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$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 Drive, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$1,295,000
4 Beds ⋅ 5 Baths
Annapolis New Turnkey Masterpiece: Welcome to 3126 Port Way - an extraordinary residential real estate transformation in the highly sought-after Anchorage waterfront community in Annapolis. This fully reimagined masterpiece 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 3126 Port Way a complete, down-to-the-studs renovation and expansion. They purchased this almost 1/2-acre property from its original owner, and they turned a 2,000 square foot home into 3,200 square feet of luxurious, modern turnkey showpiece with no detail overlooked. The four-bedrooms, all with en-suite bathrooms and walk-in-closet, two-powder room, ample 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, pool, 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.

3126 Port Way, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$1,225,000
5 Beds ⋅ 3 Baths
Welcome to your dream home nestled in the sought after water privileged community of Anchorage, where life meets comfort and recreation. This stunning 5 bedroom, 2.5 bath beauty is designed for both relaxation and entertainment, offering a perfect blend of modern updates and classic charm. Step inside to discover a bright and airy open concept living space, enhanced by an updated kitchen featuring elegant quartz countertops and sleek stainless steel appliances, including a 6 Burner Wolf Cooktop. This professional-grade cooktop is perfect for those who love to cook and entertain. Whether you’re hosting a dinner party or enjoying a casual meal, this kitchen is sure to impress. The adjacent dining area flows seamlessly into the spacious living room, providing an inviting atmosphere for family gatherings. Extend your living space outdoors where a delightful screened-in porch awaits, perfect for sipping morning coffee or enjoying evening cocktails. The deck and patio area offer additional space for alfresco dining and entertaining, all overlooking a fully fenced-in backyard…ideal for children and pets to play freely. Enjoy the numerous community amenities that make Anchorage a true gem, including access to a marina and boat ramp for your boating adventures, a basketball court for some friendly competition, and a sparkling swimming pool to cool off during warm summer days. With downtown Annapolis just a short drive or boat ride away, you’ll have the best of both worlds. Don’t miss this opportunity to make this exquisite home your own and experience the vibrant coastal lifestyle that awaits you in Annapolis!

3130 Starboard Drive, Annapolis

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

Selling Office: .

$950,000
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 Drive, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$875,000
4 Beds ⋅ 3 Baths
PRICE ADJUSTED on this wonderful 4-bedroom home! Welcome to one of Annapolis’ most sought-after waterfront communities, where residents enjoy a waterfront pool, and a private marina and boat ramp that’s just minutes to the Chesapeake Bay by boat. This beautifully updated four-bedroom home at 1141 Mainsail Drive in Anchorage is situated just down the block from all these amazing amenities and sits on a spacious one-third acre lot framed by mature trees and manicured landscaping. Inside, the home features a bright open floor plan with gorgeous hardwood floors, crown & chair-rail moldings, and large windows that fill the space with natural light. The chef’s kitchen boasts stainless steel appliances, quartz countertops, and an inviting breakfast area that opens to a cozy family room with a double-sided brick fireplace. The sliding glass doors that open to the back deck make grilling and al fresco dining a breeze. A formal living and dining room offer flexibility for entertaining, and the main level also includes a powder room and access to the oversized two car garage. Upstairs, the primary suite includes a private bath with a renovated walk-in shower and updated fixtures. Three additional bedrooms are ample in size and there’s a second renovated bathroom. There is a wonderful office nook overlooking the front yard. The finished lower level, with Pergo flooring, provides a spacious recreation and/or office space with room for storage and a workshop area. Outdoors, the circular driveway provides a gracious entry and leads to an attached two-car garage. The beautifully landscaped backyard is private and offers plenty of space for enjoyment in addition to the brick patio. Residents of Anchorage enjoy an unparalleled lifestyle centered around the community’s marina, pool, and social events, all while being just minutes from downtown Annapolis, Quiet Waters Park, and top-rated schools. Whether boating on Lake Ogleton, gathering at the waterfront picnic area, or simply enjoying evening walks around the neighborhood, life in Anchorage feels like a year-round retreat.

1141 Mainsail Drive, Annapolis

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

Selling Office: .

$850,000
5 Beds ⋅ 3 Baths
At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more. This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated within the last 4 years. Upgrades that include HVAC, tankless hot water heater, well pump, sewer line, roof, downspouts, gutters, soffit and windows make this home a low maintenance joy. A bespoke new sunroom addition off of the kitchen includes a wood burning stove. Simply delightful! The sparkling kitchen with a new double oven and stainless appliances has an easy flow with classically beautiful cabinetry and quartz counters. Wood floors continue through the living room and down the hall to 3 bedrooms which include the primary with ensuite bath and an additional half bath. Downstairs there are 2 bedrooms, a full bath, laundry room, storage room and family room with a fully lined fireplace and wood stove. Garage access is through this room. In the 2 car garage you'll find 2 EV chargers. The harmonious floor plan guides you from room to room with ease. Sitting on nearly 1/2 acre, the outdoor space won't disappoint. Entertaining is a breeze here, enjoy the spacious deck which is adjacent to the sunroom and overlooks the level, lightly treed and fenced backyard. Landscaping which has matured with the years adds to the natural charm of the property. Two storage sheds provide plenty of storage with one facing the driveway for easy bike storage access. The community waterfront on Lake Ogleton includes 49 deep water slips in the marina, community pool, kayak storage, boat ramp and basketball court. The Chesapeake Bay is a quick motor away and historic downtown Annapolis is minutes by car underscoring the desirability of this home's locale. Filled with amenities and coupled with location, Anchorage is a community that truly has it all.

1106 Mainsail Drive, Annapolis

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

Selling Office: .

$834,400
4 Beds ⋅ 3 Baths
Extensively renovated from 2022–2024, this move-in-ready, modern Colonial is a standout offering in Anchorage, an Annapolis premier water-privileged community. Set on a private, wooded half-acre lot, this 4-bedroom, 2.5-bath residence combines approximately 2,000 square feet of refined living space with the potential to add 864 square feet in the walkout basement. The home’s interior showcases high-end craftsmanship, including a custom kitchen with quartzite waterfall island and counter-tops, spa-inspired bathrooms, Pella windows/doors, and Spanish ceramic tiling alongside refinished hardwoods. Residents enjoy an unparalleled waterfront lifestyle with access to a 49-slip marina, boat ramp, pool, and lakeside amenities on Lake Ogleton. Perfectly positioned just minutes from Historic Downtown Annapolis, the Naval Academy, Thomas Point Preserve and Quiet Waters Park. This location provides easy commutes to Washington, DC and Baltimore. The property’s location offers a rare balance of secluded coastal living and metropolitan accessibility. Fully renovated homes in this sought-after community are rarely available at this price point—an exceptional opportunity for the discerning buyer to live the Annapolis lifestyle.

1126 Mainsail Drive, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$810,000
5 Beds ⋅ 4 Baths
Multiple Offers received. Deadline Sunday at Noon . Charming water-privileged split-foyer residence in the desirable Beale Manor community, offering 3,145 finished square feet of thoughtfully designed living space. Recent updates include a roof replacement, a newer water heater, fresh interior paint, and beautifully refinished flooring throughout the main level, enhancing both style and peace of mind. // The traditional layout begins with a formal living room featuring large picture windows that draw in abundant natural light and flows seamlessly into the formal dining room, creating an inviting setting for gatherings. The updated eat-in kitchen is both stylish and functional, showcasing crisp white cabinetry with sleek bar pulls, a peninsula breakfast bar, black appliances including double ovens, a built-in workstation, and a bright breakfast area with sliding door access to the screened porch. Just off the kitchen, the welcoming family room is highlighted by a white-washed brick fireplace and filled with natural light, while a convenient powder room and laundry area complete the main level. // The upper level features four generously sized bedrooms, including a spacious owner’s suite with a comfortable sitting area, dual closets—one a walk-in with a custom organization system—and a private ensuite bath with a soaking tub and separate shower. A centrally located full bathroom with an extended vanity serves the additional bedrooms. The walk-out finished lower level provides exceptional versatility, offering a large recreation space, a full bathroom, a bar area with a rough-in for a sink, and a fifth bedroom ideal for a home office, gym, or guest space. // Outdoor living is equally appealing, with a screened porch overlooking the backyard, an open-air deck that steps down to a patio, and a spacious, flat, fully fenced yard backing to trees for added privacy. // Residents of Beale Manor enjoy a wealth of community amenities, including a scenic waterfront pool, a basketball court, and a whimsical pollinator garden, fostering a vibrant, connected lifestyle.

3135 Anchorage Drive, Annapolis

Listing courtesy of Keller Williams Lucido Agency. Contact:

Selling Office: .

$765,000
5 Beds ⋅ 3 Baths
Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a partially fenced backyard and invisible fence, ideal for pets or added privacy. This move-in-ready property combines modern comfort, thoughtful upgrades, and premium waterfront community living—an absolute gem in Annapolis! Step inside to discover a bright and airy layout enhanced by large windows that invite abundant natural light and offer tranquil views of the mature landscape. The modern kitchen is a chef’s delight, featuring quartz countertops, a gas range, white cabinetry, skylights, and stainless-steel appliances. Additional highlights include a 1-car garage, generous living and dining areas, and thoughtful updates throughout. The primary bedroom features its own en-suite bathroom, providing a private retreat within the home where you fall asleep hearing the horns of ships anchored on the Chesapeake Bay. The family room offers a cozy ambiance with a wood-burning fireplace and a rough-in for gas conversion, flanked by custom wall built-ins—perfect for displaying books, décor, or media. Throughout the upstairs bedrooms, primary bath, and lower-level bedrooms, you’ll find professionally installed solid wooden doors, adding a refined and durable touch. A laundry chute conveniently located in the hallway bathroom leads to a well-equipped laundry room with ample storage space and an adjacent separate utility room for added organization. The main level boasts gleaming hardwood floors, seamlessly connecting the living, dining, and kitchen areas in a cohesive open-plan layout. Comfort meets efficiency with a high-efficiency cooling system and hydronic gas heating for year-round comfort. Additional upgrades include a water treatment system with softener, a whole-house central vacuum system, and a gas generator. A new roof was installed in April 2025, adding value and durability, while the spacious backyard provides the perfect setting for entertaining, relaxing, or enjoying outdoor activities. Located in the highly sought-after Anchorage Waterfront community, residents enjoy exceptional amenities with an HOA fee of just $118/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court. Don’t miss the chance to own this hidden gem in one of Annapolis’s most coveted neighborhoods.

3117 Port Way, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$527,400
3 Beds ⋅ 3 Baths
Welcome Home to 104 Jib Way, an elegantly designed home featuring 3 bedrooms and 2.5 baths. Inside, enjoy the warmth of newly finished hardwood floors that flow seamlessly throughout the kitchen and living spaces. The spacious owner's suite includes oversized walk-in closets, while the additional two bedrooms provide plenty of room for comfort. The kitchen showcases 42” maple cabinets and updated appliances, creating an inviting space for culinary delights. This home also features an oversized garage, providing ample storage and parking space. Step outside into a luxurious outdoor retreat, where a stunning stone patio encircles a breathtaking custom pool, transforming your backyard into a private paradise for relaxation and entertainment. The meticulously landscaped grounds boast exquisite hard-scaped garden beds and an automatic irrigation system installed throughout the entire property, ensuring vibrant greenery year-round. Stone walkways meander gracefully from the front of the home to the rear, leading you to a serene, fenced backyard that offers privacy, complete with a vinyl privacy fence and an additional access gate to the pool area. Situated on a corner lot in a sought-after waterfront community, the Anchorage community offers a picturesque park and pier with a floating dock, where you can launch canoes and kayaks or enjoy crabbing and fishing from the pier Don’t miss the chance to witness breathtaking sunsets from the community pier, providing a perfect end to any day spent by the water. With public water and sewer services and an HOA that includes trash collection, convenience is at your fingertips. Just a minute from Route 50 and within walking distance to shops, restaurants, a post office, and grocery stores, this home is perfectly positioned for easy island living. Schedule your tour today to experience this enchanting property on Kent Island! "This Home is not only turn key it's worry free"

104 Jib Way, Stevensville

Listing courtesy of Samson Properties. Contact:

Selling Office: .