Is a car needed in Deep Creek South, Chesapeake, VA?

As of early 2026, 98% of users say car is needed

Are yards well-kept in Deep Creek South, Chesapeake, VA?

As of early 2026, 95% of users say yards are well-kept

Is Deep Creek South, Chesapeake, VA dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Is parking easy in Deep Creek South, Chesapeake, VA?

As of early 2026, 90% of users say parking is easy

Does Deep Creek South, Chesapeake, VA show holiday spirit?

As of early 2026, 86% of users say there's holiday spirit

Do kids play outside in Deep Creek South, Chesapeake, VA?

As of early 2026, 80% of users say kids play outside

Would people walk alone at night in Deep Creek South, Chesapeake, VA?

As of early 2026, 77% of users say people would walk alone at night

Is Deep Creek South, Chesapeake, VA quiet?

As of early 2026, 76% of users say it's quiet

Is there wildlife in Deep Creek South, Chesapeake, VA?

As of early 2026, 74% of users say there's wildlife

Are neighbors friendly in Deep Creek South, Chesapeake, VA?

As of early 2026, 65% of users say neighbors are friendly

Do residents of Deep Creek South, Chesapeake, VA plan to stay at least 5 years?

As of early 2026, 55% of users say they plan to stay for at least 5 years

Are the streets well-lit in Deep Creek South, Chesapeake, VA?

As of early 2026, 53% of users say streets are well-lit

Are there community events in Deep Creek South, Chesapeake, VA?

As of early 2026, 41% of users say there are community events

Does Deep Creek South, Chesapeake, VA have sidewalks?

As of early 2026, 35% of users say there are sidewalks

Is Deep Creek South, Chesapeake, VA walkable to grocery stores?

As of early 2026, 26% of users say it's walkable to grocery stores

Is Deep Creek South, Chesapeake, VA walkable to restaurants?

As of early 2026, 13% of users say it's walkable to restaurants

What is 2100 Chesterfield Loop estimated to be worth?

Trulia's estimated value for 2100 Chesterfield Loop in Chesapeake, VA is $628,100 .

What is the price history for 2100 Chesterfield Loop?

2100 Chesterfield Loop in Chesapeake, VA last sold for $445,000 in July 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 $420K. That is up $6.67K from the prior month.

Does 2100 Chesterfield Loop have air conditioning?

Yes, 2100 Chesterfield Loop in Chesapeake, VA has air conditioning.

Does 2100 Chesterfield Loop have a pool?

Yes, 2100 Chesterfield Loop in Chesapeake, VA has a pool.

OFF MARKET

$628,100

Trulia Estimate

4 Beds
3 Baths
3,000 sqft (on 0.25 acres)

2100 Chesterfield Loop, Chesapeake, VA 23323

Deep Creek South

Est. Refi. Payment $3,839/mo*

Refinance Your Home

Currently Off Market - Sold Jul 7, 2020 for $445,000

Home Value

Trulia Estimate

$628K

Since last month

$700 (-0.1%)

Since last year

$20K (+3.3%)

Since last sale

$183K (+41.1%)

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

Month	Estimated value
2026
August 2026	$628K
August 2026	$627K
July 2026	$629K
June 2026	$634K
May 2026	$631K
April 2026	$629K
March 2026	$622K
February 2026	$612K
January 2026	$608K
2025
December 2025	$610K
November 2025	$607K
October 2025	$609K
September 2025	$605K
August 2025	$608K
July 2025	$623K
June 2025	$623K
May 2025	$624K
April 2025	$619K
March 2025	$611K
February 2025	$610K
January 2025	$602K
2024
December 2024	$626K
November 2024	$620K
October 2024	$615K
September 2024	$615K
August 2024	$612K
July 2024	$608K
June 2024	$609K
May 2024	$613K
April 2024	$604K
March 2024	$607K
February 2024	$601K
January 2024	$585K
2023
December 2023	$588K
November 2023	$583K
October 2023	$591K
September 2023	$594K
August 2023	$591K
July 2023	$590K
June 2023	$587K
May 2023	$581K
April 2023	$575K
March 2023	$567K
February 2023	$550K
January 2023	$535K
2022
December 2022	$536K
November 2022	$539K
October 2022	$548K
September 2022	$542K
August 2022	$542K
July 2022	$553K
June 2022	$556K
May 2022	$558K
April 2022	$557K
March 2022	$551K
February 2022	$547K
January 2022	$540K
2021
December 2021	$532K
November 2021	$525K
October 2021	$527K
September 2021	$521K
August 2021	$515K
July 2021	$505K
June 2021	$500K
May 2021	$494K
April 2021	$485K
March 2021	$473K
February 2021	$467K
January 2021	$464K
2020
December 2020	$463K
November 2020	$459K
October 2020	$457K
September 2020	$451K
August 2020	$448K
July 2020	$446K
June 2020	$409K
May 2020	$410K
April 2020	$410K
March 2020	$409K
February 2020	$404K
January 2020	$405K
2019
December 2019	$402K
November 2019	$402K
October 2019	$401K
September 2019	$399K
August 2019	$404K
July 2019	$399K
June 2019	$398K
May 2019	$409K
April 2019	$407K
March 2019	$408K
February 2019	$404K
January 2019	$402K
2018
December 2018	$398K
November 2018	$394K
October 2018	$388K
September 2018	$388K
August 2018	$388K
July 2018	$389K
June 2018	$386K
May 2018	$386K
April 2018	$385K
March 2018	$377K
February 2018	$373K
January 2018	$374K
2017
December 2017	$370K
November 2017	$368K
October 2017	$363K
September 2017	$369K
August 2017	$366K
July 2017	$368K
June 2017	$370K
May 2017	$372K
April 2017	$373K
March 2017	$368K
February 2017	$369K
January 2017	$368K
2016
December 2016	$363K
November 2016	$362K
October 2016	$363K
September 2016	$362K

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
2601 Sawtooth Cir, Chesapeake, VA	0.24	Single-Family Home	$525,000	06/15/26	5	2.5	2,926
908 Artisan Ave, Chesapeake, VA	0.07	Single-Family Home	$606,000	09/24/25	5	2.5	2,728
2616 Pitchback Ln, Chesapeake, VA	0.29	Single-Family Home	$620,000	06/24/26	5	3.5	2,891
2016 Sunset Maple Ln, Chesapeake, VA	0.45	Single-Family Home	$480,150	08/20/26	4	2.5	2,390
2129 Chesterfield Loop, Chesapeake, VA	0.23	Single-Family Home	$610,000	09/01/26	4	2.5	2,668
509 Lake Crest Dr, Chesapeake, VA	0.57	Single-Family Home	$450,000	12/12/25	4	2.5	2,088
402 Undershot Ct, Chesapeake, VA	0.61	Single-Family Home	$440,000	03/04/26	5	3	2,789
808 Winter King Ct, Chesapeake, VA	0.49	Single-Family Home	$445,000	04/07/26	3	2.5	1,700
407 Montross Ct, Chesapeake, VA	0.67	Single-Family Home	$475,000	07/20/26	4	2.5	2,209
2803 Bedstone Cir, Chesapeake, VA	0.57	Single-Family Home	$610,000	06/02/26	5	4	2,989

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
908 Artisan Ave, Chesapeake, VA 23323	0.07	$628,200	5	2.5	2,728	Off Market
803 Gresham Way, Chesapeake, VA 23323	0.13	$650,000	5	3.5	3,670	For Sale
2130 Chesterfield Loop, Chesapeake, VA 23323	0.21	$554,000	5	3	2,549	Recently Sold
2129 Chesterfield Loop, Chesapeake, VA 23323	0.23	$610,000	4	2.5	2,668	Recently Sold
317 Sawyers Mill Xing, Chesapeake, VA 23323	0.23	$520,000	4	2.5	2,710	Recently Sold
2605 Pitchback Ln, Chesapeake, VA 23323	0.24	$595,000	5	3	3,026	Recently Sold
2601 Sawtooth Cir, Chesapeake, VA 23323	0.24	$525,000	5	2.5	2,926	Recently Sold
2616 Pitchback Ln, Chesapeake, VA 23323	0.29	$620,000	5	3.5	2,891	Recently Sold
2116 Cedar Rd, Chesapeake, VA 23323	0.37	$647,499	5	3	2,500	For Sale
2016 Sunset Maple Ln, Chesapeake, VA 23323	0.45	$480,150	4	2.5	2,390	Recently Sold
913 West Rd, Chesapeake, VA 23323	0.46	$299,800	2	1	1,080	Off Market
541 Lake Crest Dr, Chesapeake, VA 23323	0.46	$555,000	4	2.5	2,781	Recently Sold

Local Information

Map ViewExplore the area around 2100 Chesterfield Loop.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2000

0.25 acre lot

3,000 sqft

$209/sqft

Garage

About this House

This single-family home is located at 2100 Chesterfield Loop, Chesapeake, VA. 2100 Chesterfield Loop is in the Deep Creek South neighborhood in Chesapeake, VA and in ZIP code 23323. This property has 4 bedrooms, 3 bathrooms and approximately 3,000 sqft of floor space. This property has a lot size of 10890 sqft and was built in 2000.

2100 Chesterfield Loop, Chesapeake, VA 23323 is a 4 bedroom, 3 bathroom, 3,000 sqft single-family home in Deep Creek South, built in 2000. It last sold for $445,000 on Jul 7, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $628,100, with a rent estimate of $3,378/month.

Home Details for 2100 Chesterfield Loop

Interior Features
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 2Floors: Carpet, Hardwood, Linoleum Vinyl
Interior Details AtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Pantry
Appliances & Utilities DishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa FireplaceJetted Bath Tub

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: Vinyl, BrickFoundation Type: OtherPatio
Pool Pool
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2000Year Updated: 2019
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 10890 sqft

Price and Tax history

Date	Event	Price
Jul 7, 2020 Source: N/A	Sold	$445,000
May 30, 2020 Source: Agent Provided	Listed For Sale	$439,000
Sep 7, 2016 Source: EXIT Realty solds #1585039185595309468	Sold	$370,000
Jul 27, 2016 Source: Agent Provided	Listed For Sale	$374,900
Jun 29, 2016 Source: N/A	Sold	$273,600
May 26, 2016 Source: Agent Provided	Listed For Sale	$0
Apr 9, 2016 Source: Agent Provided	ListingRemoved	$340,000
Feb 8, 2016 Source: Agent Provided	Listed For Sale	$340,000
Nov 21, 2014 Source: N/A	ListingRemoved	$399,000
Nov 17, 2014 Source: N/A	Listed For Sale	$399,000
Aug 20, 2014 Source: N/A	Sold	$385,000
Jan 22, 2007 Source: N/A	Sold	$440,000
Jan 15, 2002 Source: N/A	Sold	$240,000

Year	Property tax	Tax assessment
2025	$5,818	$576,000

Additional Cost

Market trends in Chesapeake

Last updated August 2026

Avg. sale price

$420K

$6.67KMoM

Sale-to-List Price

100.0%

Price per sq ft

$221

$2MoM

Available listings

986

12MoM

Around this home

Grassfield Elementary School
PK-5
Public
1307 Students
Chesapeake Public Schools
10/10
GreatSchools Rating
Parent Rating Average
I do not recommend this school. Everyone claims this is a great school but it is not. I have spoken to many other parents who also feel that the school does not have the students' best interests at heart and the administration would rather students be injured or embarrassed than be helped and show kindness.The principal doesn't like young children behaving as children and the teachers are so overly focused on SPED students they ignore non-sped.When students are injured by other students the victim is blamed.Do not believe the 8/10 rating, it is heavily inaccurate to the reality of the school.
Teacher Review
1y ago
14 Reviews

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

48 Homes For You
Buy: $49.9k - $3.54m

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
Resident
3mo ago
"Low stress area. Convenient location. Could use more restaurants. Over all the schools are awesome and the community is supportive. "
0
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Kaylermeg
Resident
1y ago
"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
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Trulia User
Resident
3y ago
"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
Resident
4y ago
"great neighborhood and it is highly recommended. this is a great place to live and you will enjoy it. "
0
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Trulia User
Visitor
4y ago
"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
Resident
5y ago
"wonderful location to raise children. great schools and the best parks. love watching the boats go by. would recommend this area to anyone. "
0
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Trulia User
Resident
5y ago
"great area! very family friendly and the best schools. I would recommend this area for big families. "
0
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Cgraes
Resident
6y ago
"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.
Resident
6y ago
"Dogs are a welcomed part of this community, I always see people walking their dogs, but I never see any droppings!!! "
3
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Leaosc
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
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Sheldongreg
Resident
7y ago
"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. (.
Resident
7y ago
"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
Resident
7y ago
"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
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Mary-elizabeth H.
Resident
7y ago
"We love our neighborhood. It’s quiet and clean. It has two playgrounds, a pond and plenty of walking trails. "
2
Flag
Sayhelo
Resident
7y ago
"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
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Sayhelo
Resident
7y ago
"Many new homes with small children. Great schools, close to shopping,tech college, A nice variety for eating out"
0
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Megan m.
Resident
7y ago
"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.
Resident
8y ago
"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
Resident
8y ago
"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
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LGBTQ Local Legal Protections

Frequently asked questions about 2100 Chesterfield Loop

What is 2100 Chesterfield Loop estimated to be worth?
Trulia's estimated value for 2100 Chesterfield Loop in Chesapeake, VA is $628,100.
What is the price history for 2100 Chesterfield Loop?
2100 Chesterfield Loop in Chesapeake, VA last sold for $445,000 in July 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 $420K. That is up $6.67K from the prior month.
Does 2100 Chesterfield Loop have air conditioning?
Yes, 2100 Chesterfield Loop in Chesapeake, VA has air conditioning.
Does 2100 Chesterfield Loop have a pool?
Yes, 2100 Chesterfield Loop in Chesapeake, VA has a pool.