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Annapolis, MD Houses for Sale

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  • 79 Windwhisper Ln, Annapolis, MD 21403
    79 Windwhisper Ln, Annapolis, MD 21403
    79 Windwhisper Ln, Annapolis, MD 21403
    /21

    $629,999

    • 4 Beds
    • 3.5 Baths
    • 2,560 Sq Ft

    79 Windwhisper Ln, Annapolis, MD 21403

    Motivated Sellers!! Price Just Improved!! Rare Opportunity in an Amazing Annapolis Neighborhood! Welcome to 79 Windwhisper. A beautiful 4 bedroom, 2500 sq foot, 3.5 bath home with an office, located in one of Annapolis’ most desirable neighborhoods. This well-maintained property offers numerous recent updates, including new carpet, hardwood flooring on main level, updated bathrooms, flooring,

    Agent Photo

    Kristen Quinn

    Realty Navigator

    (443) 402-3711

    79 Windwhisper Ln, Annapolis, MD 21403
  • 860 Woodmont Rd, Annapolis, MD 21401
    860 Woodmont Rd, Annapolis, MD 21401
    860 Woodmont Rd, Annapolis, MD 21401
    /55

    $629,000

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft

    860 Woodmont Rd, Annapolis, MD 21401

    Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the highly sought-after, amenity-rich Heritage Harbour community in Annapolis. Thoughtfully designed for comfortable main-level living, this home features a spacious primary suite with a gorgeous updated bath and walk-in closet, along with a second bedroom, 2nd updated full bath, and convenient main-level laundry.The

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 883-7342

    860 Woodmont Rd, Annapolis, MD 21401
  • 17151717 Porters Hill Rd, Annapolis, MD 21401
    17151717 Porters Hill Rd, Annapolis, MD 21401
    17151717 Porters Hill Rd, Annapolis, MD 21401
    /37

    $4,950,000

    • 7 Beds
    • 7 Baths
    • 7,500 Sq Ft

    17151717 Porters Hill Rd, Annapolis, MD 21401

    Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715-1717 Porters Hill Road is a unique heritage property with over a century of history. Set on a 2.96 acre lot with 429 ft of waterfrontage, the property is comprised of two separate parcels and includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures.

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (443) 960-7039

    17151717 Porters Hill Rd, Annapolis, MD 21401
  • 13 Alder Rd, Eastport, MD 21403
    13 Alder Rd, Eastport, MD 21403
    /2

    $499,000 Coming Soon

    • 4 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    13 Alder Rd, Eastport, MD 21403

    Agent Photo

    Mr. K Oyedele

    Cornerstone Properties and Financial Services LLC

    (410) 376-5350

    13 Alder Rd, Eastport, MD 21403
  • 3307 Harness Creek Rd, Annapolis, MD 21403
    3307 Harness Creek Rd, Annapolis, MD 21403
    3307 Harness Creek Rd, Annapolis, MD 21403
    /44

    $3,145,000

    • 3 Beds
    • 2.5 Baths
    • 2,570 Sq Ft

    3307 Harness Creek Rd, Annapolis, MD 21403

    Welcome to 3307 Harness Creek Road: a Nantucket style, coastal home set on a private peninsula with spectacular water views, a serene backyard oasis and two deep-water piers on protected Harness Creek. This waterside gem, with 190 ft of waterfrontage, is situated directly across from Quiet Waters Park and offers quick access to the South River and the Chesapeake Bay.Inside, you’re greeted by

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (410) 762-4260

    3307 Harness Creek Rd, Annapolis, MD 21403
  • 1349 Yorktown Rd, Annapolis, MD 21409
    1349 Yorktown Rd, Annapolis, MD 21409
    1349 Yorktown Rd, Annapolis, MD 21409
    /35

    $2,799,000

    • 16 Beds
    • 6 Baths
    • 5,719 Sq Ft

    1349 Yorktown Rd, Annapolis, MD 21409

    This brand new, fully renovated 16-bedroom, 6-bathroom residence in Annapolis offers an exceptional opportunity for assisted living or specialized care operations. Thoughtfully redesigned and fully permitted with the county for use as an assisted living facility, the property combines modern upgrades with full regulatory compliance. The spacious layout features three separate living areas,

    Agent Photo

    Karen Rollings

    EXP Realty, LLC

    (443) 296-5581

    1349 Yorktown Rd, Annapolis, MD 21409
  • 1116 Bay Ridge Ave, Annapolis, MD 21403
    1116 Bay Ridge Ave, Annapolis, MD 21403
    1116 Bay Ridge Ave, Annapolis, MD 21403
    /47

    $849,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,268 Sq Ft

    1116 Bay Ridge Ave, Annapolis, MD 21403

    This beautifully reimagined residence at 1116 Bay Ridge Avenue offers a sophisticated blend of classic Annapolis charm and high-end modern luxury. Located in a prime Eastport location, this home has been meticulously updated with a focus on quality craftsmanship and professional-grade amenities.The inviting exterior is defined by expert hardscaping and a welcoming stone walkway leading to a

    Agent Photo

    Charles Dwayne Hoyt

    Berkshire Hathaway HomeServices PenFed Realty

    (410) 431-3528

    1116 Bay Ridge Ave, Annapolis, MD 21403
  • 111 Janwall St, Annapolis, MD 21403
    111 Janwall St, Annapolis, MD 21403
    /2

    $540,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,754 Sq Ft

    111 Janwall St, Annapolis, MD 21403

    Charming 3-Bedroom Home on Quiet Cul-de-Sac Near Downtown Annapolis Welcome to this beautifully maintained 3-bedroom, 2.5-bath single-family home, perfectly situated on a peaceful cul-de-sac just minutes from downtown Annapolis. Offering a blend of comfort, convenience, and charm, this home is ideal for both relaxing and entertaining. Step inside to find a bright and inviting interior with a

    Agent Photo

    Amy Juras

    Long & Foster Real Estate, Inc.

    (443) 940-6438

    111 Janwall St, Annapolis, MD 21403
  • 113 Stilly Way, Annapolis, MD 21403
    113 Stilly Way, Annapolis, MD 21403
    113 Stilly Way, Annapolis, MD 21403
    /13

    $1,079,990 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,700 Sq Ft

    113 Stilly Way, Annapolis, MD 21403

    Spacious and elegant, this 4-bedroom, 4.5-bath home offers approximately 4,400 sq. ft., with the option to expand to 5,300 sq. ft. with a fourth level. The gourmet kitchen features double wall ovens (upper with air-fry), a 36" gas cooktop, and choice of cabinetry or stainless steel hood. Enjoy a sunroom, cozy fireplace, 9-foot ceilings on all levels, and a finished basement with full bath.

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 431-3849

    113 Stilly Way, Annapolis, MD 21403
  • 116 Stilly Way, Annapolis, MD 21403
    116 Stilly Way, Annapolis, MD 21403
    116 Stilly Way, Annapolis, MD 21403
    /21

    $1,099,990 New Construction

    • 4 Beds
    • 3 Baths
    • 4,400 Sq Ft

    116 Stilly Way, Annapolis, MD 21403

    Backs to Quiet Waters Park! This spacious and elegant home offers 4 bedrooms, 3.5 bathrooms and approximately 4,400 sq. ft. of living space, with the option to expand to 5,300 sq. ft. by adding a fourth level. The gourmet kitchen features double wall ovens (with the upper oven including an air-fry option), a 36-inch gas cooktop and the choice of a cabinetry hood or stainless-steel chimney hood.

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (443) 222-1215

    116 Stilly Way, Annapolis, MD 21403
  • 1165 Green Holly Ct, Annapolis, MD 21409
    1165 Green Holly Ct, Annapolis, MD 21409
    1165 Green Holly Ct, Annapolis, MD 21409
    /47

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,218 Sq Ft

    1165 Green Holly Ct, Annapolis, MD 21409

    Cape St. Claire Home sold with Extra Lot included! This lovely Cape St. Claire property boasts an extra lot, offering more space for your family to enjoy. Build a detached garage with extra living space or possible ADU. Upon entering the home, you’ll immediately feel at ease. The spacious living room, which could also serve as a formal dining area, features a cozy fireplace. The kitchen, with its

    Darlene Winegardner RE/MAX Executive

    1165 Green Holly Ct, Annapolis, MD 21409
  • 207 1st St, Annapolis, MD 21401
    207 1st St, Annapolis, MD 21401
    207 1st St, Annapolis, MD 21401
    /29

    $499,900

    • 4 Beds
    • 2 Baths
    • 1,435 Sq Ft

    207 1st St, Annapolis, MD 21401

    This home has so much to offer. The lot is larger than you think with a fenced back yard. The home itself features hardwood floors, a modern kitchen with custom cabinets, granite countertops, upgraded appliances. It boasts 3 bedrooms upstairs with hardwoods and a renovated bath (2020) with ceramic tile. Master bedroom includes full master bath with oversized shower. Lower level is great for

    James Dick Long & Foster Real Estate, Inc.

    207 1st St, Annapolis, MD 21401
  • 2942 Southaven Dr, Annapolis, MD 21401
    2942 Southaven Dr, Annapolis, MD 21401
    2942 Southaven Dr, Annapolis, MD 21401
    /41

    $949,900

    • 4 Beds
    • 2.5 Baths
    • 2,142 Sq Ft

    2942 Southaven Dr, Annapolis, MD 21401

    Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an

    Erica Baker TTR Sotheby's International Realty

    2942 Southaven Dr, Annapolis, MD 21401
  • 1787 Beachfield Rd, Annapolis, MD 21409
    1787 Beachfield Rd, Annapolis, MD 21409
    1787 Beachfield Rd, Annapolis, MD 21409
    /46

    $3,499,000

    • 5 Beds
    • 4.5 Baths
    • 6,360 Sq Ft

    1787 Beachfield Rd, Annapolis, MD 21409

    Welcome to a thoughtfully designed waterfront home on Whitehall Creek, where elevated positioning, wide open views, and a private deep-water pier with approximately 12 feet of mean low water, define the experience from the start. Step inside and the water immediately becomes the focal point. Natural light fills the home, and open sightlines carry those views throughout the main living spaces,

    Brad Kappel TTR Sotheby's International Realty

    1787 Beachfield Rd, Annapolis, MD 21409
  • 102 Oak Dr, Annapolis, MD 21403
    102 Oak Dr, Annapolis, MD 21403
    102 Oak Dr, Annapolis, MD 21403
    /22

    $498,000

    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft

    102 Oak Dr, Annapolis, MD 21403

    Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conveniently located just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes, this home provides easy access to shopping, dining, and everyday essentials. Residents of Hillsmere Shores also enjoy easy

    Amy Presley Samson Properties

    102 Oak Dr, Annapolis, MD 21403
  • 99 Summerfield Dr, Annapolis, MD 21403
    99 Summerfield Dr, Annapolis, MD 21403
    99 Summerfield Dr, Annapolis, MD 21403
    /55

    $524,900

    • 4 Beds
    • 3 Baths
    • 1,980 Sq Ft

    99 Summerfield Dr, Annapolis, MD 21403

    Thank you to everyone who has shown or is scheduled to show 99 Summerfield Drive—we truly appreciate the interest! Due to the strong activity, the seller has set an offer deadline for Monday April 6th at 12:00 PM (noon). Charming rancher in the heart of Annapolis! Hardwood throughout, updates to the kitchens and bathrooms, fully finished basement with full bathroom, screened-in porch, large

    Jack Papaleonti Academy Realty Inc.

    99 Summerfield Dr, Annapolis, MD 21403
  • 1407 Brenwoode Rd, Annapolis, MD 21409
    1407 Brenwoode Rd, Annapolis, MD 21409
    1407 Brenwoode Rd, Annapolis, MD 21409
    /34

    $575,000

    • 3 Beds
    • 3 Baths
    • 2,390 Sq Ft

    1407 Brenwoode Rd, Annapolis, MD 21409

    Welcome to 1407 Brenwoode Rd. This spacious 3-bedroom home (with potential 4th bedroom /bonus room in basement), is ideally situated in one of Annapolis’ most sought-after communities on the Broadneck Peninsula. Experience the charm of neighboring Cape St. Claire, where community, convenience, and coastal living come together. Freshly painted and ready for your finishing touches, the home

    Andrea Scheidt Engel & Völkers Annapolis

    1407 Brenwoode Rd, Annapolis, MD 21409
  • 4 Boxwood Rd, Annapolis, MD 21403
    4 Boxwood Rd, Annapolis, MD 21403
    /2

    $389,900

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    4 Boxwood Rd, Annapolis, MD 21403

    Located at the corner of Spa Road and Boxwood Drive, this property offers an excellent Annapolis location with convenient access to downtown, shopping, dining, and major commuter routes. The home sits on a prominent corner lot and presents a great opportunity for investors, builders, or buyers looking to renovate and customize a home to their own vision. The property is in need of updating and is

    Rick Gloekler RE/MAX Executive

    4 Boxwood Rd, Annapolis, MD 21403
  • 198 Acton Rd, Annapolis, MD 21403
    198 Acton Rd, Annapolis, MD 21403
    198 Acton Rd, Annapolis, MD 21403
    /50

    $2,350,000

    • 3 Beds
    • 3.5 Baths
    • 3,550 Sq Ft

    198 Acton Rd, Annapolis, MD 21403

    Experience the best of waterfront living with easy water access to historic Annapolis, Eastport, and the Chesapeake Bay. Perfectly sited in a protected area on Spa Creek, this eco-friendly contemporary home was designed by architect Gary S. Schwerzler of Fourth Street Design Studio and built by Blueford Contracting.Set on a quarter of an acre and surrounded by lush native landscaping, the

    Sarah Greenlee Morse TTR Sotheby's International Realty

    198 Acton Rd, Annapolis, MD 21403
  • 46 Lafayette Ave, Annapolis, MD 21401
    46 Lafayette Ave, Annapolis, MD 21401
    46 Lafayette Ave, Annapolis, MD 21401
    /32

    $975,000

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    46 Lafayette Ave, Annapolis, MD 21401

    46 Lafayette Ave is a Murray Hill classic, a beautifully updated Craftsman four-square where original heart-of-pine floors and a charming covered front porch meet a stunning gourmet kitchen. The open floor plan flows naturally from the marble-topped island into dining and living spaces, making it effortless for everyday living and entertaining alike. Cooks will love the stainless appliances,

    Vanessa Knight Engel & Völkers Annapolis

    46 Lafayette Ave, Annapolis, MD 21401
  • 1070 Foxcroft Run, Annapolis, MD 21401
    1070 Foxcroft Run, Annapolis, MD 21401
    1070 Foxcroft Run, Annapolis, MD 21401
    /45

    $924,999

    • 4 Beds
    • 3.5 Baths
    • 3,286 Sq Ft

    1070 Foxcroft Run, Annapolis, MD 21401

    Tucked away in the woods on a quiet cul-de-sac, this stunning single-family home sits on a private and picturesque .77-acre lot, offering the perfect blend of tranquility and modern comfort. With 4 spacious bedrooms and 3.5 bathrooms, this home features a bright, open floor plan designed for both everyday living and entertaining. The Spacious kitchen with windows on 2 sides and stainless

    Louis Pope Trademark Realty, Inc

    1070 Foxcroft Run, Annapolis, MD 21401
  • 22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    /79

    $2,550,000 Open Sat 3PM - 5PM

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    22 E Lake Dr, Annapolis, MD 21403

    Welcome to 22 E Lake Drive! This exceptional waterfront residence offers striking architectural elements with expansive, light-filled interiors and seamless indoor-outdoor living along the Chesapeake Bay.The main level open floor plan is designed for effortless flow and everyday living. The living room anchors the space, featuring a floor-to-ceiling stone fireplace and a wall of bi-fold glass

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    22 E Lake Dr, Annapolis, MD 21403
  • 707 Pilot House Dr, Annapolis, MD 21401
    707 Pilot House Dr, Annapolis, MD 21401
    707 Pilot House Dr, Annapolis, MD 21401
    /45

    $945,000

    • 4 Beds
    • 4.5 Baths
    • 4,797 Sq Ft

    707 Pilot House Dr, Annapolis, MD 21401

    Welcome to this exceptional Kingsport 4 BR, 5 BA home with over 4600+ SF of beautifully designed finished living space tailored for both everyday comfort and unforgettable entertaining. Thoughtfully enhanced by its original owners, the home features over $150K in state of the art, commercial grade electronics, seamlessly integrating lighting, whole-home audio, and premium theatre systems

    Moe Farley Coldwell Banker Realty

    707 Pilot House Dr, Annapolis, MD 21401
  • 605 Lighthouse Landing Ln, Annapolis, MD 21409
    605 Lighthouse Landing Ln, Annapolis, MD 21409
    605 Lighthouse Landing Ln, Annapolis, MD 21409
    /51

    $1,018,000

    • 6 Beds
    • 4.5 Baths
    • 4,041 Sq Ft

    605 Lighthouse Landing Ln, Annapolis, MD 21409

    Welcome to 605 Lighthouse Landing Ln, located on a quiet corner lot. This home has 6 bedrooms, 4 1⁄2 baths, designed with an open floor plan. The great room on the first level has a den with fireplace, breakfast nook, and kitchen. Also on the first floor is the living room, foyer, dining room, and a primary bedroom with shower and soak in tub also there are two large, his and hers walk in

    Nathalie Mullinix Nathalie Mullinix Realty Universal, Inc.

    605 Lighthouse Landing Ln, Annapolis, MD 21409
  • 3 Elliott Rd, Annapolis, MD 21403
    3 Elliott Rd, Annapolis, MD 21403
    3 Elliott Rd, Annapolis, MD 21403
    /44

    $745,000

    • 4 Beds
    • 2 Baths
    • 2,928 Sq Ft

    3 Elliott Rd, Annapolis, MD 21403

    3 Elliott Road offers a fantastic opportunity to own a well-maintained two-unit duplex with completely separate living spaces and entrances on opposite sides of the property—ideal for investors or owner-occupants seeking rental income. Unit 1 (Vacant) is a spacious 2-bedroom, 1-bath residence featuring high ceilings, hardwood floors, and abundant natural light. The unit includes an updated

    Benjamin Mueller Innovative Properties, Inc.

    3 Elliott Rd, Annapolis, MD 21403
  • 1519 Winchester Rd, Annapolis, MD 21409
    1519 Winchester Rd, Annapolis, MD 21409
    1519 Winchester Rd, Annapolis, MD 21409
    /34

    $849,000

    • 5 Beds
    • 3 Baths
    • 2,375 Sq Ft

    1519 Winchester Rd, Annapolis, MD 21409

    Set on a beautifully landscaped 0.34-acre corner lot in sought-after Winchester-on-the-Severn, this thoughtfully renovated residence offers a seamless blend of style, comfort, and everyday livability. A fully fenced backyard creates a private outdoor retreat, complete with a deck, patio, garden, playground, and storage shed, perfectly designed for both entertaining and relaxed daily living.

    Brad Kappel TTR Sotheby's International Realty

    1519 Winchester Rd, Annapolis, MD 21409
  • 327 Riverview Trail, Annapolis, MD 21401
    327 Riverview Trail, Annapolis, MD 21401
    327 Riverview Trail, Annapolis, MD 21401
    /40

    $2,495,000

    • 3 Beds
    • 3.5 Baths
    • 1,831 Sq Ft

    327 Riverview Trail, Annapolis, MD 21401

    Picturesque Craftsman-style waterfront cottage in Epping Forest! Mornings begin with coffee on the porch as the water glistens across Saltworks Creek and stretches out to the Severn River, while evenings are spent gathered by the firepit, watching boats drift by under painted skies. Welcome to effortless waterfront living in the private, gated community of Epping Forest where every day feels like

    Brad Kappel TTR Sotheby's International Realty

    327 Riverview Trail, Annapolis, MD 21401
  • 220 West St, Annapolis, MD 21401
    220 West St, Annapolis, MD 21401
    220 West St, Annapolis, MD 21401
    /41

    $924,900

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    220 West St, Annapolis, MD 21401

    Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced,

    Vishal Doddanna Keller Williams Realty Centre

    220 West St, Annapolis, MD 21401
  • 1223 Madison St, Annapolis, MD 21403
    1223 Madison St, Annapolis, MD 21403
    1223 Madison St, Annapolis, MD 21403
    /36

    $609,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,488 Sq Ft

    1223 Madison St, Annapolis, MD 21403

    Fully updated 4-bedroom, 2-bath home in the heart of Eastport offering modern finishes, flexible living space, and a walkable location just minutes from downtown Annapolis, marinas, restaurants, and waterfront parks. The main level features a bright living room, dining area, and upgraded kitchen with stainless steel appliances. Three bedrooms and one full bath complete this level, along with

    Michelle Boretti Coldwell Banker Realty

    1223 Madison St, Annapolis, MD 21403
  • 1576 Saint Margarets Rd, Annapolis, MD 21409
    1576 Saint Margarets Rd, Annapolis, MD 21409
    1576 Saint Margarets Rd, Annapolis, MD 21409
    /44

    $690,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    1576 Saint Margarets Rd, Annapolis, MD 21409

    Welcome to 1576 St. Margaret’s Road, a meticulously rebuilt rancher set on a peaceful 1.89-acre level lot. If you’ve been searching for single-level living with room to breathe, this is the one. The spacious layout offers a seamless flow between the living and dining areas, creating the perfect setting for both everyday living and entertaining. With two bedrooms and a full bath on each side of

    Anthony Scholl Taylor Properties

    1576 Saint Margarets Rd, Annapolis, MD 21409
  • 767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    /50

    $1,175,000

    • 5 Beds
    • 4 Baths
    • 3,255 Sq Ft

    767 Bon Haven Dr, Annapolis, MD 21401

    Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive water access community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including

    Sean O'Connor Coldwell Banker Realty

    767 Bon Haven Dr, Annapolis, MD 21401
  • 92 Clifford Blvd, Annapolis, MD 21401
    92 Clifford Blvd, Annapolis, MD 21401
    92 Clifford Blvd, Annapolis, MD 21401
    /64

    $835,000

    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    92 Clifford Blvd, Annapolis, MD 21401

    Welcome home to this beautifully maintained transitional Craftsman in sought-after Clifford Estates, NO HOA! From the moment you arrive, you’re greeted by a spacious Trex front porch, the perfect place to sip your morning coffee, unwind after a long day, and wave to neighbors passing by. Step inside to discover an inviting, light filled interior featuring Brazilian cherry hardwood flooring,

    Chad Robertson Compass

    92 Clifford Blvd, Annapolis, MD 21401
  • 101 Huse Dr, Annapolis, MD 21403
    101 Huse Dr, Annapolis, MD 21403
    101 Huse Dr, Annapolis, MD 21403
    /45

    $800,000

    • 4 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    101 Huse Dr, Annapolis, MD 21403

    YES, YOU CAN HAVE IT ALL. Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes. The kitchen, the great room... this is the hub. The heart of the home. And the best part? You’re not dreaming about what it could be—the work is already done. Big island, open flow—everyone ends up here. Whether you’re cooking, hanging out, or just

    Kristi Krankowski RE/MAX One

    101 Huse Dr, Annapolis, MD 21403
  • 2977 Southaven Dr, Annapolis, MD 21401
    2977 Southaven Dr, Annapolis, MD 21401
    2977 Southaven Dr, Annapolis, MD 21401
    /44

    $849,900

    • 4 Beds
    • 4 Baths
    • 1,936 Sq Ft

    2977 Southaven Dr, Annapolis, MD 21401

    Set on 2.48 private acres with potential subdivision opportunity, this beautiful log home offers the perfect mix of character, space, and thoughtful updates. Surrounded by mature trees and landscaping, the property provides peaceful treetop views and seasonal water views during the winter months. The two-story living room features a striking wood-burning fireplace and opens to the dining area and

    David Moore Real Broker, LLC

    2977 Southaven Dr, Annapolis, MD 21401
  • 509 Chesapeake Ave, Annapolis, MD 21403
    509 Chesapeake Ave, Annapolis, MD 21403
    509 Chesapeake Ave, Annapolis, MD 21403
    /24

    $975,000

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    509 Chesapeake Ave, Annapolis, MD 21403

    Located just moments from the shoreline, 509 Chesapeake Ave presents a rare opportunity to secure a 4-bedroom, 2-bath single-family home in one of Annapolis’s most desirable waterfront-adjacent areas. Whether you’re an investor searching for your next project or a homeowner ready to create your dream coastal retreat, this property offers incredible potential. The home features a spacious layout

    Kayla Ziegenhein LPT Realty, LLC

    509 Chesapeake Ave, Annapolis, MD 21403
  • 141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    /56

    $1,125,000

    • 5 Beds
    • 4.5 Baths
    • 5,140 Sq Ft

    141 Stilly Way, Annapolis, MD 21403

    She’s one and a half years young. She’s flawless. She’s Annapolis. Welcome to 141 Stilly Way — a barely lived-in, fully upgraded showpiece in the sought-after Parkside Preserve, offered in true mint condition. This is not a builder sale. This is the finished product — every bump-out, every upgrade, every design decision already made at the highest level. No waiting. No construction. No

    Wendy Oliver Coldwell Banker Realty

    141 Stilly Way, Annapolis, MD 21403
  • 163 Prince George St, Annapolis, MD 21401
    163 Prince George St, Annapolis, MD 21401
    163 Prince George St, Annapolis, MD 21401
    /65

    $1,425,000

    • 3 Beds
    • 2.5 Baths
    • 2,434 Sq Ft

    163 Prince George St, Annapolis, MD 21401

    Located on one of the most charming and desirable streets in Historic Annapolis, this beautifully updated home offers a rare combination of timeless character, thoughtful improvements, and an exceptional sense of space and privacy. With no direct neighbors in front or behind, the home enjoys an open, airy setting that is hard to find in such a prime downtown location.Inside, historic details

    Teresa Klem Long & Foster Real Estate, Inc.

    163 Prince George St, Annapolis, MD 21401
  • 103 Roselawn Rd, Annapolis, MD 21403
    103 Roselawn Rd, Annapolis, MD 21403
    103 Roselawn Rd, Annapolis, MD 21403
    /33

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    103 Roselawn Rd, Annapolis, MD 21403

    Discover the charm of this delightful ranch-style home nestled in the serene Primrose Acres neighborhood. Built in 1956, this well-maintained residence boasts 1,287 square feet of inviting living space, featuring three spacious bedrooms and two full bathrooms, perfect for comfortable living. Step inside to find a warm and welcoming atmosphere, enhanced by thoughtful interior features that create

    Rosalie Petsu Long & Foster Real Estate, Inc.

    103 Roselawn Rd, Annapolis, MD 21403
  • 706 Drake Way, Annapolis, MD 21401
    706 Drake Way, Annapolis, MD 21401
    706 Drake Way, Annapolis, MD 21401
    /44

    $905,000

    • 4 Beds
    • 4.5 Baths
    • 4,571 Sq Ft

    706 Drake Way, Annapolis, MD 21401

    Experience the best of Annapolis living in this beautifully cared-for Kingsport home, offering a perfect blend of comfort, style, and thoughtful upgrades. Built by Basheer & Edgemoore, this 4 bedroom, 4.5 bath residence welcomes you with a bright two-story foyer and an inviting layout designed for both everyday living and effortless entertaining.Hardwood floors, plantation shutters. recessed

    Anne Harrington Coldwell Banker Realty

    706 Drake Way, Annapolis, MD 21401
  • 1716 Severn Forest Dr, Annapolis, MD 21401
    1716 Severn Forest Dr, Annapolis, MD 21401
    1716 Severn Forest Dr, Annapolis, MD 21401
    /81

    $5,775,000

    • 5 Beds
    • 6 Baths
    • 6,573 Sq Ft

    1716 Severn Forest Dr, Annapolis, MD 21401

    Set on 4.5 scenic acres along the Severn River, this exceptional Tudor/French Country estate blends timeless architecture with high-end craftsmanship just 10 minutes from downtown Annapolis. Panoramic views of the Severn, set the tone for this exceptional property, complemented by a conditiioned detached two-car garage with private guest quarters complete with a kitchenette and full bath. Outdoor

    Georgie Berkinshaw Coldwell Banker Realty

    1716 Severn Forest Dr, Annapolis, MD 21401

Showing Results 1 - 40, Page 1 of 3

Maryland Anne Arundel County Annapolis

Houses for Sale in Annapolis, MD

Why Live in Annapolis

Steeped in maritime heritage, Annapolis combines historic colonial charm with modern waterfront living. The United States Naval Academy stands as a cornerstone of the city, where visitors can explore "The Yard" and see midshipmen in training. The Maryland State House, featuring the largest wooden dome constructed without nails in the U.S., represents the oldest state capitol in continuous legislative use. Downtown's Main Street leads to City Dock, known as "Ego Alley," where boats parade through the harbor against a backdrop of waterfront restaurants like Carrol's Creek Cafe and Chart House.

The Annapolis real estate market presents diverse housing options across distinct neighborhoods. Downtown Annapolis features historic properties with a median single family home price of $1,447,500. The waterfront community of Eastport commands a median single family home price of $1,102,500. West Annapolis Wardour provides a more suburban feel with a median single family home price of $790,000. The citywide median sale price stands at $615,000, with townhomes at $485,000 and condos ranging from $343,000 for one bedroom to $399,000 for two bedrooms.

Property taxes in Annapolis remain competitive at 0.85%, lower than Baltimore's 1.48%. The Maryland state income tax rate is 4.75%, with an additional Anne Arundel County tax rate of 2.81%. The education landscape includes several highly rated private institutions such as Indian Creek School and Key School, both rated A plus by Niche. South River High School stands out among public options with an A rating. Commuters benefit from Annapolis Transit bus service and water taxis, with Washington D.C. and Baltimore each approximately 30 miles away. The climate features humid summers and mild winters, with 47 inches of annual rainfall and 13 inches of snow.

Learn more about living in Annapolis

Home Trends in Annapolis, MD

On average, homes in Annapolis, MD sell after 37 days on the market compared to the national average of 55 days. The median sale price for homes in Annapolis, MD over the last 12 months is $625,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$625,000
Median Single Family Sale Price
$815,000
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$420,000
Median 1 Bedroom Sale Price
$459,900
Average Price Per Sq Ft
$355
Number of Homes for Sale
241
Last 12 months Home Sales
1,304
Months of Supply
2.20
Median List Price
$634,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%

Popular Home Searches in Annapolis, MD

In Annapolis, waterfront living and historic charm are top priorities, especially near Eastport and the historic district.

How to Buy a Home How to Finance a Home How to Sell a Home

In Annapolis, there are currently 117 houses for sale, offering an array of options for potential buyers. With houses priced between $338,000 to $8,750,000, there's a range to accomodate every budget. As of April, 2026 the median home price in Annapolis is $634,500, while the average sale price is $844,075, offering insights into the local housing market. On average, houses spend 37 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Annapolis, MD and find the perfect place to call home.

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