Homes Under $500K in Chester, VA

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3 beds New construction With a pool

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24 of 101 Listings

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Homes Under $500K in Chester, VA

24 of 101 Listings

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101 listings

Homes Under $500K in Chester, VA

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24 of 101 Listings

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Homes Under $500K in Chester, VA

24 of 101 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

New39

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Active

$337,000

3 bd · 3 ba · 1,644 sqft

11425 Claimont Mill Dr, Chester, VA

Tucker Greer · Shaheen Ruth Martin & Fonville

New25Active

$454,900

3 bd · 2 ba · 2,056 sqft

10662 Centralia Station Rd, Chester, VA

Alex Glaser · Long & Foster REALTORS

New1Active

$335,000

5 bd · 4 ba · 2,798 sqft

3561 Thornsett Dr, Chester, VA

Eric Walker · EXP Realty, LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

39Active

$355,000

3 bd · 3 ba · 1,700 sqft

10331 Genlou Rd, Chester, VA

Sara Tostenson · Real Broker LLC

34Active

$400,000

4 bd · 3 ba · 2,520 sqft

4601` Black Oak Rd, Chester, VA

Roberta Johnson · First Choice Realty

1Active

$289,900

3 bd · 2 ba · 2,204 sqft

4512 Greenbriar Dr, Chester, VA

Mike McCarthy · Metro DMV Realty

44Active

$385,000

4 bd · 3 ba · 1,891 sqft

1109 Walnut Dr, Chester, VA

Kacie Jenkins · Real Broker LLC

6Active

$415,000

4 bd · 3 ba · 2,679 sqft

3207 Ludgate Rd, Chester, VA

Denise Conway · Long & Foster REALTORS

52Active

$475,000

4 bd · 3 ba · 3,199 sqft

4101 Cara Hill Ct, Chester, VA

Nicole Reed · Real Broker LLC

41Active

$369,950

3 bd · 2 ba · 2,124 sqft

3421 Wood Dale Rd, Chester, VA

Victoria Brumfield · Cole Real Estate, Inc.

33Active

$385,000

3 bd · 4 ba · 2,146 sqft

6113 W Stonepath Garden Dr, Chester, VA

Tracy Girard · Real Broker LLC

37Active

$315,000

3 bd · 2 ba · 1,650 sqft

14141 Cherry St, Chester, VA

Sandy Owens · RE/MAX Commonwealth

47Active

$424,950

4 bd · 3 ba · 2,076 sqft

11119 Sweetbay Arbor Pl, Chester, VA

Kelly Bump · Share Realty

31Active

$360,000

3 bd · 2 ba · 1,759 sqft

3429 Wood Dale Rd, Chester, VA

Victoria Brumfield · Cole Real Estate, Inc.

46Active

$375,000

3 bd · 3 ba · 1,632 sqft

10501 Surry Rd, Chester, VA

Ryan Medlin · RE/MAX Commonwealth

34Active

$382,950

4 bd · 3 ba · 1,680 sqft

3313 New Found Ln, Chester, VA

Doris Gunn-Conner · Keller Williams Realty

32Active

$365,000

3 bd · 2 ba · 1,766 sqft

4504 Edenton Pl, Chester, VA

Jennifer McCray · Real Broker LLC

48Active

$395,000

4 bd · 3 ba · 1,925 sqft

4820 Cedar Cliff Rd, Chester, VA

Rebby Castro-Imobisa · Real Broker LLC

Price Reduced35Active

$432,000

3 bd · 2 ba · 2,208 sqft

612 Green Garden Cir, Chester, VA

Anthony Burch · United Real Estate Richmond

Price Reduced54Active

$419,900

4 bd · 3 ba · 2,760 sqft

12541 Winfree St, Chester, VA

Kasey Shumaker · Douglas Elliman Real Estate

40Active

$475,000

4 bd · 2 ba · 2,522 sqft

14424 Dampier Dr, Chester, VA

Dianne Stanley · Shaheen Ruth Martin & Fonville

37Active

$414,999

3 bd · 3 ba · 1,872 sqft

501 Green Orchard Dr, Chester, VA

Monier Monier · United Real Estate Richmond

32Active

$445,000

3 bd · 2 ba · 1,418 sqft

11319 Vulcan Ln, Chester, VA

Ciera Koger · Keller Williams Realty

Price Reduced38Active

$334,500

3 bd · 3 ba · 1,864 sqft

5112 Weatherby Dr, Chester, VA

Mike Hogan · The Hogan Group Real Estate

Listing data & MLS disclosures

Central Virginia Regional MLS: IDX information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listings. All CVR MLS information provided is deemed reliable but is not guaranteed accurate.The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC®. All Rights Reserved. Last Updated: 2026-09-17 20:38:52 UTC

Chester housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 46 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $388,365$343,130–$474,550 typical range
Price per sq. ft.: $195
Sales: 67
Paid in cash: 17.9%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $447,475

Chester, VA community profile

Area: 50 sq. mi.

Source: HJN community data

Explore Chester homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

Listing data & MLS disclosures

Central Virginia Regional MLS: IDX information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listings. All CVR MLS information provided is deemed reliable but is not guaranteed accurate.The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC®. All Rights Reserved. Last Updated: 2026-09-17 20:38:52 UTC

Chester, VA community profile

Area: 50 sq. mi.

Source: HJN community data

Chester housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 46 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $388,365$343,130–$474,550 typical range
Price per sq. ft.: $195
Sales: 67
Paid in cash: 17.9%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $447,475

Homes for sale

110

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -1.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 2,096 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chester housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 31, 2026

Chester, VA community profile

Explore Chester homes

Your local brokerage

Listing data & MLS disclosures

Chester, VA community profile

Chester housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026