263 properties for sale in Glebe Heights

Welcome to 293 Cedar Lane, a classic 1963 ranch on a private. 27 acre lot in the water privileged community of Hillsmere Estates, steps from Quiet Waters Park and minutes to the South River. Original hardwood floors flow through the main level, where a living room with custom built in shelving opens to a galley kitchen with an electric stove top, wall oven, and dishwasher, full of potential for your personal touch. The full bath keeps its classic pedestal sink charm. Downstairs, a full basement offers a finished rec area and bonus room alongside generous unfinished storage and utility space, ready for however you want to use it. Step outside to a rear deck made for morning coffee or evening unwinding. Ceiling fans keep the main level comfortable, while public sewer and a private well simplify utilities. Sold strictly as is, this well loved home offers real bones in one of Annapolis's most sought after neighborhoods, home to a private beach, marina, and community pool. Come discover wha

Space, flexibility & value in the south river school district! This spacious Cape Cod offers 5 bedrooms, 4 full bathrooms, nearly 2,000 square feet of finished living space above grade, a full walk-out basement and approximately ONE ACRE of property! With generous room sizes and a versatile floor plan, there's plenty of room to spread out and make this home your own! The main level features an eat-in kitchen, comfortable family room, two spacious bedrooms and a full bathroom with shower ideal for those seeking main-level living, guest accommodations or a dedicated home office. Upstairs, you'll find 2 additional generously sized bedrooms, including a primary suite with private bath, plus an additional hall bath. Oversized walk-in closets created by the Cape Cod dormers provide exceptional storage. The full walk-out basement offers even more flexibility with a 5th bedroom, a full bath and space for recreation, hobbies and abundant storage. Move right in and enjoy the space today, with th

Step inside this move in ready end unit townhome to discover new flooring and a bright, welcoming interior designed for easy everyday living. The kitchen features granite countertops and stainless appliances, creating a stylish yet functional space. A new roof and water heater add even more peace of mind and value to the next owner. Beyond the home, you will find a vibrant, active neighborhood with 2 community pools, multiple pickleball courts, tennis courts, sidewalks, and lots of green space. With downtown Annapolis, Truxton Park, Quiet Waters Park, shopping, dining and commuter routes just minutes away, this location makes it easy to enjoy the best that Annapolis has to offer!

Welcome to easy living in Annapolis desirable Heritage Harbour 55+ community. This charming two-bedroom, two-bath villa is ideally situated just a short walk from the community lodge and its many amenities. The home offers several distinctive features, including skylights, a 10-by-10-foot home-office addition, an enclosed sunroom, and a deck overlooking a wooded area that provides exceptional privacy. The interior walls, doors, and trim have been freshly painted, creating a bright, move-in-ready atmosphere. Additional features include a welcoming entrance, pull-down stairs providing attic access, a storage shed and storage chest, an upgraded heat pump, and extra-large gutters and downspouts. The roof is approximately four years old. Heritage Harbour offers an active, resort-style lifestyle with two swimming pools, a golf course, tennis courts, a fitness center, library, billiards room, walking trails, and a vibrant community lodge offering numerous clubs, activities, and social events.

Welcome to 313 Fourth St, one of only three townhomes at The Tecumseh and a rare opportunity in one of Eastports most distinctive waterfront communities. Completed in 1968 on the site of a former boatyard, The Tecumseh was Annapoliss earliest condominium communities, designed around the boating lifestyle that continues to define Eastport today. Set directly on Spa Creek, the community offers a 72-slip private marina, waterfront swimming pool and deck, and gated private parking. Located at the corner of Fourth St and Severn Ave, this three-story, approximately 2,700-square-foot residence offers three bedrooms, two-and-a-half baths, expansive third-floor bonus space, charming Eastport street appeal, and a private rear courtyard. The main level is filled with character, featuring charming arched details, a newly renovated powder room, spacious kitchen with breakfast nook, dining area, walk-in butlers pantry, and custom built-in bookshelves surrounding a gas fireplace. A generous living ar

Take advantage of an ASSUMABLE 2.25% va loan! Do NOT have to be a VA buyer! Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsmanship. Built with everyone in mind, this residence boasts timeless appeal with its classic brick-and-vinyl siding exterior, harmoniously blending with the lush surroundings. Step inside to discover a spacious layout that offers both comfort and functionality. With five generous bedrooms and three and a half bathrooms, this home is perfect for those who appreciate space and versatility. The heart of the home features a cozy fireplace, creating an inviting atmosphere for gatherings and quiet evenings alike. The partially finished basement provides endless possibilities, whether you envision a workshop, a play area, or additional storage. The expansive lot offers ample outdoor space for relaxation and recreation, while the community pool adds a r

Exceptional Lower Eastport property: tastefully updated, semi-detached home with a detached one-bedroom cottage with proven rental income. Enjoy the charm and walkability of Lower Eastport from this 2007-built home on a peaceful, tree-lined street just two blocks from the harbor and close to parks, restaurants, shops and the waterfront. The property offers over 3000 square feet of living space between the main house and the cottage. Two dwellings make up a unique configuration that allows an exceptional degree of flexibility and privacy. Enter the main residence through a classic Eastport front porch, perfect for rocking chairs and enjoying views of the neighborhood. The home features three bedrooms and three-and-a-half baths, a separate dining room, and an open kitchen adjoining a spacious living room. Sliding doors extend the living space to a covered porch overlooking the fenced backyard. Upstairs, the spacious primary suite features a large walk-in closet and adjoining newly renova

Pristine and move-in ready, 2 Silopanna Court offers just over 2000 square feet of flexible living space inside Annapolis city limits, minutes from Eastport and historic downtown. A well-planned addition expanded the home to include a spacious upstairs primary suite and a separate family room with an adjoining office area on the main level. The primary suite features a walk-in closet and a private bath, with sliding doors that open to its own balcony. Three additional generously sized bedrooms share a second full bath, keeping all four bedrooms together upstairs. A main-level powder room adds convenience for guests. A full wall of built-in shelving and cabinetry gives the living room character and ample storage. The kitchen features white cabinets and stainless steel appliances and opens to a dining area with sliding doors to the backyard patio. The family room provides space to spread out, while the adjoining office or sitting area accommodates working from home. Outside, the fenced b

Welcome to 952 Yachtsman Way an Annapolis home with space, character, and the opportunity to make it your own in the sought-after Mariners Point community. This 2-bedroom, 2-bath home features a bright, open layout with vaulted ceilings, abundant natural light, and a wood-burning fireplace that anchors the main living space. The dining area opens to a rear deck and backyard, creating an easy flow for everyday living, grilling, entertaining, or simply enjoying the outdoors. The main level offers a bedroom and full bath, while the upper level includes a second bedroom plus flexible loft-style space that can serve as a home office, reading nook, or additional living area. Recently refreshed with interior paint, the home also offers off-street parking, outdoor storage, and access to Mariners Point community amenities including the pool and clubhouse. Located just minutes from downtown Annapolis, Eastport, Quiet Waters Park, shopping, dining, marinas, and major commuter routes, 952 Yachtsma

Rare opportunity! Two homes on one lot in eastport! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shop

Welcome to 428 Penwood Drive, a beautifully maintained end-unit townhome ideally situated on a private homesite in the highly sought-after South River Colony community of Edgewater. With approximately 2,500 square feet of finished living space across three levels, this spacious three-bedroom, two-and-a-half-bath home combines comfort, style, and functionality with the added privacy and natural light of an end-unit location. The main level welcomes you with an inviting foyer and a bright, open floor plan featuring new luxury vinyl plank flooring and new carpeting. The spacious living and dining areas offer plenty of room for everyday living and entertaining, while the well-appointed kitchen provides abundant cabinetry and generous workspace. A cozy gas fireplace creates a warm and inviting focal point, and the large rear deck extends the living space outdoors, providing the perfect setting for morning coffee, outdoor dining, entertaining, or simply relaxing while enjoying the peaceful l

An exceptional offering in the heart of the Annapolis Historic District, 100 Conduit Street captures the timeless elegance and effortless lifestyle that make downtown Annapolis so coveted. Set along one of the citys most charming historic streets, this distinctive three-four bedroom, two-and-a-half-bath residence pairs beautiful architectural character with an extraordinary location just moments from the waterfront. Inside, gracious living spaces are defined by gorgeous wood floors, rich millwork, custom built-ins, and thoughtful architectural details that lend warmth, character, and a wonderful sense of place. A chef's kitchen and separate dining room provide an elegant setting for everything from intimate dinners to holiday gatherings, while the inviting side porch offers the perfect spot for morning coffee, an evening glass of wine, or simply watching the rhythm of downtown life unfold. The home feels equally suited to comfortable everyday living and sophisticated entertaining, with

This RARE opportunity to have your business right at your home LEGALLY. This C4 Non conforming use accommodates Landscapers, tree service, Auto body shop and other uses. Call for more information about this' one of a kind opportunity'. Zoned residential with a county approved C4 non confirming use granted. This C4 Non conforming use. Many, Many uses come and see to grasp the possibilities or take it for a new home site. New septic, new well. Lots of opportunity on this site. This listing is being sold'AS IS' no feasibility studies, county non confirming to be used with what it is designated for. Cannot be altered to anything else-. Check view documents to see all information. Listing agent to attend all showings. Zoned Residential so could be a new home site, or a great car collectors dream haven

Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both? !This stunning property offers the perfect blend of style and comfort with the ease of access to a plethora of sought after water-oriented community amenities! The main level features a beautiful, open kitchen with walk-in pantry, stainless steel appliances, center island, and large eat-in space. The living room is truly the heart of the home featuring a cozy gas/propane fireplace. Perfect for gathering for cozy evenings at home. The upper floor is home to all four bedrooms. Two of which have attached bathrooms and walk-in closets. And the upper level laundry adds convenience to daily living. The attached garage, with space for two vehicles and additional storage, provides practicality without compromising on style with a large driveway making it easy for guest parking. One of the standout features of this property is the spacious dec

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U. S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is

HUGE price drop on this beautiful new home. Construction is underway and something truly special is taking shape! Schaefer Homes is proud to present this stunning newly constructed Colonial in the prestigious Oyster Harbor community, with a target completion date of November 2026. From the moment construction began, every detail has been thoughtfully considered to deliver a home that is as beautiful as it is livable. Set on a sprawling 0.62-acre lot, this exceptional residence offers the kind of space and privacy that is increasingly rare plenty of room to create the outdoor oasis you've always envisioned, whether that's a garden retreat, entertaining terrace, or simply wide open space to enjoy the beauty of your surroundings. Inside, the elegant Colonial layout unfolds beautifully across a thoughtfully designed floor plan featuring 4 spacious bedrooms and 2.5 elegantly appointed bathrooms. The showstopping gourmet kitchen is the heart of the home, outfitted with upgraded design featur

Rarely available, all-brick rancher in the amenity-rich, sought-after Hillsmere Shores community. This home has been meticulously cared for and loved, and it will show from the moment you step in! Gleaming hardwood floors, freshly painted interior, and abundant natural light perfectly framed by custom plantation shutters are your first signs that this is a special home. As you make your way through the dining/eating area, you will begin to realize that there is way more space inside than you might have imagined from the outside. Prepare to be completely wow'd as you step into the four-season room! Vaulted ceilings, skylights, a brick accent wall, a pellet stove, and a dedicated Mitsubishi split heat and A/C system will quickly make you realize you have found your favorite room in the house. The second bathroom's shower was converted for accessibility to main level laundry. Enjoy the convenience, or easily convert back as there is still laundry available in the basement. Speaking of the

Welcome home to the sought-after Hardesty Estate neighborhood. This stunning Mid Century, Clerestory and contemporary home has almost 3,500 square feet on 3 levels and sits on over 2 private and pristine acres in a parklike setting. The house exterior was just painted in 2025 and the owners have updated all three bathrooms, refinished the main level hardwood floors, replaced the roof and gutters with gutter guards (2020) and all the windows and 5 oversized sliding doors (2023). There is special glazing on all the Andersen windows and sliders to deter birds. You will need to catch your breath as you take in all the beautiful natural light and picturesque views from all the windows that are strategically placed high to maximize natural light but still preserve privacy. The large composite deck is maintenance free, spans the entire rear of the home, and has stairways with upper gates on both ends for optimal convenience. Features include soaring vaulted ceilings, gleaming hardwood floors,

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer

A unique mixed-use opportunity in the heart of Annapolis! Located in the Arts District, 232 West Street offers the flexibility of commercial and residential use in a convenient location close to Downtown Annapolis, Navy-Marine Corps Memorial Stadium, and the U. S. Naval Academy. Renovated in 2018, the property is currently configured for residential use with one bedroom and one and a half baths. Skylights and abundant natural light create a bright, welcoming feel throughout. The updated kitchen features white cabinetry, stainless steel appliances, a subway tile backsplash, and an island with seating, while hardwood floors add warmth and character. The spacious primary bedroom offers two closets and direct access to a private deck. The adjoining bathroom features a dual-sink vanity and a shower with dual shower heads. A separate studio in the rear provides additional flexible space with a variety of potential uses. The fenced yard adds privacy and creates a nice connection between the p

Welcome Arundel on the Bay. A water oriented lifestyle community offering access to kayaking, paddle-boarding, beach and playground. All this with close proximity to shopping, restaurants, parks and downtown Annapolis. The quiet and calm neighborhood offers an island-like feeling. And this striking 3-story home is absolutely MOVE-IN READY! Gracious and plentiful windows leave you appreciating the timeless perennial gardens, majestic trees and peeks at Fishing Creek from multiple locations. As Fall arrives the'peeks' will become relaxing and lovely views! A bright and open floorplan features architectural lines and high ceilings which enhance the home's airy, gallery-like feel. Stunning wood floors offer warmth and continue the feeling of openness. We hope you like to cook and entertain. This Kitchen makes it not only possible but inviting and engaging. Extend your morning or evening and take a step out to the private back Deck tucked in to give you an intimate feeling with a lovely per

Welcome home to this beautifully updated 2-bedroom, 2-bathroom condo, offering comfortable living, stylish upgrades, and an unbeatable location within the community. The updated kitchen features new soft-close cabinets and new quartz countertops, creating a fresh and modern space for cooking and entertaining. The condo also boasts new flooring and fresh paint throughout, giving the entire home a bright, clean, move-in-ready feel. Relax by the cozy fireplace or step outside onto the private deck off the bedroom, where you can enjoy beautiful water views and unwind at the end of the day. For added convenience, the condo is located right next to the community pool, making it easy to enjoy resort-style amenities just steps from your door. You'll also appreciate being close to shopping, dining, and everyday conveniences. With its thoughtful updates, water views, convenient location, and community amenities, this condo is a wonderful place to call home! More than one photo virtually staged

Inside the Annapolis city limits, on a cul-de-sac, this Dutch Colonial pairs four bedrooms and two full baths with a fully fenced yard and about 1,928 finished square feet on three levels. A bedroom and full bath on the main level give guests their own space or make room for a home office, and three more bedrooms and a second full bath are upstairs. The fully finished basement adds room for a rec room, gym, or office. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. Out back, a deck steps down to the fenced yard, and a shed adds storage. The driveway parks two cars. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, the restaurants of Eastport, the Annapolis Maritime Museum, and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore, and the Eastern Shore within reach, for the commute or for the weekend. Ask your agent about a len

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 waters edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. Theres 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 fo

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 compl

Highly desirable Eastport location just a short walk to Historic Annapolis, the U. S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multigenerational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated threelevel Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines

A beautiful colonial on Private and Secluded James Way! This stunning home sits on over half an acre, and has been remodeled head to toe. Freshly Painted in Sept 2026 and boasting new flooring throughout the entire home, this house also features a fully remodeled kitchen with Shaker cabinets, quartz counters, SS appliances, a dual zone wine refrigerator, and an oversized island. The main level also features a fireplace with shiplap surround, a spacious 12x20 trex deck off the back, a 10x10 patio to the side of the deck, and a fully fenced in rear yard! The owners suite boasts a whopping 8ft x 20ft walk in closet, a fully remodeled bathroom with dual vanity and shiplap surround, a large roman shower with two shower heads and 2 body sprayers. The hall bathroom has been renovated to include a dual vanity, board and batten accents, and brand new tile floor. The third floor is fully finished with a large closet, a separate HVAC system, and a full bathroom. A new tankless HWH! This home has

GREAT PRICE and all major items replaced. Space, flexibility and the Annapolis water-oriented lifestyle come together at 1007 Harbor Drive, offering 3722 finished square feet, four bedrooms, three full and two half baths, a two car garage and a finished lower level. All in the sought-after Annapolis Roads community. The versatile floor plan provides room to spread out, work from home, entertain and accommodate guests, while the finished lower level adds a recreation room, kitchenette, full bath, bonus room and private entrance. Outdoor living is equally impressive. Enjoy the screened porch, deck, 10-person hot tub and newly built fire pit with custom paver patio overlooking the level, fenced backyard. An extra-wide driveway provides parking for additional vehicles, a boat or RV, while the two-car garage offers extensive storage with a floored attic, shelving and cabinets. Inside, hardwood and luxury vinyl plank flooring, fresh paint, new upstairs carpet and recessed lighting complement

Tucked into Homewood, just beyond the brick sidewalks of Historic Downtown Annapolis, 16 Woodlawn Avenue is a residence taken down to the studs and rebuilt in 2019, blending all the comforts of modern design with the historic charm of Homewood. A traditional front porch, turned white columns and soft buttery siding announce the home from the street while a long driveway offers the rare luxury of off street parking in one of Annapolis's most walkable in-town pockets. Inside, tall ceilings and recessed lighting set an airy tone against gorgeous oak flooring on the main level and the beautifully refinished original pine flooring on the stairs and level two. The classic period moldings that run throughout remind you that this home has been here for a time as the updates make it seem like a much newer build. The kitchen anchors the main level: white shaker cabinetry, stainless appliances, and granite countertops surround a center island with room for a kitchen table, while a separate formal

Welcome to 2566 Glen Cove, a beautifully updated three-bedroom, two-bath home offering a rare opportunity to enjoy the Heritage Harbour lifestyle without the age restriction. While this property is not age-restricted, owners have the option to join Heritage Harbour through a social membership and enjoy access to its many amenities. Inside, the home is warm, inviting, and thoughtfully updated, highlighted by a stunning brand-new kitchen completed in 2026 featuring quartz countertops, stainless steel appliances, and beautiful finishes. Wood floors flow through the home, complemented by updated bathrooms, a separate dining room, and a classic wood-burning fireplace that creates a welcoming focal point for the living space. A spacious three-season sunroom provides the perfect place to relax or entertain while overlooking professionally designed landscaping by Cindy Shuart of Harmony Gardens. An irrigation system makes maintaining the beautifully curated grounds effortless. Additional highl