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$830,000
4 Beds 4 Baths
Nestled in the highly sought-after Annapolis Roads community, this spacious Colonial offers the perfect blend of comfort, privacy, and coastal living. Featuring 4 bedrooms and 3.5 baths, this well-appointed home showcases hardwood floors, a beautifully updated kitchen with granite countertops, a formal living room, dining room, and convenient main-level laundry. The upper level boasts a spacious primary suite with a vaulted ceiling, an oversized walk-in closet, and a private en-suite bath. Three additional generously sized bedrooms and a full hall bath complete the second floor. The finished lower level provides a versatile family room, a full bath, and abundant storage space—ideal for entertaining, guests, or a home office. Step outside to your own private sanctuary. The expansive sunroom overlooks a peaceful wooded backdrop, creating the perfect setting to relax, enjoy your morning coffee, and watch the birds year-round. A custom built 10' x 8' 10' tall matching shed with electricity completes the beautiful backyard. Additional highlights include a two-car garage and ample driveway parking. For added comfort, the heat pump was replaced in 2025, which switches to propane when the temperature drops below 40F. There's added assurance of a 17kw whole-house generator that runs on propane. This Siemens System with a Generac generator kicks in automatically when the power has been out for five minutes and runs the entire house. There are three 100 gallon propane tanks that can run the generator for a week. The water softener system is less than four years old. Residents of Annapolis Roads enjoy exceptional community amenities, including a private beach, boat ramp, fishing pier, bayfront pavilion, bayside picnic area, playground, fire pit, community pier, kayak storage, extensive hiking trails, and a variety of neighborhood events throughout the year. Located just minutes from downtown Annapolis, shopping, dining, and major commuter routes.

2691 Claibourne Rd, Annapolis

Listing courtesy of Redfin Corp. Contact: 3016586186

$824,995
2 Beds 1 Baths
A rare opportunity to own one of Annapolis' most distinguished historic residences, thoughtfully restored to preserve its extraordinary heritage while seamlessly incorporating today's finest amenities. This remarkable 18th-century Tidewater Georgian Vernacular home is a recipient of the 2017 Historic Annapolis Preservation Award, is listed on the National Register of Historic Places, and offers the uncommon combination of rich history, exceptional craftsmanship, private off-street parking for two vehicles, and a spacious fenced backyard. Originally constructed before the founding of the United States, the property sits at the foot of the hill from the Maryland State House and just steps from City Dock, in the heart of Historic Annapolis. The land was originally set aside for Francis Nicholson, whose visionary 1694–1695 plan established the layout of Maryland's capital city. Every detail of the restoration was carefully executed to honor the home's original character while enhancing everyday livability. Historic architectural elements have been meticulously preserved, complemented by premium modern upgrades throughout. The beautifully designed gourmet kitchen features top-of-the-line appliances, abundant custom cabinetry, generous storage, and a discreetly integrated laundry area, making it equally suited for everyday living and elegant entertaining. Inside, light-filled, generously proportioned rooms showcase timeless architectural details, three fireplaces, and the warmth and craftsmanship that only a home of this pedigree can offer. The seamless blend of original materials, thoughtful restoration, and sophisticated modern conveniences creates a residence that is as comfortable as it is historically significant. Offering a truly unparalleled Historic Annapolis lifestyle, this is an exceptional opportunity to own an award-winning piece of American history in one of the country's most coveted waterfront communities.

45 Fleet St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$650,000
5 Beds 3 Baths
Welcome to this one-of-a-kind, fully updated rancher! Offering 5 bedrooms and 3 full bathrooms, this versatile home combines modern style, thoughtful design, and exceptional functionality—all within the desirable Broadneck School District! The main level features an open-concept layout with a stunning modern kitchen showcasing quartz countertops, stainless steel appliances, sleek finishes, and an inviting dining area centered around a charming brick wood-burning fireplace. An additional living room just off the dining area provides the perfect flex space for entertaining, relaxing, or gathering with family. Four spacious bedrooms, beautifully updated bathrooms, upgraded flooring, and contemporary fixtures complete the main level. Need space for extended family, guests, or additional income potential? The separate 1-bedroom, 1-bath apartment offers its own beautifully finished kitchen with quartz countertops, stainless steel appliances, and the same modern finishes carried throughout the home, making it ideal for multigenerational living, a private guest suite, or potential rental opportunities where permitted. Outside, enjoy a quiet, generously sized lot with room to entertain, garden, or simply unwind. The attached garage provides direct access into the living area, making everyday living and unloading groceries effortless. With designer finishes, flexible living spaces, and an unbeatable location just minutes from parks, beaches, shopping, dining, and commuter routes, this move-in-ready home truly has it all. Modern homes with this much versatility in Cape St. Claire don't come along often—schedule your private showing today!

1328 Yorktown Rd, Annapolis

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

$2,250,000
5 Beds 7 Baths
Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five-bedroom, seven-bathroom home combines timeless architecture, modern updates, and resort-inspired outdoor living. A grand two-story foyer welcomes you with a sweeping curved staircase and soaring ceilings. The main level is designed for both everyday living and entertaining, featuring a formal dining room, private office, dramatic two-story family room with a fireplace, and a sunroom connected by French doors that fills the home with natural light. The gourmet kitchen serves as the heart of the home with an oversized center island, custom cabinetry, granite countertops, a spacious breakfast area, and a butler’s pantry, creating an ideal space for gatherings large and small. The main level also features a spacious primary suite with an en-suite bath, providing flexibility for a variety of living arrangements. An additional office, laundry room, and powder room complete the main level. Upstairs, a second primary suite offers a private retreat with a sitting area and en-suite bath. Three additional bedrooms each feature their own private en-suite bathrooms, providing comfort and privacy throughout the upper level. The walkout lower level expands the home’s living and entertaining space with a large recreation room, second kitchen, half bath, and abundant storage. Completed in 2023, the backyard was transformed into an exceptional outdoor living space featuring a heated saltwater pool, expansive patio, outdoor fireplace, and a fully equipped outdoor kitchen designed for entertaining and enjoying an outdoor lifestyle. Recent improvements include a new roof (2025), two new HVAC systems (2022), new wood front and garage doors, a Tesla EV charger, and a lawn irrigation system. Located in the desirable Wyatts Hill community with no HOA, this home offers convenient access to Historic Annapolis, BWI Airport, Fort Meade, Baltimore, Washington, D.C., and major commuter routes including I-97 and Route 50.

1614 Annesley Ct, Annapolis

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

$455,000
3 Beds 2 Baths
Rare opportunity to buy into a premiun Annapolis neighborhood at a fraction of the cost and remodel /design your perfect coastal dream home in the highly coveted, water-privileged community of Annapolis Roads! Nestled on a private .40-acre lot on a quiet cul-de-sac, this charming rancher offers main level living, a spacious layout , wood-burning fireplace and access to an expansive upper level deck. The lower level features a walkout basement and two additional bedrooms and bath- great for privacy! Living in Annapolis Roads means embracing a vibrant resort lifestyle offering sandy beaches with sweeping views of the Chesapeake Bay , a waterfront pavillion, playground and firepit, community dock and boat ramp, walking trails in Ogleton Woods and Fusco althetic park and numerous community events - all within walking distance to your home! There is no HOA- it is a special tax district with taxes included in the property tax. Minutes from downtown Annapolis, shopping and restaurants and major commuting routes, this home is awaiting it's transformation!

1110 Jenniper Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$499,900
6 Beds 2 Baths
Welcome Home! This spacious 6-bedroom Split Foyer in the highly sought-after Cape St. Claire community offers Chesapeake Bay views from a prime location directly across the street from the water. With 3 bedrooms on the main level and 3 additional bedrooms on the lower level, this home provides exceptional flexibility for multi-generational living, guests, home offices, or growing households. The main level features a bright living room that flows into the dining area, kitchen, and a generously sized family/sunroom, creating an ideal space for both everyday living and entertaining. Two full bathrooms, abundant storage, and a functional layout offer comfort and convenience throughout. The lower level includes three additional bedrooms, a laundry room, storage room, and a large workshop with rear exterior access, perfect for hobbies, a home business, fitness space, or extra storage. Enjoy the unmatched amenities of Cape St. Claire, including community beaches, a fishing and crabbing pier, boat ramp, marina, playgrounds, and more. Conveniently located near shopping, dining, and everyday necessities, and just minutes from Downtown Annapolis. Commuters will appreciate the easy access to Route 50, I-97, Washington, D.C., Baltimore, and Fort Meade. A rare opportunity to enjoy Bay views, outstanding community amenities, and a fantastic location while creating the home of your dreams!

1247 River Bay Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4107407100

$750,000
3 Beds 2 Baths
You’ve experienced Eastport. You’ve admired the effortless ease of its residents, and now you’re . Embrace that coveted, walkable, waterfront lifestyle. This enchanting, fully reimagined cottage offers it in abundance. Storybook curb appeal? Effortlessly. A seamless blend of timeless character and refined modern luxury? Absolutely. A short stroll to coffee, cocktails, and the beloved Eastport-A-Rockin’ Festival? Naturally. There is a reason the white picket fence endures as a symbol of the American dream. There is an undeniable allure to a home that feels as though it has been lifted from the pages of a classic novel. Set within Eastport’s sought-after Maritime District and enhanced by an owner’s discerning eye for elevated, thoughtfully curated finishes, this residence is as captivating as it is distinctive. Inside, graceful curved archways, authentic hardwood floors, and sophisticated lighting create an atmosphere of understated elegance. Custom tilework, a beautifully appointed kitchen with travertine flooring, and bathrooms adorned with refined marble surfaces reflect a commitment to quality and design. Coastal charm and contemporary sensibility are artfully balanced, resulting in a home that feels both timeless and impeccably current. Mornings unfold with quiet indulgence: a leisurely walk to Bakers & Co. for a chocolate almond croissant, followed by a scenic stroll to Oscar’s Coffee at Horn Point Marina. There, you linger over an iced coconut milk latte, exchanging greetings with neighbors before continuing on to Horn Point Park, where the shoreline invites both relaxation and play. Eastport’s celebrated dining scene may beckon, but today is reserved for hosting. Friends arrive via water taxi from the Historic District, and your home becomes the gathering place. With three bedrooms, two full baths, and a heated and air-conditioned sunroom that effortlessly transforms into a charming sleeping porch, every guest is welcomed in comfort. As evening settles in, conversation flows easily—perhaps around the fire pit beneath the stars, or within the enclosed rear sunroom, where sliding doors open wide to invite in music, laughter, and the gentle Chesapeake breeze. The following morning begins with a simple pleasure: a walk across the street to Diehl’s Produce for fresh, seasonal ingredients. Brunch is served in the formal dining room, where everyone gathers once more before heading to the marina for an afternoon sail. This is the essence of Eastport living—refined, relaxed, and richly rewarding. All that remains is your story.

1100 Bay Ridge Ave, Annapolis

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

$959,000
4 Beds 3 Baths
Beautifully updated and thoughtfully designed, this four-bedroom home offers exceptional indoor and outdoor living in the prestigious Annapolis waterfront community of Epping Forest. Where waterfront living and exceptional amenities combine to create an unparalleled lifestyle. This sought-after, water-privileged neighborhood features a new deep-water marina, wooded trails, a clubhouse overlooking the Severn River, tennis, pickleball and basketball courts, parks, and two sandy beaches perfect for swimming, relaxing, or launching your next adventure on the water. Inside, this beautifully designed home offers four spacious bedrooms, including a convenient main-level bedroom, ideal for guests, multigenerational living, or a private home office. The open, light-filled floor plan welcomes you with abundant natural light, effortless flow, and oak hardwood floors throughout, creating inviting spaces for both everyday living and entertaining. The chef’s kitchen is thoughtfully appointed with premium GE Café appliances, striking Blue-Eyed granite countertops, and abundant cabinetry, making meal preparation both functional and enjoyable. Just beyond, the inviting living room is anchored by a charming enclosed wood-burning fireplace, creating a warm and welcoming atmosphere throughout the seasons. The spacious dining area opens directly to the side patio, seamlessly extending indoor living and entertaining outdoors. Upstairs, the luxurious primary suite serves as a private retreat, featuring an expansive walk-in closet and a spa-inspired ensuite bath designed for relaxation. A charming Juliet balcony offers the perfect spot to enjoy a cool evening breeze or a quiet morning coffee. Two additional bedrooms and a well-appointed full bathroom provide comfortable accommodations for family and guests. The bright, finished lower level offers exceptional flexibility, with generous space for a recreation room, fitness area, media room, or home office. A large utility room with walk-out access to the rear patio adds both convenience and functionality. Outdoor living is equally impressive. The private patio provides an ideal setting for al fresco dining, morning coffee, or relaxing at the end of the day. Gather around the inviting fire pit on cool evenings, while the charming garden shed keeps outdoor essentials neatly organized. Beyond, a second secluded garden creates a peaceful retreat with plenty of room for family, friends, and pets to enjoy. The professionally landscaped and hardscaped grounds provide season-long color, beauty, and privacy, creating a tranquil outdoor oasis. Combining timeless style, thoughtful design, and the unmatched lifestyle of Epping Forest, this exceptional home offers a rare opportunity to experience the very best of Annapolis waterfront living. Epping Forest is a Special Tax District with an annual assessment of $2,003 and is governed by community Rules and Regulations.”

1724 Robinhood Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$685,000
3 Beds 3 Baths
ESTATE SALE - Property being sold AS IS. Welcome to 1110 Tyler Avenue. Situated on approximately .51 acres, this loving-maintained Cape Cod shows off its old school charm with an attached garage, 3 bedrooms and 3 full baths. Ready for your updates, the main level offers an en suite primary bedroom, a second bedroom, full bath, and 2 separate living rooms. The lower level features a recreation room, dry bar with refrigerator, laundry room and full bath. The updated kitchen with stainless steel appliances, hardwood floors, light filled living room overlooking the expansive deck, impressive back yard, and updated roof are just a few of its special features. The wow factor is the long, wide driveway that leads to an oversized, detached, 2 car garage with a half bath, an upper-level flex space, and updated roof. Close to Eastport shopping and restaurants, Downtown, and everything Annapolis has to offer. Welcome home!

1110 Tyler Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$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

$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

$1,425,000
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

$1,150,000
4 Beds 2 Baths
Incredible opportunity to purchase two adjoining properties - one vacant commercial parcel and one residential property with an existing home. Situated on over half an acre combined in Annapolis, this unique offering has been owned by the same family for generations and presents endless possibilities for its next owner. The commercial parcel provides a blank slate for future development or investment, while the residential property features a 4-bedroom, 1.5-bath home with numerous updates, including a roof less than 10 years old and recently replaced HVAC system and hot water heater. Whether you're looking to develop, invest, or create your own vision, this is a rare opportunity you won't want to miss. Commercial Tax ID: 020600003497200 Residential Tax ID: 020600003498600

19 Old Solomons Island Rd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$4,600,000
5 Beds 4 Baths
An extraordinary opportunity to own one of Annapolis’ most distinctive waterfront properties, offering some of the finest views on Spa Creek and the rare privilege of owning your own private marina in your backyard with dockside parking. Perfectly positioned to capture breathtaking panoramic vistas, this elegant Nantucket-inspired residence is filled with natural light, featuring walls of glass that showcase the ever-changing waterfront from nearly every room. Multiple balconies and an expansive waterside terrace invite effortless indoor-outdoor living, creating exceptional spaces for entertaining or simply enjoying the beauty of life on the water. A dockside workshop is a great opportunity to work and enjoy waterfront living. The thoughtfully designed floor plan includes spacious living areas, a versatile 1800 square feet (approximate) lower level with an in-law suite or private guest accommodations, and endless opportunities to personalize the home to suit your lifestyle. This home even has a koi pond in the front yard. Whether you’re an avid yachtsman, seeking a multigenerational waterfront retreat, or searching for a truly one-of-a-kind Annapolis property, this exceptional offering combines luxury, privacy, and an unmatched boating lifestyle in one remarkable setting. Additional details and professional photography coming soon.

140 Spa Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$845,000
2 Beds 1 Baths
An exceptional opportunity to embrace the coveted Eastport lifestyle while planning and permitting your future dream home. Situated on a generously sized lot in one of Annapolis' most desirable waterfront communities, this property offers the rare chance to move in, enjoy, and thoughtfully design your long-term vision. The existing home is a contributing structure within the Eastport Overlay District, helping preserve the neighborhood's distinctive character and charm while offering potential for substantial expansion. Buyers are encouraged to conduct their own due diligence regarding future improvements, additions, and permitting requirements. The home features solid bones, off-street parking, and endless possibilities for customization. Perfectly positioned just moments from Safe Harbor Marina, Annapolis Yacht Club, Eastport Yacht Club, Lewnes' Steakhouse, waterfront dining, shopping, and downtown Annapolis. Start enjoying everything Eastport has to offer this summer and create a legacy property in one of the Chesapeake Bay's most sought-after locations. *The second photo is an AI concept*

513 Fifth St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$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:

$559,000
4 Beds 3 Baths
Welcome to 1424 Regent Street, where modern style meets everyday comfort. This beautifully updated home offers exceptional curb appeal with a spacious driveway, a brand-new sprinkler system, and a fully fenced backyard featuring a large deck—perfect for entertaining, relaxing, or enjoying outdoor living. Step inside to discover a stunning custom-designed living room highlighted by a striking gold and white accent wall that creates a warm, sophisticated focal point. The adjoining dining area flows seamlessly into the show-stopping custom kitchen, complete with stylish cabinetry, gorgeous quartz countertops, and designer finishes that make cooking and gathering a true pleasure. The spacious primary suite features its own en-suite bathroom featuring custom designer finishes. An additional beautifully renovated full bathroom upstairs offers both style and convenience for family and guests. Throughout the home, you'll find thoughtfully designed custom bathrooms and quality updates that create a move-in-ready experience. The lower level offer additional entertaining space with a stone fireplace, as well as a bedroom and a full bathroom. With its modern upgrades, designer touches, functional layout, and inviting spaces, 1424 Regent Street is a home you'll be proud to call your own.

1424 Regent St, Annapolis

Listing courtesy of Allfirst Realty, Inc.. Contact: 4433201344

$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

$775,000
5 Beds 3 Baths
OPEN HOUSE CANCELED PROPERTY UNDER CONTRACT Welcome to 1908 Dulaney Place! This 5-bedroom, 3-full bath home is located in the highly sought-after community of Pendennis Mount. Perfectly positioned just over the Naval Academy Bridge, this exceptional location offers quick access to the U.S. Naval Academy, Historic Downtown Annapolis, the Navy Golf Club, Sandy Point State Park, the Chesapeake Bay Bridge, and Maryland's Eastern Shore. Enjoy he highly rated Broadneck School Distric, plus easy commuting with quick access to Routes 50, 97, and 100. Designed for both everyday living and entertaining, this spacious home offers multiple gathering spaces including a bright sunroom, inviting screened porch with low-maintenance composite decking, and an extended brick patio overlooking the fully fenced backyard. The kitchen features updated appliances (2026) and natural gas is also available for the range. The living room is drenched in natural light with a large sky light with beam detail. 3 Bedrooms and 2 full bathrooms on the main level including the Primary en-suite. The cozy lower level family room is anchored by a gas fireplace insert and has built-in shelving for storage and function. 2 more bedrooms and 1 full bath, plus laundry room and access to the attached one car garage (heated and air-conditioned) on the lower level as well. The true showstopper is the incredible 600-square-foot detached garage—a rare find! Heated and air-conditioned with an oversized garage door and space for up to four vehicles, it offers endless possibilities for car enthusiasts, boat storage, a home gym, workshop, studio, hobby space, or additional recreational storage. Thoughtful updates provide peace of mind, including an updated architectural shingle roof with Velux skylights (2024), HVAC and gas furnace (2016), water heater (2016), updated windows, washer and dryer (2026), and exterior power washing (2026). Septic system was installed in 2008 with two dry wells and has been professionally maintained. Additional features include a storage shed, Lead-Free Certificate, and beautifully maintained landscaping. Offering an unbeatable combination of location, space, and one of the most versatile garage setups you'll find in the Annapolis area, this Pendennis Mount home is ready to welcome its next owners. *Square Footage is estimated. *Some photos have been virtually staged.

1908 Dulaney Pl, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425

$1,350,000
3 Beds 3 Baths
Welcome to a waterfront retreat where timeless coastal living meets modern luxury. Perfectly positioned on approximately one private acre along the tranquil waters of Mill Creek with direct access to the Chesapeake Bay, this custom-built home offers the exceptional lifestyle that Annapolis is known for. Designed to capture breathtaking water views from nearly every room, this beautifully appointed 3 bedroom, 2.5 bath Chalet features an open, light-filled floor plan with soaring ceilings, rich hardwood flooring, a cozy fireplace, and expansive windows that bring the outdoors in. The gourmet kitchen flows seamlessly into the living and dining spaces, creating an inviting atmosphere for entertaining or relaxing while enjoying picturesque waterfront vistas. The fully equipped kitchen boasts modern stainless steel appliances and ample space for entertaining. Wake up each morning in the serene primary suite overlooking the water, which features a large walk-in closet and a whirlpool soaking tub. Then, step outside to experience your own private waterfront oasis. The expansive deck is ideal for hosting family and friends, enjoying morning coffee, or taking in spectacular sunsets over Mill Creek. This property includes docking for two boats and deep-water access, perfect for boating, crabbing, and fishing. Conveniently located just five minutes from the U.S. Naval Academy, West Annapolis, and historic downtown Annapolis, this home provides easy access to shopping, dining, and entertainment. Washington, D.C and Baltimore are each only 30 minutes away. Local highlights include Cantler's Riverside Restaurant, a renowned spot for seafood and steamed crabs right on the water, as well as the charming shops and cafes along Main Street and in nearby West Annapolis. Outdoor lovers will appreciate the close proximity to Sandy Point State Park, as well as nearby golf courses and trails for year-round recreation. Whether you’re searching for a primary residence or legacy waterfront property to enjoy for generations, this extraordinary home offers a rare opportunity to own one of Annapolis’ most desirable waterfront settings. Schedule your private tour today and discover the Chesapeake lifestyle you’ve been dreaming of.

2203 Mulberry Hill Rd, Annapolis

Listing courtesy of Keller Williams Preferred Properties. Contact:

$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:

$750,000
4 Beds 3 Baths
Nestled in the sought-after water-privileged community of Lindamoor, this beautifully updated home blends timeless character with modern comfort. Original hardwood floors complement a renovated kitchen featuring natural wood cabinetry, granite countertops, stainless steel appliances, and a raised breakfast bar with decorative glass accents. The private, tree-lined setting creates a serene backdrop for the screened porch and composite deck, perfect for relaxing or entertaining. The spacious primary suite offers a vaulted ceiling, oversized walk-in closet, and a luxurious bath with a Kohler air-jet tub, double vanity, separate shower, and cathedral ceiling. The lower level features durable flooring throughout the family room and fourth bedroom or office, complete with a wall of custom built-ins and convenient access to a full bath with jetted tub. A raised-hearth gas fireplace anchors the family room, which opens to a covered paver patio overlooking the backyard and wooded buffer. Additional highlights include a 3-4 car paver parking pad, abundant indoor storage, and a dedicated outdoor storage room with workbench. Voluntary Lindamoor Improvement Association membership ($150/year) provides access to community paths leading to Cove of Cork and the Severn River, a community pier, sandy beach and a mooring area.

59 Sleepy Hollow Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$799,000
3 Beds 3 Baths
Welcome to 307 Glen Ave, a charming cedar shake home in the heart of Annapolis's highly sought after Homewood community. Originally built in 1901 and thoughtfully renovated in the mid-2000's, this 3 bedroom, 2.5 bath residence seamlessly blends historic character with modern convenience. Situated on an oversized 8,812 square-foot lot, this home offers timeless curb appeal, generous outdoor living space, and an exceptional location. The classic cedar shake and inviting front porch create a warm welcome, while the interior features comfortable living spaces filled with charm and character. Recent improvements include a new HVAC system (2024), oven/range and microwave (2022), dishwasher, washer and dryer (2021) providing peace of mind for the next owner. Newly painted front porch along with the dining and living rooms. Located just steps from the Navy-Marine Corps Memorial Stadium and within walking distance of local restaurants and coffee shops, this home offers a lifestyle that is increasingly hard to find. Enjoy easy access to Downtown Annapolis, West Street dining and entertainment, the U.S. Naval Academy, waterfront attractions and major commute routes to Baltimore and Washington, D.C. Professional photos coming soon July 8th.

307 Glen Ave, Annapolis

Listing courtesy of Corner House Realty. Contact: (443) 499-3839

$1,289,900
4 Beds 2 Baths
Rare opportunity to own a stunning newer built fully detached four bedroom home in the historic district with an attached one car garage plus a one car driveway​ —an amenity rarely found in downtown Annapolis. Tucked away on a quiet street just steps from Spa Creek and City Dock, 12 Union Street combines the charm and walkability of the Historic District with the comfort and convenience of newer construction. Spanning four levels, the home is filled with natural light and offers high ceilings throughout. The entire interior has recently undergone a significant refresh, including resurfaced hardwood floors, all-new carpet, professional interior painting throughout, new lighting fixtures, new outlets and switches, a new kitchen backsplash and quartz countertops, plus a new dishwasher, refrigerator, and hot water heater. With four bedrooms and two full baths, the flexible floor plan provides plenty of options for guests, a home office, gym, or additional living space. Outdoor living is equally inviting, featuring a screened porch off the second level and a spacious deck off the main level with additional outdoor space ideal for relaxing, entertaining, or creating a garden retreat. The unfinished basement offers exceptional storage and future potential, featuring windows that bring in natural light and unusually high ceilings rarely found in similar downtown homes. Step outside and enjoy everything that makes Annapolis special. The waterfront is just moments away, while the U.S. Naval Academy, restaurants, shops, parks, and all the attractions of downtown Annapolis are within easy walking distance. Whether you're looking for a full-time residence, a weekend escape, or a smart investment, 12 Union Street offers an exceptional opportunity in one of Annapolis' most sought-after locations.

12 Union St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$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:

$1,295,000
4 Beds 4 Baths
Rare opportunity to own a true deep-water waterfront property offering breathtaking, tranquil views of Whitehall Creek. With approximately 8 feet of water depth in the slips and 11 feet at the end of the pier, this exceptional property is a boater's dream, providing effortless access to deep water and the Chesapeake Bay beyond. The gentle approach from the backyard to the pier is an added luxury rarely found on waterfront properties. Cherished by the same family for nearly four decades and enjoyed by three generations, this special home is ready for its next chapter. Whether you choose to renovate, expand, or build the waterfront retreat you've always envisioned, the possibilities are endless. The generous footprint and public sewer connection create an outstanding opportunity to design and customize your dream waterfront residence. The main level offers expansive living spaces perfectly suited for gatherings of any size, including a spacious kitchen, oversized dining room, and an impressive family room designed for entertaining while capturing beautiful water views. A highly desirable feature, the main floor includes three bedrooms, two of which are positioned waterfront and one offering a private ensuite bath. Upstairs, the oversized primary suite serves as a peaceful retreat, showcasing stunning panoramic views of Whitehall Creek and a private ensuite bathroom. The walkout lower level adds even more living space with a large recreation/family room centered around a striking stone fireplace, along with an additional full bathroom, bringing the home's total to four full baths. Properties offering this combination of deep water, protected harbor, spectacular views, public sewer, and unlimited potential are exceptionally rare. Create the waterfront legacy property you've always dreamed of in one of Annapolis' most coveted waterfront settings!!

1668 Homewood Landing Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: