game room, fitness center, indoor lap pool, infrared sauna, wine tasting and cellar area, and countless spaces to gather ensure there is always something to enjoy for every generation. The residence itself is beautifully designed and thoughtfully appointed, with spacious living and entertaining areas, a wraparound screened porch that embraces the waterfront setting, private ensuite bedrooms throughout, and a dedicated guest or in-law suite that welcomes family and friends in comfort and style. Abundant storage, an attached two-car garage, and a detached garage with additional space for vehicles, golf carts, recreational equipment, and storage provide the functionality expected of a property of this caliber. What makes this estate truly special is not simply the remarkable list of amenities—it is the feeling it creates. The extraordinary combination of peace, beauty, privacy, and convenience is increasingly difficult to find. Just minutes from Annapolis, yet seemingly a world away, this is the kind of property where children spend their days outdoors, guests never want to leave, and every sunset reminds you why you chose to call it home. A rare opportunity to own a true Chesapeake Bay waterfront compound where every day feels like a vacation, every detail has been thoughtfully considered, and the lifestyle is every bit as exceptional as the home itself. Welcome Home!

2045 Maidstone Farm Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$315,000
1 Beds ⋅ 2 Baths
Experience the Baywoods lifestyle from Unit #202, a beautifully located 1BR/1.5BA cooperative residence in the sought-after Baywoods community of Annapolis. Nestled along the beautiful Chesapeake Bay, Baywoods offers residents the perfect blend of waterfront beauty, maintenance-free living, and a vibrant retirement lifestyle. Unit #202 is ideally located in the North Tower, just steps from the elevator and conveniently situated on the same floor as the Bistro, making dining and socializing easily accessible. Relax and enjoy peaceful wooded views from the spacious all-season enclosed patio, offering a private and serene setting year-round. Residents enjoy access to a wide range of amenities, dining venues, wellness programs, social activities, walking paths, and future care services—all within a scenic Annapolis setting. Call the listing agent for details on the cooperative ownership structure, buyer qualifications, monthly fees, and to schedule a private tour. Discover why so many residents choose Baywoods to enjoy the Chesapeake Bay lifestyle while maintaining independence and peace of mind.

7101 Bay Front Dr Unit #202, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000
$1,699,000
5 Beds ⋅ 6 Baths
** PRICE IMPROVEMENT** GREAT OPPORTUNITY TO OWN A PRIVATE LUXURY ESTATE ON THE BROADNECK PENINSULA!! Built in 2001, this stately brick Koch Colonial offers 4,648 square feet above grade and is nestled on a private 5.73-acre cul-de-sac lot in the highly sought-after Broadneck School District, delivering the perfect blend of luxury, privacy, and timeless elegance. Featuring a stunning 2022 gourmet kitchen renovation, 5 bedrooms, 5.5 baths, a 3-car garage with new epoxy flooring, an extended driveway, and a 2,392-square-foot finished walk-up basement, this exceptional estate is designed for both comfortable living and grand-scale entertaining. A magnificent front portico with oversized columns, paver entry, and private side guest entrance welcomes you into a dramatic two-story foyer featuring a sweeping staircase, Palladian window, hardwood floors, and detailed custom moldings. The home's thoughtfully designed floor plan also features dual staircases, providing both elegance and everyday convenience. The remodeled gourmet kitchen is the heart of the home, showcasing stacked custom white and light seafoam-green cabinetry, quartz countertops, designer backsplash, under-cabinet lighting, a large center island with storage, premium appliances, and a butler's pantry. The inviting family room boasts 10-foot ceilings, a wood-burning fireplace, and a wet bar, while the formal dining room is accented by crown molding, picture-frame trim, and elegant fixtures from Annapolis Lighting. The main level also features 9-foot ceilings, a private office, laundry room, updated full bath, and a versatile fifth bedroom or guest suite. Upstairs, the massive primary suite offers a sitting area, spa-inspired bath, and oversized walk-in closet. Three additional generously sized bedrooms each feature private en-suite baths and walk-in closets. Two of the secondary bedrooms have been enhanced with custom-themed murals painted by a local artist, adding character and charm. The expansive walk-out lower level adds 2,392 square feet of finished living space with abundant storage and a bath rough-in, providing endless opportunities for recreation, fitness, a home theater, guest quarters, or multi-generational living. Outside, enjoy your own private resort featuring a heated saltwater PebbleTec pool with three waterfalls and a diving rock, surrounded by multiple paver and flagstone patios, extensive hardscaping, professional landscaping, outdoor lighting, irrigation, and a combination of aluminum and wood fencing. The property is also outdoor speaker ready, making it ideal for entertaining poolside or hosting gatherings throughout the grounds. Additional amenities include Andersen windows, low HOA fees, a Generac generator, radon mitigation system, alarm system, a whole-home sound system with indoor and outdoor audio capability, and invisible fence readiness. Recent improvements include a 30-year architectural roof (2022), complete gourmet kitchen renovation (2022), main-level full bath renovation (2022), new upper-level and lower-level quality carpeting (2026), and epoxy garage flooring (2026). Offering more than 7,000 square feet of finished living space, resort-style amenities, exceptional craftsmanship, and a premier location within the highly sought-after Broadneck School District, this extraordinary Annapolis estate presents a rare opportunity to enjoy luxury living at its finest. Enjoy convenient access to the new Anne Arundel County Walking Trail, perfect for outdoor recreation and exercise. This home is located adjacent to Windsor Farm Elementary School and just minutes from Rt. 50, providing easy access to Downtown Annapolis, Washington, D.C., Baltimore, and Maryland's Eastern Shore beaches. Contact me today to schedule your private tour.

1322 Windsor Ridge Ln, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$575,000
2 Beds ⋅ 2 Baths
Welcome to 2016 Quay Village Court, Unit T-2, located in one of Annapolis' most sought-after gated waterfront communities. Tucked away in a private and secluded setting, this beautifully updated 2-bedroom, 2-bath home offers a peaceful retreat that barely feels like condo living. The walk-out location and mature landscaping create a wonderful sense of privacy, while the thoughtfully designed interior is warm, inviting, and beautifully maintained. From the patio and primary bedroom, you'll enjoy year-round views of the Chesapeake Bay beyond a natural shoreline of cattails and native grasses. The scenery changes daily, offering a peaceful backdrop filled with wildlife, sailboats, and ever-changing skies. Residents of Chesapeake Harbour enjoy exceptional amenities including a heated pool with lap lanes, a Bayfront pool, tennis courts, pickleball courts, private beaches, kayak launch and storage areas, community grilling stations, a marina, and waterfront dining. Professional interior photography and additional details will be uploaded soon. Stay tuned for a closer look at this special home and the Chesapeake Harbour lifestyle. https://youtu.be/fo_7CwN9AR8 Y

2016 Quay Village Ct Unit #T2, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$835,000
5 Beds ⋅ 5 Baths
Refreshed Listing! Buyers who may have missed 712 Coybay Drive the first time around, now is your chance to take another look. Please be sure to view the photos and floor plans to truly appreciate the layout, room sizes, and how well this home could fit your needs. Located in the sought-after Kingsport community of Annapolis, this spacious 5-bedroom, 4.5-bath home offers 4,230 finished sq ft, including 3,395 sq ft above grade and 835 sq ft finished below grade, with an additional 1,502 sq ft of unfinished lower-level space ready for future possibilities. The basement is a true bonus, offering a finished recreation room, 5th bedroom or office, full bath, and a large unfinished storage area that serves as a blank canvas for a media room, gym, hobby space, workshop, or expanded living area. The main level features a grand kitchen with tile flooring, stainless steel appliances, a large island, and walk-in pantry, with flexible adjoining space that can function as a dining area, sitting area, or family room. The dramatic two-story room with expansive windows and gas fireplace creates a beautiful focal point for everyday living and entertaining. A private office and laundry room are also located on the main level for added convenience. Upstairs, the bedroom layout is exceptional, with generously sized bedrooms and access to full baths, including a spacious primary suite with two walk-in closets and a spa-style bath. Outside, the beautifully designed garden patio offers a peaceful setting for morning coffee, grilling, relaxing, or entertaining. The home is positioned almost directly across from the Kingsport clubhouse, community pool, playgrounds, walking/jogging paths, pier/dock, common grounds, and other neighborhood amenities. At this price point, the seller understands some buyers may want to make cosmetic updates, but that is exactly what creates the opportunity. The home has been well maintained, offers plenty of functional living space, and gives the next owner room to grow, personalize, and build value over time. With similar homes in Kingsport selling in the upper $800s to $900K+ range, this is a strong opportunity to own a fabulous home in one of Annapolis’ desirable communities. Seller requires 15–30 days to secure home of choice.-Home Warranty for 1 year as well.

712 Coybay Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,495,000
5 Beds ⋅ 5 Baths
Experience timeless elegance in this exceptional colonial home, built in 2018 and sited on over two-thirds of an acre with protected conservation land ensuring lasting privacy. Thoughtfully and tastefully updated to reflect modern styles, every detail of this residence exudes sophistication, from its open floor plan to its refined finishes and light-filled interiors. The main level showcases a stunning great room with fireplace, a chef’s kitchen designed for culinary excellence with a quartz-topped island, custom cabinetry, generous eat-in space, a powder room, and a beautifully designed custom bar area perfect for entertaining. Upstairs, the lavish primary suite is a true retreat with a spa-inspired bath featuring a large shower and soaking tub, dual vanities, and two expansive custom walk-in closets. Three additional bedrooms and two full baths complete the level. The finished lower level offers a private guest suite with full bath and an expansive recreation space ideal for gatherings. Step outside to a resort-style sanctuary: a heated gunite saltwater pool with tanning ledge, integrated spa with cascading waterfall, retractable awning over the deck, and extensive hardscaping and landscaping. Additional features include an in-ground trampoline, playground, a large fully fenced and irrigated lawn, and a sizable custom shed for extra storage. An oversized attached two-car garage provides both practicality and convenience. Perfectly located - just a three-minute walk to Hillsmere Elementary, three miles from Historic Downtown Annapolis, and offering effortless access to Route 50, I-97, BWI, Fort Meade, and Washington, DC - this property seamlessly combines elegance, privacy, and convenience. Welcome Home!

962 Old Annapolis Neck Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$235,000
2 Beds ⋅ 1 Baths
Welcome to easy Annapolis living! This beautifully updated 2-bedroom, 1-bath condo offers the perfect blend of style, comfort, and convenience. Tucked away at the rear of the community, this home enjoys a private, wooded setting with large windows that fill the space with natural light and create a peaceful retreat from the everyday. The open-concept floor plan is designed for modern living, featuring updated flooring, fresh paint, and a spacious living area that flows seamlessly into the kitchen. The kitchen boasts granite countertops, stainless steel appliances, ample cabinetry, and a large breakfast bar perfect for casual dining, entertaining, or working from home. The generous primary bedroom features two large closets and ample storage, while the second bedroom offers flexibility as a guest room, home office, or fitness space. Step outside to the oversized private patio, an ideal spot to enjoy morning coffee, unwind after work, or entertain friends while surrounded by mature trees. Residents enjoy access to community amenities, including a pool available for a nominal seasonal fee. Ideally located just minutes from Downtown Annapolis, Quiet Waters Park, shopping, dining, commuter routes, and major highways, this home offers convenient access to both Washington, D.C. and Baltimore. Whether you’re a first-time buyer, downsizing, or searching for a low-maintenance lifestyle, this move-in-ready condo is one you won’t want to miss.

19 Heritage Ct, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4433727171
$275,000
2 Beds ⋅ 2 Baths
Welcome to the sought-after North Green Condominiums in Annapolis! This spacious top-floor, two-level penthouse loft condo offers an open and versatile floor plan designed for comfortable living and entertaining. The kitchen features granite countertops, stainless steel appliances, and ceramic tile flooring. Both full bathrooms were beautifully remodeled in 2024 and showcase stylish, modern finishes. The expansive loft provides endless possibilities as a home office, family room, exercise area, guest retreat, or hobby space. Step outside to your private balcony, the perfect place to enjoy your morning coffee or unwind after a long day. Recent updates include a main-level HVAC system replaced in 2022 and an upper-level HVAC system replaced in 2019. Residents enjoy outstanding community amenities, including a pool and entertainment area. Ideally located close to everything Annapolis has to offer, including downtown Annapolis, Truxtun Park, waterfront attractions, shopping, dining, and major commuter routes. This move-in-ready penthouse combines space, style, convenience, and an unbeatable location.

300 Hilltop Ln Unit #I, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$750,000
2 Beds ⋅ 3 Baths
Perched on the coveted south side of the 10th floor at GrandView Luxury Condominiums, Residence 1014 is more than a home—it is a private sanctuary above the treetops, where elegance, tranquility, and breathtaking views converge. Boasting a rare, unobstructed southern exposure, this exceptional residence captures panoramic vistas stretching more than 20 miles into Southern Maryland. Whether enjoyed from the comfort of the living spaces or from the private balcony, the ever-changing landscape provides a spectacular backdrop from sunrise to sunset. Meticulously maintained and thoughtfully enhanced, this two-bedroom, two-bathroom ensuite residence with a den showcases an impressive collection of recent upgrades, including a new hot water heater (2025), custom draperies in the primary suite (2025), and a complete KitchenAid appliance package—refrigerator, oven, dishwasher, and microwave (2026). Rich Swedish walnut hardwood flooring was installed throughout the living room, dining room, and den (2026), complemented by fresh paint in the dining room and den, new wall-to-wall carpeting in the primary bedroom, and coordinating luxury area rugs that beautifully unify the living and dining spaces (all completed in 2026). Beyond these recent improvements, this residence stands apart from every other Everest model in the building. Custom draperies throughout, California Closets in every closet, and bespoke built-in cabinetry in the den reflect a level of craftsmanship and attention to detail rarely found. Every enhancement was selected with intention and care, creating a home that is both sophisticated and deeply inviting. Residence 1014 offers a rare opportunity to experience elevated condominium living at its finest—where privacy, luxury, and spectacular views come together in perfect harmony. Beyond your front door, the very best of Annapolis Town Center is just steps away. Whole Foods for groceries, Target for everyday essentials, CVS for prescriptions, and Bin 201 Wine & Spirits for a carefully selected bottle are all within a leisurely stroll from GrandView’s secure entrance. Whether enjoying a relaxed breakfast, a business lunch, happy hour with friends, or a celebratory dinner, an exceptional variety of restaurants and gathering places await without ever needing to start the car. Life at GrandView is not only beautiful—it is effortlessly convenient. Ideally located just minutes from historic downtown Annapolis and centrally positioned between Washington, D.C., Baltimore, and the beaches of Maryland’s Eastern Shore, this is luxury living with unmatched accessibility.

1915 Towne Centre Blvd Unit #1014, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$315,000
2 Beds ⋅ 2 Baths
Welcome to Tidewater Colony, one of Annapolis' most sought-after condo communities! This wonderful 2-bedroom, 1.5-bath condo offers an exceptional opportunity to own an affordable home in a prime Annapolis location (just outside city limits, so NO CITY TAXES), minutes from the U.S. Naval Academy, Navy-Marine Corps Memorial Stadium, Anne Arundel Medical Center, downtown Annapolis, major commuter routes, shopping, dining, and more! Step inside to discover an inviting open-concept floor plan enhanced by vaulted ceilings, a spacious family room featuring custom built-in bookcases and a cozy gas fireplace, creating the perfect setting for relaxing evenings at home. The adjoining dining area provides seamless access to a private deck (with composite decking), ideal for enjoying your morning coffee or unwinding with an evening cocktail. The generously sized primary bedroom offers vaulted ceilings, a walk-in closet and direct access to the full bath, while a second bedroom, convenient half bath, and in-unit laundry provide comfort and functionality. Move in with confidence knowing that the major systems have already been updated, including a brand-new HVAC system (2026) and newer stainless steel kitchen appliances. Enjoy a low-maintenance lifestyle with outstanding community amenities, including a swimming pool, tennis court, walking trails, fitness center, clubhouse and Water and Sewer are included in your condo fees! Whether you're a first-time homebuyer, downsizing, or looking for an ideal Annapolis retreat, this home offers the perfect combination of value, convenience, and lifestyle. Don't miss your chance to make this exceptional condo your own. Schedule your private showing today and experience all that Tidewater Colony and Annapolis have to offer!

2015 Gov Thomas Bladen Way Unit #303, Annapolis

Listing courtesy of Veterans First Realty. Contact: (410) 280-5029
$1,150,000
3 Beds ⋅ 3 Baths
Open Friday, July 10th from 4-6:30 PM! Vacation every day in your stunning two-level condo with exceptional views and amazing privacy! Wonderful open floor plan and walls of glass make you feel like you are on a boat and create outstanding views from every room. Exceptional features include smart technology throughout, a wood-burning fireplace, soaring ceilings, GE Cafe appliances (new in 2024), electric blinds, separate dining area with a glass wall that beautifully reflects the water and accentuates the gorgeous natural light. Designer-selected tones throughout the home reflect the changing moods of the outdoors — soft greys and grey blues echo the water and sky, while subtle sunrise-inspired oranges and purples bring warmth and character to the interiors. Cherry wood floors and rich wood accents create a seamless connection between indoor living and the surrounding waterfront setting. The unit has been redesigned to increase the storage, creating ample closet space. Every day is a new opportunity to experience an incredible sunrise over the Chesapeake Bay Bridge and Eastern Shore, follow the tankers and watch the boat races. Chesapeake Harbour is a gated waterfront resort with outstanding water access, including private beaches, boat launch, and great piers for gathering with friends and neighbors to watch the races or cast a fishing line. Choose which of the two waterside community pools suits your mood (one is heated), enjoy a game of tennis on the multiple available courts, or launch your boat or board from the sandy beach and glide across the water. Take one of the many community paths to the marina (slips at Chesapeake Harbour Marina are available for a fee and NOT part of the HOA) or stop in for drinks or dinner at The Beacon harborside restaurant. Better still, stay home where you have the best view in the community and just relax. This amazing haven is located within a few short minutes of fun Eastport, Downtown Annapolis and its many offerings, dozens of scrumptious close-by neighborhood restaurants, 5 minutes from multiple breathtaking parks (Quiet Waters, Thomas Point, EO Moyer, Carr's), and it truly feels like a world away from it all! Bonus-100% turnkey-furniture included! Ask for more details!

2127 Beach Village Ct Unit #202, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$419,900
2 Beds ⋅ 2 Baths
Welcome to 953 Windwhisper Lane in the desirable Mariners Point community of Annapolis. This beautifully updated single-level duplex offers easy living with 2 bedrooms, 2 full baths, vaulted ceilings, and a bright open layout filled with natural light. Bamboo flooring runs throughout the home with no carpet, and the spacious family room features a wood-burning stacked stone fireplace and soaring ceilings for a warm yet airy feel. The updated kitchen and baths make this home truly move-in ready, while the primary suite offers the convenience of main-level living with vaulted ceilings and a private bath. Outside, enjoy beautifully maintained landscaping, a custom built stone fire-pit perfect, a freshly painted deck, charming shed, and a private fenced backyard designed for relaxing and entertaining. • Roof 2021 • HVAC/Heat pump 2023 • Hot Water Heater 2022 • New Gutters 2022 • Mariners Point residents enjoy a community pool and clubhouse, all just minutes from Quiet Waters Park, Thomas Point Park, Eastport, downtown Annapolis, and the waterfront amenities along Bay Ridge and Forest Drive including nearby beaches, marinas, dining, and shopping. Easy commuter access and off-street parking complete the package. A rare opportunity to find a move-in ready Annapolis home with single-level living at this price point.

953 Windwhisper Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$430,000
3 Beds ⋅ 2 Baths
Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining, ample off-street parking, and a beautifully landscaped, fenced yard with mature trees and plantings. Enjoy the best of coastal living in one of the area's most desirable communities.

406 Holly Dr, Annapolis

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$1,250,000
5 Beds ⋅ 5 Baths
Move-in ready and beautifully upgraded, welcome to 128 Stilly Way — a barely lived-in showpiece located in Annapolis’ sought-after Parkside Preserve community. Built in 2024 and offered in pristine condition, this exceptional residence combines the advantages of brand-new construction with the convenience of immediate enjoyment. No builder delays, no design center decisions, and no construction process — every upgrade, structural enhancement, and premium finish has already been thoughtfully selected and completed including a pool. One of the home’s most extraordinary features is its private backyard retreat. Situated in one of only three lots in the entire community approved for a full-size pool, this property offers a rare opportunity to enjoy resort-style outdoor living right at home. The custom heated saltwater pool and spa create a true luxury experience, with additional gas piping already in place for a future outdoor kitchen. The highly sought-after Fitzgerald model was built at the highest level with structural bump-outs that create expansive, light-filled living spaces enhanced by oversized windows and soaring 9-foot ceilings. The open-concept main level is ideal for both everyday living and entertaining, anchored by a stunning gourmet kitchen featuring upgraded cabinetry, premium countertops, and high-end appliances. Spacious living and dining and areas flow seamlessly to the composite deck, creating effortless indoor-outdoor living and entertaining space. A charming full front porch bricked adds timeless curb appeal and a warm welcome. Upstairs, beautifully appointed bedroom suites and spa-inspired baths continue the home’s sophisticated aesthetic and attention to detail. Every space has been carefully designed to feel elevated, comfortable, and functional. Includes additional living space on bedroom level. The fully finished walk-out lower level is a true extension of the home and a standout feature of the property. Offering a possible fifth bedroom, full bath, and expansive recreation area, this level is perfectly suited for guests, multigenerational living, a home gym, or movie nights. Direct backyard access further enhances the seamless connection between indoor and outdoor spaces. Perfectly located just minutes from historic downtown Annapolis and Eastport, with convenient access to major commuter routes, shopping, dining, and waterfront attractions, this exceptional home offers luxury, convenience, and modern living in one of Annapolis’ most desirable new communities. Come see this beautiful home that all you have to do is move in!

128 Stilly Way, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$335,000
3 Beds ⋅ 3 Baths
FHA APPROVED This is NOT a condo! Welcome to 10A Ironstone Ct, the BEST-PRICED 3-bedroom, 2.5-bathroom move-in-ready townhome in Annapolis. This beautifully maintained, spacious home offers the perfect blend of comfort, convenience, and the highly sought-after Annapolis lifestyle. The highlight is the stunning top-level primary suite, a private retreat complete with a cozy fireplace, soaking tub, separate shower, and walk-in closet. For everyday ease, the laundry room is conveniently located right on the bedroom level. Enjoy fantastic community amenities including a pool and clubhouse, all while being just minutes from Downtown Annapolis, waterfront dining, boutique shopping, entertainment, and major commuter routes. Competitively priced and ready for its next owner, schedule your tour today! PS HOA covers ALL exterior maintenance (roof, siding, gutters, shutters, etc)

10 Ironstone Ct, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8333357433
$635,000
4 Beds ⋅ 2 Baths
Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and living areas—perfect for everyday living and entertaining. Just off the living room, enjoy an enclosed deck that adds extra flexible space and a great place to relax or entertain. This level also includes three spacious bedrooms and an updated full bathroom. Downstairs, the home continues to impress with tiled flooring throughout, heated floors, and a large primary suite with a private full bathroom, plus walkout access to an enclosed patio featuring a heated exercise pool or hot tub. Outside, the property offers a large cleared lot with beautiful landscaping, an irrigation system, and a shed for additional storage. Hillsmere Shores is known for its exceptional community amenities including a marina, multiple boat ramps and kayak launches, a beach, playground, and access to Quiet Waters Park, with the Key School conveniently located right across the street. An electric vehicle charger is also included, adding even more value and convenience—this move-in ready home is a rare opportunity to enjoy a renovated property and an unmatched Annapolis lifestyle.

100 Carroll Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$980,000
3 Beds ⋅ 2 Baths
Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. .7460 Acres ! Make this PROPERTY Your Own! USE YOUR IMAGINATION! THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! SUPERIOR WATER ACCESS, STEPS TO COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE COMMUNITY BEACHES! & THE BIG WOODS "BAY RIDGE CONSERVATION AREA” W/TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! WALK TO COMMUNITY MARINA, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS , KASS PARK w/ BASEBALL/SOCCER, LACROSSE FIELD!! WHETHER YOU'RE A BOATER, SUP ENTHUSIAST, DOG WALKER, HIKER (PRIVATE TRAILS IN THE BIG WOODS), RUNNER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. SOLD STRICTLY AS IS.

54 Decatur Ave, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$10,850,000
4 Beds ⋅ 7 Baths
An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett Breeding and flawlessly built by Pyramid Builders. A complete refit elevated the home to an uncompromising standard where timeless architecture and modern sophistication exist in perfect harmony. An enchanting winding crushed gravel driveway framed by Belgian block curbing sets the tone for the remarkable experience that awaits. Perfectly positioned with western exposure, the property captures breathtaking sunsets as golden light melts into the horizon across the river and the surrounding landscape. Professionally designed landscaping creates a lush resort like setting that enhances the home’s striking architectural presence. Inside, high lacquered woodwork, bespoke millwork, hidden passage doors, attention to detail, and coffered ceilings create an atmosphere of refined sophistication. Ultra luxe Chesneys fireplace surrounds anchor multiple living spaces with warmth and elegance, while expansive walls of glass frame sweeping water views and seamlessly connect the indoors with the surrounding waterfront setting. A richly appointed wood-clad office with custom built ins offers an executive retreat designed for both privacy and inspiration. At the heart of the residence, the extraordinary St. Charles kitchen rivals those found in internationally celebrated estates, featuring Premier custom cabinetry, a statement Le Cornue range and island, exquisite fixtures, and an artisan-crafted focal point range hood, all designed for elevated entertaining and effortless daily living. Outdoor living reaches resort caliber with an elevated spa and a spectacular four sided overflow vanishing edge pool, where the waterline sits flush with the pool edge, creating a seamless visual connection to the river beyond. Exotic Ipe hardwood decking surrounds the pool and expansive rear terrace, while pergolas and a screened porch provide beautifully designed spaces for entertaining and relaxation. A new private pier, private beach, and panoramic river and pond views complete this extraordinary waterfront lifestyle. The upper level offers four luxurious ensuite bedrooms, including a phenomenal primary suite with sweeping water views, barrel ceiling, a fireside sitting room, a boutique inspired dressing gallery, and a spa quality bath with a soaking tub overlooking the water. Integrated Control4 home automation delivers effortless comfort and convenience throughout. Tucked away on the coveted Annapolis Neck peninsula, Wimbledon Farms offers a rare blend of tranquility, exclusivity, and convenience. Just moments from Downtown Annapolis and major commuter routes, the setting feels worlds away, defined by peaceful surroundings and an unmistakable sense of retreat. Encompassing only 19 estate homesites, this intimate waterfront enclave is gracefully bordered by Harness Creek and the South River, creating a breathtaking backdrop for both sunrise and sunset vistas. Residents enjoy a warm yet private community atmosphere, highlighted by occasional neighborhood gatherings and an expansive marina on protected Harness Creek, a prized deep water haven known for its calm, sheltered waters and exceptional boating access. Welcome Home!

3344 Harness Creek Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$365,000
2 Beds ⋅ 2 Baths
Welcome to 15 Copley Ct, ideally situated in one of Annapolis's most convenient locations! This home offers easy access to historic Downtown Annapolis, the U.S. Naval Academy, and Westfield Annapolis Mall—putting shopping, dining, and waterfront charm just minutes away. Enjoy living with HOA amenities including TWO community pools and a pickleball court, perfect for staying active and social right in your own neighborhood. Inside, you'll find brand-new carpet throughout the upper level and basement, plus major mechanicals in great shape, including a newer HVAC system installed just 2 years ago. Don't miss this opportunity to enjoy the best of Annapolis living with unbeatable convenience and community perks!

15 Copley Ct, Annapolis

Listing courtesy of RE/MAX Excellence Realty. Contact: 301-445-5900
$619,000
2 Beds ⋅ 3 Baths
Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with interior access and additional parking out front, a rare and coveted amenity in the neighborhood. The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay. Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath. Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!

2002 Dakota Pl Unit #2A, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
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