460 properties for sale in Hillsmere Shores

Welcome to this impeccably maintained and extensively updated ranch-style residence, offering an exceptional blend of luxury, comfort, and resort-inspired living just minutes from historic Annapolis. From the moment you arrive, the quality craftsmanship and meticulous attention to detail are evident throughout. At the heart of the home is a beautifully appointed gourmet kitchen featuring premium Wolf appliances, abundant custom cabinetry, granite countertops, a beverage refrigerator, and generous space for both everyday living and entertaining. Recent renovations have enhanced the home's appeal, highlighted by a spectacular oversized primary suite designed as a private retreat. The suite features a spacious walk-in closet and a spa-inspired bath complete with heated floors, instant hot water, and integrated Bluetooth speakers. The fully finished lower level offers remarkable flexibility with luxury vinyl plank flooring, a custom bar with wine refrigerator, a full bath, and a private ex

Nestled in the charming water privileged community of Woodland Beach, this delightful ranch-style home, with tremendous curb appeal, offers a perfect blend of comfort with single-level living. Built in 1930 and thoughtfully renovated with a new roofline in 2000, this residence features three bedrooms and a well-appointed full bathroom, making it an ideal retreat for those seeking a cozy atmosphere. There have been many newer updates and upgrades, too many to mention here, but are listed with the disclosures. The heart of the home boasts a functional kitchen equipped with essential appliances, including a propane gas oven/range, brand new refrigerator, and free standing microwave. The inviting layout includes an enclosed side porch and provides ample space for relaxation and gatherings. Set on a generous 8,000 square foot lot, the well manicured property includes a quaint paved patio seating area in the rear and a large side yard. The property includes a large shed/shop with electric (a

Tastefully updated Edgewater home for Sale. This Beautiful 4 bedroom 3 bathroom house will deliver on all your needs. Located at one of the most sought after water oriented communities Woodland Beach. This unique home offers the type of living where your main living area is elevated on the 2nd floor adjacent to a full front covered balcony for maximum comfort and ease. Large updated kitchen with quartz countertops, oversized island peninsula for 3-4 people and stainless steel appliances. Designated dining room area adjacent to large living room. Main owners bedroom with an en-suite bathroom with a walk in shower. Another 2nd bedroom and a 2nd full bath completes this level. The 1st level greets you with an open floor plan family room 2 more bedrooms, a custom 3rd full bath and plenty of storage. Designated Laundry area and utility room. Additional Den/Office area of the laundry room. Nice back patio and fully fenced in yard ideal for many uses. Privileged access to local beaches, piers

Move-in Ready, 3 bedroom, 2 full/2 half bath, Garage Townhome in the sought-after Greens Community in SOUTH RIVER COLONY with large deck that backs to trees and the beautiful pond. All 3 levels are finished with a 4' bump out. Gleaming hardwood floors, open concept kitchen with large center island and granite countertops with recessed lighting. Large Primary Bedroom with walk-in closet and vaulted ceilings. Ensuite primary bath features a separate shower and soaking tub and lots of cabinetry. Lower level is perfect for hosting your Superbowl parties with a spacious Recreation Room with cozy gas fireplace featuring marble surround and built-in bookcases. Paver stone patio is located under the large deck that has a view of the community pond with walking trails. Newer roof and freshly painted in most of the home. New carpet. South River Colony is a premier community in Edgewater featuring the award-winning South River Golf Course (call for membership information), 2 sets of Tennis/Pickle

Incredible opportunity to purchase two adjoining properties. One vacant commercial parcel and one residential property with an existing home. Situated on over half an acre combined in Annapolis, this unique offering has been owned by the same family for generations and presents endless possibilities for its next owner. The commercial parcel provides a blank slate for future development or investment, while the residential property features a 4-bedroom, 1.5-bath home with numerous updates, including a roof less than 10 years old and recently replaced HVAC system and hot water heater. Whether you're looking to develop, invest, or create your own vision, this is a rare opportunity you won't want to miss. Commercial Tax ID: 020600003497- Residential Tax ID: 020600003498

Welcome to 317 Kenmore Avenue, where thoughtful modern design meets the relaxed Chesapeake Bay lifestyle in the sought-after water-privileged community of Pine Whiff Beach. Perfectly situated on a spacious corner lot just one block from the water, this beautifully updated four-bedroom, two-and-a-half-bath home offers over 2,000 square feet of thoughtfully designed living space that blends style, comfort, and functionality. At the heart of the home is a stunning, renovated and expanded custom kitchen inspired by modern Montessori principles and designed around the way people truly live. Rich custom cabinetry, expansive butcher block countertops, abundant storage, open shelving, and generous prep space create an inviting gathering place where family and friends naturally come together. Whether preparing weeknight dinners, hosting holiday celebrations, or baking with little helpers, this kitchen was intentionally designed to make everyday living both beautiful and functional. The open-con

Move-in ready! Beautifully renovated 5BR/3BA home in the sought-after, water-privileged Pines on the Severn community. This turnkey home offers over three finished levels with quality updates throughout. The main level features restored hardwood floors, a bright living room, formal dining room with chair rail, two bedrooms, a full bath, and a dedicated home office. The designer kitchen showcases new cabinetry, quartz countertops, stainless steel appliances, and opens to a brand-new Trex deckperfect for entertaining. Upstairs offers two spacious bedrooms connected by a fully renovated bath. The finished walkout lower level includes a fifth bedroom, full bath, recreation room, and separate laundry area, providing excellent flexibility for guests, in-laws, or additional living space. Major updates include a new roof, new plumbing, new electrical, brand-new HVAC (A/C), new two-car garage, new asphalt driveway, and new steel garage access door for lasting peace of mind. Enjoy exceptional co

Welcome to 1424 Regent Street, where modern style meets everyday comfort. This beautifully updated home offers exceptional curb appeal with a spacious driveway, a brand-new sprinkler system, and a fully fenced backyard featuring a large deckperfect for entertaining, relaxing, or enjoying outdoor living. Step inside to discover a stunning custom-designed living room highlighted by a striking gold and white accent wall that creates a warm, sophisticated focal point. The adjoining dining area flows seamlessly into the show-stopping custom kitchen, complete with stylish cabinetry, gorgeous quartz countertops, and designer finishes that make cooking and gathering a true pleasure. The spacious primary suite features its own en-suite bathroom featuring custom designer finishes. An additional beautifully renovated full bathroom upstairs offers both style and convenience for family and guests. Throughout the home, you'll find thoughtfully designed custom bathrooms and quality updates that creat

Annapolis New Stunning Luxury Renovation: Just Completed! Experience the perfect blend of timeless elegance and modern sophistication in this stunning luxury renovation in Annapolis. Thoughtfully redesigned with impeccable craftsmanship and upscale finishes throughout, this exceptional 5-bedroom / 3.5-Bathroom residence offers refined living at its finest. A bright, open-concept floor plan showcases a designer chefs kitchen, premium appliances, custom cabinetry, and beautifully appointed living spaces ideal for both everyday living and entertaining. Luxurious baths, spacious bedrooms, and carefully curated details create a move-in-ready retreat. Situated in one of Annapolis most desirable locations, Anchorage waterfront community, this remarkable home delivers the best of coastal living with convenient access to downtown Annapolis, the Chesapeake Bay, marinas, shopping, and dining. A rare opportunity to own a brand-new luxury home in the heart of Annapolis. This extraordinary residenti

Coming soon in bay ridge! A rare coastal retreat offering the perfect blend of timeless charm, thoughtful modern updates, and an incredibly versatile floor plan. This lovingly maintained 4-bedroom, 3 full bath, 2 half bath home seamlessly combines traditional and Craftsman-inspired character with comfortable living spaces. Inside, the main level welcomes you with beautiful hardwood floors, a fully renovated kitchen, updated bathrooms, a cozy fireplace, and a flexible two-bedroom layout that is ideal for multi-generational living, guests, or a convenient home office or nursery. Upstairs find two spacious bedrooms and an additional living area where stunning water views create the perfect setting to relax. The expansive, partially finished walkout basement offers exceptional flexibility with a half bath, craft room, and abundant storage. Set on a generous 0.27-acre lot, the outdoor spaces are equally inviting, featuring a private patio, mature landscaping, plenty of room for gardening or

Experience a hassle-free waterfront lifestyle at The Point on Spa Creek, where this stunning condo offers exceptionally easy living with picturesque views overlooking Historic Annapolis and Spa Creek. This spacious 2 bedroom 2 bath condo with flexible loft space features beautifully appointed rooms and is just steps away from the clubhouse, pool, dock, and scenic walking paths. The expansive Living room with fireplace is the perfect setting to relax and take in the views. The 2 sided fireplace also provides ambiance for the adjacent cozy nook that is ideal for a desk or reading chair. The gourmet kitchen with peninsula is sure to please any chef and the gorgeous water views makes everyday feel like a vacation. Enjoy the covered deck overlooking the waterfront; perfect for entertaining or relaxing while taking in the tranquil surroundings. The primary bedroom features a spacious closet, ensuite bath and covered balcony. With an additional light-filled bedroom, hall bath and loft space,

As-is. Welcome to Loch Haven Beach. 3440 South River Terrace boasts expansive water views of the South River. Check the Loch Haven community website for more information about this unique and historical waterfront community

Experience Ultimate Flexibility with this Versatile and Spacious Contemporary Townhome offering Unique Zoning flexibility, 3 Finished levels with 3,016sf, and a Rare Live/Work Opportunity in Village Greens of Annapolis! Operate a boutique business, studio, or professional office right from your street-level commercial space with no commute. Previously a boutique shop. With a convenient Kitchenette/Wet Bar area and Half Bath. Upstairs on the Main Living Level, discover an upscale, open-concept layout flooded with natural light and fabulous Designer Touches, Crown Molding, Plantation Shutters, Gorgeous Wood Floors and a Half Bath. The Beautiful Gourmet Kitchen features a large Island, Bright White Cabinets, Stainless Appliances and Quartz Counters in addition to the Spacious Dining area, and Inviting Living Room, Cozy Gas Fireplace and Deck create the perfect hub for Entertaining! Retreat to the Upper Level offering a Serene Primary Suite with Amazing Attached Bath and Walk-in Closet in

Rare opportunity to own a stunning newer built fully detached four bedroom home in the historic district with an attached one car garage plus a one car driveway an amenity rarely found in downtown Annapolis. Tucked away on a quiet street just steps from Spa Creek and City Dock, 12 Union Street combines the charm and walkability of the Historic District with the comfort and convenience of newer construction. Spanning four levels, the home is filled with natural light and offers high ceilings throughout. The entire interior has recently undergone a significant refresh, including resurfaced hardwood floors, all-new carpet, professional interior painting throughout, new lighting fixtures, new outlets and switches, a new kitchen backsplash and quartz countertops, plus a new dishwasher, refrigerator, and hot water heater. With four bedrooms and two full baths, the flexible floor plan provides plenty of options for guests, a home office, gym, or additional living space. Outdoor living is equa

Charming 2-bed, 1-bath home in the Selby on the Bay waterfront neighborhood. This move-in-ready home features new flooring (2023), an updated kitchen (2023) with a propane stovetop, and a shed and water system installed in 2023. Major systems updated recently: HVAC replaced in 2021 and a new water heater in 2025. Driveway and front porch were added in 2025. Enjoy community amenities including a waterfront community center, community beach, waterfront playground, kayak storage and boat ramp privilegesperfect for boating and outdoor living. Ideal as a year-round home or weekend getaway

Welcome to 1906 Ridgeville Road, a meticulously cared for Cape Cod in the heart of Woodland Beach, one of Edgewater's most sought-after waterfront communities. Here, you'll enjoy a unique Chesapeake Bay lifestyle with access to multiple community beaches, a boat ramp, parks, kayak access, fishing piers, and waterfront recreationall while remaining conveniently close to Annapolis, shopping, dining, and commuter routes. Situated on a rare double lot totaling approximately 8,000 square feet, this well-maintained home offers exceptional indoor and outdoor living. A front gate, fresh stone walkway, and oversized driveway provide ample parking and space for boats, RVs, and trailers, complete with a 50-amp electric hookup. Inside, the open-concept layout is designed for both everyday comfort and entertaining. The spacious kitchen features abundant workspace, breakfast bar seating, and dual sinks. The main level includes a bedroom and full bath, while the private upper-level primary suite offe

Welcome to this bright and sunny 2 BR | 2 BA condominium in desirable Tidewater Colony of Annapolis. Superb location near hospital, Navy stadium and Mall and just off 50/97 for easy commuting. Located on top level, this inviting residence features soaring vaulted ceilings that create an open, airy feel throughout. Freshly painted with newer flooring, this home is move-in ready and filled with natural light. The updated Kitchen offers stainless appliances, granite countertops and ample cabinet space, opening seamlessly to the Living and Dining areas. Slider to your balcony and storage closet. The spacious Primary BR includes a private Bath and generous closet space, while the 2nd BR utilizes Hall Bath. Laundry Room included in list price. Residents of Tidewater Colony enjoy and exceptional array of amenities including community pool, tennis court, fitness center, and beautifully maintained grounds, all just minutes from Downtown Annapolis, shopping & dining. West Annapolis Elementary Sc

Very Nice move in ready condo with a nice deck and nice view in the back. Ask about 100 percent loans Hurry while this great home lasts

Welcome to 1908 Dulaney Place! This 5-bedroom, 3-full bath home is located in the highly sought-after community of Pendennis Mount. Perfectly positioned just over the Naval Academy Bridge, this exceptional location offers quick access to the U. S. Naval Academy, Historic Downtown Annapolis, the Navy Golf Club, Sandy Point State Park, the Chesapeake Bay Bridge, and Maryland's Eastern Shore. Enjoy he highly rated Broadneck School Distric, plus easy commuting with quick access to Routes 50, 97, and 100. Designed for both everyday living and entertaining, this spacious home offers multiple gathering spaces including a bright sunroom, inviting screened porch with low-maintenance composite decking, and an extended brick patio overlooking the fully fenced backyard. The kitchen features updated appliances (2026) and natural gas is also available for the range. The living room is drenched in natural light with a large sky light with beam detail. 3 Bedrooms and 2 full bathrooms on the main level

Rare opportunity to own a custom-designed waterfront home on the South River. Built in 2022, this exceptional residence offers more than 3,000 square feet of finished living space, panoramic water views, modern construction, and energy-efficient features. Situated on a quiet private brick-paved lane with only three homes, the property enjoys approximately 0.60 miles of open-water views across the South River toward the Riva Bridge. The open-concept main level was designed to maximize natural light and showcase the waterfront setting, featuring hardwood floors, a gourmet kitchen with GE Profile appliances, a six-burner dual-fuel gas range, granite countertops, custom cabinetry, an imported Portuguese tile backsplash, walk-in pantry, and a spacious living area with a gas fireplace and oversized sliding glass doors leading to a waterside deck. A dedicated main-level office provides the perfect work-from-home space. The upper level includes a luxurious waterfront primary suite with vaulted

Coming Soon! Nestled in the desirable water-oriented community of Riva, this beautifully maintained 5-bedroom, 3.5-bath home offers the perfect blend of comfort, updates, and outdoor living. The freshly painted interior creates a bright, inviting atmosphere, while the updated kitchen serves as the heart of the home for everyday living and entertaining. A fully finished basement, completed in 2020, provides versatile additional living space. Major updates include a new roof (2020), HVAC system (2018), and hot water heater. Outside, enjoy your own private retreat featuring a built-in grill and a stunning 10,000-gallon saltwater pool. Residents also enjoy access to a community pier and playground, all within a neighborhood served by top-rated schools

Nestled in the prestigious Wynnewood community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort. Spanning an impressive 4,708 square feet, the home features a thoughtfully designed traditional floor plan that invites warmth and connection. Step inside to discover a gourmet kitchen, complete with upgraded countertops, a spacious island, and a cozy breakfast area, perfect for casual dining. The kitchen seamlessly flows into a family room adorned with recessed lighting and a stunning gas fireplace, creating an inviting atmosphere for gatherings. Formal dining and separate living areas provide elegant spaces for entertaining. Retreat to the fully finished basement, ideal for recreation or relaxation, while the main floor laundry adds convenience to your daily routine. Each bedroom boasts ample room storage for your wardrobe. Outside, the property is a private oasis on 1.42 acres, featuring a heated saltwater pool surrounded by a fenced patio, perfect

3800 sf 4br/3ba high-end craftsman home with 2-car garage and rooftop deck in the tree canopy, built new in 2019. Located on Severn Rivers most gorgeous Chase Creek, with deep water community dock and kayak rack for your boat(s). Hundred-year-old neighborhood is surrounded by water at the end of a half mile of forest and horse farms, yet it is just 8 min from the Naval Academy, 10 min from downtown Annapolis, and 25 minutes to BWI Airport. Its also on the Baltimore to Annapolis Rail-Trail for easy commuting into Annapolis. Retreat-like setting with 360 tree and tree canopy views and seasonal water views from 65 top-of-the-line Marvin windows, with permanent clear views between the house and the tidal Chesapeake Bay tributaries below. Low maintenance lot/yard is a highly diverse mix of native species trees and shrubs that will grow more gorgeous as they continue to mature. Daylight basement family room with separate entrance that easily can be used as a separate living space to accommod

848 Deerwood Court offers a wonderful opportunity to enjoy life in Heritage Harbour, one of Annapolis' most sought-after active adult communities. Situated on a desirable corner lot at the end of a quiet cul-de-sac, this well-designed ranch-style home features three bedrooms, two full bathrooms, a spacious side addition, and a two-car garage. The home has been lovingly maintained over the years and offers a comfortable floor plan with generous living spaces, abundant natural light, and excellent flow for both everyday living and entertaining. The side addition provides valuable extra living space rarely found in many homes of this size, while the corner lot setting offers attractive curb appeal and additional privacy. This property presents an excellent opportunity for buyers to personalize a home to their own tastes and style while enjoying all that Heritage Harbour has to offer. Whether you're looking to make updates immediately or over time, the solid layout and desirable location p

One of Homewoods most distinctive homes, this 8-bedroom, 4-bath residence offers over 3,100 square feet and a truly unique story. Once known as the Gables Tourist Home Bed & Breakfast, the property (built in 1938) still carries subtle nods to its pastincluding the numbered bedroom doorswhile the current owners have thoughtfully updated the interiors and major systems for comfortable modern living. Inside, the home blends historic character with fresh, eclectic designfull of personality, flexibility, and space to live, work, and host. With eight bedrooms, the layout offers exceptional versatility for multi-generational living, guest suites, or creative uses. The fully renovated walkout basement (20212-) adds significant finished living space and includes a kitchenette and full bathideal for guests, recreation, or extended living arrangements. Recent improvements include basement waterproofing, new HVAC, boiler, water heater, roof, and the addition of a natural gas lineoffering peace of