823 Chestnut Tree Dr, Annapolis, MD 21409
Property image
Property image
OFF MARKET

$787,700

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,843 sqft

823 Chestnut Tree Dr, Annapolis, MD 21409

Est. Refi. Payment $4,792/mo*
Refinance Your Home
Currently Off Market - Sold Apr 4, 2024 for $735,000

Home Value

Trulia Estimate
$788K
Since last month
Decreased$500 (-0.1%)
Since last year
Increased$33K (+4.4%)
Since last sale
Increased$53K (+7.2%)
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 +232% in the last 10 years
MonthEstimated value
2026
September 2026$788K
August 2026$788K
July 2026$794K
June 2026$799K
May 2026$801K
April 2026$798K
March 2026$796K
February 2026$787K
January 2026$781K
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
810 Chestnut Tree Dr, Annapolis, MD
0.08
Single-Family Home
$625,000
12/19/25
4
3.5
2,667
1214 Ramblewood Dr, Annapolis, MD
0.15
Single-Family Home
$925,000
01/15/26
5
3.5
3,257
1179 Neptune Pl, Annapolis, MD
0.15
Single-Family Home
$602,000
11/18/25
4
2.5
1,870
1148 Mermaid Dr, Annapolis, MD
0.20
Single-Family Home
$664,900
04/29/26
4
2.5
1,870
935 Marine Dr, Annapolis, MD
0.29
Single-Family Home
$625,000
08/19/26
4
2.5
2,480
1294 Seabright Dr, Annapolis, MD
0.40
Single-Family Home
$735,000
08/28/26
4
3.5
2,784
1181 Ramblewood Dr, Annapolis, MD
0.26
Single-Family Home
$670,000
12/30/25
4
2.5
1,888
726 Hillcrest Dr, Annapolis, MD
0.22
Single-Family Home
$659,000
08/25/26
3
2.5
2,681
1247 Ramblewood Dr, Annapolis, MD
0.20
Single-Family Home
$555,000
01/16/26
4
2.5
1,728

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
810 Chestnut Tree Dr, Annapolis, MD 21409
0.08
$625,000
4
3.5
2,667
Recently Sold
806 Chestnut Tree Dr, Annapolis, MD 21409
0.10
$659,100
3
2.5
3,140
Off Market
1219 Ramblewood Dr, Annapolis, MD 21409
0.11
$508,100
5
2
1,736
Off Market
1228 Ramblewood Dr, Annapolis, MD 21409
0.15
$533,700
4
2.5
1,644
Off Market
1199 Southview Dr, Annapolis, MD 21409
0.16
$570,800
4
2.5
2,100
Off Market
958 Mount Holly Dr, Annapolis, MD 21409
0.18
$612,800
3
2.5
2,224
Off Market
1179 Neptune Pl, Annapolis, MD 21409
0.15
$607,500
4
2.5
1,870
Off Market
1214 Ramblewood Dr, Annapolis, MD 21409
0.15
$925,000
5
3.5
3,257
Recently Sold
1184 Neptune Pl, Annapolis, MD 21409
0.15
$566,400
4
2.5
1,870
Off Market
1247 Ramblewood Dr, Annapolis, MD 21409
0.20
$555,000
4
2.5
1,728
Recently Sold
1180 Neptune Pl, Annapolis, MD 21409
0.17
$653,900
4
2.5
2,329
Off Market

Local Information

  • Map ViewExplore the area around 823 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 2020
2,843 sqft
$277/sqft
2 Car Garage
HOA $1/mo

About this House

Welcome home to Cape St. Claire! Move right in to this stunning newer construction home completed in 2020. Designer touches throughout this 4 bedroom home with 3 full plus 1 half bathrooms and over 2,700 sq ft of finished living space across 3 levels. You'll immediately appreciate the grand, oversized front door welcoming you with a 2 story foyer, designer neutral paint and luxury flooring throughout. Open concept main living level with bright, sun filled rooms. A chef inspired kitchen offers stainless appliances, high end back splash, quartz counters, a large center island with seating and plenty of cabinets. Flowing seamlessly from the kitchen is the dining area and great room with a cozy gas fireplace and glass door to the private, fully fenced rear yard and patio. The main level additionally features a formal living room, a half bathroom and access to the garage and basement level. Travel up the grand foyer to the bedroom level complete with a full laundry room for the utmost convenience. A tranquil primary bedroom suite is sure to please with its large size, tray ceilings, walk in closet and private super bath with tiled shower and soaking tub besides a dual sink vanity. 3 additional, generously sized bedrooms all with fantastic closets and a full hallway bathroom complete the upper level. The lower level offers more living space with a bonus rec room, custom work out room, home office and newly completed full bathroom with plenty of storage and wide walk up stairs to the private rear yard. There is no shortage of space in this modern home. Ample parking with a front loading 2 car garage and bonus parking pad. Just a short walk to schools, beaches, playground and the clubhouse. Broadneck School District. Close to shopping, dining & entertainment with easy commuter access. Schedule your private tour today!
823 Chestnut Tree Dr, Annapolis, MD 21409 is a 4 bedroom, 4 bathroom, 2,843 sqft single-family home built in 2020. It last sold for $735,000 on Apr 4, 2024 (1% above the $725,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $787,700, with a rent estimate of $4,516/month.
Last check for updates: about 11 hours ago
Listed by David Orso, (443) 691-0838
Berkshire Hathaway HomeServices PenFed Realty
Co-Listing Agent: Jessica L Verde, (443) 994-5481
Berkshire Hathaway HomeServices PenFed Realty
Bought with: Kimberly McGrath, (301) 351-5792, Long & Foster Real Estate, Inc.
Source: Bright MLS, MLS#MDAA2077200

Home Details for 823 Chestnut Tree Dr

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2843 Square Feet
Appliances & Utilities
Utilities: Underground UtilitiesAppliances: Disposal, Exhaust Fan, Ice Maker, Stainless Steel Appliance(s), Refrigerator, Water Heater, Cooktop, Oven/Range - Electric, Microwave, Washer, Dryer, Electric Water HeaterDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Gas/PropaneHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Insulated Windows, ScreensDoor: InsulatedFlooring: Wood, Ceramic Tile, Carpet, Laminate
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Wood, Ceramic Tile, Carpet, Laminate
View
Has a ViewView: Garden
Security
Security: Smoke Detector(s), Fire Sprinkler System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, PatioOther Structures: Above Grade, Below GradeFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Faces Front,Inside Entrance,Oversized,Asphalt,Driveway,Attached
Pool
Pool: Community
Frontage
Waterfront: Canoe/Kayak, Boat - Powered, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard, BayResponsible for Road Maintenance: City/CountyRoad Surface Type: Black TopNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Chesapeake Bay
Finished Area
Finished Area (above surface): 1997 Square FeetFinished Area (below surface): 846 Square Feet

Property Information

Year Built
Year Built: 2020
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Craftsman,Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionNo Additional Parcels
Property Information
Condition: ExcellentNot Included in Sale: 2 Chandeliers Located In Child's Bedroom And Kitchen, Wine Fridge & Fridge / Freezer In GarageIncluded in Sale: Shelves In Basement PantryParcel Number: 020316590013891

Price & Status

Price
List Price: $725,000
Status Change & Dates
Off Market Date: Sat Apr 06 2024Possession Timing: 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 Details
Builder Name: Cedar Square Homes
Building Area
Building Area: 2843 Square Feet

Community

Community Features: PoolNot Senior Community

HOA

HOA Fee Includes: Common Area MaintenanceHOA Name: CAPE ST. CLAIRE IMPROVEMENT ASSOCIATIONHas an HOAHOA Fee: $10/Annually

Lot Information

Lot Area: 9000 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2077200Above Grade Unfinished Area: 1997

Additional Information

HOA Amenities: Baseball Field,Basketball Court,Beach Access,Bike Trail,Boat Ramp,Clubhouse,Common Grounds,Community Center,Jogging Path,Marina/Marina Club,Meeting Room,Picnic Area,Pier/Dock,Pool Mem Avail,Tot Lots/Playground,Water/Lake Privileges

Price and Tax history

DateEventPrice
Apr 4, 2024
Source: Bright MLS #MDAA2077200
Sold
$735,000
Mar 2, 2024
Source: Bright MLS #MDAA2077200
Pending
$725,000
Mar 2, 2024
Source: Bright MLS #MDAA2077200
ListingRemoved
Mar 1, 2024
Source: Bright MLS #MDAA2077200
Listed For Sale
$725,000
Jan 12, 2021
Source: N/A
Sold
$599,000

Market trends in Annapolis

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$643K
$1KMoM
Sale-to-List Price
100.0%
Price per sq ft
$331
$6MoM
Available listings
344
11MoM

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."
    1
    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

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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. Click here for more information

Frequently asked questions about 823 Chestnut Tree Dr

  • What is 823 Chestnut Tree Dr estimated to be worth?
    Trulia's estimated value for 823 Chestnut Tree Dr in Annapolis, MD is $787,700.
  • What is the price history for 823 Chestnut Tree Dr?
    823 Chestnut Tree Dr in Annapolis, MD last sold for $735,000 in April 2024.
  • 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 $643K. That is down $1K from the prior month.
  • Does 823 Chestnut Tree Dr have air conditioning?
    Yes, 823 Chestnut Tree Dr in Annapolis, MD has air conditioning.
  • Does 823 Chestnut Tree Dr have a pool?
    Yes, 823 Chestnut Tree Dr in Annapolis, MD has a pool.

Explore by feature - Pet Friendly

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