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)

$661,200

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $3,792/mo*
Refinance Your Home

$661,200

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $3,792/mo*
Refinance Your Home
5 Beds
4 Baths
3,556 sqft
(on 0.31 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 2139 Chesterfield Loop

DatePriceEventSource
01/24/2014$330,000Sold
N/A
11/06/2013$349,900PriceChange
Agent Provided
10/18/2013$364,900PriceChange
Agent Provided
08/17/2013$379,900Listed For SaleAgent Provided
04/29/2013$353,793Sold
N/A
01/16/2013$359,900Listed For SaleAgent Provided
01/10/2005$3,600,000Sold
N/A
09/29/2000$228,500Sold
N/A
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Property Tax and Assessment

Year2025
Tax$5,980
Assessment$592,100
Home facts updated by county records

Comparable Sales for 2139 Chesterfield Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1013 Artisan Ave, Chesapeake, VA
0.21
Single-Family Home
$665,000
06/06/25
5
2.5
3,200
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
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
2121 Chesterfield Loop, Chesapeake, VA
0.15
Single-Family Home
$625,000
05/28/25
5
3
3,194
501 Cassway Arch, Chesapeake, VA
0.63
Single-Family Home
$480,000
05/30/25
4
2.5
1,944
523 Lynnfield Rd, Chesapeake, VA
0.66
Single-Family Home
$530,000
06/13/25
4
2.5
2,318
2605 Pitchback Ln, Chesapeake, VA
0.27
Single-Family Home
$595,000
03/06/26
5
3
3,026
2500 Garth Way, Chesapeake, VA
0.75
Single-Family Home
$470,000
05/20/25
4
2.5
2,051

Assigned Schools

These are the assigned schools for 2139 Chesterfield Loop.
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.

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

Learn more about our methodology.
  • 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!"
    1
    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
  • deweyfrenchbulldog
    "A great place to live! The community is quiet, quant and a joy to come home to after work! Love it!"
    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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Explore by feature

2139 Chesterfield Loop, Chesapeake, VA 23323 is a 5 bedroom, 4 bathroom, 3,556 sqft single-family home built in 1999. 2139 Chesterfield Loop is located in Deep Creek South, Chesapeake. This property is not currently available for sale. 2139 Chesterfield Loop was last sold on Jan 24, 2014 for $330,000. The current Trulia Estimate for 2139 Chesterfield Loop is $661,200.