107

Homes for Sale in 21403

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  • 1132 Bay Ridge Rd, Annapolis, MD 21403
    1132 Bay Ridge Rd, Annapolis, MD 21403
    1132 Bay Ridge Rd, Annapolis, MD 21403
    /56

    $720,000

    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft

    1132 Bay Ridge Rd, Annapolis, MD 21403

    Live the Annapolis dream in this beautiful, well maintained, quality home surrounded with professional landscaping. This home delivers the ultimate move in ready experience. Fantastic location on private lane with lots of “New”. New roof, skylight and gutters in 2026, New heat pump in 2026 (with 10-year parts and labor warranty that transfers), New hot water heater 2026, New carpet 2026, New

    Wendy Trebbe Blackwell Real Estate, LLC

    1132 Bay Ridge Rd, Annapolis, MD 21403
  • 105 Mansion Dr, Annapolis, MD 21403
    105 Mansion Dr, Annapolis, MD 21403
    105 Mansion Dr, Annapolis, MD 21403
    /29

    $550,000

    • 2 Beds
    • 1 Bath
    • 1,240 Sq Ft

    105 Mansion Dr, Annapolis, MD 21403

    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

    Danielle Franz EXP Realty, LLC

    105 Mansion Dr, Annapolis, MD 21403
  • 20 Ironstone Ct Unit 20 F, Annapolis, MD 21403
    20 Ironstone Ct Unit 20 F, Annapolis, MD 21403
    20 Ironstone Ct Unit 20 F, Annapolis, MD 21403
    /49

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    20 Ironstone Ct Unit 20 F, Annapolis, MD 21403

    Beautiful end-unit townhome located in the desirable Annapolis Overlook community, featuring a sunny garden and charming white picket fence. This well-designed home offers an inviting open floor plan with spacious living and dining areas, a living room with a charming bump-out window, a well-appointed kitchen with pantry storage, and a convenient main-level half bath. Recent updates include a new

    Wendy Foard Coastal Realty Maryland

    20 Ironstone Ct Unit 20 F, Annapolis, MD 21403
  • 15 Copley Ct, Annapolis, MD 21403
    15 Copley Ct, Annapolis, MD 21403
    15 Copley Ct, Annapolis, MD 21403
    /23

    $374,900

    Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 1,704 Sq Ft

    15 Copley Ct, Annapolis, MD 21403

    Nestled in the charming community of Painters Hill, this contemporary townhouse offers a perfect blend of comfort and style. Step inside to discover a spacious open living and dining area, ideal for everyday living and easy entertaining. The kitchen features upgraded countertops and stainless steel appliances, making everyday cooking a pleasure. With two generous bedrooms, including a walk-in

    Marielys Montero RE/MAX Excellence Realty

    15 Copley Ct, Annapolis, MD 21403
  • 7 Mizzen Ct, Annapolis, MD 21403
    7 Mizzen Ct, Annapolis, MD 21403
    7 Mizzen Ct, Annapolis, MD 21403
    /28

    $390,000

    • 2 Beds
    • 2.5 Baths
    • 1,319 Sq Ft

    7 Mizzen Ct, Annapolis, MD 21403

    This spacious, well-maintained townhouse in desirable Annapolis offers comfortable, move-in-ready living. The main level features a welcoming living room centered on a classic wood-burning fireplace with back slider that flood the space with light and open to the backyard. A dedicated dining area adjoins the living room, creating an ideal flow for both casual and formal gatherings. The fully

    Lauren Emrick Innovative Properties, Inc.

    7 Mizzen Ct, Annapolis, MD 21403
  • 2002 Dakota Place Unit 2A, Annapolis, MD 21403
    2002 Dakota Place Unit 2A, Annapolis, MD 21403
    2002 Dakota Place Unit 2A, Annapolis, MD 21403
    /28

    $650,000

    • 2 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    2002 Dakota Place Unit 2A, Annapolis, MD 21403

    Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an

    Brad Kappel TTR Sotheby's International Realty

    2002 Dakota Place Unit 2A, Annapolis, MD 21403
  • 3365 Arundel on The Bay Rd, Annapolis, MD 21403
    3365 Arundel on The Bay Rd, Annapolis, MD 21403
    3365 Arundel on The Bay Rd, Annapolis, MD 21403
    /47

    $499,999

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    3365 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome Home!!! Beautiful Single Family Home, a peaceful retreat nestled in the water-privileged community of Oyster Harbor. Updates include all new oak hardwood flooring, custom kitchen cabinets with island and lots of counter space, quartz countertops and stainless steel appliances, sun filled living room, dining room, upscale bathrooms w/ custom tile and vanities, large bedrooms, private

    Olisa Akpati Fairfax Realty Select

    3365 Arundel on The Bay Rd, Annapolis, MD 21403
  • 735 Warren Dr, Annapolis, MD 21403
    735 Warren Dr, Annapolis, MD 21403
    735 Warren Dr, Annapolis, MD 21403
    /55

    $579,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 3 Baths
    • 2,041 Sq Ft

    735 Warren Dr, Annapolis, MD 21403

    Welcome to 735 Warren Drive, nestled in the heart of Greenacres. This beautifully updated 3-bedroom, 3-bath rancher is the perfect blend of modern comfort and timeless charm. The fully renovated kitchen is a chef’s dream, featuring custom cabinetry, gleaming quartz countertops, and top-of-the-line JennAir appliances. Adjacent to the kitchen, the light-filled sunroom offers the ideal space to

    Jaime Watt Compass

    735 Warren Dr, Annapolis, MD 21403
  • 2562 Carrollton Rd, Annapolis, MD 21403
    2562 Carrollton Rd, Annapolis, MD 21403
    2562 Carrollton Rd, Annapolis, MD 21403
    /54

    $6,500,000

    • 7 Beds
    • 8.5 Baths
    • 9,026 Sq Ft

    2562 Carrollton Rd, Annapolis, MD 21403

    A truly iconic Annapolis offering, this extraordinarily rare waterfront estate is gracefully set on 7.5 remarkably private acres, showcasing what may be the most breathtaking panoramic views in all of Annapolis. With endless, horizon-stretching vistas that evoke the feel of an oceanfront retreat, the Chesapeake Bay unfolds before you with the Bay Bridge creating a dramatic backdrop in the

    Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

    2562 Carrollton Rd, Annapolis, MD 21403
  • 124 E Bay View Dr, Annapolis, MD 21403
    124 E Bay View Dr, Annapolis, MD 21403
    124 E Bay View Dr, Annapolis, MD 21403
    /21

    $1,025,000

    Open House 6/06 Coming Soon
    • 4 Beds
    • 3 Baths
    • 4,061 Sq Ft

    124 E Bay View Dr, Annapolis, MD 21403

    Welcome to 124 E Bay View Drive, beautifully remodeled and ideally located in Hillsmere Shores, one of Annapolis’ most beloved water-oriented communities. Set along picturesque East Bay View Drive with water views, this thoughtfully updated home is just one block from the neighborhood beach with stunning water views, around the corner from the community marina, and a block away from the boat ramp

    Jennifer Gregorski Washington Fine Properties

    124 E Bay View Dr, Annapolis, MD 21403
  • 2004 Quay Village Ct Unit T1, Annapolis, MD 21403
    2004 Quay Village Ct Unit T1, Annapolis, MD 21403
    2004 Quay Village Ct Unit T1, Annapolis, MD 21403
    /37

    $415,000

    • 1 Bed
    • 1.5 Baths
    • 1,100 Sq Ft

    2004 Quay Village Ct Unit T1, Annapolis, MD 21403

    Beautifully maintained and move-in ready, this spacious 1-bedroom, 1.5-bath condo offers an exceptional opportunity to enjoy the waterfront community lifestyle in sought-after Chesapeake Harbour. Ideally located just steps from the community pool and adjoining tennis/pickleball courts, this light-filled home features an open-concept layout with generous living and dining spaces, floor-to-ceiling

    Melanie Wood Berkshire Hathaway HomeServices PenFed Realty

    2004 Quay Village Ct Unit T1, Annapolis, MD 21403
  • 209 Garden Gate Ln, Annapolis, MD 21403
    209 Garden Gate Ln, Annapolis, MD 21403
    209 Garden Gate Ln, Annapolis, MD 21403
    /19

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    209 Garden Gate Ln, Annapolis, MD 21403

    Spacious and thoughtfully updated, this 4-bedroom, 2.5-bath single-family home offers comfort, functionality, and modern improvements throughout. Over the past two years, the property has seen numerous upgrades, including a new rear privacy fence, concrete walkway, expansive Trex deck with dual staircases, luxury vinyl plank flooring in the primary bedroom, and an updated walk-in shower on the

    Carolyn Braun Keller Williams Flagship

    209 Garden Gate Ln, Annapolis, MD 21403
  • 7036 Harbour Village Ct Unit 1, Annapolis, MD 21403
    7036 Harbour Village Ct Unit 1, Annapolis, MD 21403
    7036 Harbour Village Ct Unit 1, Annapolis, MD 21403
    /49

    $625,000

    • 1 Bed
    • 1.5 Baths
    • 1,000 Sq Ft

    7036 Harbour Village Ct Unit 1, Annapolis, MD 21403

    Waterfront living at its finest. Welcome to this marina-front gem in the highly sought-after, 24-hour gated Chesapeake Harbour community. This beautifully renovated 1-bedroom, 1.5-bath terrace-level condo offers effortless coastal living paired with resort-style amenities and some of the most breathtaking views in Annapolis. Completely rehabbed from top to bottom, this home features all-new

    Steven Lane LPT Realty, LLC

    7036 Harbour Village Ct Unit 1, Annapolis, MD 21403
  • 2020 Quay Village Ct Unit T1, Annapolis, MD 21403
    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
    /32

    $700,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    2020 Quay Village Ct Unit T1, Annapolis, MD 21403

    OPEN all weekend noon - 3PM === WATERFRONT= ONE BEDROOM "C" FLOOR PLAN = EXTRA WIDE CONDO: Four pane sliders in living room and there are 4 glass pane windows in master bedroom == Master has a private exit door to a beach front patio == Front row seats for the Blue Angels flyover and weekly regatta races ... Amenities galore with two community pools / pool house complexes - one directly on the

    Candice Friday Coastal Realty Maryland

    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
  • 422 First St, Annapolis, MD 21403
    422 First St, Annapolis, MD 21403
    422 First St, Annapolis, MD 21403
    /19

    $870,000

    • 2 Beds
    • 1.5 Baths
    • 1,094 Sq Ft

    422 First St, Annapolis, MD 21403

    Welcome to Eastport—just steps from downtown Annapolis. This adorable duplex offers the perfect blend of charm, convenience, and a coastal lifestyle. This inviting two-bedroom, 1.5-bath home is freshly painted and features numerous updates, including new hardwood floors throughout, new windows in the living room and kitchen, a new wood-burning stove, and a new A/C heat pump—making it move-in

    Cindy Nairn Coldwell Banker Realty

    422 First St, Annapolis, MD 21403
  • 3328 Shore Dr, Annapolis, MD 21403
    3328 Shore Dr, Annapolis, MD 21403
    3328 Shore Dr, Annapolis, MD 21403
    /19

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    3328 Shore Dr, Annapolis, MD 21403

    Amazing opportunity! Situated in one of Annapolis’ most desirable waterfront communities, Oyster Harbor, 3328 Shore Drive offers a premier corner-lot location with beautiful second-floor water views. Enjoy the coastal lifestyle with easy access to marinas, parks, the community beach, local dining, and the charm of nearby historic Annapolis. This property presents an incredible opportunity for

    Joanna Dalton Coldwell Banker Realty

    3328 Shore Dr, Annapolis, MD 21403
  • 15 Landings Ct, Annapolis, MD 21403
    15 Landings Ct, Annapolis, MD 21403
    15 Landings Ct, Annapolis, MD 21403
    /55

    $575,000

    Open Wed 5:30PM - 8PM
    • 4 Beds
    • 3.5 Baths
    • 1,736 Sq Ft

    15 Landings Ct, Annapolis, MD 21403

    Large, beautifully maintained contemporary home in the sought-after Stone Creek community of Annapolis. Professional photos of this bright and airy property are coming soon.Features of this 4-bedroom, 3.5-bathroom home include:Renovated Interior: Recently painted throughout with an open-concept layout, remodeled kitchen and bathrooms, and vinyl plank flooring in the living and dining

    Agent Photo

    Gina White

    Coldwell Banker Realty

    (410) 632-6739

    15 Landings Ct, Annapolis, MD 21403
  • 7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
    /80

    $899,000

    • 3 Beds
    • 3 Baths
    • 2,041 Sq Ft

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403

    LOCK AND LEAVE CAREFREE LIFESTYLE IN A WATERFRONT GATED COMMUNITY! DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design

    Ann Chumney Coldwell Banker Realty

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
  • 2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    /53

    $739,000

    • 2 Beds
    • 2 Baths
    • 1,618 Sq Ft

    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    Life at Chesapeake Harbour feels like being on vacation every single day. Mornings begin with coffee on the balcony as the sun rises over the marina and the Chesapeake Bay. Even simple moments feel special here, whether it’s curling up with a book by the fireplace on a rainy afternoon, taking an evening stroll along the shoreline, or enjoying dinner on the deck as the sky changes colors over the

    Jennifer Schaub EXP Realty, LLC

    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • 15 President Point Dr Unit B2, Annapolis, MD 21403
    15 President Point Dr Unit B2, Annapolis, MD 21403
    15 President Point Dr Unit B2, Annapolis, MD 21403
    /25

    $975,000

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft

    15 President Point Dr Unit B2, Annapolis, MD 21403

    Eastport Waterfront Condo – 2BR/2BA – 1250 sq ft. 2 outdoor decks – 1 deck with amazing full city and waterfront view. Open Concept Living Room with cooks kitchen. Living Room has hardwood floors and fireplace. Newer windows and sliding doors with blinds. Full size front loader washer/dryer. Designer style Bathrooms. Community has pool, pier and tennis courts. Walk to town and live the life.

    Lauren Emrick Innovative Properties, Inc.

    15 President Point Dr Unit B2, Annapolis, MD 21403
  • 520 Harbor Dr, Annapolis, MD 21403
    520 Harbor Dr, Annapolis, MD 21403
    520 Harbor Dr, Annapolis, MD 21403
    /59

    $800,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    520 Harbor Dr, Annapolis, MD 21403

    520 Harbor Drive isn’t simply another home hitting the market — it’s the opportunity buyers spend months waiting to find in Hillsmere and rarely secure. Perfectly positioned in the heart of one of Annapolis’ most loved waterfront communities, this home delivers the lifestyle that keeps people here for years: private beaches, marina access, boat ramps, a community pool, playgrounds, and effortless

    Wendy Oliver Coldwell Banker Realty

    520 Harbor Dr, Annapolis, MD 21403
  • 121 Conley Dr, Annapolis, MD 21403
    121 Conley Dr, Annapolis, MD 21403
    121 Conley Dr, Annapolis, MD 21403
    /38

    $330,000

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    121 Conley Dr, Annapolis, MD 21403

    Welcome to this home nestled in the heart of Annapolis. Offering a blend of comfort, functionality, and convenience, this property features spacious living areas, abundant natural light, and a layout designed for everyday living and entertaining. Enjoy a generous backyard perfect for relaxing or hosting gatherings, along with easy access to local shopping, dining, marinas, parks, and major

    Ms. Kristina Boyd Keller Williams Preferred Properties

    121 Conley Dr, Annapolis, MD 21403
  • 19 Boucher Place, Annapolis, MD 21403
    19 Boucher Place, Annapolis, MD 21403
    19 Boucher Place, Annapolis, MD 21403
    /55

    $819,000

    • 3 Beds
    • 3.5 Baths
    • 1,800 Sq Ft

    19 Boucher Place, Annapolis, MD 21403

    Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offers a perfect blend of coastal and traditional architectural styles, creating a warm and inviting atmosphere. Built in 2013, this residence boasts 1,800 square feet of thoughtfully designed living space, ideal for those seeking comfort and elegance. The kitchen is a chef's dream, featuring upgraded

    Deborah Savoie Long & Foster Real Estate, Inc.

    19 Boucher Place, Annapolis, MD 21403
  • 2 Highland Ave, Annapolis, MD 21403
    2 Highland Ave, Annapolis, MD 21403
    /2

    $485,000

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    2 Highland Ave, Annapolis, MD 21403

    Charming 2 bedroom 1 bathroom home in Eastport. Home has large fenced yard, finished attic, and large unfinished basement.

    Michelle Greenwaldt Innovative Properties, Inc.

    2 Highland Ave, Annapolis, MD 21403
  • 1180 Bay Highlands Dr, Annapolis, MD 21403
    1180 Bay Highlands Dr, Annapolis, MD 21403
    1180 Bay Highlands Dr, Annapolis, MD 21403
    /47

    $710,000

    • 3 Beds
    • 2.5 Baths
    • 1,758 Sq Ft

    1180 Bay Highlands Dr, Annapolis, MD 21403

    Beautifully maintained and filled with natural light, this inviting home offers an open floor plan with vaulted ceilings, hardwood floors, and comfortable living spaces designed for both relaxing and entertaining. The spacious primary suite features a private sitting area and en-suite bath, while the cozy fireplace and rear deck create the perfect setting for everyday living. A fenced backyard

    Gary Durand CENTURY 21 New Millennium

    1180 Bay Highlands Dr, Annapolis, MD 21403
  • 1126 Mainsail Dr, Annapolis, MD 21403
    1126 Mainsail Dr, Annapolis, MD 21403
    1126 Mainsail Dr, Annapolis, MD 21403
    /62

    $865,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    1126 Mainsail Dr, Annapolis, MD 21403

    New in the Market! Extensively renovated from 2022–2024, this move-in-ready, modern Colonial is a standout offering in Anchorage, an Annapolis premier water-privileged community. Set on a private, wooded half-acre lot, this 4-bedroom, 2.5-bath residence combines approximately 2,000 square feet of refined living space with a full basement. The home’s interior showcases high-end craftsmanship,

    Ani Gonzalez-Brunet Coldwell Banker Realty

    1126 Mainsail Dr, Annapolis, MD 21403
  • 3448 Cohasset Ave, Annapolis, MD 21403
    3448 Cohasset Ave, Annapolis, MD 21403
    3448 Cohasset Ave, Annapolis, MD 21403
    /30

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    3448 Cohasset Ave, Annapolis, MD 21403

    Located in the sought-after waterfront community of Arundel on the Bay, this 3-bedroom, 2.5-bath rancher offers relaxed coastal living with stunning bay views just minutes from downtown Annapolis. Stroll just blocks to the community beach, dock, boat ramp and playground to experience the charm of Chesapeake Bay living. Inside, an open floor plan features a cozy family room with a wood-burning

    Sarah Ernest Cummings & Co. Realtors

    3448 Cohasset Ave, Annapolis, MD 21403
  • 774 Fairview Ave Unit F, Annapolis, MD 21403
    774 Fairview Ave Unit F, Annapolis, MD 21403
    774 Fairview Ave Unit F, Annapolis, MD 21403
    /20

    $635,000

    • 2 Beds
    • 2 Baths
    • 1,060 Sq Ft

    774 Fairview Ave Unit F, Annapolis, MD 21403

    Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautifully renovated, this top-floor 2-bedroom, 2-bath condominium in the sought-after Severn House community offers direct views of Back Creek, a deeded boat slip, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle. Inside, the residence has been thoughtfully updated with a clean,

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (443) 673-5707

    774 Fairview Ave Unit F, Annapolis, MD 21403
  • 755 Fairview Ave Unit 755 D, Annapolis, MD 21403
    755 Fairview Ave Unit 755 D, Annapolis, MD 21403
    755 Fairview Ave Unit 755 D, Annapolis, MD 21403
    /43

    $574,999

    • 3 Beds
    • 2 Baths
    • 1,295 Sq Ft

    755 Fairview Ave Unit 755 D, Annapolis, MD 21403

    WELCOME HOME!This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool.This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring

    Carey Laycock RE/MAX Leading Edge

    755 Fairview Ave Unit 755 D, Annapolis, MD 21403
  • 763 Fairview Ave Unit 763 F, Annapolis, MD 21403
    763 Fairview Ave Unit 763 F, Annapolis, MD 21403
    763 Fairview Ave Unit 763 F, Annapolis, MD 21403
    /6

    $375,000

    Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 1,058 Sq Ft

    763 Fairview Ave Unit 763 F, Annapolis, MD 21403

    This well‐maintained and recently rehabbed 2-bedroom, 1.5-bath unit is located in Severn House, one of Eastport’s most desirable waterfront condominium communities, offering exceptional amenities and a true Annapolis lifestyle. Residents enjoy a waterfront swimming pool with a large patio, deck, marina views, and community WiFi, along with a small‐craft launch ideal for kayaks, canoes, and

    Kyle Jones Berkshire Hathaway HomeServices PenFed Realty

    763 Fairview Ave Unit 763 F, Annapolis, MD 21403
  • 1022 Harbor Dr, Annapolis, MD 21403
    1022 Harbor Dr, Annapolis, MD 21403
    1022 Harbor Dr, Annapolis, MD 21403
    /37

    $735,000

    Open Sat 11AM - 2PM
    • 5 Beds
    • 3 Baths
    • 2,600 Sq Ft

    1022 Harbor Dr, Annapolis, MD 21403

    Discover a truly one-of-a-kind property in the highly sought-after Annapolis Roads community. This exceptional 5-bedroom, 3-bathroom single-family home sits on 0.4 acres and includes a detached, oversized two-car garage with a newly renovated one-bedroom, one-bathroom apartment above—perfect for guests or extended family. The main residence, apartment, and garage have all been freshly painted.

    Jeremy McDonough Mr. Lister Realty

    1022 Harbor Dr, Annapolis, MD 21403
  • 3712 Gateshead Dr, Annapolis, MD 21403
    3712 Gateshead Dr, Annapolis, MD 21403
    3712 Gateshead Dr, Annapolis, MD 21403
    /74

    $1,949,000

    Open Sat 11AM - 1PM $51K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,620 Sq Ft

    3712 Gateshead Dr, Annapolis, MD 21403

    Price reduced!!! Nestled along the banks of Watergate Harbor with direct access to the South River, in the prestigious Watergate neighborhood of Annapolis, 3712 Gateshead Drive offers the ultimate waterfront lifestyle with waterviews from every room in the home. When you enter the home you are greeted with the marble flooring in the foyer which transitions beautifully to the gleaming hardwood

    Melissa Murray Compass

    3712 Gateshead Dr, Annapolis, MD 21403
  • 317 Canterfield Rd, Annapolis, MD 21403
    317 Canterfield Rd, Annapolis, MD 21403
    317 Canterfield Rd, Annapolis, MD 21403
    /66

    $735,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,352 Sq Ft

    317 Canterfield Rd, Annapolis, MD 21403

    Welcome to 317 Canterfield Road in the highly sought-after Hunt Meadow community! Situated on a beautifully landscaped corner lot, this well-maintained home offers the perfect combination of space, comfort, and location. Step inside to find a bright and inviting main level featuring hardwood floors, spacious living and dining areas, and a well-appointed kitchen that opens to a cozy family

    Rick Gloekler RE/MAX Executive

    317 Canterfield Rd, Annapolis, MD 21403
  • 1227 Creek Dr, Annapolis, MD 21403
    1227 Creek Dr, Annapolis, MD 21403
    1227 Creek Dr, Annapolis, MD 21403
    /13

    $25,000

    • Land
    • 17,859 Sq Ft
    • $60,976 per Acre

    1227 Creek Dr, Annapolis, MD 21403

    ONLINE AUCTION: Bidding begins 05/25/2026 @ 10:00 AM. Bidding ends 05/27/2026 @ 11:50 AM. List Price is Suggested Opening Bid. Deposit: $5,000. Tucked inside the sought-after Oyster Harbor community of Annapolis, this 0.41-acre homesite at 1227 Creek Dr offers something increasingly rare in Anne Arundel County: land in an established waterfront neighborhood just minutes from the heart of

    Adam Shpritz

    1227 Creek Dr, Annapolis, MD 21403
  • 34 Enclave Ct, Annapolis, MD 21403
    34 Enclave Ct, Annapolis, MD 21403
    /2

    $725,000

    Coming Soon
    • 3 Beds
    • 3.5 Baths
    • 2,556 Sq Ft

    34 Enclave Ct, Annapolis, MD 21403

    Welcome to 34 Enclave Court, a beautifully appointed and spacious townhome in one of Annapolis's most desirable and convenient locations. Built in 2019 by K. Hovnanian, this meticulously maintained residence offers over 2,700 square feet of refined living space across three thoughtfully designed levels-all within walking distance of Downtown Annapolis, the Naval Academy, and major commuter

    Beth Viscarra Cummings & Co. Realtors

    34 Enclave Ct, Annapolis, MD 21403
  • 996 Headwater Rd, Annapolis, MD 21403
    996 Headwater Rd, Annapolis, MD 21403
    996 Headwater Rd, Annapolis, MD 21403
    /59

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 2,288 Sq Ft

    996 Headwater Rd, Annapolis, MD 21403

    Waterfront home nestled in the serene enclave of Kitty Creek; located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy

    Amanda Greenfield Engel & Völkers Annapolis

    996 Headwater Rd, Annapolis, MD 21403
  • 417 Chesapeake Ave, Annapolis, MD 21403
    417 Chesapeake Ave, Annapolis, MD 21403
    417 Chesapeake Ave, Annapolis, MD 21403
    /78

    $1,399,000

    $96K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,259 Sq Ft

    417 Chesapeake Ave, Annapolis, MD 21403

    This exceptional 3-bedroom, 2.5-bath sun-drenched contemporary home sits on a spacious Eastport corner lot. Enjoy the vibrant Eastport lifestyle from your newly updated, well-maintained oasis featuring warm hardwood floors and generous living, dining, and kitchen areas. The open layout complements the coastal Eastport vibe, while the inviting wraparound porch is great for morning coffee or an

    Barbara Birkbeck White Coldwell Banker Realty

    417 Chesapeake Ave, Annapolis, MD 21403
  • 40 Greystone Ct Unit L, Annapolis, MD 21403
    40 Greystone Ct Unit L, Annapolis, MD 21403
    40 Greystone Ct Unit L, Annapolis, MD 21403
    /40

    $299,900

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,229 Sq Ft

    40 Greystone Ct Unit L, Annapolis, MD 21403

    Welcome to this fully renovated penthouse condo in the highly desirable Annapolis Overlook community. This spacious 2-bedroom, 2-bath residence features soaring 10-foot ceilings in the main living area, creating an airy, open feel filled with natural light, along with a cozy wood-burning fireplace perfect for cooler evenings. The thoughtfully designed open-concept layout flows seamlessly from the

    Kara Shaffer Engel & Völkers Annapolis

    40 Greystone Ct Unit L, Annapolis, MD 21403
  • 7004 Channel Village Ct Unit 102, Annapolis, MD 21403
    7004 Channel Village Ct Unit 102, Annapolis, MD 21403
    7004 Channel Village Ct Unit 102, Annapolis, MD 21403
    /40

    $575,000

    • 2 Beds
    • 2 Baths

    7004 Channel Village Ct Unit 102, Annapolis, MD 21403

    Don’t miss this beautifully updated, move-in-ready condo in the highly sought-after, amenity-rich community of Chesapeake Harbour, offering serene marina views and the perfect backdrop to relax and watch the boats drift by. This inviting home is bright and cheery and features neutral paint and carpeting. There are two spacious bedrooms with two full baths. The open-concept living and dining areas

    Colleen Smith EXP Realty, LLC

    7004 Channel Village Ct Unit 102, Annapolis, MD 21403
  • 3280 Arundel on The Bay Rd, Annapolis, MD 21403
    3280 Arundel on The Bay Rd, Annapolis, MD 21403
    3280 Arundel on The Bay Rd, Annapolis, MD 21403
    /40

    $799,900

    Open Sat 1PM - 3PM $25K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,144 Sq Ft

    3280 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome to this beautifully maintained custom built Tudor Style home! With a primary suite and full bath on the main level and another primary suite with full bath on the upper level, this home is perfect for multi-generational living! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 bedroom and 1.5 bath; and the lower level has another full bath and several

    Deanna Marshall The KW Collective

    3280 Arundel on The Bay Rd, Annapolis, MD 21403

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