A significant price reduction has been made on this stunning home! Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort.A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable.Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

There is something special about life near the Chesapeake Bay—and 1221 Bast Lane captures it beautifully. Completely remodeled from top to bottom, this charming one-level Coastal Craftsman combines fresh, sophisticated interiors with incredible outdoor space and one of the most impressive detached garages you will find. Set on a beautiful lot just shy of an acre in Shady Side, the home offers four bedrooms and an easy, comfortable floor plan filled with natural light, beautiful windows, gorgeous flooring, and thoughtful finishes throughout. At the heart of the home is a stunning gourmet kitchen featuring beautiful cabinetry, warm butcher-block countertops, stainless steel appliances, a stylish backsplash, generous workspace, and a fresh coastal aesthetic that makes the entire space feel inviting. The primary suite is a wonderful retreat with an enormous walk-in closet and a sleek, spa-inspired bath featuring a beautiful walk-in shower with glass doors. Additional bathrooms carry the same clean, sophisticated design, while the incredible laundry room proves that even the most practical spaces can be beautiful. Step outside onto the spacious deck and imagine summer dinners, weekend cookouts, morning coffee, or a glass of wine as the sky changes color at sunset. The huge yard offers nearly an acre to spread out, garden, play, entertain, or simply enjoy having space around you. And then there is the garage. More than 1,500 square feet of detached garage and workspace with THREE bays and electric creates an absolute dream setup for car enthusiasts, collectors, hobbyists, contractors, or anyone who wants room for vehicles, tools, storage, and projects without sacrificing the house or yard. The home and garage roofs date to 2023, along with the home's siding. Beyond the property, Shady Side delivers the Chesapeake lifestyle people fall in love with: water views, beautiful sunsets, neighbors walking their dogs, kids playing, and the relaxed sense of community that makes evenings feel a little slower and weekends feel a little longer. Here, you can enjoy the character of a coastal community while coming home to a beautifully renovated property where the transformation has already been completed. Beautiful inside, extraordinary outside, and filled with unexpected features, 1221 Bast Lane isn't simply move-in ready—it's the kind of place that makes you excited to come home.

RECENT PRICE REDUCTION! Step into a charming piece of history with this stunning Colonial home, built in 1879, nestled in the desirable Queenstown neighborhood, water community and GOLF. Spanning 1,920 square feet, this residence seamlessly blends classic elegance with modern comforts, making it the perfect sanctuary for today's discerning buyer. As you enter, you'll be greeted by exquisite details such as crown moldings and chair railings that evoke a sense of timeless sophistication. The gourmet kitchen is a chef's dream, featuring upgraded countertops and essential appliances, including a refrigerator, stove, dishwasher, and icemaker, ensuring every culinary endeavor is a delight. The inviting dining area is perfect for hosting gatherings, while the cozy living room, complete with a charming fireplace, sets the stage for intimate evenings. This home boasts three spacious bedrooms, including a primary suite with an en-suite bath, providing a private retreat. Outside, enjoy the serenity of a quarter-acre lot, beautiful gardens and ponds, with off-street parking and a detached garage, providing both convenience and privacy. With its rich character and modern amenities, this home is not just a place to live; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this enchanting property your own!

Welcome to 2566 Glen Cove, a beautifully updated three-bedroom, two-bath home offering a rare opportunity to enjoy the Heritage Harbour lifestyle without the age restriction. While this property is not age-restricted, owners have the option to join Heritage Harbour through a social membership and enjoy access to its many amenities.Inside, the home is warm, inviting, and thoughtfully updated, highlighted by a stunning brand-new kitchen completed in 2026 featuring quartz countertops, stainless steel appliances, and beautiful finishes. Wood floors flow through the home, complemented by updated bathrooms, a separate dining room, and a classic wood-burning fireplace that creates a welcoming focal point for the living space.A spacious three-season sunroom provides the perfect place to relax or entertain while overlooking professionally designed landscaping by Cindy Shuart of Harmony Gardens. An irrigation system makes maintaining the beautifully curated grounds effortless.Additional highlights include a two-car garage and a new architectural shingle roof installed in 2026 with a transferable warranty, offering peace of mind for years to come.Beautifully maintained, thoughtfully improved, and surrounded by mature landscaping, 2566 Glen Cove offers comfortable Annapolis living with the added opportunity to become part of the vibrant Heritage Harbour community.

Ooh la la, Eastport. There is something unmistakably special about life here—and 820 Bay Ridge Avenue captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence delivers the rare combination of space, sophistication, outdoor living, and walkability, all just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and a gracious brick front porch create a picture-perfect welcome. Step inside to more than 4,000 square feet of beautifully finished living across FOUR levels, where rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters create a home that feels polished without ever feeling fussy. Thoughtfully customized during construction, the residence includes numerous builder upgrades, enhanced electrical features, and details designed to make everyday living as effortless as the home is beautiful. At its heart is a fabulous kitchen with honed granite countertops, premium appliances, abundant cabinetry, and a generous center island opening seamlessly to the family room and upgraded gas fireplace. The formal dining room is ready for holidays, celebrations, and memorable dinners, while the adjoining sitting room or study is perfect for working from home, curling up with a favorite book, or ending the evening with a bourbon. And then there is the outdoor living. Morning coffee on the front porch overlooking the flower garden. Dinner in your private English courtyard. Cocktails under the stars on the second-floor terrace. Professionally enhanced landscaping creates an intimate retreat, while ceiling fans, a dedicated natural gas line for grilling, and the opportunity for a future fire feature make these spaces as functional as they are beautiful. Upstairs, the primary suite feels like a private escape, with a custom walk-in closet, spa-inspired bath, and expansive sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft brings even more possibilities—a home office, fitness studio, media room, guest retreat, or whatever life calls for next. The finished lower level adds a spacious family room and full bath, providing even more flexibility for entertaining, extended stays, or multigenerational living. And in a feature rarely found, the home was designed with the future in mind with a framed elevator shaft, allowing an elevator to be added without compromising the architecture or thoughtful floor plan. But perhaps the greatest luxury of 820 Bay Ridge Avenue is everything waiting just outside your front door. Walk to St. Mary’s. Walk to dinner. Walk to neighborhood cafés and marinas. Walk to the Annapolis Yacht Club and Eastport Yacht Club. Cross the Spa Creek Drawbridge into Historic Downtown Annapolis and City Dock. Spend the afternoon on the Chesapeake, meet friends for dinner on the water, browse the shops and galleries downtown, or take the water taxi home after an evening out. Morning coffee around the corner. An afternoon on the water. Dinner in Eastport. Ice cream at City Dock. School, sailing, restaurants, shopping, marinas, yacht clubs, and downtown Annapolis—all without having to get in the car. And somehow, you still come home to more than 4,000 square feet, four finished levels, beautiful outdoor spaces, exceptional privacy, extensive custom upgrades, and future elevator capability. No need to choose between space, sophistication, and walkability. Here, you get all three. Polished. Coastal. Effortlessly Annapolis. Ooh la la, indeed.

NOW $1,249,000—a $100,000 price improvement. This distinctive Historic Annapolis home offers buyers an opportunity to put that difference toward updates tailored to their own vision. Just steps from Spa Creek in the Annapolis Historic District, 8 Revell Street is a 1903 home offering more than 3,600 square feet across three finished levels, with 5 bedrooms and 2 full baths. Beautiful original character, mature gardens and an exceptional downtown location set the stage. With its classic wood-shingle exterior, recently resurfaced standing-seam metal roof and freshly painted interior, the home presents an opportunity to thoughtfully update its spaces while preserving the details that make it so memorable.An elevated front porch sits above the street and offers a charming glimpse of Spa Creek—a lovely perch for enjoying breezes off the water. Inside, hardwood floors, generous room sizes, original built-ins, distinctive tile work, classic radiators and an unforgettable stained-glass window give this home its remarkable charm.The third floor is one of the home's most beautiful spaces. The fifth bedroom, currently staged as an elegant office, is a light-filled retreat with elevated views of Spa Creek. An adjoining full bath and access to generous attic storage add versatility to this special level.Outside, a large terraced brick patio offers space for dining, entertaining and relaxing. Mature gardens surround the patio, while established wisteria climbs the trellis to provide natural shade and a beautiful sense of enclosure. A garden shed provides additional storage.And then there is the location. From Revell Street, stroll to City Dock, St. Mary's, the shops and restaurants of Main Street, the waterfront and so much of downtown Annapolis. Walk to the end of the street and catch a water taxi to explore Annapolis from the water. A morning paddle on Spa Creek, downtown dining and shopping, historic streets and the Chesapeake Bay lifestyle are all within easy reach.With its generous scale, original architectural details, beautiful outdoor spaces, Spa Creek views and exceptional Historic District location, 8 Revell Street offers a rare combination of history, character and possibility. Enjoy what makes it special today while thoughtfully making it your own for its next chapter. Property is being sold As-Is.

Price adjusted to reflect market response. AND it's open 10/31 & 11/1 ! There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

New construction from acclaimed local builder, Sturbridge Homes! This spectacular home offers over 3,900 square feet of finished space in the heart of Annapolis's Homewood neighborhood, close to all of the entertainment and enjoyment available in our historic town. Located near the new Annapolis Public Library, Maryland Hall, Annapolis Town Center, and the Naval Academy Stadium, this home is situated for you to enjoy the best of in-town life, yet relax in a tree-lined neighborhood environment. This home is excellently upgraded with 9-foot ceilings on all three levels, quartz countertops, ceramic tile, stainless appliances, and more! The main level features a flexible den/office/bedroom with an attached full bathroom, so guests and family can have private space. The primary suite is a luxurious oasis with plenty of space to enjoy with a huge customizable walk-in closet. The lower level features a separate entrance, a bedroom and a full bathroom, and a large rec room, making it perfect for entertaining guests, caregiving, or multi-generational living. The builder has included many thoughtful touches throughout. The front porch is a perfect spot to savor your morning coffee, and the backyard with deck offers endless possibilities. The home comes with green building features, a package of smart home features, and a 10-year limited warranty. Enjoy the low-maintenance lifestyle of a new construction home for many years to come!