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866 Chestnut Tree Dr, Annapolis, MD 21409
866 Chestnut Tree Dr, Annapolis, MD 21409
Sold for $600,000
866 Chestnut Tree Dr, Annapolis, MD 21409
Sold for $600,000
866 Chestnut Tree Dr, Annapolis, MD 21409
866 Chestnut Tree Dr, Annapolis, MD 21409
866 Chestnut Tree Dr, Annapolis, MD 21409
866 Chestnut Tree Dr, Annapolis, MD 21409

866 Chestnut Tree Dr Annapolis, MD 21409

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$600,000

CLOSED
Beds
5
Baths
3
Sqft
2,842
Acres
0.21
Year
1960
Close Date
Aug 25, 2026
Property Type
Residential
Sub Type
Per Square Foot
$211
Date Listed
Aug 6, 2026

Description of 866 Chestnut Tree Dr, Annapolis, MD 21409

Listing details for 866 Chestnut Tree Dr, Annapolis, MD 21409 : 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.
Listing Updated : 10-11-2026 at 8:30 AM EDT
Listing Provided By : Kevin Brown, 4102122477, [email protected], Samson Properties

Properties displayed may be listed or sold by various participants in the MLS

Source :

Bright MLS, MLS#: MDAA2153252

What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$515K – $715K
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Comments
What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$515K – $715K
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Property History

DateEventPrice
8/25/2026
Sold
$600,000 +4.3%
$211/sqft
Source:Bright MLS #MDAA2153252
8/8/2026
Pending sale
$575,000 0%
$202/sqft
Source:Bright MLS #MDAA2153252
8/6/2026
Listed for sale
$575,000 0%
$202/sqft
Source:Bright MLS #MDAA2153252
8/3/2026
Coming Soon
$575,000 +49.4%
$202/sqft
Source:Bright MLS #MDAA2153252
11/1/2019
Sold
$385,000
$135/sqft
Source:Bright MLS #MDAA400186
5/17/2019
Listed for sale
—
Source:Bright MLS #MDAA400186

Location of 866 Chestnut Tree Dr, Annapolis, MD 21409

Streetview of 866 Chestnut Tree Dr, Annapolis, MD 21409

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$515K – $715K
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Comments

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc.
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