866 Chestnut Tree Dr, Annapolis, MD 21409
Property image
Property image
SOLD
AUG 25, 2026

$600,000

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 2,842 sqft

866 Chestnut Tree Dr, Annapolis, MD 21409

Est. Refi. Payment $3,543/mo*
Refinance Your Home
Currently Off Market - Sold Aug 25, 2026 for $600,000 (4% above list price)

Home Value

Trulia Estimate
$600K
Since last month
Increased$53K (+9.7%)
Since last year
Increased$79K (+15%)
Since last sale
$100 (0%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +61% in the last 10 years
MonthEstimated value
2026
August 2026$600K
July 2026$547K
June 2026$557K
May 2026$545K
April 2026$541K
March 2026$536K
February 2026$523K
January 2026$518K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
982 Highpoint Dr, Annapolis, MD
0.16
Single-Family Home
$555,000
03/18/26
4
3
2,190
970 Highpoint Dr, Annapolis, MD
0.19
Single-Family Home
$610,000
06/04/26
4
3
2,062
987 Saint Johns Dr, Annapolis, MD
0.19
Single-Family Home
$878,930
09/30/25
4
2.5
2,740
1207 Hampton Rd, Annapolis, MD
0.14
Single-Family Home
$562,500
05/01/26
4
2
2,412
1223 Hampton Rd, Annapolis, MD
0.14
Single-Family Home
$565,000
10/07/25
3
2.5
1,960
1219 Hampton Rd, Annapolis, MD
0.14
Single-Family Home
$1,010,525
02/06/26
4
2.5
3,600
1227 Hampton Rd, Annapolis, MD
0.15
Single-Family Home
$585,000
10/31/25
4
2
2,068

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
989 Dogwood Tree Dr, Annapolis, MD 21409
0.08
$486,500
3
2
1,612
Off Market
1207 Hampton Rd, Annapolis, MD 21409
0.14
$562,500
4
2
2,412
Recently Sold
1217 Hampton Rd, Annapolis, MD 21409
0.14
$896,000
4
2.5
2,700
For Sale
1219 Hampton Rd, Annapolis, MD 21409
0.14
$1,010,525
4
2.5
3,600
Recently Sold
1213 Hampton Rd, Annapolis, MD 21409
0.14
$665,800
3
3
2,500
Off Market
1223 Hampton Rd, Annapolis, MD 21409
0.14
$570,800
3
2.5
1,960
Off Market
975 Dogwood Tree Dr, Annapolis, MD 21409
0.12
$500,700
4
2
1,860
Off Market
919 Blue Ridge Dr, Annapolis, MD 21409
0.13
$464,900
3
2
1,272
Recently Sold
1227 Hampton Rd, Annapolis, MD 21409
0.15
$590,600
4
2
2,068
Off Market
1199 Hampton Rd, Annapolis, MD 21409
0.17
$439,500
3
1
1,227
Off Market
1192 Hampton Rd, Annapolis, MD 21409
0.17
$552,600
4
2.5
1,356
Off Market

Local Information

  • Map ViewExplore the area around 866 Chestnut Tree Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
2,842 sqft
$211/sqft
Open Parking

About this House

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.
866 Chestnut Tree Dr, Annapolis, MD 21409 is a 5 bedroom, 3 bathroom, 2,842 sqft single-family home built in 1960. It last sold for $600,000 on Aug 25, 2026 (4% above the $575,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $600,000, with a rent estimate of $3,802/month.
Last check for updates: about 3 hours ago
Listed by Kevin Brown, (410) 212-2477
Samson Properties
Bought with: Brittany Gough, (301) 367-3616, Samson Properties
Source: Bright MLS, MLS#MDAA2153252

Home Details for 866 Chestnut Tree Dr

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 5Main Level Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2842 Square Feet
Appliances & Utilities
Utilities: Cable ConnectedAppliances: 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 HeaterDishwasherDryerLaundry: In Basement,Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,OilHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Brick, Equipment, Mantel(s), MarbleHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 2.5Levels: Two and One HalfAccessibility: NoneFloors: Hardwood, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, PorchFencing: VinylOther Structures: Above Grade, Below GradeExterior: Lighting, Flood LightsFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Asphalt,Driveway
Pool
Pool: None
Frontage
Waterfront: RiverNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1722 Square FeetFinished Area (below surface): 1120 Square Feet

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Parcel Number: 020316523329332

Price & Status

Price
List Price: $575,000Price Per Sqft: $211/sqft
Status Change & Dates
Off Market Date: Tue Aug 25 2026Possession Timing: 0-30 Days CD, 31-60 Days CD, Immediate, Negotiable, Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: ANNAPOLISCommunity: Cape St Claire
School Information
Elementary School: Cape St ClaireElementary School District: Anne Arundel County Public SchoolsJr High / Middle School: Magothy RiverJr High / Middle School District: Anne Arundel County Public SchoolsHigh School: BroadneckHigh School District: Anne Arundel County Public Schools

Building

Building Area
Building Area: 2842 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 9000 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2153252Above Grade Unfinished Area: 1722

Additional Information

Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Aug 25, 2026
Source: Bright MLS #MDAA2153252
Sold
$600,000
Aug 10, 2026
Source: Bright MLS #MDAA2153252
Pending
$575,000
Aug 10, 2026
Source: Bright MLS #MDAA2153252
ListingRemoved
$575,000
Aug 8, 2026
Source: Bright MLS #MDAA2153252
Pending
$575,000
Aug 6, 2026
Source: Bright MLS #MDAA2153252
Listed For Sale
$575,000

Market trends in Annapolis

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$646K
$11.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$326
$7MoM
Available listings
355
3MoM

Around this home

What Locals Say about Annapolis

At least 470 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 83 % Say car is needed

  • 75 % Say there's holiday spirit

  • 73 % Say parking is easy

  • 73 % Say there are sidewalks

  • 70 % Say yards are well-kept

  • 68 % Say people would walk alone at night

  • 68 % Say kids play outside

  • 66 % Say streets are well-lit

  • 65 % Say it's quiet

  • 63 % Say there's wildlife

  • 57 % Say it's walkable to restaurants

  • 57 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 49 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly neighborhood. But not a lot of green space other than other peoples’ yards. "
    0
    Flag
  • Shannon Chatlos
    "If you like coastal living and a laid-back lifestyle, and are willing to pay for it, this a wonderful place to live."
    0
    Flag
  • Sylvie Bracke
    "It’s a very dog friendly place - I just can’t help wondering why some people don’t clean up after their pets? It’s a nice neighborhood with high end properties & I don’t get that dissonance."
    0
    Flag
  • Erin
    "Safe. On water. Paths in woods. Friendly. Dog play area. Lots of open spaces. Areas are walkable, clean. "
    0
    Flag
  • Halljanie68
    "Community Pool convenient shopping. Easy access to major routes 50/95 Easy access to downtown Annapolis "
    0
    Flag
  • Sheila Wilson
    "A lot of traffic on forest drive very hard to come onto the street. It need a red light or stop sign. Before a serious accident happens. People speed over 40mph"
    0
    Flag
  • Diana H.
    "I’m not sure, I don’t own a dog. Plenty walk by my dead end street house daily though and the neighborhood seems safe for both dogs and owners. "
    0
    Flag
  • Paul Eric Watson
    "Love the urban feel. Lots of history and near the water is a bonus. Very walkable and always something going on. "
    5
    Flag
  • Trulia User
    "Access to Route 50, the Bay Bridge, and Sandy Point State Park. Thirty minutes to Baltimore. Forty minutes to Washington D.C."
    2
    Flag
  • Trulia User
    "It’s a great neighborhood for kids and dogs Lots of walking areas, parks, water park and boat to downtown Annapolis "
    2
    Flag
  • Trulia User
    "It’s a tad busy commute rush hour traffic is something to consider small town lots of people takes about 10-15 min or so to get from one side of town to the other without traffic "
    1
    Flag
  • Trulia User
    "Great school public and private well maintained parks great public libraries close downtown Annapolis shopping for everything is conveniently close "
    0
    Flag
  • Trulia User
    "Lots of families with dogs. Poop bag stations throughout the neighborhood. Lots of woods to walk thru and sidewalks too. "
    1
    Flag
  • Trulia User
    "Nothing is special about my neighborhood. So quiet and nobody talks to anybody. The play area was demolished so no kids can hang out to play."
    4
    Flag
  • Trulia User
    "This is an excellent neighborhood for families and the neighbors are wonderful. Cape St. John gives you access to everything in Annapolis with the tranquility of living along the river."
    0
    Flag
  • Trulia User
    "While Truxton is dog friendly it would be nice to have a dedicated dog park closer than Quiet Waters. "
    0
    Flag
  • Trulia User
    "Wonderful family neighborhood. This neighborhood is very convenient to Hway 50 and all of the Annapolis area. The people here are terrific neighbors."
    0
    Flag
  • Trulia User
    "Good to walk. And parks are nice to play with kids. Stores are close by. And dog walkers all around. "
    0
    Flag
  • Trulia User
    "Summer beach parties, puppy happy hours, annual sock burning, lots of parks and the people are wonderful!"
    0
    Flag
  • Trulia User
    "the history Open napolis is amazing the people around here are kind and friendly and the schools are phenomenal"
    0
    Flag
  • Singletonad
    "the public school system in Annapolis needs to get significantly stronger overall. The private school system here is quite reliable."
    0
    Flag
  • Keren_molina
    "Lovely place and definitely good place to live and have a dog and a lot sores to go buy stuff ..........."
    5
    Flag
  • Singletonad
    "There is no community dog run here and no sidewalks so it can feel awkward letting your dog poop in someone else's yard even if you pick it up. The vast majority of neighbors are dog friendly, but not all, and that is their perogative."
    0
    Flag
  • Raddisob07
    " N/A school are great parking is great close to everything ppl are friendly and been living in Annapolis all my life "
    4
    Flag
  • Tery_hodges
    "I walk my son to elementary school. We can walk to many restaurants and “tourist” shops but do have to drive to get to a grocery store."
    2
    Flag
  • Stephanie.ward0715
    "I've been around this area for years. People are friendly and always willing to help each other. The restaurant's and shopping are also a plus. Everything you are looking for is 5 minutes away."
    0
    Flag
  • Raddisob07
    "None that I know of. The community should definitely do more collaborative events at least at least Quarterly they are family friendly."
    5
    Flag
  • Stella
    "Feel good living here Parking so easy Location very good Many things nearby Old town and new town "
    3
    Flag
  • Jennifer B.
    "It's super quiet and funny, I've leving here for 1 year and I feel safe my neighbors are nice.. Down town is amazing.. ❤️ "
    0
    Flag
  • Kwisniewski805
    "Holiday events and many boating events. There are street fairs, food markets, holiday markets. Community is very close. "
    0
    Flag
  • Cara M. E.
    "I teach at a school that is less than 10 minutes from my house. But there are times that Forest Dr gets incredibly backed up, or there is an accident that causes the road to be shut down. "
    1
    Flag
  • Beth S.
    "Bad area is close by, so kids need to understand boundaries. Private schools are important here, so save your money. Sports are good here, with lots of good coaching."
    0
    Flag
  • Linda D.
    "I've been visiting a dear close friend - helping them recuperate from serious surgery. traffic is atrocious- I miss living in the rural countryside area!"
    0
    Flag
  • Liza
    "The schools in Annapolis are not as good as they are in Severna Park which is where I grew up originally. But Annapolis has many great amenities including local places to eat and shop."
    0
    Flag
  • Rodwellsantos6
    "I like it this community is pretty good as so matters fact for elders we looking to buy in this areas I don’t know frankly about this gorgeous homes we will see."
    0
    Flag
  • Jeffrey H.
    "Lived here for 4 years. Loved the area, including the park across the street. Hate the maintenance of the building including the attention to detail of maintenance of property. "
    0
    Flag
  • jfh4k0
    "Local traffic is not too bad. Beach traffic and rush hour traffic to DC and Baltimore is pretty terrible. "
    2
    Flag
  • Nadja Maril
    "I lived in this neighborhood over 20 years and walk downtown with my dog every morning for coffee. On pretty days we visit City Dock and admire the views and the boats."
    1
    Flag
  • Markkimethanmolly
    "We’ve lived here for 18 years, and everyone is very friendly. Our neighborhood is very safe and quiet."
    0
    Flag
  • Debwill64
    "There is a bus stop close enough to walk to but I have to drive to DC. The bus only goes to Annapolis and maybe Baltimore, not sure though."
    0
    Flag

LGBTQ Local Legal Protections

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. Click here for more information

Frequently asked questions about 866 Chestnut Tree Dr

  • What is 866 Chestnut Tree Dr estimated to be worth?
    Trulia's estimated value for 866 Chestnut Tree Dr in Annapolis, MD is $600,000.
  • What is the price history for 866 Chestnut Tree Dr?
    866 Chestnut Tree Dr in Annapolis, MD last sold for $600,000 in August 2026.
  • Is Annapolis a buyer's or seller's market?
    Annapolis is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Annapolis?
    The median sale price in Annapolis is $646K. That is up $11.67K from the prior month.
  • Does 866 Chestnut Tree Dr have air conditioning?
    Yes, 866 Chestnut Tree Dr in Annapolis, MD has air conditioning.
  • Does 866 Chestnut Tree Dr have laundry facilities?
    Yes, 866 Chestnut Tree Dr in Annapolis, MD has in-unit laundry.

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