38,877

Annapolis, MD Homes

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  • 1247 River Bay Rd, Annapolis, MD 21409
    1247 River Bay Rd, Annapolis, MD 21409
    1247 River Bay Rd, Annapolis, MD 21409
    /48

    $499,900

    • 6 Beds
    • 2 Baths
    • 1,936 Sq Ft

    1247 River Bay Rd, Annapolis, MD 21409

    Welcome Home! This spacious 6-bedroom Split Foyer in the highly sought-after Cape St. Claire community offers Chesapeake Bay views from a prime location directly across the street from the water. With 3 bedrooms on the main level and 3 additional bedrooms on the lower level, this home provides exceptional flexibility for multi-generational living, guests, home offices, or growing households. The

    Agent Photo

    Justin Akchurin

    Coldwell Banker Realty

    1247 River Bay Rd, Annapolis, MD 21409
  • 174 Acton Rd, Annapolis, MD 21403
    174 Acton Rd, Annapolis, MD 21403
    174 Acton Rd, Annapolis, MD 21403
    /32

    $7,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 4,574 Sq Ft
    • House for Rent

    174 Acton Rd, Annapolis, MD 21403

    Welcome to this exceptional 4-bedroom, 4-bath Colonial home ideally situated along Spa Creek. Designed to capture the beauty of its waterfront setting, the residence features a spacious living room with a cathedral ceiling, creating an open and airy atmosphere, along with a dining room and kitchen combination perfect for everyday living and entertaining. Three private balconies overlook the

    Agent Photo

    Cheryl Jersey-Lecourt

    Long & Foster Real Estate, Inc.

    174 Acton Rd, Annapolis, MD 21403
  • 1035 Boucher Ave, Annapolis, MD 21403
    1035 Boucher Ave, Annapolis, MD 21403
    1035 Boucher Ave, Annapolis, MD 21403
    /75

    $1,399,000

    Sold Jun 30, 2026

    1035 Boucher Ave, Annapolis, MD 21403

    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 2021

    Last Sold Summary

    • $583/SF
    • 1 Day On Market

    Current Estimated Value $1,354,006

    Last Listing Agent Kate Liscinsky Compass

    1035 Boucher Ave, Annapolis, MD 21403
    • 116 Lejeune Way, Annapolis, MD 21401
      116 Lejeune Way, Annapolis, MD 21401
      116 Lejeune Way, Annapolis, MD 21401
      /35

      Not Listed For Sale

      116 Lejeune Way, Annapolis, MD 21401

      • 2 Beds
      • 2.5 Baths
      • 1,600 Sq Ft
      • Built 2016
      116 Lejeune Way, Annapolis, MD 21401

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Kellie Gough McLendon Long & Foster Real Estate, Inc.

  • 2758 Bon Haven Ln, Annapolis, MD 21401
    2758 Bon Haven Ln, Annapolis, MD 21401
    2758 Bon Haven Ln, Annapolis, MD 21401
    /25

    $1,150,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    2758 Bon Haven Ln, Annapolis, MD 21401

    Set above the South River on 1.28 acres, 2758 Bon Haven Lane offers the feeling of a private waterfront retreat without sacrificing everyday convenience. Mature trees and over 100 feet of shoreline frame water views and offer the property a wonderfully serene quality. The private pier has approximately five feet of mean low water, two lifts (jet ski and 10,000 lbs), and immediate access to the

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    2758 Bon Haven Ln, Annapolis, MD 21401
  • 2494 Riva Rd, Annapolis, MD 21401
    2494 Riva Rd, Annapolis, MD 21401
    2494 Riva Rd, Annapolis, MD 21401
    /68

    Starting at $1,982 Per Month

    • Studio - 2 Beds

    2494 Riva Rd, Annapolis, MD 21401

    Welcome to the brand-new apartments at Avalon Annapolis, located near the Annapolis historic downtown and adjacent to the Annapolis Town Center. We understand that where you live, is where you come alive, which is why our thoughtfully crafted studio, one-bedroom, and two-bedroom apartment homes feature modern kitchens with sleek quartz countertops and stainless-steel appliances in a variety of

    Avalon Annapolis

    2494 Riva Rd, Annapolis, MD 21401
  • 922 Yachtsman Way, Annapolis, MD 21403
    922 Yachtsman Way, Annapolis, MD 21403
    922 Yachtsman Way, Annapolis, MD 21403
    /23

    $465,000

    Sold Mar 27, 2026

    922 Yachtsman Way, Annapolis, MD 21403

    • 2 Beds
    • 2 Baths
    • 1,354 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Above List Price
    • $343/SF
    • 1 Day On Market

    Current Estimated Value $459,093

    Last Listing Agent Della Edwards Curtis Real Estate Company

    922 Yachtsman Way, Annapolis, MD 21403
    • 706 Riverview Terrace, Annapolis, MD 21401
      706 Riverview Terrace, Annapolis, MD 21401
      706 Riverview Terrace, Annapolis, MD 21401
      /68

      Est $974,695

      Not Listed For Sale

      706 Riverview Terrace, Annapolis, MD 21401

      • 4 Beds
      • 2.5 Baths
      • 2,448 Sq Ft
      • Built 2009
      706 Riverview Terrace, Annapolis, MD 21401

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Cheryl Jersey-Lecourt Long & Foster Real Estate, Inc.

  • 1717 Porters Hill Rd, Annapolis, MD 21401
    1717 Porters Hill Rd, Annapolis, MD 21401
    1717 Porters Hill Rd, Annapolis, MD 21401
    /27

    $1,300,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1717 Porters Hill Rd, Annapolis, MD 21401

    Welcome to 1717 Porters Hill Road, a light-filled contemporary home designed around volume and a seamless connection to its natural surroundings. Framed by expansive windows and soaring architectural lines, the home offers a fresh, airy interior where natural light moves beautifully throughout the day.Inside, the main living spaces unfold with an open floor plan that feels both modern and

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    1717 Porters Hill Rd, Annapolis, MD 21401
  • 1036 Hyde Park Dr, Annapolis, MD 21403
    1036 Hyde Park Dr, Annapolis, MD 21403
    1036 Hyde Park Dr, Annapolis, MD 21403
    /21

    $2,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,254 Sq Ft
    • House for Rent

    1036 Hyde Park Dr, Annapolis, MD 21403

    Lovely home available for immediate occupancy. Main level features a large living room, hardwood floors throughout the kitchen and dining room, a wood-burning fireplace, and a huge primary bedroom with vaulted ceilings, lots of closet space, and a full primary bathroom. Two more bedrooms and a full bath upstairs, and a basement rec room with additional storage space. Beautiful back yard is fully

    Agent Photo

    Andrew Cerrito

    Cerrito Realty, LLC

    1036 Hyde Park Dr, Annapolis, MD 21403
  • 1176 Green Holly Dr, Annapolis, MD 21409
    1176 Green Holly Dr, Annapolis, MD 21409
    1176 Green Holly Dr, Annapolis, MD 21409
    /44

    $865,000

    Sold May 07, 2026

    1176 Green Holly Dr, Annapolis, MD 21409

    • 4 Beds
    • 2.5 Baths
    • 2,594 Sq Ft
    • Built 2022

    Last Sold Summary

    • 3% Below List Price
    • $333/SF
    • 13 Days On Market

    Current Estimated Value $868,982

    Last Listing Agent Michael Klugo Coldwell Banker Realty

    1176 Green Holly Dr, Annapolis, MD 21409
    • 301 Burnside St Unit B202, Annapolis, MD 21403
      301 Burnside St Unit B202, Annapolis, MD 21403
      301 Burnside St Unit B202, Annapolis, MD 21403
      /56

      Est $754,120

      Not Listed For Sale

      301 Burnside St Unit B202, Annapolis, MD 21403

      • 2 Beds
      • 1 Bath
      • 728 Sq Ft
      • Built 1978
      301 Burnside St Unit B202, Annapolis, MD 21403

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Chris May May Realty

  • 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 Under Contract
    • 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
  • 721 S Cherry Grove Ave, Annapolis, MD 21401
    721 S Cherry Grove Ave, Annapolis, MD 21401
    721 S Cherry Grove Ave, Annapolis, MD 21401
    /74

    Starting at $1,966 Per Month

    • 1 - 3 Beds

    721 S Cherry Grove Ave, Annapolis, MD 21401

    Modern, spacious and serene garden style apartments with open breezeways for rent in Annapolis Bay, MD with desirable amenities and a dedicated team. Available one-, two-, and three-bedroom apartment homes with optional garages within a gate community providing comfort, convenience and the best rental experience in the area.

    Annapolis Bay

    721 S Cherry Grove Ave, Annapolis, MD 21401
  • 228 Dubois Rd, Annapolis, MD 21401
    228 Dubois Rd, Annapolis, MD 21401
    228 Dubois Rd, Annapolis, MD 21401
    /93

    $660,000

    Sold Jan 09, 2026

    228 Dubois Rd, Annapolis, MD 21401

    • 4 Beds
    • 3 Baths
    • 2,900 Sq Ft
    • Built 1950

    Last Sold Summary

    • $228/SF
    • 61 Days On Market

    Current Estimated Value $595,014

    Last Listing Agent Deborah Savoie Long & Foster Real Estate, Inc.

    228 Dubois Rd, Annapolis, MD 21401
    • 219 Bowen Ct, Annapolis, MD 21401
      219 Bowen Ct, Annapolis, MD 21401
      219 Bowen Ct, Annapolis, MD 21401
      /58

      Est $925,124

      Not Listed For Sale

      219 Bowen Ct, Annapolis, MD 21401

      • 5 Beds
      • 4.5 Baths
      • 4,601 Sq Ft
      • Built 2008
      219 Bowen Ct, Annapolis, MD 21401

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Jennifer Chino Compass

  • 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 with an Assumable 4.25% VA loan located 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

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    709 Skippers Ln, Annapolis, MD 21401
  • 629 Tripp Creek Ct, Annapolis, MD 21401
    629 Tripp Creek Ct, Annapolis, MD 21401
    629 Tripp Creek Ct, Annapolis, MD 21401
    /10

    $3,200 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,662 Sq Ft
    • Townhouse for Rent

    629 Tripp Creek Ct, Annapolis, MD 21401

    Beautifully updated and move-in ready, this spacious rental offers modern finishes, thoughtful upgrades, and an unbeatable Annapolis location. The interior features updated flooring throughout the main living areas, creating a fresh and inviting atmosphere. The kitchen is equipped with black stainless steel smart appliances, a drop-in sink, and an over-the-range microwave, making meal preparation

    Agent Photo

    Litra Simms

    Simms and Associates

    629 Tripp Creek Ct, Annapolis, MD 21401
  • 1534 Lodge Pole Ct, Annapolis, MD 21409
    1534 Lodge Pole Ct, Annapolis, MD 21409
    1534 Lodge Pole Ct, Annapolis, MD 21409
    /33

    $385,000

    Sold Mar 09, 2026

    1534 Lodge Pole Ct, Annapolis, MD 21409

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 1984

    Last Sold Summary

    • $271/SF
    • 23 Days On Market

    Current Estimated Value $384,991

    Last Listing Agent Gary Durand CENTURY 21 New Millennium

    1534 Lodge Pole Ct, Annapolis, MD 21409
    • 86 Summerfield Dr, Annapolis, MD 21403
      86 Summerfield Dr, Annapolis, MD 21403
      86 Summerfield Dr, Annapolis, MD 21403
      /28

      Est $479,777

      Not Listed For Sale

      86 Summerfield Dr, Annapolis, MD 21403

      • 5 Beds
      • 2 Baths
      • 2,340 Sq Ft
      • Built 1962
      86 Summerfield Dr, Annapolis, MD 21403

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Barry Hess Keller Williams Flagship

  • 2102 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2102 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2102 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    /52

    $685,000

    • 3 Beds
    • 3 Baths
    • 1,666 Sq Ft

    2102 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    Welcome to coastal living at its finest in Annapolis’ gated Chesapeake Harbour community! Enjoy sweeping marina views, fantastic people watching, and resort style amenities including 2 pools, tennis/pickleball courts, kayak access, walking trails, beaches, cocktails and entertainment at the dock bar and waterfront dining at The Beacon Restaurant. This sun drenched 3 bedroom, 3 full bath condo

    Agent Photo

    Lorna Kaim

    Compass

    2102 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • 225 N Calvert St, Baltimore, MD 21202
    225 N Calvert St, Baltimore, MD 21202
    225 N Calvert St, Baltimore, MD 21202
    /34

    Starting at $1,522

    Total Monthly Price

    • 1 - 2 Beds

    225 N Calvert St, Baltimore, MD 21202

    Introducing Baltimore’s newest high-rise apartments, 225 North Calvert Street. With impressive amenities from the lobby to the rooftop. Community programming and social happenings. Open layouts with views of the cityscape from your private balcony. And an ideal, central location that puts you within easy reach of the city’s exciting restaurants, lively nightlife, sporting events, museums, and

    225 N Calvert

    225 N Calvert St, Baltimore, MD 21202
  • 103 Stilly Way, Annapolis, MD 21403
    103 Stilly Way, Annapolis, MD 21403
    103 Stilly Way, Annapolis, MD 21403
    /33

    $1,161,840

    Sold Dec 24, 2025

    103 Stilly Way, Annapolis, MD 21403

    • 5 Beds
    • 5.5 Baths
    • 5,200 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $223/SF
    • 5 Days On Market

    Current Estimated Value $1,169,129

    Lennar Parkeside Preserve - Manor

    103 Stilly Way, Annapolis, MD 21403
    • 806 Coachway, Annapolis, MD 21401
      806 Coachway, Annapolis, MD 21401
      806 Coachway, Annapolis, MD 21401
      /43

      Est $7,002,317

      Not Listed For Sale

      806 Coachway, Annapolis, MD 21401

      • 5 Beds
      • 8 Baths
      • 12,635 Sq Ft
      • Built 2009
      806 Coachway, Annapolis, MD 21401

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Brad Kappel TTR Sotheby's International Realty

  • 605 Admiral Dr, Annapolis, MD 21401
    605 Admiral Dr, Annapolis, MD 21401
    605 Admiral Dr, Annapolis, MD 21401
    /31

    $359,000

    $11K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,214 Sq Ft

    605 Admiral Dr, Annapolis, MD 21401

    Fully Renovated 2 Bedroom Condo in Annapolis! Step into effortless, modern living in this beautifully renovated 2 bedroom, 2 bath one floor condo at 605 B Admiral Dr, Unit 108. Thoughtfully updated from top to bottom, this home offers stylish finishes including crown molding, exceptional storage, and the comfort of truly move in ready living.The renovated kitchen features brand new

    Agent Photo

    Kristen Quinn

    Realty Navigator

    605 Admiral Dr, Annapolis, MD 21401
  • 655 Americana Dr, Annapolis, MD 21403
    655 Americana Dr, Annapolis, MD 21403
    655 Americana Dr, Annapolis, MD 21403
    /28

    Starting at $1,566 Per Month

    • Studio - 3 Beds

    655 Americana Dr, Annapolis, MD 21403

    Our community is operating as normal. Please call or stop by for a tour.

    Nautilus Point

    655 Americana Dr, Annapolis, MD 21403
  • 244 Puritan Place, Annapolis, MD 21409
    244 Puritan Place, Annapolis, MD 21409
    244 Puritan Place, Annapolis, MD 21409
    /95

    $1,500,000

    Sold Apr 30, 2026

    244 Puritan Place, Annapolis, MD 21409

    • 4 Beds
    • 2.5 Baths
    • 3,700 Sq Ft
    • Built 1969

    Last Sold Summary

    • $405/SF
    • 3 Days On Market

    Current Estimated Value $1,489,285

    Last Listing Agent Bobbi Farquhar Engel & Völkers Annapolis

    244 Puritan Place, Annapolis, MD 21409
    • 48 Cornhill St, Annapolis, MD 21401
      48 Cornhill St, Annapolis, MD 21401
      48 Cornhill St, Annapolis, MD 21401
      /42

      Est $904,771

      Not Listed For Sale

      48 Cornhill St, Annapolis, MD 21401

      • 3 Beds
      • 2 Baths
      • 1,448 Sq Ft
      • Built 1850
      48 Cornhill St, Annapolis, MD 21401

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Dawn Riley Deep Roots Real Estate

  • 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
  • 2445 Holly Ave, Annapolis, MD 21401
    2445 Holly Ave, Annapolis, MD 21401
    2445 Holly Ave, Annapolis, MD 21401
    /41

    Starting at $1,984

    Total Monthly Price

    • Studio - 2 Beds

    2445 Holly Ave, Annapolis, MD 21401

    Maris Annapolis: Luxury Apartments in the Heart of Maryland's CapitalExperience a lifestyle unlike any other at Maris in Annapolis. Our pet-friendly community offers resort-inspired living with unmatched amenities, including a state-of-the-art fitness center, yoga and spin studio, outdoor kitchen with BBQ, rooftop pool with private cabanas, and even a rooftop movie theater. Discover refined

    Maris

    2445 Holly Ave, Annapolis, MD 21401
  • 48 Rockwell Ct, Annapolis, MD 21403
    48 Rockwell Ct, Annapolis, MD 21403
    48 Rockwell Ct, Annapolis, MD 21403
    /21

    $337,000

    Sold May 15, 2026

    48 Rockwell Ct, Annapolis, MD 21403

    • 2 Beds
    • 1.5 Baths
    • 1,222 Sq Ft
    • Built 1981

    Last Sold Summary

    • 4% Below List Price
    • $276/SF
    • 5 Days On Market

    Current Estimated Value $338,725

    Last Listing Agent Joshua Shapiro Douglas Realty, LLC

    48 Rockwell Ct, Annapolis, MD 21403
    • 2714 Cabernet Ln, Annapolis, MD 21401
      2714 Cabernet Ln, Annapolis, MD 21401
      2714 Cabernet Ln, Annapolis, MD 21401
      /41

      Est $711,047

      Not Listed For Sale

      2714 Cabernet Ln, Annapolis, MD 21401

      • 4 Beds
      • 3.5 Baths
      • 3,105 Sq Ft
      • Built 2006
      2714 Cabernet Ln, Annapolis, MD 21401

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Nick Waldner Keller Williams Realty Centre

  • 774 Fairview Ave Unit F, Annapolis, MD 21403
    774 Fairview Ave Unit F, Annapolis, MD 21403
    774 Fairview Ave Unit F, Annapolis, MD 21403
    /21

    $545,000

    $90K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,060 Sq Ft

    774 Fairview Ave Unit F, Annapolis, MD 21403

    PRICE ADJUSTED AS SELLERS HAVE FOUND THEIR NEXT HOME! 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, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle.Inside, the residence has been

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    774 Fairview Ave Unit F, Annapolis, MD 21403
  • 116 Stone Point Dr, Annapolis, MD 21401
    116 Stone Point Dr, Annapolis, MD 21401
    116 Stone Point Dr, Annapolis, MD 21401
    /60

    Starting at $2,029

    Total Monthly Price

    • 1 - 3 Beds

    116 Stone Point Dr, Annapolis, MD 21401

    Resort living, Annapolis style. Discover the essentials of living well at Stone Point Apartments. Here, you'll enjoy an unparalleled mix of luxury, convenience and recreation, including a spectacular 10,000 sq. ft. clubhouse with swimming and hydrotherapy pools. With one-, two- and three-bedroom apartments as well as beautiful townhome residences to choose from, you'll think you've arrived at a

    Stone Point Apartments

    116 Stone Point Dr, Annapolis, MD 21401
  • 116 Vanguard Ln, Annapolis, MD 21401
    116 Vanguard Ln, Annapolis, MD 21401
    116 Vanguard Ln, Annapolis, MD 21401
    /72

    $587,500

    Sold Jun 05, 2026

    116 Vanguard Ln, Annapolis, MD 21401

    • 4 Beds
    • 5 Baths
    • 2,450 Sq Ft
    • Built 2016

    Last Sold Summary

    • $240/SF
    • 7 Days On Market

    Current Estimated Value $589,183

    Last Listing Agent Michele Cordle Long & Foster Real Estate, Inc.

    116 Vanguard Ln, Annapolis, MD 21401
    • 1500 Chester Town Cir, Annapolis, MD 21409
      1500 Chester Town Cir, Annapolis, MD 21409
      1500 Chester Town Cir, Annapolis, MD 21409
      /27

      Est $506,748

      Not Listed For Sale

      1500 Chester Town Cir, Annapolis, MD 21409

      • 4 Beds
      • 2.5 Baths
      • 2,069 Sq Ft
      • Built 1999
      1500 Chester Town Cir, Annapolis, MD 21409

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Brian Gearhart Benson & Mangold, LLC

  • 2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    /69

    $569,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,237 Sq Ft

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403

    AMENITY RICH LOCATION!!! Welcome to this beautiful 2 bedroom, 2 bath coveted, spacious and serene 2nd floor end unit condo, located in Second Village just steps away from all of the amenities found in Chesapeake Harbour. Imagine yourself enjoying the Bay front swimming pool, the sandy beach, kayaks, grills, picnic tables, fishing/crabbing piers, jog/walking paths, pickleball and tennis courts,

    Agent Photo

    Lorna Kaim

    Compass

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
  • 1293 Thom Ct, Annapolis, MD 21403
    1293 Thom Ct, Annapolis, MD 21403
    1293 Thom Ct, Annapolis, MD 21403
    /53

    Starting at $1,436 Per Month

    • 1 - 3 Beds

    1293 Thom Ct, Annapolis, MD 21403

    Welcome to Quiet Waters Landing. Our gorgeous apartment community offers one, two, and three bedroom apartments ready for you to move in and call your own. From fantastic in-home features to convenient community amenities, we have it all. Schedule a personalized tour of Quiet Waters Landing and see for yourself.

    Quiet Waters Landing

    1293 Thom Ct, Annapolis, MD 21403
  • 1105 Van Buren St, Annapolis, MD 21403
    1105 Van Buren St, Annapolis, MD 21403
    1105 Van Buren St, Annapolis, MD 21403
    /45

    $660,000

    Sold Aug 21, 2026

    1105 Van Buren St, Annapolis, MD 21403

    • 3 Beds
    • 2 Baths
    • 1,595 Sq Ft
    • Built 1947

    Last Sold Summary

    • 10% Above List Price
    • $414/SF
    • 2 Days On Market

    Current Estimated Value $520,391

    Last Listing Agent Chad Robertson Compass

    1105 Van Buren St, Annapolis, MD 21403
    • 1253 Destiny Cir, Annapolis, MD 21409
      1253 Destiny Cir, Annapolis, MD 21409
      1253 Destiny Cir, Annapolis, MD 21409
      /51

      Est $685,787

      Not Listed For Sale

      1253 Destiny Cir, Annapolis, MD 21409

      • 3 Beds
      • 3 Baths
      • 3,248 Sq Ft
      • Built 2004
      1253 Destiny Cir, Annapolis, MD 21409

      Last Sold Summary

      Last Listing Agent Justin Baker Hyatt & Company Real Estate LLC

Showing Results 1 - 40, Page 1 of 18

Maryland Anne Arundel County

Real Estate & Homes

Home Prices in Annapolis, MD

The median home sale price in Annapolis, MD is $640,000, up 3% year-over-year. Homes in Annapolis sell in 35 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$640,000
Median Single Family Sale Price
$834,700
Median Townhouse Sale Price
$465,000
Median 2 Bedroom Sale Price
$450,000
Median 1 Bedroom Sale Price
$453,700
Average Price Per Sq Ft
$357
Number of Homes for Sale
288
Last 12 months Home Sales
1,295
Months of Supply
2.70
Median List Price
$650,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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