2139 Chesterfield Loop, Chesapeake, VA 23323
OFF MARKET

2139 Chesterfield Loop
Chesapeake, VA 23323

Deep Creek South
  • 5 Beds
  • 4 Baths
  • 3,556 sqft (on 0.31 acres)

$657,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,879/mo*
Refinance Your Home

$657,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,879/mo*
Refinance Your Home
5 Beds
4 Baths
3,556 sqft
(on 0.31 acres)

Home Value

Trulia Estimate
$658K
Since last month
Decreased$3K (-0.4%)
Since last year
Increased$2K (+0.3%)
Since last sale
Increased$327K (+99.2%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$657K
July 2026$656K
June 2026$660K
May 2026$658K
April 2026$654K
March 2026$648K
February 2026$636K
January 2026$633K
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
2616 Pitchback Ln, Chesapeake, VA
0.32
Single-Family Home
$620,000
06/24/26
5
3.5
2,891
2601 Sawtooth Cir, Chesapeake, VA
0.33
Single-Family Home
$525,000
06/15/26
5
2.5
2,926
908 Artisan Ave, Chesapeake, VA
0.30
Single-Family Home
$606,000
09/24/25
5
2.5
2,728
402 Undershot Ct, Chesapeake, VA
0.48
Single-Family Home
$440,000
03/04/26
5
2.5
2,800
2803 Bedstone Cir, Chesapeake, VA
0.55
Single-Family Home
$610,000
06/02/26
5
4
2,989
509 Lake Crest Dr, Chesapeake, VA
0.58
Single-Family Home
$450,000
12/12/25
4
2.5
2,088
2130 Chesterfield Loop, Chesapeake, VA
0.07
Single-Family Home
$554,000
03/10/26
5
3
2,549
2605 Pitchback Ln, Chesapeake, VA
0.27
Single-Family Home
$595,000
03/06/26
5
3
3,026
408 Mallet Way, Chesapeake, VA
0.73
Single-Family Home
$550,000
07/30/26
5
2.5
2,379
407 Montross Ct, Chesapeake, VA
0.71
Single-Family Home
$475,000
07/20/26
4
2.5
2,209

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
2130 Chesterfield Loop, Chesapeake, VA 23323
0.07
$554,000
5
3
2,549
Recently Sold
807 Gresham Way, Chesapeake, VA 23323
0.06
$610,000
5
2.5
3,188
For Sale
803 Gresham Way, Chesapeake, VA 23323
0.10
$669,000
5
3.5
3,670
For Sale
2605 Pitchback Ln, Chesapeake, VA 23323
0.27
$595,000
5
3
3,026
Recently Sold
908 Artisan Ave, Chesapeake, VA 23323
0.30
$627,200
5
2.5
2,728
Off Market
2616 Pitchback Ln, Chesapeake, VA 23323
0.32
$620,000
5
3.5
2,891
Recently Sold
2601 Sawtooth Cir, Chesapeake, VA 23323
0.33
$525,000
5
2.5
2,926
Recently Sold
317 Sawyers Mill Xing, Chesapeake, VA 23323
0.34
$520,000
4
2.5
2,710
Recently Sold
541 Lake Crest Dr, Chesapeake, VA 23323
0.42
$555,000
4
2.5
2,781
Recently Sold
536 Lake Crest Dr, Chesapeake, VA 23323
0.46
$499,300
4
2
2,368
Off Market
402 Undershot Ct, Chesapeake, VA 23323
0.48
$545,000
5
2.5
2,800
For Sale
509 Lake Crest Dr, Chesapeake, VA 23323
0.58
$450,000
4
2.5
2,088
Recently Sold

Local Information

  • Map ViewExplore the area around 2139 Chesterfield Loop.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
0.31 acres
Living Area
3,556 sqft
Price/Sqft
$185
Parking
Garage

About this House

This single-family home is located at 2139 Chesterfield Loop, Chesapeake, VA. 2139 Chesterfield Loop is in the Deep Creek South neighborhood in Chesapeake, VA and in ZIP code 23323. This property has 5 bedrooms, 4 bathrooms and approximately 3,556 sqft of floor space. This property has a lot size of 0.31 acres and was built in 1999.
2139 Chesterfield Loop, Chesapeake, VA 23323 is a 5 bedroom, 4 bathroom, 3,556 sqft single-family home in Deep Creek South, built in 1999. It last sold for $330,000 on Jan 24, 2014. It is currently off market. The Trulia Estimate is $657,600, with a rent estimate of $3,743/month.

Home Details for 2139 Chesterfield Loop

Interior Features

Heating & Cooling
Heating: Heat Pump, GasAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood, Linoleum Vinyl
Interior Details
AtticIn-law unitNumber of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, PantryCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl, BrickFoundation Type: OtherSprinkler System
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Price and Tax history

DateEventPrice
Jan 24, 2014
Source: N/A
Sold
$330,000
Nov 6, 2013
Source: Agent Provided
PriceChange
$349,900
Price decreased by 4%
Oct 18, 2013
Source: Agent Provided
PriceChange
$364,900
Price decreased by 4%
Aug 17, 2013
Source: Agent Provided
Listed For Sale
$379,900
Apr 29, 2013
Source: N/A
Sold
$353,793

Market trends in Chesapeake

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$390K
$4.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$216
$3MoM
Available listings
930
19MoM
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Around this home

Neighborhood Overview

Deep Creek South
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Deep Creek South

At least 81 Trulia users voted on each feature.

  • 98 % Say car is needed

  • 95 % Say yards are well-kept

  • 91 % Say it's dog friendly

  • 90 % Say parking is easy

  • 86 % Say there's holiday spirit

  • 80 % Say kids play outside

  • 77 % Say people would walk alone at night

  • 76 % Say it's quiet

  • 74 % Say there's wildlife

  • 65 % Say neighbors are friendly

  • 55 % Say they plan to stay for at least 5 years

  • 53 % Say streets are well-lit

  • 41 % Say there are community events

  • 35 % Say there are sidewalks

  • 26 % Say it's walkable to grocery stores

  • 13 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Sonya Cunningham
    "Low stress area. Convenient location. Could use more restaurants. Over all the schools are awesome and the community is supportive. "
    0
    Flag
  • Kaylermeg
    "Halloween is soo much fun! Everyone hangs out in their garages and makes it extra special for all of the kids with fun drinks and snacks, they usually have a DJ too! Usually there is a neighborhood bar crawl in the summer!"
    2
    Flag
  • Trulia User
    "I lived in this neighborhood for two years now. The Folks are very friendly. The neighborhood is very pet friendly and well suited for family."
    1
    Flag
  • Trulia User
    "great neighborhood and it is highly recommended. this is a great place to live and you will enjoy it. "
    0
    Flag
  • Trulia User
    "There is a nice long path running along the length of the dismal swamp that would be great for walking dogs. "
    2
    Flag
  • Trulia User
    "wonderful location to raise children. great schools and the best parks. love watching the boats go by. would recommend this area to anyone. "
    0
    Flag
  • Trulia User
    "great area! very family friendly and the best schools. I would recommend this area for big families. "
    0
    Flag
  • Cgraes
    "This is a safe, quiet, and a great place for families. The tolls and traffic are the downers. Very congested considering tons of communities connected to two main low capacity roads available."
    2
    Flag
  • Christy R.
    "Dogs are a welcomed part of this community, I always see people walking their dogs, but I never see any droppings!!! "
    3
    Flag
  • Leaosc
    "Large dog friendly community. Some owners don’t know how to pick up after their furry family members. That makes it frustrating."
    2
    Flag
  • Sayhelo
    "I love my neighbors, and the people who live here. Good schools, nice shops, clean here. I have many food stores to choose from and other shops. The only thing I don’t like is the tolls, and the large amount of gun shot I hear in this area, which I guess is for control of wild life in the area."
    6
    Flag
  • Ddaniels36
    "We have lived in this neighborhood for 20 years. My children grew to be smart and strong here, and they had many friends. The schools are great and the teachers are wonderful. The neighbors are kind and caring. Our jobs are taking us to another state, but we will always treasure the memories and friends we have made here in this safe and secure neighborhood."
    0
    Flag
  • Sheldongreg
    "People walk they’re Dogs regularly on a leash and pick up any waste as the dog leaves it. There’s a waste can especially for Dog Waste while on your walk with your Dog. It’s very pleasant in my neighborhood to walk the Dog."
    2
    Flag
  • Michael S. S. (.
    "Neighborhood park and community pool. Meetings and holiday gatherings, parties, festivals, hay rides, parades and night out activities keep this diverse community connected."
    1
    Flag
  • Sayhelo
    "There are many folks with dogs, horses. I have also seen people with Gooses,and one guy who walks his chickens around the neighborhood. Never a problem with people who complain about others animals."
    4
    Flag
  • Mary-elizabeth H.
    "We love our neighborhood. It’s quiet and clean. It has two playgrounds, a pond and plenty of walking trails. "
    2
    Flag
  • Sayhelo
    "They have a really nice school system, although the new bridge was built, the toll is a little Steep. We don’t have much shopping on this side of the bridge . We have a few food stores, Walmart, food loin, but we need a place that will offer fresh fruit, and vegetables. "
    0
    Flag
  • Sayhelo
    "Many new homes with small children. Great schools, close to shopping,tech college, A nice variety for eating out"
    0
    Flag
  • Megan m.
    "I have lived in the area for 10 years Have seen lots of wildlife Friendly neighbors And easy to get around"
    2
    Flag
  • Yunilda B.
    "Love this neighborhood. It’s peaceful, beautiful, friendly and good for raising kids. I wish has more restaurants around so we can have options for dining. "
    4
    Flag
  • Sasha_The_Great
    "Loveeeeee my community! It’s very friendly and quiet. They are always having fun community events at the pool and club house. You will love this sought after friendly neighborhood. "
    1
    Flag

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Homes for sale near 2139 Chesterfield Loop

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Off Market Homes Near 2139 Chesterfield Loop

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Frequently asked questions about 2139 Chesterfield Loop

  • What is 2139 Chesterfield Loop estimated to be worth?
    Trulia's estimated value for 2139 Chesterfield Loop in Chesapeake, VA is $657,600.
  • What is the price history for 2139 Chesterfield Loop?
    2139 Chesterfield Loop in Chesapeake, VA last sold for $330,000 in January 2014.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $390K. That is up $4.67K from the prior month.
  • Does 2139 Chesterfield Loop have air conditioning?
    Yes, 2139 Chesterfield Loop in Chesapeake, VA has air conditioning.
  • Does 2139 Chesterfield Loop have laundry facilities?
    Yes, 2139 Chesterfield Loop in Chesapeake, VA has in-unit laundry.