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.

Priced to sell: Annapolis Stunning Contemporary - Located in the highly sought-after waterfront community of Anchorage, this stunning 3,000+ square foot contemporary 4-bedroom/3-bathroom home offers the perfect blend of architectural sophistication, modern upgrades, and serene coastal living. Main level living and open layout floor plan at its finest! This elegant home sits on a professionally landscaped corner lot and has a 2-car garage. Enjoy exclusive community amenities, including a private dock, newly raised boat slips, boat ramp, and a waterfront pool overlooking Lake Ogleton and the marina. A rare lifestyle opportunity just minutes from downtown Annapolis.The home boasts impeccable curb appeal, with pristine steps leading to an etched glass front door. Step into the elegant marble foyer, adorned with a compass rose inlay, skylights, and ambient recessed lighting, setting the tone for the refined details throughout.Enjoy main-level living at its finest; highlighted by a Great Room, recessed lighting, and double sliding doors that open to a screened-in porch complete with skylights, a hot tub rough-in, and a block platform ready for hot tub installation. From the porch step out onto a 14’ x 16’ IPE Brazilian mahogany architect designed deck; featuring a solid hardwood support structure, grilling area, and stair access to a professionally landscaped, meticulously manicured backyard. In addition, there is a climate-controlled dry storage areas below the great room and another storage below the deck (each approx. 20’ x 20’) which offer abundant space for water toys, tools, and seasonal items.The remodeled, open layout kitchen is a showpiece featuring white Corian countertops, Travertine tile backsplash, bar-height countertop with breakfast bar seating, upgraded white shaker cabinetry, stainless appliances and a sun-filled breakfast nook with ceiling fan. Off the kitchen enjoy a versatile room (family room, dining room or office) with a wood burning fireplace.The expanded owner’s suite is a true retreat featuring skylights, recessed lighting, walk-in closet, and direct access to the screened-in porch, ideal for morning coffee. The en-suite bath showcases Carrara marble tile flooring, a glass-enclosed shower, Carrara marble vanity and abundant natural light. An additional main-level bedroom and fully remodeled hall bath feature marble tile, a 60-inch custom vanity with marble top, a Mother of Pearl-framed mirror, and a soaking tub. The lower level with mostly ceramic tile flooring; features a cozy family/recreation room with fireplace and built-ins, two bedrooms, a full hallway bathroom and office area, plus a laundry/utility room with direct access to a two-car garage. Additional upgrades include; plantation shutters on most windows, hardwood and bamboo flooring throughout the main level, tray ceilings and crown molding, professionally painted walls and ceilings, Dual HVAC systems (Trane & Carrier) and architectural shingle roof.Set on a beautifully landscaped corner lot with year-round perennials, this remarkable property offers an unmatched lifestyle in a prestigious Annapolis location. 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. Currently two boat slips available (06/06/25). Don’t miss your chance to call Anchorage home!

Annapolis Renovated Charming HomeWelcome to 1128 Mainsail Drive - a beautifully renovated 4/5-bedroom, 2-bathroom home offering 2,613 square feet on a generous half-acre lot. Brimming with character and enhanced by over $60,000 in recent improvements, this charming residence combines timeless appeal with modern convenience. Nestled in the desirable waterfront community of Anchorage, this property blends modern upgrades, thoughtful details, and community amenities designed for the ultimate Annapolis lifestyle.Step inside to discover an open-concept layout filled with natural light, fresh finishes, and stylish updates. The gourmet kitchen has been completely remodeled with quartz countertops, an elegant backsplash, a center island with pendant lights, white cabinetry, stainless steel appliances, and a gas line for the range - perfect for any home chef.One of the home’s standout features is the spectacular sunroom - a warm and inviting space filled with natural light, framed by exposed wood beams that add rustic charm and architectural character. This bright and airy retreat is perfect for year-round enjoyment, whether you’re sipping morning coffee or hosting gatherings. Sliding glass doors lead directly out to the brand-new deck, creating a seamless flow between indoor and outdoor living and offering the perfect setup for entertaining or relaxing in the peaceful backyard setting.Step outside and discover your own private oasis - an approximately half-acre yard surrounded by mature landscaping that offers beauty, privacy, and tranquility in every season. Whether you’re entertaining on the new deck, relaxing under the covered patio, or simply soaking in the peaceful atmosphere, this backyard is a true retreat.Tucked into the corner of the yard is a brand-new shed with charming details that make it feel more like a storybook playhouse - a perfect hideaway for office, hobbies, or stylish storage. The lush greenery and natural setting make this outdoor space feel like an extension of the home, ideal for gardening, recreation, or quiet moments under the trees.The one-car garage has also been fully upgraded with insulation, new drywall, fresh paint, and an epoxy floor, making it both functional and polished.Warm up by one of two fireplaces: one wood-burning and one gas-burning - adding cozy ambiance to both the main living area and the lower level. Every detail has been considered, including updated outlets and light switches, recessed lighting, and blinds throughout. Hardwood floors in main level and luxury vinyl plank in lower level.As a resident of Anchorage, you’ll enjoy access to an exclusive waterfront lifestyle, including 49-boat slips, a community marina, boat ramp, outdoor pool, picnic area, and half basketball court—all just moments from your doorstep. Whether you’re a boating enthusiast or simply looking for a peaceful neighborhood with resort-style amenities, Anchorage offers something special.Located just minutes from historic downtown Annapolis, the U.S. Naval Academy, local marinas, shops, and restaurants - this move-in-ready gem is the perfect blend of comfort, community, and coastal charm.

Priced to Sell: 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.

St. Michaels Renovated Historic Gem: Step into a turnkey, fully renovated 1890 historic home that blends timeless charm with modern luxury. Completely transformed in 2023—inside and out—this move-in-ready residence is the perfect pied-à-terre, vacation retreat, or low-maintenance full-time home.Just one block from the heart of historic St. Michaels, a vibrant waterfront town on Maryland’s Eastern Shore known for its brick-lined streets, boutique shops, award-winning dining, and lively boating scene, this property offers a rare blend of small-town warmth and upscale coastal living.The home sits just down the street from the picturesque Waterfront Town Park by San Domingo Creek, with its public dock, kayak launch, walking trail with a covered bridge, picnic areas, and playground. The town’s popular “rails-to-trails” walking and biking path passes right through, connecting you to scenic waters and the Chesapeake Bay.Inside, approximately 1,500 sq. ft. of thoughtfully designed living space features an open floor plan with natural light, two bedrooms, and two full bathrooms, with the potential for a main-level primary bedroom. The brand-new kitchen showcases Diamond® Vibe™ Series Semi-Custom Cabinetry in an elegant coconut color finish, granite countertops, and all-new stainless-steel appliances.Every detail has been updated—granite countertops on all bathrooms and kitchen, recessed lighting throughout, fresh new paint, luxury vinyl plank flooring in the foyer, dining, kitchen, laundry, and baths, electrical and plumbing systems “up to code”, new crawl space encapsulation with spray foam insulation, French drains, and dehumidifier, three Carrier multi-zone mini-splits and new furnace, all-new windows, doors, hardware, and a “lifetime” blue metal roof. Lead-Free Certification obtained from the Maryland Department of the Environment (August 8, 2023). Also, this gem is outside of the historic restrictions of St. Michaels which is not subject to the extra layer of review and approval from the Historic District Committee.The property includes a flat, fenced backyard with a detached shed that could serve as a studio, workshop, or hobby space. French drains also in backyard. A charming front porch and a stone patio offer perfect spots for morning coffee or evening gatherings.With its lock-and-leave convenience, and prime location near the waterfront, 204 West Chew Avenue is more than a home—it’s a gateway to the St. Michaels lifestyle.