2108 Chesterfield Loop, Chesapeake, VA 23323
Property image
Property image
OFF MARKET

2108 Chesterfield Loop
Chesapeake, VA 23323

Deep Creek South
  • 5 Beds
  • 3 Baths
  • 3,030 sqft (on 0.25 acres)

$616,400

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $3,534/mo*
Refinance Your Home

$616,400

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $3,534/mo*
Refinance Your Home
5 Beds
3 Baths
3,030 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 2108 Chesterfield Loop.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

* CURRENTLY UNDER RENOVATION, AVAILABLE FOR SHOWING AT END OF MONTH*

BEAUTIFUL 2-STORY, BRICK FRONT, 2-CAR GARAGE,SINGLE FAMILY HOME. 5 BR 3 FULL BATH, LOCATED IN MARSH CREEK IN THE HIGHLY COVETED GRASSFIELD HIGHSCHOOL SCHOOL DISTRICT. NEWLY RENOVATED:

* UPDATED KITCHEN W/ GRANITE COUTER TOPS
* FRESH PAINT
* NEW FLOORS
* NEW ROOF
* LARGE COVERED DECK GREAT FOR ENTERTAINING/ RELAXING

LOCATED CLOSE TO MOST MAJOR BASES, 10 MINUTES AWAY FROM GREENBRIAR MALL FOR CONVIENIENT SHOPPING AND 30 MINUTES FROM THE BEACH. THIS HOME IS A "MUST SEE

* RENT 1-3 YEARS
2108 Chesterfield Loop, Chesapeake, VA 23323 is a 5 bedroom, 3 bathroom, 3,030 sqft single-family home in Deep Creek South, built in 1999. It last sold for $342,700 on Jan 7, 2009. More recently, it was listed as a rental in January 2023 with an asking price of $2,300 per month. That rental listing was removed on February 1, 2023. It is currently off market. The Trulia Estimate is $616,400, with a rent estimate of $3,644/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 2108 Chesterfield Loop

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Interior Details
Additional StorageAtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Dining RoomStorage
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: CompositionExterior: BrickFoundation Type: OtherLawn
Parking & Garage
GarageParking: None, Garage

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 2108 Chesterfield Loop

DatePriceEventSource
02/01/2023ListingRemovedZillow Rentals
01/05/2023$2,900PriceChange
Zillow Rentals
01/03/2023$2,300Listed For RentZillow Rentals
03/24/2021ListingRemovedN/A
11/16/2017$2,300ListingRemovedN/A
10/18/2017$2,300PriceChange
N/A
09/26/2017$2,400Listed For RentN/A
08/22/2017$365,000ListingRemovedAgent Provided
06/01/2017$365,000PriceChange
Agent Provided
03/15/2017$369,800PriceChange
Agent Provided
02/07/2017$369,900Listed For SaleAgent Provided
01/07/2009$342,700Sold
N/A
09/24/1999$222,000Sold
N/A

Market trends in Chesapeake

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$386K
$3.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$213
$3MoM
Available listings
909
54MoM
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Property Tax and Assessment

Year2025
Tax$5,522
Assessment$546,700
Home facts updated by county records

Comparable Sales for 2108 Chesterfield Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2601 Sawtooth Cir, Chesapeake, VA
0.20
Single-Family Home
$525,000
06/15/26
5
2.5
2,926
908 Artisan Ave, Chesapeake, VA
0.10
Single-Family Home
$606,000
09/24/25
5
2.5
2,728
2616 Pitchback Ln, Chesapeake, VA
0.24
Single-Family Home
$620,000
06/24/26
5
3.5
2,891
2803 Bedstone Cir, Chesapeake, VA
0.52
Single-Family Home
$610,000
06/02/26
5
4
2,989
509 Lake Crest Dr, Chesapeake, VA
0.53
Single-Family Home
$450,000
12/12/25
4
2.5
2,088
402 Undershot Ct, Chesapeake, VA
0.57
Single-Family Home
$440,000
03/04/26
5
2.5
2,800
808 Winter King Ct, Chesapeake, VA
0.49
Single-Family Home
$445,000
04/07/26
3
2.5
1,700
2605 Pitchback Ln, Chesapeake, VA
0.19
Single-Family Home
$595,000
03/06/26
5
3
3,026
532 Shelview Cir, Chesapeake, VA
0.66
Single-Family Home
$475,000
04/30/26
4
2.5
2,006
2130 Chesterfield Loop, Chesapeake, VA
0.18
Single-Family Home
$554,000
03/10/26
5
3
2,549

Nearby homes

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Assigned Schools

These are the assigned schools for 2108 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

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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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Outdoor Space

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Homes for sale near 2108 Chesterfield Loop

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Off Market Homes Near 2108 Chesterfield Loop

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