100 Chestnut Dr, Williamsburg, VA 23185
Bedroom 1 with en-suite half bath
Bedroom 4
OFF MARKET

100 Chestnut Dr
Williamsburg, VA 23185

  • 4 Beds
  • 2.5 Baths
  • 2,024 sqft

$450,000

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,499/mo*
Refinance Your Home

$450,000

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,499/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,024 sqft

Local Information

  • Map ViewExplore the area around 100 Chestnut Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Amazing spacious four-bedroom house with garage, deck and fenced yard. This beautiful property is just minutes to the historic Williamsburg area with access to a bike path to the Colonial Parkway. This well-cared for home features hardwood floors throughout the main level, a formal living room with wood burning fireplace, and a fully updated kitchen with a dining area looking out onto the large, beautiful fenced-in backyard with mature landscaping and fig and maple trees. Down the hall find a full bath, the primary bedroom with en-suite half bath, and 4th bedroom. Move upstairs to a comfortable family room and two additional large bedrooms with laminate flooring throughout. Front porch looks out onto a tulip magnolia, crepe myrtles, and roses. Back deck perfect for bird-watching and enjoying seasonal blooms with lots of space for dogs to run. One-car garage with new washer and dryer. Ample parking on the driveway and along the street. A commuter's dream, enjoy easy access to Route 199 for all points east and west.

1-year lease duration minimum (over 1-year negotiable). Unfurnished. Renter responsible for all utilities (e.g., electric, water, sewer, trash, recycling, Internet). Up to 3 pets total allowed (certain breeds restricted). No smoking/vaping allowed. No illegal substances or activities allowed. Renter responsible for yard maintenance. All adult renters must be on lease.
100 Chestnut Dr, Williamsburg, VA 23185 is a 4 bedroom, 3 bathroom, 2,024 sqft single-family home. It last sold for $340,000 on Mar 24, 2023 (12,043% above the $2,800 asking price). More recently, it was listed as a rental in August 2025 with an asking price of $2,800 per month. That rental listing was removed on August 11, 2025. It is currently off market. The Trulia Estimate is $450,000, with a rent estimate of $2,903/month.

Home Highlights

Parking
Attached Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 100 Chestnut Dr

Interior Features

Heating & Cooling
Heating: Forced Air, FireplaceAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached, On Site

Price History for 100 Chestnut Dr

DatePriceEventSource
08/11/2025$2,800ListingRemovedZillow Rentals
08/07/2025$2,800Listed For RentZillow Rentals
03/24/2023$340,000Sold
WMLS #2300435
03/07/2023$329,000PendingWMLS #2300435
03/07/2023$329,000ContingentREIN Inc. #10476519
03/03/2023$329,000Listed For SaleWMLS #2300435

Market trends in Williamsburg

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$472K
$8.33KMoM
Sale-to-List Price
99.8%
0.7%MoM
Price per sq ft
$217
$2MoM
Available listings
504
14MoM
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Property Tax and Assessment

Year2025
Tax$2,677
Assessment$322,500
Home facts updated by county records

Comparable Sales for 100 Chestnut Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2967 Lake Powell Rd, Williamsburg, VA
0.02
Single-Family Home
$365,000
03/12/26
3
2.5
1,682
102 Dogwood Dr, Williamsburg, VA
0.14
Single-Family Home
$397,500
04/16/26
4
2.5
1,700
2847 Hidden Lake Dr, Williamsburg, VA
0.26
Single-Family Home
$428,000
03/23/26
4
2.5
2,249
103 Laurel Ct, Williamsburg, VA
0.27
Single-Family Home
$344,000
05/14/26
3
1.5
1,500
110 Brookwood Dr, Williamsburg, VA
0.30
Single-Family Home
$300,000
11/12/25
3
1.5
1,500
5515 Rolling Woods Dr, Williamsburg, VA
0.28
Single-Family Home
$449,000
10/03/25
5
3.5
2,540
105 Laurel Ct, Williamsburg, VA
0.26
Single-Family Home
$152,000
03/25/26
3
2
1,272
5520 Brixton Rd, Williamsburg, VA
0.51
Single-Family Home
$480,000
05/28/26
3
2.5
2,367
180 Exmoor Ct, Williamsburg, VA
0.44
Single-Family Home
$525,000
04/30/26
4
3.5
2,788
1410 Jamestown Rd, Williamsburg, VA
0.56
Single-Family Home
$400,000
10/30/25
3
2
1,636

Nearby homes

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Assigned Schools

These are the assigned schools for 100 Chestnut Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Williamsburg

At least 503 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 87 % Say car is needed

  • 83 % Say parking is easy

  • 80 % Say there's holiday spirit

  • 78 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 73 % Say yards are well-kept

  • 69 % Say kids play outside

  • 60 % Say there's wildlife

  • 55 % Say neighbors are friendly

  • 55 % Say there are sidewalks

  • 52 % Say they plan to stay for at least 5 years

  • 49 % Say streets are well-lit

  • 36 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 34 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Yfz4k7khrd
    "great access, good people, nice place to live"
    0
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  • Smancilla10
    "Many families with dogs in my neighborhood. It feels safe to walk during the day and at night. All owners pick up after their dogs. "
    0
    Flag
  • Amy Guerin
    "There is a local concert series in spring and summer seasons. Many locals attend, and it’s amazing. "
    0
    Flag
  • Patsy7
    "Ability to walk your dog safely, 99% of the time. Minimum traffic to be concerned about, and it is clean in the streets mostly."
    0
    Flag
  • Laila Richard
    "Colonial Williamsburg is nearby and has community events every holiday. William & Mary College also has many activities and events. "
    0
    Flag
  • R6hqhw7b4c
    "No dogs larger than minis allowed, it is very sad. "
    0
    Flag
  • Carter25102000
    "Easy commute. I’m right by major highways and streets. My drive to work isn’t that bad and drive to Richmond isn’t too bad either"
    0
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  • Betticushing
    "There are many people walking their dogs on leashes and they seem to enjoy the neighborhood. Most people pick up after their dogs, though I’ve seen an occasional pile of doggie poop on the edge of the road. "
    0
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  • Mrs. Alicia D. roberts
    "Nice walking trails, a lot of bark parks, there is nothing they would t like as long as they are taken care of."
    0
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  • Romamer
    "We have Veteran’s Park a mile away that has play area for kids, free pickleball courts, and beautiful gardens with a picnic area. "
    0
    Flag
  • Aiden Mills
    "Unless your work is in Williamsburg a car is always needed. Traffic is not bad and only really gets congested around the tourist areas and even then it’s not too bad."
    0
    Flag
  • Casheeish
    "The historic area of Colonial Williamsburg is located conveniently nearby and provides an excellent venue for dog walking"
    0
    Flag
  • Aiden Mills
    "Dog owners would love the grass and dog park in my area. Owners would not like the amount of cars going through my neighborhood."
    0
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  • Casheeish
    "The Grand Illumination and Independence Day festivities in the historic area of Colonial Williamsburg are celebrations unique to our community. "
    0
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  • Ashlee C
    "My commute can range anywhere from seven to eleven minutes depending on traffic. It’s a very easy ride to work and I’m greatful for that!"
    0
    Flag
  • Jygz8p77tx
    "Wonderful town to call home. Safe and friendly community. Good schools and hospitals. Many community businesses as well as churches. "
    0
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  • Trulia User
    "It’s a very nice family friendly neighborhood, very quiet. Well maintained, and centrally located to lots of stores and highway"
    0
    Flag
  • Christine Carter
    "They would love that it’s animal friendly and quiet. Filled with dog lovers. Very wonderful place to live and raise a dog family. "
    0
    Flag
  • Trulia User
    "The area has a great holiday spirit, nobody is too neighborly per se, but people do check on each other. During the holidays ie. Christmas time a lot of the people here decorate their houses and people drive around and look at the holiday lights. Also, during Halloween a lot of the kids go and trick-or-treat together."
    4
    Flag
  • Trulia User
    "Quiet, safe close to schools and stores. Lots of pet owners who watch out for neighbors pets and houses"
    4
    Flag
  • Trulia User
    "pretty good neighborhood. we have a store and 3 churches all within a vert short walking distance. There is also a school with a park for kids."
    2
    Flag
  • Trulia User
    "Small, can be busy with kids in the summer of course, but clean, small trail along the front, community pool and playground, nice neighbors in my experience. Management? Eh. "
    1
    Flag
  • Trulia User
    "we love this neighborhood! it is great for raising a family! we are close to lots of cool places and a wonderful church!"
    1
    Flag
  • Sharon H.
    "My neighborhood is in a great location and has a very diverse population. The public transportation is at the entrance of my neighborhood.The lawns are well manicured. The busses are clean and social distancing is practiced. It is a comfortable ride and the people are nice. There are stores and eateries are right on the line."
    3
    Flag
  • Jessica W.
    "Very warming, clean sides roads and lots of deers!!. "
    21
    Flag
  • Tara B.
    "Obly has a 20 minute drive to Fort Eustis military installation every day. Newly paved highway lanes make it even more accessible."
    1
    Flag
  • Betsyedwards11
    "Great school district and neighborhood- one way in one way out - never farther than 20 min from anywhere in Williamsburg "
    0
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  • Joy B.
    "There’s a lot of families here, activities for the children is abundant, then you have the historical side which is great for learning. "
    8
    Flag
  • Julie C.
    "Williamsburg is a safe community with great schools. I especially like to different cultural event available. "
    0
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  • Adam D.
    "Williamsburg is exciting not because of what it *is*, but because of what it is *going to* be, or what it *could* be. Lots of southern passive aggression, but also lots of truly friendly, laid back people. Look for the city to get younger and younger as the "college town" infrastructure continues to expand."
    23
    Flag
  • Trulia User
    "Great for families. Plenty of places to eat and shop. As well as loads of history to see and visit. "
    3
    Flag
  • Jvshelton
    "Its a nice place to bring up children and many places in History to learn about And places to have fun Moderate temps all year great schools "
    0
    Flag
  • Caroline C.
    "The Williamsburg farmers market is my favorite community event. Everyone brings their families and pets, and it feels good to support small farmers. "
    0
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  • Latrelle J.
    "I was born and raised here and if I could afford to live here I’d stay! The chills are ok if you stay in touch with the teachers and up to date with your child’s progress yourself. It’s clean too."
    2
    Flag
  • Peter L.
    "People are nice and it feels safe to walk around at night. I never had a problem with anyone. It's great gor kids and family to visit."
    0
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  • Shane C.
    "Safe older neighborhood with long time owners. Many of the homes are being updated making the neighborhood retain value."
    0
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  • Ruca60
    "It’s friendly, cultured, good values, easy to get around in your car, lots restaurants, lots to do. And the beach is only an hour and a half away."
    0
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  • Kelly
    "I’ve lived in this neighborhood for 3 years... lots of long time residents and houses do not come up for sale often. Kid and dog friendly. Close to the York river State Park"
    4
    Flag
  • Laura W.
    "Colonial Williamsburg is wonderful for company and for every day adventures. There are a good mix of people and a large dog community. "
    0
    Flag
  • Gonzalez
    "It’s a great neighborhood because is very quiet. There is nothing more complacent then coming home from a long day of work and being able to relax and enjoy the calming and peaceful atmosphere of your home and neighborhood "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 100 Chestnut Dr

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Off Market Homes Near 100 Chestnut Dr

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