1108 Chesslawn Cir E, Chesapeake, VA 23320
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Property image
OFF MARKET

1108 Chesslawn Cir E
Chesapeake, VA 23320

Greenbrier West
  • 4 Beds
  • 2 Baths
  • 1,767 sqft (on 0.39 acres)

$460,600

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,740/mo*
Refinance Your Home

$460,600

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,740/mo*
Refinance Your Home
4 Beds
2 Baths
1,767 sqft
(on 0.39 acres)

Home Value

Trulia Estimate
$461K
Since last month
Decreased$1K (-0.3%)
Since last year
Increased$11K (+2.5%)
Since last sale
Increased$140K (+43.6%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$460K
July 2026$461K
June 2026$464K
May 2026$462K
April 2026$461K
March 2026$454K
February 2026$447K
January 2026$445K
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
1129 Valmire Dr, Chesapeake, VA
0.21
Single-Family Home
$380,000
09/19/25
4
2
1,675
152 Thrasher Rd, Chesapeake, VA
0.12
Single-Family Home
$350,000
11/25/25
3
2
1,975
1121 Battlefield Blvd N, Chesapeake, VA
0.21
Single-Family Home
$300,000
06/29/26
3
2
1,754
205 Kalmar Dr, Chesapeake, VA
0.17
Single-Family Home
$405,000
05/01/26
3
2
1,500
1248 Kingsway Dr, Chesapeake, VA
0.18
Single-Family Home
$490,000
05/07/26
3
2
2,203
140 Haviland Rd, Chesapeake, VA
0.06
Single-Family Home
$505,000
06/01/26
5
3
2,800
1032 Valmire Dr, Chesapeake, VA
0.34
Single-Family Home
$325,000
07/30/26
3
1.5
1,276
105 Cottonwood Ln, Chesapeake, VA
0.41
Single-Family Home
$275,000
07/21/26
3
2
1,663
1220 Kingsway Dr, Chesapeake, VA
0.35
Single-Family Home
$410,000
08/28/25
3
2
2,008
1105 Birchwater Arch, Chesapeake, VA
0.33
Single-Family Home
$495,000
04/29/26
4
2.5
2,370

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
1120 Chesslawn Cir E, Chesapeake, VA 23320
0.06
$380,000
4
2.5
2,400
Recently Sold
140 Haviland Rd, Chesapeake, VA 23320
0.06
$505,000
5
3
2,800
Recently Sold
113 Thrasher Rd, Chesapeake, VA 23320
0.14
$349,900
3
2
1,269
Recently Sold
205 Kalmar Dr, Chesapeake, VA 23320
0.17
$405,000
3
2
1,500
Recently Sold
1256 Kingsway Dr, Chesapeake, VA 23320
0.14
$417,900
3
2
1,771
Recently Sold
152 Thrasher Rd, Chesapeake, VA 23320
0.12
$350,000
3
2
1,975
Recently Sold
1129 Valmire Dr, Chesapeake, VA 23320
0.21
$393,500
4
2
1,675
Off Market
1248 Kingsway Dr, Chesapeake, VA 23320
0.18
$490,000
3
2
2,203
Recently Sold
1253 Kingsway Dr, Chesapeake, VA 23320
0.18
$365,000
3
2
1,800
Recently Sold
224 Essex Dr, Chesapeake, VA 23320
0.26
$430,000
4
2
2,300
Recently Sold
200 Essex Dr, Chesapeake, VA 23320
0.28
$410,000
4
2
2,200
Recently Sold
244 Kalmar Dr, Chesapeake, VA 23320
0.26
$452,000
4
3
1,717
Recently Sold

Local Information

  • Map ViewExplore the area around 1108 Chesslawn Cir E.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1963
Lot Size
0.39 acres
Living Area
1,767 sqft
Price/Sqft
$261
Parking
Garage

About this House

Large detached garage offers spectacular upstairs in law suite with central heat and air, living area open with plenty of cabinets, sink, microwave, refrigerator, nice full bath, bedroom with huge walk in closet and recessed lighting throughout. Main house, 4 Bedrooms and 2 baths, lots of hard wood flooring, light oak cabinets in kitchen, new gas logs in family room, newer reverse osmosis, Side Loading 576 square foot attached garage with abundance of cabinets and counter space. Attached garage has AC vent if you like! Huge patio with covered awning for your cookouts and entertaining. Large fenced yard. Quality Built Home and Won't Last!!
1108 Chesslawn Cir E, Chesapeake, VA 23320 is a 4 bedroom, 2 bathroom, 1,767 sqft single-family home in Greenbrier West, built in 1963. It last sold for $320,000 on Aug 13, 2020. More recently, it was listed as a rental in May 2014 with an asking price of $2,100 per month. That rental listing was removed on July 5, 2014. It is currently off market. The Trulia Estimate is $460,600, with a rent estimate of $2,511/month.

Home Details for 1108 Chesslawn Cir E

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
AtticIn-law unitNumber of Rooms: 7Types of Rooms: Breakfast Nook, Family Room, Master Bath, Mud Room, WorkshopCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: BrickFoundation Type: OtherPatio
Parking & Garage
GarageParking: On Street, Garage

Property Information

Year Built
Year Built: 1963Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
Aug 13, 2020
Source: N/A
Sold
$320,000
Jul 20, 2020
Source: Agent Provided
Listed For Sale
$315,000
Jul 5, 2014
Source: N/A
ListingRemoved
$1,850
Jun 4, 2014
Source: N/A
PriceChange
$1,850
Price decreased by 12%
May 27, 2014
Source: N/A
Listed For Rent
$2,100

Market trends in Greenbrier West

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$354K
$27.17KMoM
Sale-to-List Price
100.0%
Price per sq ft
$212
$3MoM
Available listings
90
16MoM
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Around this home

Neighborhood Overview

Greenbrier West
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greenbrier West

At least 199 Trulia users voted on each feature.

  • 87 % Say it's dog friendly

  • 86 % Say car is needed

  • 82 % Say parking is easy

  • 72 % Say there's holiday spirit

  • 70 % Say it's quiet

  • 70 % Say there are sidewalks

  • 64 % Say yards are well-kept

  • 63 % Say streets are well-lit

  • 60 % Say people would walk alone at night

  • 59 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 48 % Say it's walkable to restaurants

  • 47 % Say they plan to stay for at least 5 years

  • 45 % Say neighbors are friendly

  • 40 % Say there's wildlife

  • 20 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Caryn Mckee
    "Very good location and well kept neighborhood. Close to the high way as well as to the downtown greenbrier"
    0
    Flag
  • Kelsee Majette
    "This entire area is absolutely family friendly, have lived in a few neighborhoods in the area and it’s super nice. Cozy and safe. You’ll love it "
    0
    Flag
  • Cat Lady
    "This is a family oriented neighborhood. We have the Chesapeake Park for events, good schools, some shopping, restaurants and overall low crime. We are also close to a hospital and medical offices. We are near an interstate & close to Virginia Beach & Norfolk."
    1
    Flag
  • CL
    "I’ve lived here for 7 months and haven’t heard of any community events, but neighbors are pretty friendly. "
    0
    Flag
  • Trulia User
    "We had lived in the neighborhood for a few years and are currently looking again in the neighborhood. always felt safe. "
    5
    Flag
  • Trulia User
    "The people in the neighborhood are friendly and mind there business. No one bothers your packages and they speak when spoken too."
    2
    Flag
  • Trulia User
    "Food trucks, recreational center, neighborhood rummage sales, gardening events, neighborhood events, etc…"
    3
    Flag
  • Trulia User
    "It’s a family friendly neighborhood with a lot of nice people. a lot of home owners like to walk their dogs, exercise (walk, bike etc) "
    1
    Flag
  • Trulia User
    "I just moved in and I'm loving the vibes of the stores and the restaurants. such a lively place to live. quiet and safe."
    1
    Flag
  • Trulia User
    "Great community with lots of amenities. Lots of sidewalks for walking/running and lots of streetlights to keep the neighborhood well lit at nighttime."
    0
    Flag
  • Trulia User
    "Plenty of space to walk dogs. Plenty of sidewalks, parks and dog parks. Also a great selection of nearby pet stores and clinics"
    0
    Flag
  • Helen J.
    "Nice area of Chesapeake.Quite area. Easy to get to places.Close to hospital.Close to shopping centers."
    4
    Flag
  • Brad C.
    "Most all dogs are walked on a leach...sometimes a guy and his lab play frisbee, but the lab is well trained. All dog owners pick up after their dogs. A bunch of areas for homeowners and dogs to play"
    2
    Flag
  • Aaron P.
    "Good neighborhood so far. Recently moved here not so long ago and be liking the areas. With the water and trails being nearby it makes everything great so far!"
    11
    Flag
  • Vince N.
    "It’s a pleasant area with above average schools. They are building new developments constantly so traffic is worsening. Plus the increase in development and is making public facilities such as rec centers, libraries etc more crowed than usual because no new facilities are being built for the influx of ppl. Also my son has 30 students in his class which is way too much ."
    4
    Flag
  • Mdhrrt1
    "Super quiet and cozy. Beautiful public pool and park area. Lots of trees, birds and squirrels. Great place to walk and jog. "
    1
    Flag
  • Gene W.
    "The park is right next door. I walk around the lake almost everyday. It is safe and I have lost 40 pounds and lowered my blood sugar. This neighbor has added years to my life."
    17
    Flag
  • Phuong N.
    "Very good place and very nice neighbors, I love this place, so close Food lion and many shops. We can walk to their easy."
    1
    Flag
  • Duran.carol.cheek
    "Plenty of space to walk. Nearby parks. Business park nearby creates lots of street traffic in afternoon. "
    1
    Flag
  • Phuong N.
    "I’m a stay at home mom. I don’t drive to work. My son’s school is close by and grocery store even closer"
    1
    Flag
  • Frederick K.
    "Recent homeowner, disabled veteran. It's super safe here. Literally nothing happens. Best decision I ever made."
    1
    Flag
  • JJ D. L.
    "Dogs are welcome and friendly people pick up after the dogs every where they might go. They would not like it if dogs were not picked up after or if they were allowed to run loose a leash is a must have "
    0
    Flag
  • Tainya H.
    "I've lived in this neighborhood for 3 years now It's a quiet neighborhood with an awesome school district "
    8
    Flag
  • Margecrittendon
    "Dog friendly neighborhood for sure! I have two dogs and they are well received by the neighbors. Happy Guly recommend this community!"
    0
    Flag
  • Joseph J.
    "it's a great place to live in love of places to go and things to do. I would love to move here with my family."
    0
    Flag
  • Rachel J.
    "Local park has family movie nights, food truck round ups, farmers markets, jubilees and wine festivals."
    0
    Flag
  • Ashley H. Y.
    "food lion is walking distance or bbn like distance. gas station about the same. greenbrier about 10 minutes away. norfolk about 15 minutes away with no traffic and va beach about 20 to 25 minutes away depending on what part you go to."
    1
    Flag
  • Unknown N.
    "It is a great family neighborhood with active families. Riverwalk has great amenities for families to enjoy...as well as some excellent walking paths and bike trails "
    0
    Flag
  • Ashley H. Y.
    "quiet clean and friendly. neighbors are extremely eager to lend a helping hand and are always watching out for you. "
    0
    Flag

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Homes for sale near 1108 Chesslawn Cir E

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Off Market Homes Near 1108 Chesslawn Cir E

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Frequently asked questions about 1108 Chesslawn Cir E

  • What is 1108 Chesslawn Cir E estimated to be worth?
    Trulia's estimated value for 1108 Chesslawn Cir E in Chesapeake, VA is $460,600.
  • What is the price history for 1108 Chesslawn Cir E?
    1108 Chesslawn Cir E in Chesapeake, VA last sold for $320,000 in August 2020.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $354K. That is up $27.17K from the prior month.
  • Does 1108 Chesslawn Cir E have air conditioning?
    Yes, 1108 Chesslawn Cir E in Chesapeake, VA has air conditioning.
  • How big is the lot at 1108 Chesslawn Cir E?
    The lot at 1108 Chesslawn Cir E in Chesapeake, VA is about 0.39 acres (16,901 sq ft).