Refine Search
Map
Sort by
$2,615,000
6 Beds ⋅ 6 Baths
Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributaries, this extraordinary waterfront residence at 529 Lee Circle offers an exceptional blend of sophisticated coastal design and effortless indoor-outdoor living. Privately nestled among mature trees, the home enjoys a peaceful setting with panoramic water views, a private pier, a boat house and a floating dock, creating the ultimate Annapolis waterfront retreat. The impressive rear elevation is designed to embrace the waterfront lifestyle, featuring expansive walls of glass that flood the interiors with natural light while framing picturesque water views from nearly every level. Multiple outdoor living spaces—including a spacious waterside deck, an upper-level balcony, and an expansive lawn leading to the 114 feet shoreline—provide the perfect backdrop for entertaining or relaxing while enjoying spectacular sunsets. The boat house with lift, private pier, and protected water dockage offer immediate access to boating, paddleboarding, kayaking, and all the Chesapeake Bay has to offer. Whether departing for a day on the water or enjoying quiet evenings along the shoreline, this property delivers an unmatched waterfront experience. Architecturally, the home combines classic coastal elegance with contemporary comfort. Soft gray siding, crisp white trim, multiple gables, and oversized windows create a timeless façade that complements its natural surroundings. The residence offers approximately 6,000 square feet of living space with two owners suite (one on the main level), generous entertaining areas, multiple fireplaces, and luxurious accommodations designed for both everyday living and grand-scale gatherings. The home was originally built in 1965. In 2016 it went through a complete, down-to-the-studs renovation and expansion to the creation of stunning luxurious waterfront home. Custom-Built by Architect Teresa Todd and Timberlake Homes into a 6-bedroom and 5.5-bathroom residence. Located within the sought-after Hillsmere Shores community, residents enjoy a coveted Annapolis lifestyle with access to a private beach, marina, community pool, playgrounds, and convenient proximity to Historic Downtown Annapolis, waterfront dining, yacht clubs, and the U.S. Naval Academy. This is more than a waterfront home—it is a private Chesapeake Bay sanctuary where luxury, recreation, and timeless coastal beauty come together in one exceptional offering.

529 Lee Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

$1,030,000
3 Beds ⋅ 3 Baths
Welcome to 122 E Bay View Drive in sought-after Hillsmere—where lifestyle and comfort come together just minutes from downtown Annapolis. Ideally located just steps from the community marina, this home also offers water peeks, bringing a touch of the Chesapeake Bay into your everyday living. This well-maintained home features generous living spaces, highlighted by hardwood floors and a thoughtfully updated kitchen designed for both everyday living and entertaining. The spacious room sizes provide flexibility for modern lifestyles, while the inviting wood stove adds warmth and character. Upstairs, the primary suite includes a private full bath, creating a comfortable retreat at the end of the day. Outside, enjoy your own backyard oasis with a fully fenced yard and an in-ground pool—perfect for summer gatherings, relaxing weekends, and entertaining guests. A two-car garage adds convenience and additional storage. Community amenities include beaches, boat ramps, marinas, community pool and playgrounds. Residents also enjoy close proximity to Quiet Waters Park, local dining, and all that historic Annapolis has to offer. This is a rare opportunity to enjoy space, location, and a vibrant waterfront lifestyle in one of Annapolis’ most desirable neighborhoods. Updates: Roof (2008), Heat pump (2020), Windows (2018), Appliances (2018)

122 E Bay View Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Fathom Realty MD, LLC.

$997,300
3 Beds ⋅ 2 Baths
Set in the sought-after Hillsmere neighborhood of Annapolis, this 2,200-square-foot rancher offers a calm, coastal feel enhanced by a single serene water view and a long list of significant updates. The home features a brand new kitchen with fully custom cabinets and a Wolf Range, newly renovated bathrooms, a roof replaced in 2021 with a 10-year warranty as reported by the seller, new windows added in 2022 according to seller-provided information, a new HVAC system also installed in 2022 per seller records, a new hot water heater from 2023 as stated by the seller, and a water softener from 2019 based on the seller’s account, along with numerous additional upgrades throughout the property that collectively elevate its comfort and appeal. The single-level layout maintains an easy, welcoming flow while showcasing the care invested in every improvement. Outdoors, a backyard oasis awaits with a new 2023 hot tub and a peaceful water view that creates a private haven for relaxation. Schedule your showing for this meticulously maintained home today! Hillsmere provides the full Annapolis lifestyle experience with beaches, a marina, playgrounds, walking paths, BBQ areas and extensive kayak storage, which are amenities described in publicly available community information. The neighborhood’s waterfront facilities include a main marina with a newly constructed lving shore line (part of the Shoreline Resiliency Program), multiple boat ramps and launch points, and storage areas for boats, kayaks and trailers, as outlined in community resources. Just outside the neighborhood entrance, Quiet Waters Park offers recreation such as water activities, pavilions, a playground, ice skating and food options, all features publicly noted by the park’s information sources.

150 E Bay View Dr, Annapolis

Listing courtesy of Mr. Lister Realty. Contact:

Selling Office: Compass.

$925,000
4 Beds ⋅ 4 Baths
Welcome home to this fantastic contemporary style where coastal charm meets modern connivence only blocks from the sandy beach. Located in water amenity rich Hillsmere Shores, this four bedrooms, three and a half bath home has plenty of space to spread out. Enter into a sun filled living room with vaulted ceilings catwalk on the upper level. Find a gourmet kitchen centered between the dining room with built-in cabinets and spacious family room. Through the doors in the dining room pass into a wonderful panoramic view of the back yard in an all season sun room. Step from the sunroom or family room to the huge deck and enjoy the tranquil back yard. On the upper level is the vaulted ceiling primary bedroom, with two closets, and a super full bath. Bedrooms 2 and 3 have great closet systems, and share the hall full bath with the 4th bedroom. On the lower level rests the gigantic rec room, a great bonus room with attached bath, and storage. The back yard is fully fenced and backs to woods*** Updates include new roof Sept 2024, complete backyard renovation 2023, in 2025 new refrigerator, 2024 new dishwasher, 2023 new washer and dryer. Sellers updated kitchen quartz countertops and new backsplash after moving in as well. The community offers a private beach, picnic, and play area, boat ramp and boat slips. Minutes from Eastport and downtown Annapolis, shops and restaurants, and adjacent to Quiet Waters Park.

161 E Bay View Dr, Annapolis

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

Selling Office: Coldwell Banker Realty.

$885,000
3 Beds ⋅ 3 Baths
Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores community one block from the marina, private beach, waterfront playground/parks, community pool, and boat ramp. Thoughtfully redesigned with high-end finishes throughout, this turnkey home offers the perfect blend of style, flexibility, and everyday comfort. The bright, open main level is designed for gathering, featuring a beautifully updated white kitchen with quartz countertops, stainless appliances, custom backsplash, generous workspace, and seamless flow into a dining and seating area accented by shiplap details and French doors opening to an expansive entertaining deck overlooking the oversized, fully fenced backyard. The spacious primary suite includes a sitting area, custom California Closets walk-in, and a bathroom with 4' vanity, an extra large Smart Mirror/Medicine Cabinet and marble shower. The walkout lower level offers exceptional flexibility with a large room currently enjoyed as a family room but could easily serve as a fourth bedroom, complete with fireplace, closet, full egress, and direct access to a private covered deck with hot tub. Two additional bedrooms, both with California Closet systems, a beautifully renovated full bath with double vanity, extended tub and an updated laundry room complete this level. A bonus feature of this house is the separate, flex space adjacent to the garage with its own beautifully renovated powder room, mini-split HVAC, large deck, with endless possibilities as a home office, fitness studio, media room, teen hangout, creative workspace, or guest overflow. Outside, the oversized fenced-in back yard provides rare privacy and room to play, entertain, or garden, complemented by multiple outdoor living areas and a detached shed/workshop with power and air conditioning. The large two car garage features Flow Wall storage system, epoxy floor coating, and an EV charging plug as well as direct access to the rear yard. Extensive renovations throughout include the kitchen, baths, roof, siding, windows, HVAC, flooring, lighting, garage, landscaping, and countless custom details, creating a truly move-in-ready home. Enjoy one of Annapolis' most beloved waterfront communities with a voluntary HOA, private beach on the South River, marina, community pool, playgrounds, and year-round neighborhood events—all just minutes from Downtown Annapolis.

117 Sunset Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Douglas Realty LLC.

$825,000
3 Beds ⋅ 2 Baths
Offer Received, Seller respectfully requests best and final offers be submitted by 12 PM, Monday, February 23. Welcoming rancher in water-privileged Hillsmere Shores, set on a sunny, impeccably landscaped lot just a few blocks from the beach. This beauty offers an unexpectedly spacious layout with a desirable open floor plan, a bright year-round sunroom, a versatile bonus room on the lower level, and updates that are tasteful, timeless and thoughtfully executed. Located in one of Annapolis’s most sought-after waterfront communities, Hillsmere Shores isn’t just a place to live—it’s a lifestyle. Neighbors enjoy sunset beach picnics, gathering at the community pool, launching kayacks and paddleboards from one of several private marinas, and weekends are spent exploring the Chesapeake Bay from the community boat ramp. Just seconds from these amenities, this warm and welcoming home provides the perfect backdrop for every season—from cozy holiday gatherings by the fire, to summer crab feasts on the back deck. A rare opportunity to enjoy classic Annapolis living.

108 Huse Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$689,900
4 Beds ⋅ 4 Baths
An absolute must see! Stunning 4 bed 3 1/2 bath updated home in sought after Hillsmere Shores. This home just had cosmetic upgrades including but not limited to fresh paint throughout, new carpet, new fixtures, new appliances more. Home features two bedrooms upstairs to include a primary with his and hers walk in closets and a spa like primary bath. The second floor boasts two additional bedrooms. One being a second primary with an en suite and fireplace. The home includes a large deck outback and completely fenced back yard. This property is available for immediate occupancy. Come check it out. Seller will provide home warranty with full price offer.

110 Kuethe Dr, Annapolis

Listing courtesy of JAK Real Estate. Contact:

Selling Office: Park Modern Realty.

$655,000
4 Beds ⋅ 2 Baths
Offer deadline of 6pm Sunday 3/22/2026. The main level greets you with rich hardwood floors flowing throughout, three well-appointed bedrooms, and an upgraded full bath. The heart of the home is the renovated kitchen, featuring granite countertops and sleek slate-finished stainless appliances. The kitchen opens effortlessly into a stunning addition with soaring cathedral ceilings and wood burning fireplace, filling the space with natural light and leading directly to a Trex rear deck — perfect for entertaining and outdoor relaxation. A classic front porch completes the curb appeal. The finished lower level is a standout, offering versatile living with a spacious family room, den/office, fourth bedroom, kitchenette, laundry, and a full bath. Dedicated laundry and utility area. A walkout leads to a sunroom with high ceiling, creating a bright and peaceful retreat ideal for morning coffee or year-round enjoyment. Step outside to a fully fenced yard on a generous one-third acre lot — plenty of room to play, garden, or simply unwind in your own private outdoor space. Location doesn't get much better. Stroll to the nearby Shopping Center, public library, or the beloved Quiet Waters Park. And as a resident of Hillsmere Shores, you'll enjoy access to an outstanding array of community amenities: a marina, sandy beach, playground, community pool, and boat, kayak, and small watercraft ramps and storage. Whether you're a water enthusiast or simply love an active, connected neighborhood, Hillsmere Shores delivers a lifestyle as impressive as the home itself.

115 Edgemere Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: RE/MAX Executive.

$625,000
2 Beds ⋅ 1 Baths
Open House on 5/31/26 has been cancelled. Multiple offers received. Charming two-bedroom rancher with all the right updates! Remodeled kitchen (2020) features a pantry and opens to comfortable living spaces with LVP flooring throughout. Fireplace included. Bedrooms are nicely sized with generous closet storage. A light-filled breezeway connecting the one-car garage to the home and rear deck round out this move-in ready gem. Nestled on .41 acres, there's plenty of room to breathe and enjoy the outdoors. And the best is yet to come — an unfinished basement offers an additional 1,200 sq ft of potential, ready to be transformed into the space you've always wanted. All this plus the incredible Hillsmere community amenities just a short walk away — pool, marina, beach, and kayak and small boat storage. Easy, comfortable living with room to grow!

105 Mansion Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Anne Arundel Properties, Inc..

$585,000
4 Beds ⋅ 2 Baths
OPEN SATURDAY, 6/6, 10AM-12PM and SUNDAY, 6/7, 12-2PM Nestled in one of Annapolis's most beloved water-oriented communities, this 4-bedroom, 2 full bath home offers the space, updates, and lifestyle you've been waiting for. The spacious kitchen is perfect for entertaining with a passthrough window to make serving an ease. Unwind on the screened porch or take full advantage of the large fenced yard — perfect for garden parties or simply enjoying the outdoors. The finished basement offers a large family room with a cozy fireplace, full bath and 4th bedroom. Hillsmere Shores amenities include a private deep-water marina with direct access to the South River, sandy beaches, designated swim area, playgrounds, community pool, boat ramps, and waterfront pavilions. The neighborhood sits between Duvall Creek and Quiet Waters Park — 340 acres of trails, open space, and South River waterfront right outside your door. Downtown Annapolis, City Dock, and the Naval Academy are just minutes away. Roof (2024). Make your appointment today to view this wonderful home!

129 Meade Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: EXP Realty, LLC.

$570,000
3 Beds ⋅ 2 Baths
Coming soon in water priveledged community on the South River! Well maintained ranch style home on large corner lot, with fenced yard, oversized 2 car garage addition, extensive hardscaping, whole house Generac genterator, fireplace, wood floors through-out main level, updated kitchen and bath, full basement and more! New roof installed 2 years ago, gutter helmets, and owner installed new well pressure tank. Replacement wondows and the list continues. Fenced yard has DB gate accomodate boat storage or what ever else you want to store on the property. Detached shed for yard tools, even the driveway has been repaved! Side yard used to feature an inground pool, so plenty of room to meet buyers desires. Voluntary Imporovement Assiciation at $25 per year gives you access to the Beach, marina & boat ramps. Special Tax Assessment district $285 per year included in property tax bill.

98 Pine Dr, Annapolis

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

Selling Office: Coldwell Banker Realty.

$531,000
3 Beds ⋅ 2 Baths
**OFFER DEADLINE MONDAY 8/10 @ 12 NOON** Welcome to 282 Cedar Lane, a beautifully updated rancher nestled in one of Annapolis' most sought-after waterfront communities. This move-in ready home blends timeless charm with thoughtful updates, beginning with a stunning magazine-worthy kitchen featuring nautical navy cabinetry, warm butcher block countertops, and stainless steel appliances—a space that's both stylish and functional. Beautiful oak hardwood floors flow throughout the main level, where you'll find three comfortable bedrooms and a full hall bath. The finished lower level provides additional living space perfect for a family room, home office, gym, or playroom and includes a half bath, the laundry room and additional unfinished storage space. Major updates provide peace of mind, including a new roof (2017) and hot water heater (2019). Life in Hillsmere Shores is about so much more than the home itself. This beloved waterfront community offers a private marina with direct access to the South River, a community pool, sandy beach, waterfront pavilions, and multiple playgrounds. Residents also enjoy walking access to Quiet Waters Park, Hillsmere Elementary School, the Eastport-Annapolis Library, PAL Park, and Bay Ridge Plaza shopping and dining. Just 3 miles from Historic Downtown Annapolis, Hillsmere Shores combines the charm of an established neighborhood with the convenience of nearby restaurants, boutiques, marinas, and waterfront attractions. PLEASE NOTE: Hillsmere is part of a Special Community Benefit District with the annual fee built into the annual property tax bill.

282 Cedar Ln, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: Paul Wesley Real Estate.

$495,000
3 Beds ⋅ 1 Baths
Big Reduction of $24,000! Start your new year off in this 3-bedroom, 1-bath home situated on a spacious lot in the desirable, water-privileged community of Hillsmere Shores. This home features an updated bathroom, beautiful hardwood floors, and a cozy fireplace (as-is). A ductless air conditioning system adds comfort and efficiency. The property offers ample parking and walking to stores, restaurants, county library and Quiet Waters Park. This home is ready for you to move in, with potential for updates to match your personal style. Basement features laundry and utility space with open space and walk out egress. Residents of Hillsmere Shores enjoy access to community amenities including a private beach, marina, boat ramps, pool, and playgrounds—all just minutes from downtown Annapolis. Don’t miss this rare opportunity to own in one of Annapolis’ most sought-after neighborhoods!

289 Hillsmere Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Cummings & Co. Realtors.

$450,000
4 Beds ⋅ 3 Baths
Welcome to this split-level 4-bedroom, 2.5-bath home in the desirable, water-privileged community of Hillsmere Shores. The home has solid bones and has been consistently cared for over the years, offering a great opportunity for cosmetic updates to suit your style. The entry level features the kitchen, a family room with a wood-burning fireplace, and convenient main-level laundry. A few steps up is a roomy living area, perfect for gatherings. Continue upward to the bedroom level, which includes four bedrooms—among them a primary suite with its own ensuite bath. The lowest level includes a utility room and additional storage. Hillsmere Shores offers exceptional amenities, including a community beach, playgrounds, marina, kayak storage, boat ramps, and a community pool. This home is just a short distance from both the pool and the community field. With some sweat equity, this property presents a rare chance to secure a true 4-bedroom home in Annapolis for under $500,000—an excellent opportunity for a buyer looking to add value in a prime location.

129 Pinecrest Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Keller Williams Legacy.

$420,000
3 Beds ⋅ 2 Baths
Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining, ample off-street parking, and a beautifully landscaped, fenced yard with mature trees and plantings. Enjoy the best of coastal living in one of the area's most desirable communities.

406 Holly Dr, Annapolis

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Coldwell Banker Realty.

$410,000
2 Beds ⋅ 1 Baths
Welcome to 98 Carroll Drive, a charming single-level home in the sought-after Hillsmere Shores community of Annapolis. This 2-bedroom, 1-bath property sits on a fenced corner lot with beautiful landscaping and a full irrigation system. Inside, the home offers a cozy layout with a spacious three-season room perfect for relaxing or entertaining, and it includes a full-home generator for reliable backup power. While ready for updates, the home is full of potential and waiting for a buyer’s personal touch. Living in Hillsmere Shores means access to bay front playgrounds, a private marina, boat ramp, community beach, and pool — all offering unmatched access to the Chesapeake Bay — plus close proximity to Quiet Waters Park and downtown Annapolis.

98 Carroll Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Coldwell Banker Realty.