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Historic Homes for Sale in Annapolis, MD

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  • /49

    $699,000

    $21K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft

    1132 Bay Ridge Rd, Annapolis, MD 21403

    Motivated Seller - Bring all offers! Beautiful, well maintained, quality one level living home with basement with water privileges at the end of Lake Ogleton, delivering the ultimate move-in ready experience. Fantastic location on private lane with lots of “New” in 2026 including new roof, skylight with remote shade, kitchen window, heat pump, hot water heater, carpet, sliding glass door, freshly

    Wendy Trebbe Blackwell Real Estate, LLC

    1132 Bay Ridge Rd, Annapolis, MD 21403
  • /17

    $305,000

    • 3 Beds
    • 2 Baths
    • 1,333 Sq Ft

    10 Sandstone Ct, Annapolis, MD 21403

    Spring has arrived, and this beautifully updated 3-bedroom, 2-bath condo offers the perfect opportunity to enjoy the best of the Annapolis lifestyle. Located on the 3rd floor, this light-filled home combines modern upgrades, comfort, and unbeatable access to outdoor recreation and waterfront attractions. Inside, the open-concept living, dining, and kitchen area creates a warm and inviting flow,

    Sharee Covington Smart Realty, LLC

    10 Sandstone Ct, Annapolis, MD 21403
  • /42

    $464,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1 Bath
    • 1,368 Sq Ft

    410 Walnut Dr, Annapolis, MD 21403

    A CHERISHED FAMILY CLASSIC IN WATERFRONT HILLSMERE ESTATES! 410 Walnut Road presents a rare opportunity in one of Annapolis’s most coveted water-privileged communities. Lovingly maintained by the same family, this home serves as a beautiful foundation for your future memories and personal design touches. Three bedrooms with a traditional layout which include rich hardwood flooring, adding a layer

    Linda Pelton Taylor Properties

    410 Walnut Dr, Annapolis, MD 21403
  • /2

    $1,500,000

    Open Sun 1PM - 3PM Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,159 Sq Ft

    107 Monticello Ave, Annapolis, MD 21401

    Nestled in the highly coveted Murray Hill neighborhood, one of Annapolis' most picturesque enclaves, this exceptional 1925 Craftsman masterpiece effortlessly blends historic charm with sophisticated modern luxury. Rich in architectural character and thoughtfully enhanced with extensive renovations, this remarkable residence offers an unparalleled lifestyle defined by elegance, convenience, and

    Alexandra Ryan EXP Realty, LLC

    107 Monticello Ave, Annapolis, MD 21401
  • /51

    $2,295,000

    $155K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,178 Sq Ft

    83 Market St, Annapolis, MD 21401

    This exceptional Historic District home combines the charm of a classic Annapolis address with a substantial 2026 renovation in all the right places. A stunning new kitchen, custom wet bar, expanded pantry area, completely reimagined third floor, new full bath, and new HVAC system bring modern function and style to this timeless home. Water access is at the end of the block, Acton's Cove

    Elizabeth Dooner Coldwell Banker Realty

    83 Market St, Annapolis, MD 21401
  • /37

    $639,900

    • 3 Beds
    • 2 Baths
    • 1,910 Sq Ft

    852 Woodmont Rd, Annapolis, MD 21401

    Welcome to easy, one-level living in Heritage Harbour, Annapolis's premier 55+ active adult community. This detached, single-family home offers 3 bedrooms, 2 full baths, and a desirable floor plan designed for comfort and convenience. A spacious family room addition provides extra living space for relaxing, entertaining, or gathering with family and friends. The cozy natural gas fireplace creates

    Deborah Randall Next Step Realty

    852 Woodmont Rd, Annapolis, MD 21401
  • /32

    $369,900

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    1008 Cedar Ridge Ct, Annapolis, MD 21403

    Welcome to this updated 3-bedroom, 2 full and 1 half bath townhome in the Cedar Ridge community, just minutes from downtown Annapolis! From the moment you arrive, this home invites you to slow down, settle in, and enjoy a lifestyle filled with comfort, convenience, and charm. Step inside and discover fresh updates that make everyday living feel special. New luxury vinyl plank flooring flows

    Diane Donnelly Keller Williams Flagship

    1008 Cedar Ridge Ct, Annapolis, MD 21403
  • /34

    $1,295,000

    New Construction
    • 3 Beds
    • 5 Baths
    • 3,100 Sq Ft

    108 Sellew Rd, Annapolis, MD 21401

    Hard Hat Tours are now available by appointment! Early buyers have the opportunity to customize their home's finish colors and materials. Don't wait! Construction is moving along and the builder will make selections for any unreserved homes.This listing is for an interior home on Lot 6. Sturbridge Homes is offering a generous pre-construction incentive package for early buyers. Submit your

    Alison Wisnom Coldwell Banker Realty

    108 Sellew Rd, Annapolis, MD 21401
  • /26

    $1,495,000

    $104K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,033 Sq Ft

    158 Prince George St, Annapolis, MD 21401

    RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significant residence with a gambrel roof structure and features header and English bond brick walls. This property has been thoughtfully adapted for modern living while preserving its timeless character and craftsmanship. Ideally located

    Marion Brenner Long & Foster Real Estate, Inc.

    158 Prince George St, Annapolis, MD 21401
  • /46

    $12,500,000

    • 5 Beds
    • 6.5 Baths
    • 5,993 Sq Ft

    5 Franklin St, Annapolis, MD 21401

    A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and

    Brad Kappel TTR Sotheby's International Realty

    5 Franklin St, Annapolis, MD 21401
  • /62

    $750,000

    • 2 Beds
    • 2.5 Baths
    • 1,672 Sq Ft

    1915 Towne Centre Blvd Unit 1014, Annapolis, MD 21401

    Perched on the coveted south side of the 10th floor at GrandView Luxury Condominiums, Residence 1014 is more than a home—it is a private sanctuary above the treetops, where elegance, tranquility, and breathtaking views converge.Boasting a rare, unobstructed southern exposure, this exceptional residence captures panoramic vistas stretching more than 20 miles into Southern Maryland. Whether

    David Yee Coldwell Banker Realty

    1915 Towne Centre Blvd Unit 1014, Annapolis, MD 21401
  • /43

    $589,000

    • 3 Beds
    • 3 Baths
    • 1,730 Sq Ft

    1016 Timber Creek Dr, Annapolis, MD 21403

    Welcome to 1016 Timber Creek Drive, a well maintained home nestled in the sought-after Timber Creek community of Annapolis. Featuring 3 bedrooms, 3 full baths, and three levels of living space, this home offers the perfect blend of comfort, functionality, and style. The main level showcases hardwood floors, a gas fireplace with marble surround, and an updated kitchen remodeled by Realistic

    Georgie Berkinshaw Coldwell Banker Realty

    1016 Timber Creek Dr, Annapolis, MD 21403
  • /49

    $995,995

    • 4 Beds
    • 4 Baths
    • 3,759 Sq Ft

    553 Choptank Cove Ct, Annapolis, MD 21401

    Tax records are incorrect the house has approximately 4000 square feet of living space.English Tudor featuring large slate patio, flagstone retaining wall and small covered front porch, surrounded by mature trees and extensive landscaping. HVAC 2 zone system replaced with high efficiency units in 2021 & 2022. Driveway repaved and expanded in 2020. Great room with cathedral beamed ceiling,

    Linda Patterson Long & Foster Real Estate, Inc.

    553 Choptank Cove Ct, Annapolis, MD 21401
  • /60

    $1,099,500

    $51K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,288 Sq Ft

    996 Headwater Rd, Annapolis, MD 21403

    Annapolis Waterfront home 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 living room with a wood-burning

    Amanda Greenfield Engel & Völkers Annapolis

    996 Headwater Rd, 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
  • /37

    $2,150,000

    • 5 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    250 Prince George St, Annapolis, MD 21401

    Perfectly positioned in the heart of downtown Annapolis, this distinguished historic residence offers a rare opportunity to own a piece of the city’s architectural legacy while enjoying the convenience of two coveted off-street parking spaces. Overlooking the beautifully preserved grounds of St. John’s College, the home captures timeless views that enhance its already exceptional setting. Steeped

    Brad Kappel TTR Sotheby's International Realty

    250 Prince George St, Annapolis, MD 21401
  • /48

    $725,000

    Open Sat 10AM - 12PM
    • 4 Beds
    • 5 Baths
    • 2,500 Sq Ft

    103 Norma Aly, Annapolis, MD 21403

    Welcome to Primrose Hill, one of Annapolis' most desirable hidden gems, where modern luxury meets the unmatched lifestyle of Maryland's capital city. Perfectly positioned just minutes from Downtown Annapolis, Eastport, City Dock, the United States Naval Academy, waterfront restaurants, marinas, parks, and endless Chesapeake Bay adventures, this stunning four-level residence offers the rare

    Wendy Oliver Coldwell Banker Realty

    103 Norma Aly, Annapolis, MD 21403
  • /6

    $579,900

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,280 Sq Ft

    40 Munroe Ct, Annapolis, MD 21401

    3 Level Colonial Brimming with Classic Charm and Timeless Character. This Home Features a Welcoming Covered Front Porch, Perfect for Relaxing and Enjoying the Neighborhood Setting. Inside, you’ll Find Spacious Bedrooms and Hardwood Floors that Add Warmth and Potential Throughout.This Property is Ready for a Full Renovation, Offering an Incredible Opportunity for Investors, Builders or Buyers

    Matthew Altizer ANR Realty, LLC

    40 Munroe Ct, Annapolis, MD 21401
  • /92

    $3,849,000

    • 6 Beds
    • 4.5 Baths
    • 4,474 Sq Ft

    16 Maryland Ave, Annapolis, MD 21401

    A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends

    Joanna Dalton Coldwell Banker Realty

    16 Maryland Ave, Annapolis, MD 21401
  • /24

    $374,900

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

    15 Copley Ct, Annapolis, MD 21403

    Welcome to 15 Copley Ct, ideally situated in one of Annapolis's most convenient locations! This home offers easy access to historic Downtown Annapolis, the U.S. Naval Academy, and Westfield Annapolis Mall—putting shopping, dining, and waterfront charm just minutes away. Enjoy living with HOA amenities including TWO community pools and a pickleball court, perfect for staying active and social

    Marielys Montero RE/MAX Excellence Realty

    15 Copley Ct, Annapolis, MD 21403
  • /15

    $1,265,000

    New Construction
    • 3 Beds
    • 5 Baths
    • 3,300 Sq Ft

    109 Sellew Rd, Annapolis, MD 21401

    Hard Hat Tours are now available by appointment! Early buyers have the opportunity to customize their home's finish colors and materials. Don't wait! Construction is moving along and the builder will make selections for any unreserved homes.This listing is for an interior home on Lot 16. Sturbridge Homes is offering a generous pre-construction incentive package for early buyers. Submit your

    Alison Wisnom Coldwell Banker Realty

    109 Sellew Rd, Annapolis, MD 21401
  • /46

    $3,495,000

    • 3 Beds
    • 2.5 Baths
    • 2,621 Sq Ft

    9 Shipwright St, Annapolis, MD 21401

    Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5

    Brad Kappel TTR Sotheby's International Realty

    9 Shipwright St, Annapolis, MD 21401
  • /55

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 2,307 Sq Ft

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Set elegantly along the marina within the prestigious Chesapeake Harbour, this waterfront townhouse presents a refined composition of craftsmanship, material integrity, and coastal elegance. Moments from the historic charm of Annapolis and the open horizon of the Chesapeake Bay, the residence captures a rare harmony between luxury living and a serene waterfront setting.The interiors reveal a

    Alexander Esfahani Coldwell Banker Realty - Washington

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
  • /35

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 1,524 Sq Ft

    1529 Ritchie Ln, Annapolis, MD 21401

    Nestled in the sought-after Southwoods community just off West Street, this beautifully updated single-family home offers the perfect blend of comfort, style, and convenience with easy access to everything Annapolis has to offer. Inside, luxury vinyl plank flooring flows throughout the inviting two-story floor plan featuring arched entryways, a cozy fireplace, and flexible living spaces designed

    Dee Dee Miller Paul Wesley Real Estate

    1529 Ritchie Ln, Annapolis, MD 21401
  • /24

    $317,000

    $11K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft

    2001 Warners Terrace N Unit 102, Annapolis, MD 21401

    Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the **new price**Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the efficient gas furnace and hot water heater, this well-maintained 2-bedroom, 2-bathroom condominium offers 1,065 square feet of comfortable living space with one standout

    Barbara Bohan Long & Foster Real Estate, Inc.

    2001 Warners Terrace N Unit 102, Annapolis, MD 21401
  • /47

    $774,900

    Open Sat 2PM - 4PM $25K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,064 Sq Ft

    32 Cornhill St, Annapolis, MD 21401

    Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely renovated and remodeled in 2023. New kitchen, new bathroom, recessed lights, new ceiling fans, lighting. Stainless steel appliances. Original hardwood floors. Front bedroom has cathedral ceiling. Exterior home has been completely painted in 2025. New decking off rear of home with a patio. Walking distance to

    Mark Feen Coldwell Banker Realty

    32 Cornhill St, Annapolis, MD 21401
  • /19

    $599,000

    $76K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    3328 Shore Dr, Annapolis, MD 21403

    Price reduced!! 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

    Joanna Dalton Coldwell Banker Realty

    3328 Shore Dr, Annapolis, MD 21403
  • /42

    $424,500

    • 2 Beds
    • 2 Baths
    • 1,464 Sq Ft

    930 Astern Way Unit 204, Annapolis, MD 21401

    Set within the coveted South River condominium in Heritage Harbour, 930 Astern Way #204 offers refined, low-maintenance living in one of Annapolis’s most desirable 55+ waterfront communities. This beautifully appointed residence combines generous proportions, timeless finishes, and effortless elegance, all complemented by the rare and highly sought-after convenience of a deeded garage parking

    Corey Kayea TTR Sotheby's International Realty

    930 Astern Way Unit 204, Annapolis, MD 21401
  • /53

    $2,950,000

    • 4 Beds
    • 5 Baths
    • 3,750 Sq Ft

    238 King George St, Annapolis, MD 21401

    Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps from State Circle, the United States Naval Academy, City Dock, waterfront dining, boutiques, and yacht clubs, 238 King George Street offers a rare opportunity to own a completely reimagined luxury residence in the heart of Maryland’s capital city. Blending timeless historic charm with the modern conveniences

    Wendy Oliver Coldwell Banker Realty

    238 King George St, Annapolis, MD 21401
  • /47

    $1,950,000

    • 6 Beds
    • 4 Baths
    • 3,415 Sq Ft

    192 Duke of Gloucester St, Annapolis, MD 21401

    Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street

    Hanh Pham Samson Properties

    192 Duke of Gloucester St, Annapolis, MD 21401
  • /58

    $1,100,000

    • 4 Beds
    • 4.5 Baths
    • 4,032 Sq Ft

    216 Bowen Ct, Annapolis, MD 21401

    Stately brick traditional in sought-after Bowen Manor community. - Turn key,move- in ready just minutes from Historic Annapolis, major commuter routes, and marinas. Offering spacious, bright living throughout. Built with numerous custom upgrades and additions by the original owner, this beautifully maintained residence combines timeless elegance with thoughtful design and very low maintenance

    Connie Cadwell Coldwell Banker Realty

    216 Bowen Ct, Annapolis, MD 21401
  • /25

    $525,000

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

    8 Spa Creek Landing Unit 8A2, Annapolis, MD 21403

    OPEN SATURDAY 6/6_ 12-2 and SUNDAY 6/7_ 1-3 Come enjoy the ease of single-level living, secure community, and the unmatched lifestyle of waterfront. The warm and inviting living room opens to sweeping Spa Creek Views, while a dazzling kitchen with a picturesque window makes creating a meal a delight...with a wood-buring fireplace and engineered hardwoods. Step outside through sliding doors to a

    Connie Cadwell Coldwell Banker Realty

    8 Spa Creek Landing Unit 8A2, Annapolis, MD 21403
  • /71

    $989,000

    Open Sat 1PM - 3PM
    • 8 Beds
    • 4 Baths
    • 3,108 Sq Ft

    1422 West St, Annapolis, MD 21401

    One of Homewood’s most distinctive homes, this 8-bedroom, 4-bath residence offers over 3,100 square feet and a truly unique story. Once known as the “Gables Tourist Home” Bed & Breakfast, the property (built in 1938) still carries subtle nods to its past—including the numbered bedroom doors—while the current owners have thoughtfully updated the interiors and major systems for comfortable modern

    Rachel Holmes Coldwell Banker Realty

    1422 West St, Annapolis, MD 21401

Showing Results 41 - 73, Page 2 of 2

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