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Sold for $600,000
  • $600,000

    866 Chestnut Tree Dr, Annapolis, MD 21409

    5beds
    2,842sqft
    Single Family Residence
    Built in 1960
    9,000 Square Feet Lot
    $600,000 Zestimate®
    $211/sqft
    $3,802 Estimated rent

    Home value

    $600,000

    $564,000 - $636,000

    $3,802/mo

    Zestimate® history
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    What's special

    Sunlight fills the homeSpacious fenced backyardBeautiful hardwood floorsLong driveway
    The best part of coming home isn’t the house. It’s the life waiting for you. Picture yourself pulling into the long driveway after a day in Downtown Annapolis, just minutes away. Sunlight fills the home as you step onto beautiful hardwood floors, and the kitchen with its timeless white cabinetry becomes the place where everyone naturally gathers. Whether you’re hosting friends, helping with homework, or enjoying a quiet morning coffee, every space feels warm, bright, and welcoming. Upstairs, the primary suite offers a peaceful retreat with its own bathroom and walkout deck, while two additional bedrooms and another full bath provide room for everyone. Need extra flexibility? The bonus room is ready to become your home office, playroom, game room, or the storage space you’ve always wanted. Downstairs, you’ll find two more bedrooms, a full bathroom, and a spacious recreation area that’s perfect for movie nights, guests, or multigenerational living. Step outside to a spacious, fenced backyard that’s ready for everything from backyard games to summer cookouts and relaxing evenings under the stars. And when you’re ready to explore, Cape St. Claire offers one of Annapolis’ most sought-after lifestyles, with community beaches, parks, marinas, boat ramps, and Chesapeake Bay access just moments away. With Route 50 nearby, commuting to Baltimore or Washington, D.C. is easy, while Downtown Annapolis, local restaurants, shopping, and the Broadneck Peninsula’s waterfront charm are all just minutes from your front door. This isn’t just a place to live. It’s a place to build your next chapter.

    Zillow last checked:

    Listing updated:

    Listed by:

    Kevin Brown 410-212-2477,

    Samson Properties

    Bought with:

    Brittany Gough, 668074

    Samson Properties

    Source: Bright MLS,MLS#: MDAA2153252MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 3
    • Full bathrooms: 3
    • Main level bathrooms: 2
    • Main level bedrooms: 3
    Basement
    • Area: 1120
    Heating
    • Central, Electric, Oil
    Cooling
    • Central Air, Electric
    Appliances
    • Included: Microwave, Dishwasher, Dryer, Self Cleaning Oven, Oven, Oven/Range - Electric, Range Hood, Refrigerator, Washer, Washer/Dryer Stacked, Water Heater, Stainless Steel Appliance(s), Electric Water Heater
    • Laundry: In Basement, Main Level
    Features
    • Attic, Breakfast Area, Ceiling Fan(s), Combination Dining/Living, Recessed Lighting, Bathroom - Stall Shower, Upgraded Countertops, Dry Wall
    • Flooring: Hardwood, Wood
    • Basement: Finished
    • Number of fireplaces: 1
    • Fireplace features: Brick, Equipment, Mantel(s), Marble
    Interior area
    • Total structure area: 2,842
    • Total interior livable area: 2,842 sqft
    • Finished area above ground: 1,722
    • Finished area below ground: 1,120

    Property

    Parking
    • Parking features: Asphalt, Driveway
    • Has uncovered spaces: Yes
    Accessibility
    • Accessibility features: None
    Features
    • Levels: Two and One Half
    • Stories: 2.5
    • Patio & porch: Deck, Porch
    • Exterior features: Lighting, Flood Lights
    • Pool features: None
    • Fencing: Vinyl
    • Waterfront features: River
    Lot
    • Size: 9,000 Square Feet
    Details
    • Additional structures: Above Grade, Below Grade
    • Parcel number: 020316523329332
    • Zoning: R5
    • Special conditions: Standard

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Ranch/Rambler
    • Property subtype: Single Family Residence
    Materials
    • Vinyl Siding
    • Foundation: Slab
    • Roof: Shingle
    Condition
    • New construction: No
    • Year built: 1960

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Well
    • Utilities for property: Cable Connected

    Community & HOA

    Community
    • Subdivision: Cape St Claire
    HOA
    • Has HOA: No
    Location
    • Region: Annapolis

    Financial & listing details

    • Price per square foot: $211/sqft
    • Tax assessed value: $404,833
    • Annual tax amount: $4,617
    • Date on market: 8/6/2026
    • Listing agreement: Exclusive Right To Sell
    • Listing terms: Cash,Conventional,FHA,VA Loan
    • Ownership: Fee Simple

    Price history

    DateEventPrice
    8/25/2026Sold$600,000+4.3%$211/sqft
    Source: Bright MLS #MDAA2153252 Report a problem
    8/10/2026Pending sale$575,000$202/sqft
    Source: Bright MLS #MDAA2153252 Report a problem
    8/10/2026Listing removed$575,000$202/sqft
    Source: Bright MLS #MDAA2153252 Report a problem
    8/8/2026Pending sale$575,000$202/sqft
    Source: Bright MLS #MDAA2153252 Report a problem
    8/6/2026Listed for sale$575,000+49.4%$202/sqft
    Source: Bright MLS #MDAA2153252 Report a problem
    11/15/2019Sold$385,000+1.6%$135/sqft
    Source: Public Record Report a problem
    9/13/2019Pending sale$379,000$133/sqft
    Source: Cottage Street Realty LLC #MDAA400186 Report a problem
    6/22/2019Price change$379,000+5.6%$133/sqft
    Source: Cottage Street Realty LLC #MDAA400186 Report a problem
    5/17/2019Listed for sale$359,000$126/sqft
    Source: Cottage Street Realty LLC #MDAA400186 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$4,575 +14.5%$384,867 +5.5%
    2024$3,996 +4%$364,900 +3.7%
    2023$3,843 +8.5%$351,933 +3.8%
    2022$3,542 +4%$338,967 +4%
    2021$3,407 +5.3%$326,000 +5.4%
    2020$3,235 +5.6%$309,267 -5.1%
    2019$3,063 +9.5%$326,000 +18.2%
    2018$2,797 +0.8%$275,800 +1.3%
    2017$2,775 $272,267 +1.3%
    2016-- $268,733 +1.3%
    2015-- $265,200
    2014-- $265,200
    2013-- $265,200 -2.9%
    2012-- $273,000
    2011-- $273,000
    2010-- $273,000 -15.9%
    2009-- $324,670 +11.7%
    2008-- $290,622 +13.3%
    2007-- $256,576 +15.3%
    2006-- $222,530 +16.7%
    2005-- $190,762 +20%
    2004-- $158,996 +25%
    2003-- $127,230 +2%
    2002-- $124,796 +2%
    2001-- $122,363
    Find assessor info on the county website

    Neighborhood: 21409

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Cape St Claire
    • Middle: Magothy River
    • High: Broadneck
    • District: Anne Arundel County Public Schools

    Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value
    $600,000
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $600,000