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Historic Homes for Sale in Annapolis, MD

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  • 2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403
    /96

    $610,000

    $65K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403

    Dramatic Price Reduction just taken on this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. This 2nd Village location provides the perfect short walk to Chase Pond, the Bay View pool, the kayak beach, tennis and pickleball courts and both community piers on Chesapeake Bay, no car needed. When the autumn leaves fall you have even more of a water view until they bloom

    Agent Photo

    Lorna Kaim

    Compass

    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403
  • 1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    /52

    $3,750,000

    $200K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 6,594 Sq Ft

    1715 Porters Hill Rd, Annapolis, MD 21401

    Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715 Porters Hill Road is a unique heritage property with over a century of history. Set on a 1.7 acre lot with 265 ft of waterfrontage, the property includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 7+ ft water depth and can

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    1715 Porters Hill Rd, Annapolis, MD 21401
  • 709 Skippers Ln, Annapolis, MD 21401
    709 Skippers Ln, Annapolis, MD 21401
    709 Skippers Ln, Annapolis, MD 21401
    /45

    $590,000

    $5K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 3,016 Sq Ft

    709 Skippers Ln, Annapolis, MD 21401

    Experience Ultimate Flexibility with this Versatile and Spacious Contemporary Townhome offering Unique Zoning flexibility , 3 Finished levels with 3,016sf, and a Rare Live/Work Opportunity in Village Greens of Annapolis! Operate a boutique business, studio, or professional office right from your street-level commercial space with no commute - previously a boutique shop - with a convenient

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    709 Skippers Ln, 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.

    17151717 Porters Hill Rd, Annapolis, MD 21401
  • 165 King George St, Annapolis, MD 21401
    165 King George St, Annapolis, MD 21401
    165 King George St, Annapolis, MD 21401
    /61

    $1,375,000

    • 4 Beds
    • 3 Baths
    • 2,649 Sq Ft

    165 King George St, Annapolis, MD 21401

    There are very few multifamily dwelling units in the City of Annapolis. This creates a rare and amazing opportunity for buyers to own one of the few existing multifamily dwelling units that’s a triplex. There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term

    Michele Michael CENTURY 21 New Millennium

    165 King George St, Annapolis, MD 21401
  • 2002 Dakota Place Unit 2A, Annapolis, MD 21403
    2002 Dakota Place Unit 2A, Annapolis, MD 21403
    2002 Dakota Place Unit 2A, Annapolis, MD 21403
    /31

    $619,000

    $31K PRICE DROP
    • 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
  • 1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    /87

    $2,999,900

    • 5 Beds
    • 4.5 Baths
    • 5,260 Sq Ft

    1486 Downham Market, Annapolis, MD 21401

    There are waterfront homes...and then there are waterfront estates that redefine luxury. Welcome to 1486 Downham Market, an extraordinary deep-water retreat in the prestigious Downs on the Severn, where timeless architecture, exceptional craftsmanship, and one of the finest protected waterfront settings in the region come together to create a home that is truly without equal. Perfectly positioned

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • 2734 Gingerview Ln, Annapolis, MD 21401
    2734 Gingerview Ln, Annapolis, MD 21401
    2734 Gingerview Ln, Annapolis, MD 21401
    /48

    $665,000

    • 3 Beds
    • 3.5 Baths
    • 2,727 Sq Ft

    2734 Gingerview Ln, Annapolis, MD 21401

    Pristine, freshly painted townhome in the Summer Village section of Riva Trace offers over 2,700 square feet of living space on three finished levels. Ideally positioned on the northeast side of Gingerview Lane, the back of the home opens out to private wooded and winter water views. The living room, screened porch, and primary suite overlook a thick canopy of mature trees leading to the banks of

    Sarah Greenlee Morse TTR Sotheby's International Realty

    2734 Gingerview Ln, Annapolis, MD 21401
  • 979 Bramleigh Ln, Annapolis, MD 21401
    979 Bramleigh Ln, Annapolis, MD 21401
    979 Bramleigh Ln, Annapolis, MD 21401
    /53

    $1,125,000

    • 4 Beds
    • 3.5 Baths
    • 4,080 Sq Ft

    979 Bramleigh Ln, Annapolis, MD 21401

    Welcome to this exceptional single-family home nestled in one of Annapolis' most desirable neighborhoods. Offering more than 4,000 square feet of thoughtfully designed living space, this beautiful residence features 4 spacious bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. Step inside to an inviting open floor plan highlighted by a dramatic two-story great

    Robert Breeden Berkshire Hathaway HomeServices Homesale Realty

    979 Bramleigh Ln, Annapolis, MD 21401
  • 1501 Ritchie St, Annapolis, MD 21401
    1501 Ritchie St, Annapolis, MD 21401
    1501 Ritchie St, Annapolis, MD 21401
    /68

    $1,295,000

    $130K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,017 Sq Ft

    1501 Ritchie St, Annapolis, MD 21401

    Welcome to this impeccably maintained and extensively updated ranch-style residence, offering an exceptional blend of luxury, comfort, and resort-inspired living just minutes from historic Annapolis. From the moment you arrive, the quality craftsmanship and meticulous attention to detail are evident throughout. At the heart of the home is a beautifully appointed gourmet kitchen featuring premium

    Bob Chew Samson Properties

    1501 Ritchie St, Annapolis, MD 21401
  • 1286 Ketch Ct, Annapolis, MD 21403
    1286 Ketch Ct, Annapolis, MD 21403
    1286 Ketch Ct, Annapolis, MD 21403
    /80

    $925,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,856 Sq Ft

    1286 Ketch Ct, Annapolis, MD 21403

    Welcome to Ketch Court, tucked away in the highly sought-after waterfront community of Annapolis Cove. With four bedrooms, two-and-a-half bathrooms, a finished basement with brand-new flooring, and a huge backyard, this home offers the space and flexibility to fit just about any stage of life. Hardwood floors create a warm, welcoming feel throughout the main level, while the family room fireplace

    Jennifer Schaub EXP Realty, LLC

    1286 Ketch Ct, Annapolis, MD 21403
  • 219 Lockwood Ct, Annapolis, MD 21403
    219 Lockwood Ct, Annapolis, MD 21403
    219 Lockwood Ct, Annapolis, MD 21403
    /38

    $1,750,000

    • 4 Beds
    • 4 Baths
    • 1,848 Sq Ft

    219 Lockwood Ct, Annapolis, MD 21403

    Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center

    John Collins Long & Foster Real Estate, Inc.

    219 Lockwood Ct, Annapolis, MD 21403
  • 10 Ironstone Ct, Annapolis, MD 21403
    10 Ironstone Ct, Annapolis, MD 21403
    10 Ironstone Ct, Annapolis, MD 21403
    /22

    $335,000

    Open Sat 11AM - 1PM $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    10 Ironstone Ct, Annapolis, MD 21403

    IGNORE DAYS ON MARKET BUYER FAILED TO PERFORM**FHA APPROVED!** This is **NOT a condominium**—it's a townhome with the convenience of condo-style exterior maintenance. The HOA takes care of **the roof, siding, gutters, shutters, pressure washing, and other exterior maintenance**, giving you more time to enjoy homeownership and less time worrying about upkeep. Can we say, BONUS?! Welcome to 10A

    Kimberlee Randall Group EXP Realty, LLC

    10 Ironstone Ct, Annapolis, MD 21403
  • 6 President Point Dr Unit B3, Annapolis, MD 21403
    6 President Point Dr Unit B3, Annapolis, MD 21403
    6 President Point Dr Unit B3, Annapolis, MD 21403
    /38

    $975,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    6 President Point Dr Unit B3, Annapolis, MD 21403

    Experience a hassle-free waterfront lifestyle at The Point on Spa Creek, where this stunning condo offers exceptionally easy living with picturesque views overlooking Historic Annapolis and Spa Creek. This spacious 2 bedroom 2 bath condo with flexible loft space features beautifully appointed rooms and is just steps away from the clubhouse, pool, dock, and scenic walking paths. The expansive

    Brad Kappel TTR Sotheby's International Realty

    6 President Point Dr Unit B3, Annapolis, MD 21403
  • 7048 Harbour Village Ct Unit 202, Annapolis, MD 21403
    7048 Harbour Village Ct Unit 202, Annapolis, MD 21403
    7048 Harbour Village Ct Unit 202, Annapolis, MD 21403
    /36

    $625,000

    • 2 Beds
    • 2.5 Baths
    • 1,592 Sq Ft

    7048 Harbour Village Ct Unit 202, Annapolis, MD 21403

    Welcome to the sought-after waterfront community of Chesapeake Harbour! This beautiful 2-bedroom, 2.5-bath end unit condo offers a spacious, light-filled floor plan with a rare combination of features. Transom windows above sliding doors and windows in the living and dining rooms adds even more light. The updated kitchen is designed for both everyday living and entertaining, showcasing granite

    Catherine Hamel Long & Foster Real Estate, Inc.

    7048 Harbour Village Ct Unit 202, Annapolis, MD 21403
  • 936 Bay Ridge Ave Unit 201, Annapolis, MD 21403
    936 Bay Ridge Ave Unit 201, Annapolis, MD 21403
    /2

    $388,000

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft

    936 Bay Ridge Ave Unit 201, Annapolis, MD 21403

    Welcome to Conte Gardens, one of Eastport's most desirable condominium communities! Thisspacious and beautifully maintained 2-bedroom, 2-bath residence offers comfort, security, and easylow-maintenance living. With elevator access and secure building entry. This move-in-ready home isideally located in the heart of Eastport, just minutes from downtown Annapolis.This

    Florence Calvert Coldwell Banker Realty

    936 Bay Ridge Ave Unit 201, Annapolis, MD 21403
  • 111 Conduit St, Annapolis, MD 21401
    111 Conduit St, Annapolis, MD 21401
    111 Conduit St, Annapolis, MD 21401
    /24

    $985,000

    $10K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft

    111 Conduit St, Annapolis, MD 21401

    111 Conduit Street is historic Annapolis living at its finest. Nestled in the heart of Historic Annapolis, this charming semi-detached residence seamlessly blends timeless character with modern convenience. Located just moments from Main Street, the City Dock, shops, restaurants, and waterfront attractions, this home offers the quintessential Annapolis lifestyle. Inside, original hardwood floors,

    Benjamin Mueller Innovative Properties, Inc.

    111 Conduit St, Annapolis, MD 21401
  • 1622 Secretariat Dr, Annapolis, MD 21409
    1622 Secretariat Dr, Annapolis, MD 21409
    1622 Secretariat Dr, Annapolis, MD 21409
    /26

    $424,900

    • 3 Beds
    • 1.5 Baths
    • 1,060 Sq Ft

    1622 Secretariat Dr, Annapolis, MD 21409

    Located in the sought after Revell Downs community and blue ribbon Broadneck School District, this move in ready home features tasteful updates throughout and is just minutes from waterfront parks, marinas, shopping, dining, and historic Annapolis. It provides the perfect balance of neighborhood charm, everyday convenience, and the Chesapeake Bay lifestyle! The solar panels are owned by the

    Michael Patrick RE/MAX United Real Estate

    1622 Secretariat Dr, Annapolis, MD 21409
  • 1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
    /63

    $675,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,602 Sq Ft

    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401

    Welcome to the highly sought-after “Davenport” corner unit in the prestigious GrandView community — perfectly positioned in one of the most desirable locations in the Annapolis Town Center. This exceptional residence is filled with natural light thanks to a stunning wall of windows, offering breathtaking sunset views each evening. Step outside to your private covered corner balcony and enjoy the

    David Yee Coldwell Banker Realty

    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
  • 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
  • 124 Treblis Way, Annapolis, MD 21403
    124 Treblis Way, Annapolis, MD 21403
    124 Treblis Way, Annapolis, MD 21403
    /40

    $725,000

    • 4 Beds
    • 5 Baths
    • 2,180 Sq Ft

    124 Treblis Way, Annapolis, MD 21403

    Experience the perfect blend of style, space, and low maintenance living in this beautifully appointed Lennar townhome, built in 2023. Thoughtfully designed across four finished levels, this truly turnkey home offers 4 bedrooms, 3 full baths, 2 half baths, and the flexibility today's lifestyle demands. From the moment you enter, you'll appreciate the abundance of natural light streaming through

    Jackie Reinauer Long & Foster Real Estate, Inc.

    124 Treblis Way, Annapolis, MD 21403
  • 214 Bowen Ct, Annapolis, MD 21401
    214 Bowen Ct, Annapolis, MD 21401
    214 Bowen Ct, Annapolis, MD 21401
    /5

    $1,080,000

    Coming Soon
    • 6 Beds
    • 4.5 Baths
    • 4,685 Sq Ft

    214 Bowen Ct, Annapolis, MD 21401

    Prepare to be absolutely wowed. Nestled in one of Annapolis's most sought-after communities, this stunning six-bedroom, four-and-a-half-bathroom Colonial has been completely and thoughtfully renovated from top to bottom, delivering a rare combination of timeless elegance, modern luxury and exceptional space across three beautifully finished levels. Step inside and immediately feel the difference.

    Kathleen Moore Engel & Völkers Annapolis

    214 Bowen Ct, Annapolis, MD 21401
  • 927 Old Annapolis Neck Rd, Annapolis, MD 21403
    927 Old Annapolis Neck Rd, Annapolis, MD 21403
    /2

    $1,100,000

    $700K PRICE DROP
    • Land
    • 1.5 Acres
    • $733,333 per Acre

    927 Old Annapolis Neck Rd, Annapolis, MD 21403

    Lots 2, 3 & 4 For Sale – Rare Builder/Developer Opportunity in Annapolis, MD (Anne Arundel County) Exceptional opportunity to acquire three fully buildable lots in a newly approved minor subdivision in one of Annapolis’ most desirable locations. These three premium lots comprise approximately 1.5 acres and are ideally suited for luxury custom homes. Large buildable parcels in Annapolis are

    Ana Lopez Equity Property Investments

    927 Old Annapolis Neck Rd, Annapolis, MD 21403
  • 202 Wardour Dr, Annapolis, MD 21401
    202 Wardour Dr, Annapolis, MD 21401
    202 Wardour Dr, Annapolis, MD 21401
    /59

    $2,149,000

    $616K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,100 Sq Ft

    202 Wardour Dr, Annapolis, MD 21401

    Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    202 Wardour Dr, Annapolis, MD 21401
  • 146 Duke of Gloucester St, Annapolis, MD 21401
    146 Duke of Gloucester St, Annapolis, MD 21401
    146 Duke of Gloucester St, Annapolis, MD 21401
    /58

    $1,999,999

    • 4 Beds
    • 3.5 Baths
    • 3,042 Sq Ft

    146 Duke of Gloucester St, Annapolis, MD 21401

    Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this

    Rob Carter Douglas Realty, LLC

    146 Duke of Gloucester St, Annapolis, MD 21401
  • 413 Blossom Tree Ct, Annapolis, MD 21409
    413 Blossom Tree Ct, Annapolis, MD 21409
    413 Blossom Tree Ct, Annapolis, MD 21409
    /36

    $385,000

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,494 Sq Ft

    413 Blossom Tree Ct, Annapolis, MD 21409

    Welcome to 413 Blossom Tree Court, a beautifully cared‐for duplex in the highly sought‐after Whispering Woods community on the Broadneck Peninsula. This lovingly maintained 3‐bedroom, 2‐full‐bath home offers a functional layout, thoughtful updates, and exceptional access to parks, trails, and everyday conveniences. The main level features a bright, renovated (2023) kitchen with granite

    Lynn Gardner Coldwell Banker Realty

    413 Blossom Tree Ct, Annapolis, MD 21409
  • 114 Sellew Rd, Annapolis, MD 21401
    114 Sellew Rd, Annapolis, MD 21401
    114 Sellew Rd, Annapolis, MD 21401
    /35

    $1,350,000

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

    114 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 end unit home on Lot 9. Sturbridge Homes is offering a generous pre-construction incentive package for early buyers. Submit your

    Alison Wisnom Coldwell Banker Realty

    114 Sellew Rd, Annapolis, MD 21401
  • 20 Shaw St, Annapolis, MD 21401
    20 Shaw St, Annapolis, MD 21401
    20 Shaw St, Annapolis, MD 21401
    /41

    $1,049,900

    Open Sun 1PM - 3PM $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    20 Shaw St, Annapolis, MD 21401

    Imagine walking a block to a delightful waterside park or a hot new Annapolis restaurant or a classic rock and roll concert and walk a block or two back home! Nestled in the heart of downtown Annapolis in the highly sought-after neighborhood of Murray Hill, this charming Colonial, originally built in 1925 and extensively remodeled in 2016, offers the perfect blend of historic character with

    Kate Hopkins Coldwell Banker Realty

    20 Shaw St, Annapolis, MD 21401
  • 11 1/2 College Ave, Annapolis, MD 21401
    11 1/2 College Ave, Annapolis, MD 21401
    11 1/2 College Ave, Annapolis, MD 21401
    /59

    $1,295,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,501 Sq Ft

    11 1/2 College Ave, Annapolis, MD 21401

    2 OPEN HOUSE OPPORTUNITIES THIS WEEKEND! Saturday, 8/8 from 12-2PM and Sunday 8/9 from 1-3PM! Now offered at an exceptional value in today's market. A rare opportunity to own a completely renovated home in the heart of the Historic District, featuring all-new plumbing, electrical, and high-end finishes throughout. This completely reimagined home is ideally situated on prestigious College Avenue

    Joanna Dalton Coldwell Banker Realty

    11 1/2 College Ave, Annapolis, MD 21401
  • 14 E Lake Dr, Annapolis, MD 21403
    14 E Lake Dr, Annapolis, MD 21403
    14 E Lake Dr, Annapolis, MD 21403
    /49

    $3,997,000

    • 5 Beds
    • 6 Baths
    • 6,234 Sq Ft

    14 E Lake Dr, Annapolis, MD 21403

    Bay Ridge Waterfront! Built by Pilli Custom Homes and beautifully curated by Erin Paige Pitts Interiors, this exceptional waterfront residence blends timeless architecture, impeccable craftsmanship, and extraordinary attention to detail. Rich custom millwork, extensive crown molding, elegant wainscoting, and coffered ceilings create an atmosphere of refined luxury throughout. A welcoming

    Brad Kappel TTR Sotheby's International Realty

    14 E Lake Dr, Annapolis, MD 21403
  • 75 Shipwright St, Annapolis, MD 21401
    75 Shipwright St, Annapolis, MD 21401
    75 Shipwright St, Annapolis, MD 21401
    /94

    $1,449,000

    $101K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,557 Sq Ft

    75 Shipwright St, Annapolis, MD 21401

    75 Shipwright Street is an enchanting Victorian semi-detached home located in the heart of the Historic District of downtown Annapolis. This is a rare opportunity to own a five-bedroom historic home directly across from St. Mary's School (Pre-K-12), allowing students to walk to class while enjoying all that Historic Annapolis has to offer. Built around 1910, this four-level residence offers a

    Norman Lee III Anne Arundel Properties, Inc.

    75 Shipwright St, Annapolis, MD 21401
  • 1227 Creek Dr, Annapolis, MD 21403
    1227 Creek Dr, Annapolis, MD 21403
    1227 Creek Dr, Annapolis, MD 21403
    /13

    $15,000

    $10K PRICE DROP
    • Land
    • 17,859 Sq Ft
    • $36,585 per Acre

    1227 Creek Dr, Annapolis, MD 21403

    ONLINE AUCTION: Bidding begins 7/30/2026, 10:00 AM. Bidding ends 8/03/2026, 12:40 PM. 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 Maryland's

    Adam Shpritz Ashland Auction Group

    1227 Creek Dr, Annapolis, MD 21403
  • 100 Oak Dr, Annapolis, MD 21403
    100 Oak Dr, Annapolis, MD 21403
    100 Oak Dr, Annapolis, MD 21403
    /49

    $845,000

    • 4 Beds
    • 3 Baths
    • 2,229 Sq Ft

    100 Oak Dr, Annapolis, MD 21403

    OPEN HOUSE FRIDAY 8/7/26 2-4PM Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle.The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025),

    Lauren Emrick Innovative Properties, Inc.

    100 Oak Dr, Annapolis, MD 21403
  • 607 Melvin Ave, Annapolis, MD 21401
    607 Melvin Ave, Annapolis, MD 21401
    607 Melvin Ave, Annapolis, MD 21401
    /58

    $899,000

    • 2 Beds
    • 2 Baths
    • 1,102 Sq Ft

    607 Melvin Ave, Annapolis, MD 21401

    Open House Saturday July 11th, 11AM - 1PM! Come Join us to see this adorable bungalow in a prime West Annapolis Location! Easy one-level living with a great fenced-in yard and a large, detached garage. Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe, Always Ice Cream Company & more! Just a short distance to Downtown

    Joanna Dalton Coldwell Banker Realty

    607 Melvin Ave, Annapolis, MD 21401
  • 1019 President St, Annapolis, MD 21403
    1019 President St, Annapolis, MD 21403
    1019 President St, Annapolis, MD 21403
    /25

    $390,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft

    1019 President St, Annapolis, MD 21403

    * Price Drop! Don't miss out on this beautiful fully updated Eastport home for less than $400k! * Welcome to 1019 President St in the heart of Eastport—where charm, space, and modern upgrades come together just minutes from the water and Historic Annapolis. This beautifully renovated 3-bedroom, 2-bath home offers a rare combination of cozy living and exceptional outdoor space. Situated on an

    Aderyn Bright CENTURY 21 New Millennium

    1019 President St, Annapolis, MD 21403
  • 50 Sandstone Ct, Annapolis, MD 21403
    50 Sandstone Ct, Annapolis, MD 21403
    50 Sandstone Ct, Annapolis, MD 21403
    /10

    $280,000

    • 2 Beds
    • 2 Baths
    • 1,010 Sq Ft

    50 Sandstone Ct, Annapolis, MD 21403

    Welcome to 50-G Sandstone Court, nestled in the desirable Annapolis Overlook community, where comfort, convenience, and easy living come together. This beautifully maintained 2-bedroom, 2-bath condominium is truly move-in ready and offers a bright, welcoming atmosphere you'll be proud to call home. Step inside to discover a spacious, open-concept living area that creates the perfect setting for

    Karen Richardson Coldwell Banker Realty

    50 Sandstone Ct, Annapolis, MD 21403
  • 104 Groh Ln, Annapolis, MD 21403
    104 Groh Ln, Annapolis, MD 21403
    104 Groh Ln, Annapolis, MD 21403
    /53

    $745,000

    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    104 Groh Ln, Annapolis, MD 21403

    There are homes that impress you. Then there are homes that make you imagine a completely different way of living. Imagine ending your workday with a walk to the beach to watch the sun set over the Chesapeake Bay. Weekend mornings begin with coffee on your deck surrounded by mature trees, afternoons are spent boating on the South River, swimming at the community pool, or exploring Quiet Waters

    Wendy Oliver Coldwell Banker Realty

    104 Groh Ln, 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
    /49

    $799,900

    • 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 in this small coastal community! NO HOA!! Pride of ownership shows! With a primary suite on the main level and another primary suite on the upper level, this home is perfect for multi-generational living and accessibility! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 large bedroom with a

    Deanna Marshall The KW Collective

    3280 Arundel on The Bay Rd, Annapolis, MD 21403
  • 1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    /46

    $2,250,000

    • 5 Beds
    • 7 Baths
    • 8,278 Sq Ft

    1614 Annesley Ct, Annapolis, MD 21401

    Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five-bedroom, seven-bathroom home combines timeless architecture, modern updates, and resort-inspired outdoor living. A grand two-story foyer welcomes you with a sweeping curved staircase and soaring ceilings. The main level is

    Brad Kappel TTR Sotheby's International Realty

    1614 Annesley Ct, Annapolis, MD 21401
  • 8 Constitution Square, Annapolis, MD 21401
    8 Constitution Square, Annapolis, MD 21401
    8 Constitution Square, Annapolis, MD 21401
    /26

    $995,000

    $33K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,751 Sq Ft

    8 Constitution Square, Annapolis, MD 21401

    Live the ultimate Downtown Annapolis lifestyle at 8 Constitution Square. Tucked away on a quiet, neighborly cul-de-sac in Murray Hill, this home offers a seamless blend of tranquility and effortless downtown walkability. Skip the parking headaches of historic downtown. Here, you'll enjoy your own private driveway on a low traffic street, giving you a true neighborhood feel right in the heart of

    Whitney Jerdal Compass

    8 Constitution Square, Annapolis, MD 21401

Showing Results 1 - 40, Page 1 of 2

Maryland Anne Arundel County

Real Estate & Homes for Sale in Annapolis, MD

Home Prices in Annapolis, MD

The median home sale price in Annapolis, MD is $638,250, up 4% year-over-year. Homes in Annapolis sell in 36 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$638,250
Median Single Family Sale Price
$840,000
Median Townhouse Sale Price
$470,000
Median 2 Bedroom Sale Price
$452,450
Median 1 Bedroom Sale Price
$399,375
Average Price Per Sq Ft
$360
Number of Homes for Sale
269
Last 12 months Home Sales
1,314
Months of Supply
2.50
Median List Price
$650,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%

Popular Home Searches in Annapolis, MD

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

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