Refine Search
Map
Sort by
$439,800
2 Beds ⋅ 2 Baths
Two years young, 55+ elevator condominium community enjoy this beautifully upgraded 2-bedroom + den residence with a balcony. Priced just shy at $100K less than current builder pricing includes surface assigned parking and storage (purchased for $7500). Offering a bright, modern kitchen filled with natural light and showcases crisp white cabinetry, a stylish (upgraded) tiled backsplash, stainless steel appliances, and sleek quartz countertops—perfect for entertaining. Throughout the home, you’ll find enhanced and recessed lighting, complemented by elegant light-toned luxury vinyl plank flooring for a completely carpet-free, sophisticated finish. The spacious primary suite is a true retreat, featuring a custom-designed oversized walk-in closet and a luxurious ensuite bath with a double vanity and upgraded tilework. Additional enhancements throughout the home include beautifully updated bathrooms and high-end finishes that elevate both comfort and style. The Element offers an exceptional, resort-style lifestyle with amenities thoughtfully designed for active adult living, including: • Landscaping with walking paths • sophisticated lobby featuring a golf simulator and billiards • Pickleball courts, dog park, and outdoor grilling areas • Fitness equipment and inviting social spaces Minutes from downtown Annapolis, Naval Academy with quick access to waterfront dining, boutique shopping, and the Bay Bridge. Schedule your viewing today and discover luxury living in Annapolis!

78 Old Mill Bottom Rd N Unit #209, Annapolis

Listing courtesy of Cottage Street Realty LLC. Contact:

$340,000
2 Beds ⋅ 2 Baths
Location, convenience, and peaceful surroundings come together in this well-maintained two-bedroom, two-full-bath condo. This unique end unit offers added privacy and relaxing views from the deck overlooking a wooded area and nearby walking path. Inside, the home provides a clean, neutral canvas ready for its next owner to personalize. The kitchen flooring and carpeting are only a few years old, and both the HVAC system and water heater have been updated in recent years. Ideally situated just minutes from downtown Annapolis, with quick access to Route 50 for convenient travel toward Washington, D.C., Baltimore, and the surrounding area. Whether you’re commuting, exploring downtown, or simply enjoying the quiet wooded setting, this condo offers an excellent combination of comfort and location.

2026 Gov Thomas Bladen Way Unit #204, Annapolis

Listing courtesy of Taylor Properties. Contact:

$494,000
2 Beds ⋅ 2 Baths
Welcome to this beautiful 2 Bedroom + Den, 2 Bath condo in N Haven Cove of Heritage Harbour. This inviting home is a popular floor plan with a spacious, updated eat-in kitchen, attached one car garage and is very well maintained. A vibrant 55+ community offering an exceptional lifestyle and an array of amenities including golf, tennis, pickleball, canoe and kayaking, plus The Lodge featuring indoor and outdoor pools, fitness facilities, library, card room and more. Conveniently located between Baltimore and Washington, DC with easy access to BWI airport.

2514 N Haven Cove Unit #102, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$3,375,000
5 Beds ⋅ 7 Baths
Nestled in the serene enclave of Cape St. John, this exquisite coastal residence offers a harmonious blend of luxury and comfort, perfectly designed for an elevated lifestyle. Built in 2012, this stunning detached home showcases timeless architectural elegance with its brick and HardiPlank exterior, inviting you into a world of sophistication. Step inside to discover an expansive open floor plan adorned with rich hardwood and tile flooring, creating a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, featuring a commercial-grade range, stainless steel appliances, and a spacious island, perfect for culinary creations and entertaining. The butler's pantry adds an extra touch of convenience, while the adjoining dining area flows seamlessly into the living space, highlighted by an elegant gas fireplace that provides a cozy ambiance. Waterfront views from every room.The primary suite is a true sanctuary, boasting breathtaking views and a luxurious en-suite bathroom complete with a soaking tub and walk-in shower. Each of the five bedrooms is generously sized with ensuite baths offering ample space for relaxation and privacy. Thoughtful details such as crown moldings, recessed lighting, and wainscoting enhance the home's refined aesthetic. Venture to the fully finished daylight basement, where natural light pours in through large windows, creating an inviting space for recreation or relaxation. This versatile area includes a wet/dry bar, perfect for hosting gatherings or enjoying quiet evenings at home, another bedroom and 2 full baths. Outside, the property is a true oasis. The extensive hardscape is complemented by lush landscaping and an underground lawn sprinkler system, ensuring a vibrant outdoor space year-round. Enjoy evenings on the screened porch or patio, where you can take in the tranquil views of the South River. With private access to the water, indulge in boating, fishing, or simply basking in the beauty of your surroundings. A standout waterfront designed for the boating lifestyle, featuring a 6' × 115' private pier with a spacious 10' × 20' platform and 3' × 12' finger pier - a total of 125 ft. length from the MHWL at the bulkhead. With approximately 10 feet of water at Mean Low Water (MLW) at the slips, the property offers exceptional deep-water access, along with a 12' × 14' boat lift with guide pole and an approximately 18' × 50' mooring slip. A timber bulkhead and riprap-protected shoreline complete this impressive waterfront setting—offering outstanding access to the Chesapeake and everything that comes with life on the water. The pier also includes a dock box, kayak rack, and lighthouse-style power pedestal. Additional features include a two-car attached garage with inside access, energy-efficient appliances, and a comprehensive water treatment system, ensuring comfort and convenience at every turn. This home is not just a residence; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Experience the best of coastal living in this remarkable property, where every detail has been thoughtfully curated for your enjoyment.

203 Cape St John Rd, Annapolis

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

$349,000
4 Beds ⋅ 3 Baths
Located just 5 minutes from Downtown Annapolis in the quiet Gentry subdivision, this contemporary 4-bedroom, 2.5-bath home offers comfortable living across three finished levels. The main level features a bright, open living area, separate dining space, updated powder room, and a cozy kitchen with quartz countertops, modern backsplash, and painted cabinetry. A large sliding glass door fills the living room with natural light and opens to a balcony, perfect for some fresh air in the afternoons. Upstairs, the spacious primary suite includes a walk-in closet, private bath, and separate vanity area with a quartz countertop. Two additional bedrooms and a full hall bath complete the upper level. The finished walk-out lower level offers plenty of flexibility for a rec room, home gym, office, media space, or another bedroom. A separate laundry and utility area provides abundant storage and room for a potential workshop. Fresh paint and thoughtful updates provide a welcoming canvas for you to make this home your own. Enjoy access to the community pool and a convenient Annapolis location close to Downtown, the U.S. Naval Academy, Spa Creek, Quiet Waters Park, shopping, dining, and much more. Easy access to Routes 50 and 97 makes getting around a breeze.

24 Gentry Ct, Annapolis

Listing courtesy of Compass. Contact: (410) 886-7342
$414,900
3 Beds ⋅ 4 Baths
Nestled in the serene community of Whispering Woods, this charming townhouse offers a perfect blend of comfort and functionality. Built in 1991, this well-maintained home boasts 1,672 square feet of inviting living space, ideal for creating lasting memories. Step inside to discover a warm and welcoming interior featuring a harmonious mix of engineered wood and neutral, freshly-painted interiors. Equipped with newer appliances and graced by maple cabinetry, recessed lighting and granite countertops, the kitchen is both practical and stylish. Newer deck overlooks a quite wooded area. Newer architectural-grade roof. The home features three generously sized bedrooms, providing ample space for relaxation and personalization. With two full bathrooms and two convenient half-bathrooms, morning routines will be a breeze. Owner's bedroom delights in an en-suite bath, dressing area and walk-in closet. Natural light floods the home through quality Andersen double-pane windows, a new front storm door, and new sliding glass doors, enhancing the inviting atmosphere and offering lovely views of the surrounding trees and woods. The full basement, complete with a connecting stairway and walkout level, presents endless possibilities. Whether you envision a bedroom, a cozy family room, a home office, or additional storage, this versatile space can be tailored to meet your needs and offers ample storage space and a workshop. The basement outside entrance opens up at grade, adding convenience, making it easy to enjoy the outdoors. The Whispering Woods community offers common grounds and tot lots/playgrounds, perfect for leisurely strolls or enjoying time outdoors. The association fee includes management, ensuring the community remains well-maintained and inviting. Parking is plentiful. The property sits on a lovely, landscaped 0.05-acre lot, providing a serene outdoor living space for gardening or relaxation. This townhouse is not just a house; it's a place to call home. With its blend of comfort, functionality, community amenities, and proximity to all major thoroughfares and the town of Annapolis, it's an exciting opportunity. Experience the tranquility of Whispering Woods and envision your future in this delightful residence.

311 Sloping Woods Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$2,499,500
6 Beds ⋅ 6 Baths
There are houses that simply check the boxes, and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighborhood, this beautifully crafted custom home is filled with the details that make a house memorable: gorgeous millwork, custom built-ins, gracious rooms, beautiful gardens and spaces designed for both gathering and retreat. At the heart of the home is a stunning chef’s kitchen that opens seamlessly to the spacious family room and screened porch, equally suited to busy mornings, relaxed weekends and a house full of friends. Custom built-ins surround the breakfast area, while formal living and dining rooms offer elegant spaces for entertaining without feeling overly formal. Upstairs, the expansive primary suite feels like a true retreat, with an oversized walk-in closet and spa-inspired bath featuring dual vanities, a soaking tub and separate shower. Two additional bedroom suites, a generous bonus room perfect for a family room, library, playroom or home office, and a large laundry room complete the second level. The third floor adds two more bedrooms and a full bath, offering tremendous flexibility for guests, work or hobbies. The lower level adds another layer of versatility, with its own private entrance, living room, full kitchen, bedroom, full bath and separate laundry. Ideal for extended family, an au pair or long-term guests, this completely independent apartment has also historically rented for $2,100 per month. Outside, the grounds are every bit as special as the home itself. Beautifully established English-style gardens surround the property, with professional landscaping, lush plantings and masses of mature hydrangeas creating a setting that feels almost Nantucket-like in the summer. The screened porch overlooks this private garden retreat and may quickly become your favorite room in the house. A circular driveway provides generous off-street parking, while the oversized two-car garage includes custom built-in storage. Significant recent improvements include three new HVAC systems installed approximately three years ago, along with an upgraded sprinkler system. And perhaps the most Annapolis detail of all: step outside in the morning and you can hear reveille from the U.S. Naval Academy; in the evening, taps carries through the air. Downtown Annapolis, the Naval Academy, marinas, restaurants and shopping are all just minutes away, with easy access to Route 50 making commuting simple and convenient. As an added benefit, the entire home has historically rented for approximately $16,000 during Naval Academy Commissioning Week, an exceptional opportunity unique to this sought-after Annapolis location. Beautifully built, wonderfully livable and unmistakably Annapolis, this is a home with room for everyone, and then some.

4 Ridge Rd, Annapolis

Listing courtesy of Cummings & Co Realtors. Contact: 4108230033
$825,000
3 Beds ⋅ 4 Baths
Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

2691 Claibourne Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$299,900
2 Beds ⋅ 2 Baths
Discover this charming 2-bedroom, 2-bathroom unit in the desirable Annapolis Overlook community. Spanning 1,229 sq. ft. , this well-maintained garden-style apartment offers a blend of comfort and modern living. The open floor plan seamlessly connects the dining and living areas, enhanced by recessed lighting and a cozy wood-burning fireplace, perfect for relaxation. The kitchen is equipped with upgraded countertops and essential appliances, including a built-in microwave, dishwasher, and self-cleaning electric oven. Enjoy the convenience of a stacked washer and dryer within the unit, making laundry days a breeze. The primary suite features a spacious walk-in closet and an en-suite bathroom, providing a private retreat. Step outside to your private deck, ideal for morning coffee or evening gatherings. The community amenities include a refreshing outdoor pool, exercise room, and playground, catering to an active lifestyle. With assigned parking and maintenance services included in the association fee, convenience is at your fingertips. This property is not only a home but a lifestyle, offering a perfect balance of tranquility and accessibility. Experience the best of community living in a well-appointed space that meets all your needs. Schedule a tour today! Furniture can be sold with the unit as well for a turn-key option if the buyer(s) are looking for that. Please inquire!

20 Greystone Ct Unit #I, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$775,000
2 Beds ⋅ 2 Baths
There is something special about life on the Chesapeake Bay, and this exceptional end-unit residence captures it beautifully. Ideally positioned where the Channel meets the Marina, the home enjoys an unobstructed view up the Channel toward the Chesapeake Bay and Bay Bridge, with expansive water vistas from nearly every room. A waterside wraparound patio, abundant green space, and fabulous interior upgrades further distinguish this unique waterfront setting. Morning begins with the sun rising over the Bay, visible from the primary bedroom and throughout the residence, while the ever-changing waterfront provides a spectacular backdrop to everyday life. From Wednesday night sailing races and Blue Angels flyovers to fireworks, passing boats, and expansive rainbows over the water, there is always something memorable to take in. Inside, the home feels bright, comfortable, and beautifully connected to its waterfront surroundings. The spacious living room is filled with natural light from an abundance of windows framing the incredible views. The electric fireplace provides a warm, relaxing atmosphere for quiet evenings or gathering with friends. Two bedrooms and two full baths provide a comfortable and versatile floor plan, whether used as a full-time residence, weekend retreat, or easy lock-and-leave Annapolis getaway. Just beyond the living room, the covered wraparound patio extends the living space outdoors and overlooks both the water and a large grassy area, an unexpected luxury in condominium living. A second patio off the kitchen offers its own highly sought-after private, no-stair walkway, allowing access to the beautifully appointed kitchen with an immediate view right out to the Bay Bridge. Together with the surrounding green space and multiple outdoor living areas, the residence offers a wonderful sense of privacy and lives much more like a single-family home than a traditional condo. Beyond the front door, Chesapeake Harbor offers a lifestyle centered around the water. Spend summer days at one of two swimming pools, including the waterfront pool, launch a kayak from the community beach, play tennis or pickleball, or follow the walking trails along the shoreline. When the day winds down, stroll to The Beacon for waterfront dining and return home as the evening light settles over the Bay. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, world class dining, shopping, and historic attractions, this exceptional residence also offers convenient access to Washington, DC, Baltimore, and BWI Airport. Whether as a full-time residence or lock-and-leave waterfront retreat, this is a rare opportunity to experience Chesapeake Harbor from a truly special vantage point.

7026 Channel Village Ct Unit #T2, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$534,000
3 Beds ⋅ 2 Baths
Welcome to 1017 Hyde Park Dr, a charming two-story Dutch Colonial nestled in Annapolis, where classic character meets a convenient location. This 3-bedroom, 2-bath home offers 1,272 square feet of living space on a 5,971-square-foot lot, with a basement providing additional flexible space for storage, recreation, hobbies, or a home office. The inviting interior features a cozy fireplace and traditional Dutch Colonial character, creating a warm backdrop for everyday living and entertaining. With its versatile layout and established charm, this home offers an opportunity to personalize the space and make it your own. Enjoy an exceptional Annapolis location just minutes from the Severn River, Annapolis Maritime Museum, and downtown Annapolis. Spend the day exploring waterfront attractions, local shops, restaurants, and historic downtown, or enjoy easy access to the Eastern Shore and major commuter routes to Washington, D.C., Baltimore, and beyond. If you're looking for a home that combines architectural charm, flexible living space, and an outstanding Annapolis location, 1017 Hyde Park Dr is ready to welcome you. Come see all this home and location have to offer!

1017 Hyde Park Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$344,900
2 Beds ⋅ 2 Baths
Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo in the desirable Admiral Reach at Harbor Gates community of Annapolis! Ideally situated just minutes from historic downtown Annapolis, the U.S. Naval Academy, Luminis Health Anne Arundel Medical Center, and major commuter routes including Route 50 and I-97, this inviting third-floor home offers the perfect blend of comfort, convenience, and low-maintenance living. Step inside to a bright and welcoming interior featuring a comfortable open layout with luxury vinyl tile and carpet flooring throughout. The updated kitchen is ready for everyday living and entertaining, featuring new countertops and stainless-steel appliances. Two spacious bedrooms and two full bathrooms provide flexibility for guests, roommates, or a work-from-home arrangement, while the in-unit laundry adds everyday convenience. Step outside onto the private covered balcony and enjoy your own outdoor retreat—perfect for morning coffee, an evening unwind, or simply enjoying the surrounding community. As a third-floor unit, the home offers an elevated perspective while providing the convenience of condo living. Harbor Gates offers an exceptional array of amenities designed to complement an active and social lifestyle. Residents enjoy access to a community swimming pool, exercise room, clubhouse, walking trails, basketball court, tennis courts, and pickleball courts. The combination of recreational amenities, convenient location, and low-maintenance living makes this community an outstanding place to call home. Whether you’re searching for a convenient primary residence, a low-maintenance second home, or an investment opportunity in the Annapolis market, 631 Admiral Drive offers an excellent combination of location, updates, outdoor living, and resort-style community amenities. Come see all this wonderful condo and community have to offer!

631 Admiral Dr Unit #304, Annapolis

Listing courtesy of Taylor Properties. Contact:

$449,000
3 Beds ⋅ 3 Baths
Open House Saturday 10AM - 12PM! Beautifully updated and move-in ready in an ideal Annapolis location! HVAC, ROOF, & HOT WATER HEATER ALL REPLACED APPROX. 2021. This inviting home has been thoughtfully refreshed with updated kitchen finishes, new flooring, fresh interior paint and beautifully updated bathrooms, creating a bright, fresh feel throughout. The main level offers a comfortable, functional layout with generous living and entertaining spaces and a beautifully updated kitchen at the heart of the home. Upstairs, spacious bedrooms and refreshed bathrooms continue the clean, updated feel. Enjoy additional living space and flexibility throughout the home, along with outdoor space perfect for relaxing or entertaining. Ideally located in Annapolis just minutes from Quiet Waters Park, downtown Annapolis, Eastport, shopping, dining and major commuter routes. With so many of the important updates already completed, this home offers an incredible opportunity to move right in and enjoy everything the Annapolis lifestyle has to offer!

150 Quiet Waters Pl, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$269,900
2 Beds ⋅ 2 Baths
This exceptional 2nd level unit, ideally located in North Green Condos offers a harmonious blend of contemporary design and modern amenities. Spanning 1,082 square feet, this well-maintained condo features two spacious bedrooms and two full bathrooms, including a primary bath with walk-in shower. The open floor plan enhances the living space, complemented by wood floors, dining room and a bright breakfast area that invites natural light. The kitchen is equipped with 42inch cabinets, stone countertops, and NEW stainless-steel appliances, including a built-in microwave, dishwasher, and electric oven/range, ensuring a seamless cooking experience. You will appreciate the new luxury carpet in bedrooms and fresh paint throughout. Additional conveniences include in-unit laundry washer and dryer, as well as a walk-in closet for ample storage. Residents can enjoy community amenities such as an outdoor pool, patio area, and beautifully maintained common grounds. The property is surrounded by sidewalks, public transport and fitness center amenities. Situated in a vibrant neighborhood, North Green Condos is conveniently located near shopping centers and local parks, providing recreational opportunities for outdoor enthusiasts. The community is well-served by public services, pet friendly, and is in proximity to schools and recreation facilities, making it a desirable location for those seeking a balanced lifestyle. The association fee covers essential services, including maintenance, building insurance, water/sewer and trash removal, ensuring worry-free living. This property represents an excellent opportunity for those seeking a modern, well-appointed home to enjoy the historic maritime experience of Annapolis. Just minutes from the United States Naval Academy and downtown city dock.

300 Hilltop Ln Unit #300E, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$1,050,000
2 Beds ⋅ 2 Baths
Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own.

412 Third St, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000
$419,900
4 Beds ⋅ 2 Baths
Spacious Duplex located in Sought After Revell Downs! Over 1800 square feet of Finished Living Space with Recent Updates Including 35 Year Architectural Shingle Roof, Maple Kitchen Cabinets, Granite Counters, Kitchen Appliances, Marble Floor Tile in Kitchen, Ceramic Wall Tile and Vanities in Bathrooms, Luxury Vinyl Plank in Living and Dining Room and New Washer and Dryer. The Main Level Features 3 Bedrooms, Bathroom, Kitchen, Living Room and Separate Dining. Downstairs you have a Big Family Room with a Fireplace, 4th Bedroom, 1/2 Bath and a Huge Storage/Laundry Room. Outside is Nicely Landscaped and Great for Entertaining with a Fully Fenced Back Yard, Big Custom Sundeck, Three Storage Sheds and a Patio. This Wonderful Community is Just minutes from Schools, Annapolis Mall, Riva Festival Shopping Center, Quiet Waters Park, Sandy Point State Park, and downtown Annapolis, with quick access to Route 50, I-97, and the Naval Academy. You can also enjoy the newly completed Broadneck Peninsula Trail with a Multi-Use path that connects the existing Baltimore and Annapolis Trail directly to Sandy Point State Park!

1660 Secretariat Dr, Annapolis

Listing courtesy of ABR. Contact: 4102127332
$9,500,000
6 Beds ⋅ 10 Baths
Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

3285 Harness Creek Rd, Annapolis

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

$995,000
2 Beds ⋅ 3 Baths
Experience the best of downtown Annapolis living from this exceptional corner residence in highly sought-after Acton’s Landing. This 2 bedroom, with an extra den unit, offers nearly 2,000 square feet of beautifully designed living space. This extraordinary condominium combines the ease of maintenance-free living with a rare feature that truly sets it apart: its own exterior entrance. Step directly outside and begin enjoying the restaurants, shops, waterfront, events, and unmistakable charm of downtown Annapolis without ever having to walk through the building. The private exterior entrance also provides exceptional convenience for guests, particularly after concierge hours, allowing them to arrive directly at your door. Inside, the spacious, open-concept floor plan has been freshly painted and features brand-new carpeting, abundant natural light, and a wall of windows overlooking the outdoor patio area. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, stainless steel appliances—including gas cooktop and a new refrigerator —and a generous island/breakfast bar that opens seamlessly to the main living area. The thoughtfully designed layout provides excellent separation between the two expansive bedroom suites. The primary suite features two closets, including a walk-in, along with a spacious private bath complete with a separate soaking tub. On the opposite side of the residence, the second bedroom offers its own en-suite bath, creating an ideal private retreat for overnight guests. A separate den/office provides valuable additional living space and offers the flexibility to serve as a home office, library, media room, or occasional guest space. A conveniently located powder room makes entertaining especially easy. Adding to the exceptional convenience are two garage parking spaces located just steps from the residence, along with an owned private storage unit—valuable amenities for downtown Annapolis living. Acton’s Landing further enhances the lifestyle with a fitness center, library, recreation/community room, beautifully landscaped courtyard, and concierge service. And when you are ready to venture out, downtown Annapolis is right outside your door. Few residences offer this combination of nearly 2,000 square feet, two garage parking spaces, private storage, luxury amenities, and the rare convenience of a direct entrance/exit with its own outdoor, covered patio—all within walking distance of everything that makes Annapolis such an extraordinary place to live. This is more than simply a downtown condo; it is an opportunity to enjoy the Annapolis lifestyle with the space, comfort, convenience, and accessibility of a true luxury residence.

66 Franklin St Unit #102, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$610,000
4 Beds ⋅ 3 Baths
Discover the charm of this beautifully renovated ranch-style home in Hillsmere Estates, where modern comfort meets serene living. Major renovations completed in 2020 have transformed this residence into a warm and inviting retreat, featuring solid hardwood flooring throughout and a fully finished basement that offers ample space for relaxation or entertainment. With four spacious bedrooms and three full bathrooms, this home is designed to accommodate your lifestyle needs. The cozy fireplace in the living area creates a perfect ambiance for gatherings, while the well-appointed kitchen is ready for your culinary adventures. Step outside to enjoy the expansive 0.32-acre lot, where you can unwind in your private outdoor space or explore the community amenities, including a refreshing pool. For water enthusiasts, the property is just 2 miles from the South River, providing easy access for boating, fishing, and kayaking. With multiple slips available by lease, your aquatic adventures are just a stone's throw away. This home also features a convenient driveway for parking and a shed for additional storage. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities. This is more than just a house; it's a place to create lasting memories. Don't miss your chance to make it your own!

301 Cedar Ln, Annapolis

Listing courtesy of ExecuHome Realty. Contact:

$175,000
1 Beds ⋅ 2 Baths
List Price is Opening bid at Online Auction to be conducted on auctioneer's website. Online Auction Only! Bidding begins Saturday, September 26th and ends Thursday October 1, 2026 at 1:00 PM. Waterfront-Inspired Annapolis Living with Exceptional Community Amenities Experience the appeal of Annapolis living at 2004 Quay Village Court, Unit T-1, a desirable main-level condominium in the water-privileged First Village of Chesapeake Harbour community. Offering an inviting blend of comfort, privacy, and resort-style amenities, this residence presents an exceptional opportunity to create a refined retreat in one of Maryland’s most desirable waterfront communities. Inside, The main-level design offers effortless one-floor living, with an open living and dining area (with a fireplace), Powder room, designated laundry area, and kitchen. The living space extends outdoors via the rear patio, creating a welcoming setting for morning coffee, evening cocktails, or relaxing at the end of the day. The space is completed by the generous primary suite, providing a peaceful private escape, featuring a spacious walk-in closet and large en-suite bathroom. Beyond your doorstep, First Village offers an enviable water-oriented lifestyle with an impressive collection of community amenities. Residents enjoy two swimming pools, four tennis courts, grilling areas, a beach area, and a boat rack, creating countless opportunities for recreation, relaxation, and entertaining without ever straying far from home. The residence offers an opportunity for thoughtful updating, allowing its next owner to introduce their own aesthetic and finishes while taking full advantage of the spacious layout and exceptional community setting. Ideally positioned in Annapolis, this property places you close to the area’s renowned dining, shopping, waterfront destinations, and vibrant coastal lifestyle. A spacious primary suite, private outdoor space, and resort-inspired community amenities come together to offer an exciting opportunity to create your own Annapolis retreat. Property Highlights: • Water Privileged Community • Premier Annapolis Location • Numerous Community Amenities • Main Level Unit • 1bd/1.5ba Please visit auctioneer's website for additional information.

2004 Quay Village Ct Unit #T1, Annapolis

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

$2,695,000
4 Beds ⋅ 4 Baths
Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and lightly lived in, the home captures everything that makes Eastport so desirable, from its welcoming front porch, charming architectural details, and beautifully curated landscaping to a location just steps from marinas, restaurants, waterfront parks, and the vibrant streets of Downtown Eastport and Annapolis. Lush, thoughtfully designed landscaping brings the property to life, framing the home with color, texture, and greenery and creating an inviting sense of arrival. A gracious front porch sets the tone for the warm and welcoming interiors. Just inside, a dedicated office provides a quiet workspace, while hardwood floors, shiplap accents, custom millwork, and thoughtful details lend character throughout. The open floor plan unfolds into the heart of the home, where a spectacular kitchen features GE Monogram appliances, an expansive island, abundant cabinetry, and generous workspace. The adjoining dining area flows seamlessly into the living room, anchored by a fireplace framed with custom built-ins. Doors extend the living space to a large rear patio surrounded by beautiful landscaping, creating a private and inviting setting for outdoor dining, entertaining, and relaxed evenings at home. The main-level primary suite offers the convenience of one-level living with a beautifully appointed ensuite bath and conveniently located laundry room. A thoughtfully designed mudroom with built-in cubbies provides everyday functionality and an organized transition into the home. Additionally, the home features advanced technology throughout, including a Tesla Powerwall 3 for backup power, Tesla EV charger, and professionally installed Control4 home automation. The integrated system provides centralized control of lighting, climate, security, electronic locks, TVs, and built-in ceiling speakers throughout the home. Upstairs, two spacious bedrooms share a hall bath, while a large finished attic adds a wonderfully flexible dimension to the floor plan. Currently ideal as a bunk room, this charming bonus space can easily adapt as a playroom, additional sleeping quarters, creative studio, or whatever best suits your lifestyle. The finished lower level takes entertaining and recreation to another level with a spacious family room, game area, wet bar, full bath, and golf simulator. A separate bonus room currently serves as a home gym, while an expansive storage area provides the practical space that is often difficult to find in Eastport. Beyond the front door, the best of Annapolis is within easy reach. Launch a kayak from nearby Horn Point Park, stroll to Eastport's celebrated restaurants, pubs, marinas, and street-end parks, or cross the Spa Creek Bridge into Downtown Annapolis and the U.S. Naval Academy. Boaters will appreciate immediate proximity to the Chesapeake Bay and some of the region's most sought-after cruising destinations. Membership at the nearby Annapolis Capital Yacht Club marina also provides permission to enjoy the Chesapeake Landing community swimming pool, adding yet another way to embrace the waterfront lifestyle just steps from home. Offering the charm and personality of an Eastport Craftsman with the advantages of newer construction, beautiful landscaping, a main-level primary suite, exceptional entertaining spaces, and an enviable walkable location, this is a rare opportunity to experience one of Annapolis' most beloved neighborhoods with comfort, style, and ease. Welcome Home!

507 1st St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,795,000
3 Beds ⋅ 3 Baths
Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$989,000
3 Beds ⋅ 2 Baths

23 Hull Ave, Annapolis

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

$419,900
3 Beds ⋅ 3 Baths
​3 BEDS | 2.5 BATHS | WHISPERING WOODS | COLONIAL TOWNHOUSE ​Welcome to This Charming 3-bedroom, 2.5-bathroom Colonial Townhouse in Whispering Woods. Great Lot that Backs to Tranquil, Wooded Views, this Move-In Ready Home Offers a Blend of Style, Comfort, and Functional Living Space. ​KEY HIGHLIGHTS: ​Gourmet Kitchen: Quartz Countertops, Stainless Steel Appliances, Hardwood Floors and Seamless Open Flow into the Dining Area—Ideal for Hosting and Entertaining. ​Spacious Living: Open Main Level with Hardwood Floors Throughout, Recessed Lighting and Ceiling Fans. ​Outdoor Oasis: Private Deck and Patio Overlooking Trees. ​Walkout Basement: Full, With Large Family Room with Walkout Access, Full Bath, Laundry and Loads of Storage. ​Parking and Amenities: Assigned Parking with Ample Overflow Parking and Community Access to Playgrounds and Common Area. ​HVAC 3 Years Old. Pella Windows and Sliders. Schedule your private tour today!

1740 Woodtree Cir, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$225,000
3 Beds ⋅ 2 Baths
Wonderful Opportunity in Annapolis! Unlock the potential of this 3-bedroom townhome and bring your vision to life. Whether you're looking for your next renovation project or an opportunity to create a home with your own personal style, this property offers outstanding potential. The home features a walkout basement, a spacious backyard with room for outdoor enjoyment, and a convenient location with easy access to shopping, dining, and major commuter routes. This property is ready for renovation and offers an excellent opportunity to add value through updates and improvements. With the right vision, this townhome has the potential to truly shine. Don't miss this chance to transform this Annapolis property into something special. Schedule your showing today and imagine the possibilities! Please see the Documents section for complete offer submission instructions. All offers must be submitted through the VRM Properties offer portal. Agents must register as a user, enter the property address, and select "Start Offer." This property may qualify for Seller Financing (Vendee). If the property was built prior to 1978, Lead-Based Paint Potentially Exists.

608 Greenbriar Ln, Annapolis

Listing courtesy of Coast To Coast Home Consultants INC. Contact: 760-927-8001
$335,900
4 Beds ⋅ 4 Baths
Bring your vision and unlock the potential of this spacious three-level end-unit townhome in the sought-after community of The Gentry, just off Spa Road. Set amid a wooded landscape, the property features mature trees along the side and rear yard, with the community pool nestled down a small hill and a backdrop of additional trees beyond. This unique setting offers a wonderful sense of privacy and a peaceful backdrop while still being close to everything Annapolis has to offer. The main level features hardwood flooring, full kitchen, a convenient half bath, a wood-burning fireplace, and a bright living area opening to a rear deck overlooking the natural surroundings and pool area; a perfect place to have your morning coffee to start your day. Upstairs, you'll find three bedrooms, including an owner’s suite with a private full bath, plus a full hall bath. The walk-out lower level adds even more versatility with a fourth bedroom, full bath, laundry, storage areas and direct access to the private backyard. The home is being sold "as is" and requires repairs and updating. It is priced accordingly, offering an excellent opportunity for a buyer ready to bring their vision to life and build equity. With its desirable end-unit location, spacious three-level layout, four bedrooms, three-and-a-half baths, outdoor spaces, and proximity to downtown Annapolis, this property offers an ideal canvas to create a home that reflects your own style!

57 Gentry Ct, Annapolis

Listing courtesy of Redfin Corp. Contact: 4102028454
$669,000
3 Beds ⋅ 2 Baths
Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and high-end upgrades from top to bottom. The open, light-filled layout features stylish new LVP flooring (Oct 2024) and contemporary lighting throughout (2024). Cook and entertain in the updated kitchen with custom cabinetry and quartz countertops (Dec 2024), plus brand-new appliances (Jan 2025). Relax in the primary suite with its custom Closet America walk-in closet (Sept 2025). Living in Chesapeake Harbour gives you direct access to a deep-water marina, private beach, pools, tennis courts, 24/7 security, and an on-site waterfront restaurant, all just minutes from historic Downtown Annapolis.

2104 Chesapeake Harbour Dr E Unit #202, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$285,000
3 Beds ⋅ 2 Baths
Move-in ready top-floor 3-bedroom, 2-bath condo in Fairwinds of Annapolis, offering comfortable living and an unbeatable location just minutes from Bay Ridge and Downtown Annapolis. This large floorplan home features a bright, open layout and a private balcony. The updated kitchen features a new flooring, countertop, gas cooking, ample cabinet storage, and a new refrigerator to be installed. New flooring in both bathrooms. The HVAC system was replaced in 2022, providing added peace of mind. The spacious primary bedroom offers a private full bath, while the two generously sized secondary bedrooms share an additional full bath. Enjoy the convenience of natural gas for heating, hot water, and cooking, along with access to the community pool and tennis courts. Free off-street parking is available, with reserved off-street parking also available for a fee through the condo association. The location is hard to beat. Walking distance to grocery stores, coffee shops, restaurants, and Rita's Italian Ice. Easy access to shopping, Downtown Annapolis, Eastport, the Naval Academy, and major commuter routes. This won't last long. Schedule a tour today!

142 Georgetown Rd Unit #9, Annapolis

Listing courtesy of Redfin Corp. Contact: 4102028454
$750,000
4 Beds ⋅ 3 Baths
** Offer deadline, please submit your best offers by Monday September 14th at 12 noon ** Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, and privacy, this home provides plenty of space for everyday living and entertaining. The impressive lofted living room is filled with natural light and features skylights that create an open, airy atmosphere. The inviting family room offers a propane fireplace, providing a cozy gathering space for relaxing evenings. The spacious kitchen offers plenty of cabinet and counter space, providing a functional and inviting setting for preparing meals and gathering with family and friends. A convenient half bath completes the main level. The spacious primary bedroom features its own ensuite bathroom and private laundry, creating a comfortable retreat with added convenience. Three additional bedrooms provide flexibility for family, guests, a home office, or hobby space. Outside, the expansive 1.8-acre property offers room to enjoy the outdoors and plenty of privacy, while the attached 2-car garage provides ample parking and storage. With its generous lot, versatile floor plan, lofted living space, and sought-after Annapolis location, 580 Pinedale Dr offers an opportunity to enjoy both space and convenience.

580 Pinedale Dr, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033
$575,000
4 Beds ⋅ 2 Baths
EARLY ACCESS! Be among the first to preview this home before it officially goes Active on the MLS. Private showings are available now. Call Lesa Clark at 301-410-6009 for a private tour. Welcome to this beautifully updated split-foyer home nestled on a gorgeous corner lot in the sought-after Cape St. Claire community of Annapolis. Offering an exceptional combination of modern updates, thoughtful improvements, and outstanding community amenities, this move-in ready home has been meticulously maintained inside and out. Inside, you'll enjoy modern fixtures, recessed lighting, granite countertops, and an updated kitchen featuring stainless steel appliances, including a refrigerator, dishwasher, and electric range replaced in 2022. The kitchen flows seamlessly onto a brand-new wood deck (2023, freshly stained in 2026), creating the perfect space for outdoor dining, entertaining, or simply relaxing. The inviting living room is centered around a beautifully renovated wood-burning fireplace (2023), while major system upgrades provide added peace of mind, including a new HVAC system (2024) and a whole-house humidifier (2025) for year-round comfort. The main level offers three bedrooms, including a primary suite with a private bath and two additional bedrooms with a shared hall bath. The finished lower level features a spacious flex area that can easily serve as a recreation room, home office, workout space, guest area, or potential fourth bedroom, along with a dedicated laundry area and convenient side-entry mudroom. Step outside and discover extensive outdoor improvements completed between 2022 and 2024. The property has been professionally regraded and enhanced with retaining walls, a stone walkway, additional gravel parking, and a completely restructured driveway offering improved functionality and expanded parking. An engineered drainage system, including underground front-yard downspouts and a complete backyard French drain, helps keep the property dry and functional throughout the seasons. Thoughtfully selected native, non-invasive flowers and shrubs provide beautiful color and interest throughout the year. Located in the highly desirable Cape St. Claire community of Annapolis, Maryland, residents enjoy access to outstanding neighborhood amenities, including a private community beach, community marina, boat ramp, fishing and crabbing pier, playgrounds, parks, and community events throughout the year. Conveniently located just minutes from downtown Annapolis, Broadneck Park, Sandy Point State Park, the Chesapeake Bay, the U.S. Naval Academy, shopping, dining, waterfront attractions, and everyday conveniences. Commuters will appreciate easy access to Route 50, I-97, Baltimore, Washington, D.C., Fort Meade, and BWI Airport. Whether you're looking for a beautifully updated home, a move-in ready property with major system upgrades, or the lifestyle that comes with living in one of Annapolis' premier water-access communities, this exceptional Cape St. Claire home offers the perfect opportunity to enjoy the very best of Maryland's Chesapeake Bay lifestyle.

1178 Glenwood Dl, Annapolis

Listing courtesy of Redfin Corp. Contact: 3016586186