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$899,900
3 Beds 2 Baths
Some homes simply have a soul—and this is one of them. For more than 100 years, this impeccably maintained Annapolis treasure has been the backdrop for holidays, celebrations, and everyday moments that become cherished memories. Lovingly cared for through the generations, it now awaits its next chapter. Perfectly positioned on an oversized corner lot overlooking the Poplar Trail, this enchanting property offers an increasingly rare combination of historic character, generous outdoor space, and an unbeatable walkable location. Stroll to Downtown Annapolis, West Annapolis, Navy-Marine Corps Memorial Stadium, restaurants, shops, parks, and waterfront attractions while enjoying the tranquility of this picturesque neighborhood. From the moment you arrive, you'll appreciate the home's original slate roof, timeless architecture, and meticulous care throughout the years. Inside, authentic details tell the story of its rich history—from gleaming hardwood floors and original crystal doorknobs to the charming laundry chute and elegant built-in dining room cabinetry. The spacious main level offers exceptional flexibility with a welcoming living room anchored by a cozy fireplace, an expansive dining room perfect for hosting family gatherings, a full bath, and a thoughtfully expanded kitchen featuring granite countertops, oak cabinetry, and a pantry. Hardwood floors are believed to be preserved beneath much of the main-level carpeting, offering even more timeless appeal. Two enclosed side porches add valuable year-round living space and endless possibilities, including the potential for a main-level bedroom, home office, or inviting sunroom. Upstairs, you'll find three generously sized bedrooms, a full bath, and access to a fully floored attic offering exciting possibilities for future finished living space. Downstairs, the expansive lower level offers abundant storage, workshop space, and plenty of room for hobbies, projects, or future creative use. Step outside and discover a backyard designed for making lifelong memories. Whether you're cooling off in the in-ground pool, relaxing beside the peaceful fish pond, gardening, entertaining family and friends, or simply enjoying the privacy of the expansive yard, this outdoor oasis offers something for everyone. A detached one-car garage, private parking pad, storage shed, and mature landscaping complete the property. Additional highlights include Thompson Creek replacement windows, timeless architectural details throughout, and an unbeatable location that perfectly balances convenience with neighborhood charm. Homes like this rarely come to market. Rich with character, impeccably maintained, and filled with endless possibilities, this is more than just a home—it's an opportunity to become part of its story and create a lifetime of memories for generations to come.

916 Poplar Ave, Annapolis

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

$350,000
3 Beds 1 Baths
Updated images to be uploaded. Completely renovated and perfectly located, this move-in-ready Annapolis ranch is proof that great things come in the perfect size. Thoughtfully redesigned for today's lifestyle, this beautifully updated one-level home offers the modern finishes buyers love without the maintenance of a larger property. Step inside to discover bright, inviting living spaces filled with natural light and quality finishes throughout. The stunning renovated kitchen serves as the centerpiece of the home, featuring stylish cabinetry, upgraded countertops, modern fixtures, and a layout designed for everyday living and effortless entertaining. Every room has been refreshed to create a home that feels both timeless and welcoming. The convenience of single-level living makes this home ideal for first-time buyers, downsizers, professionals, or anyone looking for low-maintenance living without sacrificing style or comfort. Outside, the yard offers space to entertain, garden, relax, or simply enjoy the outdoors. Located just minutes from Historic Downtown Annapolis, the U.S. Naval Academy, Quiet Waters Park, Chesapeake Bay waterfront, Annapolis Town Center, shopping, dining, marinas, entertainment, and major commuter routes including Routes 50 and 97, you'll enjoy everything that makes Annapolis one of Maryland's most sought-after destinations. Spend weekends exploring waterfront restaurants, local boutiques, festivals, boating, and scenic parks while still enjoying an easy commute to Washington, DC and Baltimore. Whether you're searching for your first home, your forever home, or a turnkey investment property, 1803 Lincoln Drive offers the perfect combination of location, modern updates, and exceptional value. Homes like this don't stay available for long. Schedule your private showing today.

1803 Lincoln Dr, Annapolis

Listing courtesy of Goldmine Realty. Contact: (240) 343-3441

$1,150,000
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 The subject includes two adjoining parcels of land, totaling 23,993 square feet (SF), generally level and elongated, rectangular-shaped, improved by a 1,660 SF, one and one-half story, frame single-family dwelling, with four bedrooms and 1 & 2/3 baths. Built in 1955, condition is good, above average for age. The front lot contains 12,345 SF, with 59 feet of frontage on Old Solomons Island Road. This parcel has PM Professional Mixed Office zoning and is sodded. The rear parcel contains 11,648 SF with R3 residential zoning. It is improved by the dwelling, a 920 SF carport, a 300 SF storage shed and a paved parking area.

19 Solomons Island Rd, Annapolis

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

$1,999,900
4 Beds 5 Baths
COMING SOON – Available August 16, 2026! Floor plans, and a full virtual tour are coming soon. The current online photos are only a preview of what is truly one of the most spectacular waterfront properties to hit the market this year. Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just minutes from Exit 22, approximately 10 minutes to Route 50, and only 15 minutes to historic downtown Annapolis. For boating enthusiasts, this property is truly second to none. The private pier features a 10,000-pound boat lift, water and electric service, including two 220-volt outlets, three boat slips, floating dock and approximately 5+ feet of water at mean low water, making it ideal for larger vessels. A nearby marina and gas dock provide exceptional convenience for fueling, maintenance, and everyday boating adventures. The owners have meticulously maintained and updated the home with major improvements, including a new roof (2021) and upper-level HVAC system (2025). The exterior is equally impressive, featuring an attached two-car garage and driveway parking for up to six additional vehicles. Whether you're hosting family gatherings or waterfront celebrations, there's room for everyone. Step inside and you'll immediately be captivated by breathtaking water views. The welcoming living room features the first of two fireplaces and overlooks the creek, creating the perfect setting to relax year-round. As you continue into the heart of the home, you'll discover an expansive dining area surrounded by panoramic water views that will have you lingering over every meal. Sliding doors lead to a covered brick patio and an incredible backyard designed for entertaining on any scale—from everyday cookouts to milestone celebrations, weddings, corporate events, and unforgettable waterfront parties. Pet owners will appreciate the professionally installed invisible fence, allowing your four-legged family members to safely enjoy the expansive yard. The main level also offers a spacious kitchen, large family room, private office with a convenient half bath, a generously sized bedroom, and a full laundry room. Upstairs, the luxurious owner's suite offers stunning sunrise views over the creek and features an incredible layout with his-and-her bathrooms, a walk-in closet, and a true owner's retreat experience. Two additional bedrooms share a spacious full bath, while the loft provides the perfect second gathering space for movie nights, gaming, reading, or studying. A second laundry room on the upper level adds everyday convenience, and the walk-up attic with pull-down stairs provides abundant storage. Need even more flexibility? A detached waterfront office equipped with its own mini-split heating and cooling system creates the ideal work-from-home environment, art studio, or private retreat—all while enjoying incredible views of Gingerville Creek. Properties offering this combination of panoramic waterfront views, exceptional boating amenities, generous living space, thoughtful updates, and an unbeatable Annapolis-area location are extraordinarily rare. Complete photos, floor plans, and additional details will be available soon. Don't miss your opportunity to own one of the area's premier waterfront homes

120 Island View Dr, Annapolis

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com

$509,900
3 Beds 2 Baths
Welcome to 282 Cedar Lane, a beautifully updated rancher nestled in one of Annapolis' most sought-after waterfront communities. This move-in ready home blends timeless charm with thoughtful updates, beginning with a stunning magazine-worthy kitchen featuring nautical navy cabinetry, warm butcher block countertops, and stainless steel appliances—a space that's both stylish and functional. Beautiful oak hardwood floors flow throughout the main level, where you'll find three comfortable bedrooms and a full hall bath. The finished lower level provides additional living space perfect for a family room, home office, gym, or playroom and includes a half bath, the laundry room and additional unfinished storage space. Major updates provide peace of mind, including a new roof (2017) and hot water heater (2019). Life in Hillsmere Shores is about so much more than the home itself. This beloved waterfront community offers a private marina with direct access to the South River, a community pool, sandy beach, waterfront pavilions, and multiple playgrounds. Residents also enjoy walking access to Quiet Waters Park, Hillsmere Elementary School, the Eastport-Annapolis Library, PAL Park, and Bay Ridge Plaza shopping and dining. Just 3 miles from Historic Downtown Annapolis, Hillsmere Shores combines the charm of an established neighborhood with the convenience of nearby restaurants, boutiques, marinas, and waterfront attractions.

282 Cedar Ln, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

$549,995
3 Beds 2 Baths
Welcome Home! Don't let summer slip away before you have the chance to relax by this beautiful pool while enjoying one of the best waterfront views around .This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool. This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butler’s pantry and laundry cabinetry for smart, hidden storage. A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit. Enjoy exclusive ownership of a deeded deep water 30+ foot boat slip—one of the few in Annapolis with direct vehicle access, allowing you to drive right to the dock for easy loading and unloading. Located in the heart of Eastport, Severn House offers a waterfront pool, beautifully maintained grounds, and the area’s most protected deep-water marina. Sidewalks lead to Downtown Annapolis, the U.S. Naval Academy, and the city’s famed restaurants and shops. This turnkey waterfront condo perfectly balances luxury, comfort, and location—schedule your private showing today.

755 Fairview Ave Unit #755 D, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

$899,999
4 Beds 3 Baths
Nestled at the end of a quiet court in sought-after Admiral Heights, 1 King Ct offers 3,125 square feet of comfortable, updated living across four bedrooms and two and a half baths. This home is ready for its next chapter—thoughtfully improved and move-in ready. The showpiece is the 2022-renovated kitchen, where warm wood flooring meets crisp quartz countertops and a custom marble backsplash. GE Café appliances—including a gas range with matching hood, refrigerator, and dishwasher, plus a GE microwave—elevate everyday cooking, while fresh cabinetry, a center island, and LED recessed lighting bring both function and style. Throughout the home, hardwood floors sanded and refinished in 2022 pair with new carpet for an inviting flow. Custom California Closets keep every room organized, and a whole-house humidifier adds year-round comfort. Peace of mind comes standard: a brand-new HVAC system (2026), a 2023 water heater, and fresh fencing installed in 2024 and 2025. Sellers replaced roof in 2024! Living here means embracing a water-privileged community. Residents enjoy Dewey Dock at Heineman Park for fishing, swimming, and launching kayaks on Weems Creek; the Williams Drive Park & Boat Club with private slips and gear storage; Halsey Park's open green space for gatherings; and the Admiral Heights Swim Club with a summer swim team. Downtown Annapolis is minutes away, offering fine dining, boutique shopping, the City Dock, and the Naval Academy—while Route 50 provides easy access to Baltimore and Washington, D.C. At 1 King Ct, refined updates meet an unbeatable Annapolis lifestyle

1 King Ct, Annapolis

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

$1,650,000
5 Beds 3 Baths
Welcome to this spacious and beautifully maintained 5-bedroom, 3-bath home in the highly sought-after Murray Hill neighborhood of Annapolis. Blending timeless charm with modern comfort, this exceptional home offers generous living spaces designed for both everyday living and entertaining. The thoughtfully designed floor plan features an abundance of natural light throughout and gleaming hardwood floors. The welcoming Foyer that flows seamlessly into the Living Room complemented by a warm, inviting fireplace. The gracious Dining Room flows effortlessly to the centerpiece of the home, the beautifully appointed Kitchen. Featuring a chef's gas range, stone countertops, wine refrigerator and stainless appliances and an island provides generous workspace. Adjacent to the Kitchen is the Family room with large windows you can mingle with the laughter of family and friends while entertaining. After a long day retreat to the upper level which includes four generously sized bedrooms. The serene Primary Suite includes a large walk-in closet with second laundry area and an en-suite bathroom with an extra large stand up shower. A standout feature of the home is the expansive third-floor level. Offering incredible flexibility as the fifth bedroom, media room, artist's studio or whatever best fits your needs. The large unfinished basement provides laundry, mechanicals and an exceptional storage space. Relax on the inviting, spacious front porch sipping your morning coffee, evening cocktails or simply watching the neighbors stroll by. Or entertain family and friends on the beautiful backyard patio, an unexpectedly expansive tree-framed yard creates a secluded outdoor retreat-an uncommon luxury featuring a built-in grill—perfect for outdoor dining and gatherings. A two-car garage and ample off-street parking provide a rare convenience in this desirable downtown location. Enjoy the best of Annapolis living with easy access to the waterfront, parks, marinas, restaurants, shopping, and the Historic District. Offering an unbeatable combination of space, charm, and location, this is a rare opportunity to own a beautiful home in one of Annapolis’ most coveted neighborhoods. Walk to the many coffee shops, compete in the May Day flower basket contest or hop on a water taxi. Dine under the stars on West Street with friends and neighbors. The Historic Charm of Annapolis blended with the boater's paradise of the Chesapeake Bay is a quick commute to D.C., Baltimore and BWI which attracts so many to this area. This is more than just a home; it's an exciting opportunity to live your best life, enjoying family and friends. This coveted Murray Hill address delivers luxury, space and lifestyle. MUST SEE!

137 Monticello Ave, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$599,000
3 Beds 2 Baths
Offer deadline Monday 27th at 5:00PM Seller reserves right to accept offer at anytime. Welcome to Colony Hills, one of Eastport's most coveted neighborhoods, where charm, convenience, and community come together with no HOA. This exceptionally stylish Cape Cod is full of character and timeless appeal, offering thoughtfully updated spaces inside and incredible outdoor living areas you'll enjoy year round. Step inside to discover a freshly painted interior accented by beautiful hardwood floors throughout the main level. Natural light pours into two inviting living spaces, creating a warm and welcoming atmosphere. The dining room is perfect for intimate dinners or entertaining family and friends and features two charming built ins that add both character and functionality. The beautifully updated kitchen is designed for gathering, complete with updated countertops, a large center island, stainless steel appliances, gas cooking, and exposed beams that create the perfect blend of warmth and style. Just beyond the kitchen, a spacious rear family room provides even more room to relax or entertain. The main level also features a generously sized bedroom and full bathroom, making it ideal for guests or flexible living. The bedroom offers two closets, including a unique bonus space that could easily serve as a small workshop, craft room, or creative studio. A full laundry room provides excellent storage and everyday convenience. Upstairs, you'll find the private primary suite and an updated bathroom, along with an additional bedroom. Charming nooks and architectural details throughout the upper level add to the home's undeniable character. The outdoor spaces truly set this home apart. Relax in the three season porch, soak in the brand new, top tier, hot tub on the expansive new Trex deck, or gather around the fire pit on crisp fall evenings, all with a fully fenced yard. Whether you're hosting friends or enjoying a quiet night at home, this backyard was designed for making memories. Don't miss the large shed, great for storing lawn and gardening equipment. Parking is a breeze with the large concrete driveway. Living in Colony Hills means you're just a short stroll to Eastport favorites like Vin 909, Adam's on Fourth, and Sammy's Italian Kitchen, or a quick bike ride to Historic Downtown Annapolis, Quiet Waters Park, and the Pip Moyer Recreation Center. Commuters will appreciate easy access to the U.S. Naval Academy, NSA Annapolis, Fort Meade, Baltimore, Washington, D.C., and BWI Airport. This is Eastport living at its finest. Don't miss your opportunity to call this special home your own, schedule your private showing today! *Updates include: Finished three season room/side porch (2025), Deck (2025), Hot Tub (2025), HVAC (2023), Crawl Space Encapsulation/Sump Pump/Dehumidifer (2023), Fence (2022), Roof/Siding/Windows (2021), Plantation Shutters (2021)

1105 Van Buren St, Annapolis

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

$1,575,000
4 Beds 4 Baths
Nestled along one of the most prestigious streets in Historic Annapolis, 268 King George Street presents a rare opportunity to own a beautifully renovated residence just steps from the U.S. Naval Academy, St. John's College, City Dock, Main Street, Spa Creek, and the Chesapeake Bay. Offering the perfect blend of historic charm and sophisticated modern living, this exceptional home places you at the center of everything that makes Downtown Annapolis one of Maryland's most desirable destinations. A welcoming covered front porch sets the tone for the home, providing the perfect place to relax, greet neighbors, or enjoy the charm of one of Annapolis' most iconic streets. Inside, timeless architectural details, including rich heart pine floors, soaring ceilings, elegant moldings, and oversized windows, are beautifully complemented by thoughtful, high-end renovations. Designed for both everyday living and effortless entertaining, the main level features elegant formal spaces, including a gracious dining room anchored by a beautiful fireplace and a spacious living room filled with natural light. The gourmet kitchen is appointed with premium appliances, custom cabinetry, generous workspace, and opens seamlessly to a sun-filled four-seasons room, creating an inviting gathering space for family and friends. Upstairs, the luxurious primary suite offers a peaceful retreat highlighted by two walk-in closets with custom built-in organization systems, providing exceptional storage rarely found in Historic Annapolis homes. The beautifully renovated bathrooms showcase designer-inspired tilework, custom vanities, and sophisticated finishes that blend timeless style with modern comfort. Additional bedrooms offer generous accommodations, while the private third-floor suite provides the ideal space for guests, a home office, fitness studio, or additional living area.Outside, a beautifully landscaped courtyard offers remarkable privacy and a tranquil setting for outdoor dining, entertaining, or quiet evenings in the heart of downtown. From your front door, enjoy easy access to award-winning restaurants, boutique shopping, waterfront parks, marinas, sailing, museums, galleries, and the vibrant energy of City Dock. Whether you're looking for a full-time residence or an exceptional Annapolis retreat, 268 King George Street offers an extraordinary opportunity to experience luxury living in one of Maryland's most treasured historic waterfront communities.

268 King George St, Annapolis

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848

$2,400,000
4 Beds 5 Baths
Nestled on one of the most picturesque streets in Annapolis, this utterly charming Murray Hill home blends timeless character with thoughtful modern updates. A welcoming wraparound porch overlooks the beautifully landscaped front yard, complete with a stunning dogwood tree, while the fenced backyard offers a private courtyard patio that's perfect for outdoor entertaining. A rare 24' x 22' detached two-car garage provides exceptional storage and convenience. Inside, classic architectural details create a warm and inviting atmosphere. The gracious foyer opens to gleaming hardwood floors, oversized moldings, and elegant French doors connecting the living and dining rooms. Two gas fireplaces—one in the living room and another in the family room—add warmth and charm throughout the home. The beautifully appointed kitchen features custom cabinetry, granite countertops, a four-burner gas range with griddle and hood, and a wine refrigerator. A conveniently located powder room completes the main level. Plantation shutters throughout the home add timeless style and privacy. The spacious family room off the kitchen features a fireplace & custom built-ins for abundant storage, while double French doors open to the delightful courtyard, seamlessly blending indoor and outdoor living. Upstairs, the generous primary suite offers a walk-in closet and an en suite bath with dual vanities and a walk-in shower. Two additional bedrooms share a charming hall bath featuring a classic clawfoot tub and a custom vanity installed in 2020. An open sitting area creates the perfect reading nook or home office, and the laundry is conveniently located on this level. The third floor is home to a delightful fourth bedroom with cathedral ceilings, exposed beams, a large walk-in closet, and a private full bath—an ideal guest suite or private retreat. The finished lower level provides exceptional flexibility with a spacious second family room featuring built-in shelving, plus an additional room currently used as a home office and fitness area. A half bath completes this level. Additional highlights include three-zone heating and cooling, a new roof installed in 2020, and a fully encapsulated crawl space. Ideally located on Southgate Avenue, this exceptional home offers easy walkability to downtown Annapolis, the U.S. Naval Academy, and the city's renowned shops, restaurants, and waterfront. At the end of the street, enjoy water access to Spa Creek—perfect for launching a kayak or stand-up paddleboard and embracing the Annapolis lifestyle.

62 Southgate Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$874,900
Welcome to 220 West Street in Annapolis, Maryland: a rare, fully gut-renovated detached property in the heart of the Downtown Arts District, offered at a row home's price and carrying MX mixed-use zoning that opens the door to residential, commercial, and income-producing use alike. Completed in 2024, the property has been transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for a buyer seeking a lifestyle home, an investment asset, or a business address in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached building, not a rowhome or townhouse, giving it enhanced privacy, natural light, and a far more versatile footprint for adaptive use. The mixed-use zoning is the story. Under Annapolis MX, the building can serve as a full-time residence, a furnished short-term or corporate rental, or a range of commercial uses including professional and medical office, a personal-care or boutique fitness studio, a gallery or arts studio, or hospitality and food-and-beverage concepts such as a wine bar or cafe, with boutique lodging and inn use available through the City's approval process. The property's own history proves the point: it has previously operated as a furniture store, office space, and a duplex residence. Few Downtown Annapolis addresses offer this much optionality. The extensive renovation includes a brand-new roof, all-new electrical and plumbing, a new high-efficiency mini-split HVAC system, a redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. A modern fire sprinkler system is in place, a meaningful head start for any commercial or lodging adaptation. Outside, the spaces have been completely upgraded with a new deck, brick patio pavers, new fencing, and ambient lighting made for evening entertaining. Inside, a bright two-story entry foyer opens to a professionally curated interior that blends modern comfort with intentional functionality. Three bedrooms and two full bathrooms give the layout the flexibility to support full-time living, guest accommodations, workspace, or commercial conversion. The main-level primary suite opens directly to a private brick patio, while the second bedroom accesses a rear deck overlooking the fully fenced yard: indoor-outdoor connections rarely found downtown. The reimagined kitchen, with new cabinetry, countertops, and appliances, and an open dining area, supports both daily living and gatherings. Step outside into a fully fenced private yard with a brick patio, outdoor dining, lounge seating, and ambient lighting: a genuine urban retreat steps from the energy of Downtown Annapolis. Moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, with easy access to Baltimore, Washington D.C., and BWI, it is equally compelling for owner-users, investors, commuters, and second-home buyers. Adding further value, the property can be sold fully furnished, with every piece professionally selected, so the next owner can move in immediately, operate it as a short-term rental, or transition it into a commercial or mixed-use setup with minimal effort. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000

$898,000
3 Beds 2 Baths
OPEN HOUSE SATURDAY 7/25 and SUNDAY 7/26 FROM 11-1pm Situated on one of Annapolis' widest and most desirable, dead end streets, this beautifully updated 3-bedroom, 1.5-bath Colonial blends timeless charm with thoughtful modern improvements. Meticulously maintained by its current owners, nearly every inch of the home has been enhanced. The renovated kitchen was thoughtfully redesigned to open the main living space, creating the perfect layout for everyday living and effortless entertaining. It features stainless steel appliances, granite countertops, a beverage refrigerator, and an exposed brick fireplace that adds warmth and character. The adjoining breakfast nook provides an inviting spot to enjoy morning coffee or serve family and guests. The spacious living room offers an open, airy feel while remaining cozy during the winter months with its wood-burning fireplace. Upstairs, you'll find three comfortable bedrooms and a beautifully renovated full bath, completed in August 2025. Step outside to discover an exceptional backyard designed for year-round enjoyment. A large covered deck creates the ultimate outdoor living room, allowing you to watch TV, grill, and entertain regardless of the weather. Professionally designed hardscaping wraps gracefully around two mature oak trees and leads to a premium artificial turf lawn—providing a lush, low-maintenance play and entertaining space in every season, from hot summer days to cool, rainy afternoons. Additional recent improvements include a new portico, Hardie Plank siding, and Andersen windows, all installed just two years ago, enhancing both curb appeal and energy efficiency. The unfinished basement offers abundant storage and flexible space for a home gym, workshop, or future office. This home has been meticulously maintained and thoughtfully upgraded, with significant improvements completed since 2017, including: New roof, New front walkway and portico, Hardie Plank siding, Andersen replacement windows, Fully remodeled kitchen, Beautifully renovated bathrooms, New rear deck, Extensive hardscaping and low-maintenance artificial turf, Chimney repairs and corrective improvements. The home has also been professionally maintained with annual service contracts through Griffith Energy Services for the HVAC and furnace, as well as Ardmore for termite protection, providing peace of mind for future homeowners.

209 S Cherry Grove Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$695,000
1 Beds 2 Baths
Tucked along a quiet one-way street in the heart of Historic Downtown Annapolis, this charming residence offers the perfect blend of character, convenience, and an exceptional in-town lifestyle. Leave the car behind and enjoy easy access to waterfront parks, City Dock, award-winning restaurants, boutiques, coffee shops, the Naval Academy, and all of the events that make downtown Annapolis such a sought-after place to call home. A rare one-car garage provides coveted off-street parking and is complemented by a versatile finished space on the entry level—complete with its own private entrance and half bath—making it ideal for a home office, studio, fitness room, or countless other possibilities. Upstairs, the light-filled main level is warm and inviting, featuring an updated kitchen with granite countertops and high-end appliances that flows seamlessly into the cozy living room centered around a fireplace. Just beyond, the adjoining sunroom creates a bright and relaxing space with access to a private balcony, perfect for morning coffee or unwinding after a day on the water or exploring town. The spacious bedroom enjoys an attached bath that also functions as a convenient powder room for guests, creating a thoughtful and efficient layout. Whether you're searching for a full-time residence, an easy lock-and-leave weekend getaway, or the perfect Annapolis pied-à-terre, this delightful home offers an opportunity to enjoy one of the city's most desirable downtown locations with the rare luxury of a garage. Welcome Home!

16 Dean St, Annapolis

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

$899,900
4 Beds 2 Baths
Welcome to 1169 Latrobe Drive in the sought after Cape St. Claire community on Annapolis’ Broadneck Peninsula. This is more than a home. It’s an opportunity that’s becoming harder and harder to find. Filled with natural light, this four bedroom, two bathroom home sits on an expansive lot with endless possibilities. Start your mornings in the bright glass enclosed sunroom overlooking the backyard, spend summer afternoons by your private pool, and enjoy beautifully maintained landscaping with multiple outbuildings that provide incredible flexibility for hobbies, storage, or future projects. Whether you’re entertaining friends, relaxing with loved ones, or simply enjoying the privacy of your own outdoor retreat, this property offers the space to do it all. The oversized lot is the true centerpiece. Renovate the existing home, expand to fit your lifestyle, explore investment opportunities, or build the custom home you’ve always envisioned. The property has already been subdivided!! Life in Cape St. Claire is about more than just your home. Enjoy community beaches, fishing piers, a marina, waterfront parks, playgrounds, and the Chesapeake Bay lifestyle that makes this one of Annapolis’ most beloved communities. Launch your kayak, spend evenings watching sunsets over the water, meet neighbors at community events, and enjoy the convenience of being just minutes from downtown Annapolis, shopping, restaurants, commuter routes, and top Broadneck area amenities. With an expansive lot, incredible outdoor living, a highly desirable location, and outstanding long term potential, this is a rare opportunity to enjoy today while investing in tomorrow.

1169 Latrobe Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 7033788810

$1,795,000
3 Beds 3 Baths
A rare opportunity to own a beautifully reimagined residence in the heart of Eastport, where timeless architecture meets modern comfort. Rich in history and craftsmanship, the home showcases an antique fireplace mantel with a hand-carved frieze, artisan wrought iron banister and fencing created by a metalsmith and co-founder of the renowned Niermann Weeks design atelier, and wide lintels that reflect the character of a bygone era. A thoughtfully designed 1986 renovation introduced a two-story addition and reconfigured the home around a central hallway, creating the exceptional floor plan enjoyed today while preserving its historic charm. The kitchen was beautifully renovated in 2022 by designer Nicole Rauzi of Chroma Kitchens, featuring updated custom cabinetry, fixtures, appliances, and a 6-burner Wolf range, blending contemporary function with classic style. Plantation shutters throughout the home add timeless elegance and privacy. French doors open from the living room to a newly completed screened porch (2026), overlooking a private garden filled with mature perennials and seasonal blooms, creating an inviting extension of the home's living space. Rarely found in Eastport, the property provides a two-car garage and three off-street parking spaces. Above the garage, the finished living space with a full bath and its own mini-split HVAC system (2022), offers flexibility as a guest suite, private office, studio and more. Additional home improvements include Hardie Plank siding (2020), washer and dryer (2022), and irrigation system (2017). Previously featured on the prestigious Annapolis Home & Garden Tour, this exceptional residence places you just moments from Eastport's celebrated restaurants, marinas, boutiques, galleries, and waterfront parks, with easy access across the Spa Creek Bridge to Historic Downtown Annapolis. A home where historic character, thoughtful updates, and an unmatched Eastport lifestyle come together in one extraordinary offering.

526 Sixth St, Annapolis

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

$2,650,000
6 Beds 6 Baths
Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributaries, this extraordinary waterfront residence at 529 Lee Circle offers an exceptional blend of sophisticated coastal design and effortless indoor-outdoor living. Privately nestled among mature trees, the home enjoys a peaceful setting with panoramic water views, a private pier, a boat house and a floating dock, creating the ultimate Annapolis waterfront retreat. The impressive rear elevation is designed to embrace the waterfront lifestyle, featuring expansive walls of glass that flood the interiors with natural light while framing picturesque water views from nearly every level. Multiple outdoor living spaces—including a spacious waterside deck, an upper-level balcony, and an expansive lawn leading to the 114 feet shoreline—provide the perfect backdrop for entertaining or relaxing while enjoying spectacular sunsets. The boat house with lift, private pier, and protected water dockage offer immediate access to boating, paddleboarding, kayaking, and all the Chesapeake Bay has to offer. Whether departing for a day on the water or enjoying quiet evenings along the shoreline, this property delivers an unmatched waterfront experience. Architecturally, the home combines classic coastal elegance with contemporary comfort. Soft gray siding, crisp white trim, multiple gables, and oversized windows create a timeless façade that complements its natural surroundings. The residence offers approximately 6,000 square feet of living space with two owners suite (one on the main level), generous entertaining areas, multiple fireplaces, and luxurious accommodations designed for both everyday living and grand-scale gatherings. The home was originally built in 1965. In 2016 it went through a complete, down-to-the-studs renovation and expansion to the creation of stunning luxurious waterfront home. Custom-Built by Architect Teresa Todd and Timberlake Homes into a 6-bedroom and 5.5-bathroom residence. Located within the sought-after Hillsmere Shores community, residents enjoy a coveted Annapolis lifestyle with access to a private beach, marina, community pool, playgrounds, and convenient proximity to Historic Downtown Annapolis, waterfront dining, yacht clubs, and the U.S. Naval Academy. This is more than a waterfront home—it is a private Chesapeake Bay sanctuary where luxury, recreation, and timeless coastal beauty come together in one exceptional offering.

529 Lee Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,750,000
4 Beds 4 Baths
Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center island, black granite countertops, stainless steel appliances, a pantry, and an expansive dining area that seamlessly flows into the inviting living room. The main-level primary suite is a true retreat with a spa-inspired bath featuring a soaking tub, walk-in shower, and generous walk-in closet. Upstairs, you'll find two large bedrooms, that share a full bath and an additional bedroom with its own private full bath, and a versatile sun-drenched sitting area with a dramatic vaulted ceiling. The walk-out lower level includes a full bath and versatile space to suit your lifestyle. Outside, a private rear deck perfect for relaxing or entertaining and charming stone walkways and welcoming front porch add historic like charm. A private driveway is for convenient off-street parking, and a storage shed is perfect to house all of your outdoor needs. Ideally located within walking distance of historic downtown Annapolis, you'll enjoy easy access to waterfront dining, boutique shopping, historic landmarks, entertainment, and all the vibrant attractions this sought-after area has to offer. The Eastport lifestyle truly one of a kind!

219 Lockwood Ct, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 224-4999

$675,000
4 Beds 3 Baths
Welcome to Pleasant Plains, one of Annapolis' most sought-after communities, where generous lots, mature trees, and a peaceful setting are just minutes from Downtown Annapolis, the Naval Academy, shopping, dining, and commuter routes. Perfectly positioned on a spacious large lot, this beautifully maintained home offers the ideal blend of classic charm and thoughtful updates. Inside, you'll find fresh, inviting spaces featuring an updated kitchen with new countertops, backsplash, sink, faucet, butcher block accent counter, new flooring, newer appliances, and abundant storage for everyday living and entertaining. The home has been meticulously cared for with numerous major improvements already completed, giving buyers peace of mind. Recent updates include a new roof (2020), new air conditioning system (2023), new well pump (2024), new well pressure tank (2025), updated fuel line and filter systems, roof inspection and tune-up completed in 2026 with a transferable warranty. The upper level featuring 4 large bedrooms, newer carpeting -wood floors underneath, custom closet systems, updated bathrooms including a beautifully remodeled primary bath with a new walk-in shower, vanity, and flooring, plus refreshed finishes throughout. The finished lower level offers brand-new carpeting, providing flexible space for recreation, a home office, gym, or playroom. Step outside and discover your own private nature retreat. The fully fenced backyard offers the perfect balance of privacy and open space, creating a peaceful setting for everything from morning coffee to evening gatherings around the fire pit. Surrounded by mature trees and lush landscaping, the yard is ideal for gatherings and pets to play freely while still offering plenty of room for gardening, entertaining, outdoor games, or simply unwinding after a long day. It's the kind of backyard that's becoming increasingly difficult to find in Annapolis. Additional highlights include ceiling fans throughout, updated lighting, fresh interior paint, attic ventilation improvements, and wiring for both Verizon Fios and Comcast Xfinity. With major mechanical systems already updated and an unbeatable location in coveted Pleasant Plains, this move-in ready home offers the perfect opportunity to enjoy the Annapolis lifestyle with space, privacy, and convenience.

1917 Cherry Rd, Annapolis

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

$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

$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:

$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

$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

$1,475,000
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

$1,295,000
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:

$464,000
3 Beds 1 Baths
A CHERISHED FAMILY CLASSIC IN WATERFRONT HILLSMERE ESTATES! 410 Walnut Road presents a rare opportunity in one of Annapolis’s most coveted water-privileged communities. Lovingly maintained by the same family, this home serves as a beautiful foundation for your future memories and personal design touches. Three bedrooms with a traditional layout which include rich hardwood flooring, adding a layer of warmth and timeless style serviced by a central, streamlined full bath. Kitchen includes custom cabinets, inviting living room features large picture window & hardwood floors. Expansive unfinished basement ideal for a future recreation room, premium home gym, personal workshop, or private guest suite +potential is there for adding an additional bath. HUGE Level, park-like fenced-in yard offering endless space for upscale outdoor living, mature gardens and entertaining. Enjoy unparalleled private neighborhood amenities just steps from your door along the South River and Duvall Creek. A private, sandy community beach with beautiful expansive water views. A crystal-clear community swimming pool. Multiple deep-water community piers and an extensive marina network. Dual neighborhood boat ramps and a dedicated low-profile launch for kayaks and paddleboards. Scenic waterfront picnic pavilions and community playground areas. Experience a serene coastal neighborhood, exceptional lot size, and close proximity to Quiet Waters Park and historic downtown Annapolis. Welcome home!

410 Walnut Dr, Annapolis

Listing courtesy of Taylor Properties. Contact:

$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

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