Vintage homes for sale & real estate in Chesterfield County, VA

36 homes

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NEW 19 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesterfield County, VA:
$5,000 SELLER CREDIT TO BUYER! Classic charm meets stylish finishes in this inviting 4-bedroom, 3-full-bath home. A generous covered front porch, distinctive exterior, and picket fence create memorable curb appeal. Inside, warm wood floors, abundant natural light, recessed lighting, and crisp trim complement the thoughtfully designed layout. The main level offers a welcoming living room, separate dining room, and breakfast nook adjoining a kitchen with white cabinetry, stainless steel appliances, and ample counter space. The spacious main-level primary suite features a beautifully appointed bathroom with a double-sink vanity, glass-enclosed shower, and freestanding soaking tub. A second bed

$454,999

4 beds3 baths2,025 sq ft

12105 Mathenay Dr, Chester, VA 23831

Covered front porch • Picket fence • Warm wood floors

ABOUT THIS HOME
Vintage Home for sale in Chesterfield County, VA:
Investor / Rehab Opportunity! This 4 Bedroom - 1 Bath Home Situated on a Double Sized Lot is Priced to Sell & Ready for Renovations. Enclosed Side Porch, Fenced Yard, Double Width Driveway, Detatched Deck, Spacious Kitchen & Updated Bathroom are just some of the Highlights of this Home. Strong Bones with Clear Upside Potential. Flooring still in Good Condition, Above Ground Swimming Pool Still Operable & Detached Large Work Shop Located on the Side of the Property could be Salvaged (Need Extra TLC). CASH OFFERS ONLY with No Contingencies. .. This Property is NOT Eligible for Traditional Financing & will not Qualify for FHA, VA or Conventonal Loans. HOME SOLD-AS-IS. S

$230,000

4 beds1 bath1,238 sq ft

6741 Strathmore Rd, North Chesterfield, VA 23237

Enclosed side porch • Detached deck • Fenced yard

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Chesterfield County, VA:
Don't let the square footage deter you. .. this home is on a large oversized corner lot with plenty of room to make it your own. Full roof replacement in 2025, plus owner has a home warranty in place that will be transferred to new buyers. Appliances were purchased in 2024. Its incredibly hard to find something at this price point in Chesterfield County within a good school district so come check it out for yourself!

$222,500

2 beds1 bath704 sq ft

15909 Hill St, South Chesterfield, VA 23834

Oversized corner lot • Home warranty • Good school district

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Chesterfield County, VA:
Welcome to this beautifully updated 4-bedroom, 2-bath home in Chesterfield, offering a comfortable layout, stylish finishes, and plenty of space inside and out. Step inside to a bright and inviting living room featuring a vaulted ceiling, recessed lighting, LVP flooring, and an open feel that carries throughout the main living spaces. Continue into the kitchen, where white cabinetry, granite countertops, stainless steel appliances, and generous workspace create a functional space for both everyday living and entertaining. The adjoining dining area provides an easy place to gather and features sliding glass doors that open directly to the back deck. Outside, the Trex deck overlooks a spaciou

$290,000

4 beds2 baths1,240 sq ft

2912 Bensley Rd, North Chesterfield, VA 23237

Updated finishes • Granite countertops • Trex deck

ABOUT THIS HOME
Vintage Home for sale in Chesterfield County, VA:
15-25 minutes to shopping, schools, and jobs, and far enough out to enjoy nature's gifts. This property offers beautiful 6.92 acres as a peaceful setting for either a new home, renovating the existing one, occupying the home as is, or a blend of the options. The land is about half cleared, with gently sloping acres of grass and a wooded portion which acts as a quiet privacy buffer with the back and side neighbors. The house has a sun porch to the front, a comfortable and charming living room, the primary bedroom, a second bedroom/family room, dining room and kitchen. The back enclosed porch serves as the laundry center. The rear deck is a wonderful place to gather friends and family. Numer

$250,000

2 beds1 bath864 sq ft

9209 Hickory Rd, South Chesterfield, VA 23803

Sun porch • Roof and siding • Deck

Property at 2406 Mcrae Rd, North Chesterfield, VA 23235, 3 beds, 2 baths

$515,000

3 beds2 baths1,984 sq ft

2406 Mcrae Rd, North Chesterfield, VA 23235

Property at 8403 Halidan Dr, North Chesterfield, VA 23235, 3 beds, 1.5 baths

$445,000

3 beds1.5 baths2,026 sq ft

8403 Halidan Dr, North Chesterfield, VA 23235

Property at 15101 Woods Edge Rd, South Chesterfield, VA 23834, 4 beds, 3 baths

$415,000

4 beds3 baths2,247 sq ft

15101 Woods Edge Rd, South Chesterfield, VA 23834

Property at 5317 River Rd, South Chesterfield, VA 23803, 3 beds, 1 bath

$249,900

3 beds1 bath1,146 sq ft

5317 River Rd, South Chesterfield, VA 23803

Property at 8409 Hopkins Rd, North Chesterfield, VA 23237, 5 beds, 2 baths

$375,000

5 beds2 baths1,874 sq ft

8409 Hopkins Rd, North Chesterfield, VA 23237

Property at 2800 Kingsdale Rd, North Chesterfield, VA 23237, 4 beds, 2.5 baths

$324,750

4 beds2.5 baths2,081 sq ft

2800 Kingsdale Rd, North Chesterfield, VA 23237

Property at 12541 Winfree St, Chester, VA 23831, 4 beds, 3 baths

$419,900

4 beds3 baths2,760 sq ft

12541 Winfree St, Chester, VA 23831

Property at 7213 Bennington Rd, North Chesterfield, VA 23225, 3 beds, 2 baths

$299,950

3 beds2 baths1,035 sq ft

7213 Bennington Rd, North Chesterfield, VA 23225

Property at 2813 Parkdale Rd, North Chesterfield, VA 23234, 3 beds, 2 baths

$359,900

3 beds2 baths1,368 sq ft

2813 Parkdale Rd, North Chesterfield, VA 23234

Property at 1808 Bellwood Rd, North Chesterfield, VA 23237, 3 beds, 2 baths

$289,990

3 beds2 baths1,412 sq ft

1808 Bellwood Rd, North Chesterfield, VA 23237

Property at 170 Charlotte Ave Ave, Colonial Heights, VA 23834, 2 beds, 1 bath

$140,000

2 beds1 bath748 sq ft

170 Charlotte Ave Ave, Colonial Heights, VA 23834

Property at 1310 Enon Ave, Chester, VA 23836, 3 beds, 1 bath

$285,000

3 beds1 bath977 sq ft

1310 Enon Ave, Chester, VA 23836

Property at 2905 Plotkin Rd, Richmond, VA 23234, 3 beds, 1 bath

$249,999

3 beds1 bath864 sq ft

2905 Plotkin Rd, Richmond, VA 23234

Property at 21210 Winfree Ave, South Chesterfield, VA 23803, 3 beds, 1 bath

$289,000

3 beds1 bath800 sq ft

21210 Winfree Ave, South Chesterfield, VA 23803

Property at 10035 Wycliff Rd, North Chesterfield, VA 23236, 3 beds, 2 baths

$342,500

3 beds2 baths1,500 sq ft

10035 Wycliff Rd, North Chesterfield, VA 23236

Property at 9916 S Wagstaff Cir, North Chesterfield, VA 23236, 4 beds, 2 baths

$450,000

4 beds2 baths2,274 sq ft

9916 S Wagstaff Cir, North Chesterfield, VA 23236

Property at 21204 Orange Hill Ave, South Chesterfield, VA 23803, 3 beds, 1.5 baths

$299,900

3 beds1.5 baths1,700 sq ft

21204 Orange Hill Ave, South Chesterfield, VA 23803

Property at 4819 Arundel Ave, North Chesterfield, VA 23234, 3 beds, 1 bath

$300,000

3 beds1 bath1,400 sq ft

4819 Arundel Ave, North Chesterfield, VA 23234

Property at 21310 Chesterfield Ave, South Chesterfield, VA 23803, 4 beds, 3 baths

$260,000

4 beds3 baths1,704 sq ft

21310 Chesterfield Ave, South Chesterfield, VA 23803

Property at 2800 Milhorn St, South Chesterfield, VA 23834, 2 beds, 1 bath

$171,000

2 beds1 bath720 sq ft

2800 Milhorn St, South Chesterfield, VA 23834

Property at 2459 Osborne Rd, Chester, VA 23831, 2 beds, 1 bath

$229,500

2 beds1 bath672 sq ft

2459 Osborne Rd, Chester, VA 23831

Property at 9700 Old Cannon Rd, North Chesterfield, VA 23237, 8 beds, 3.5 baths

$1,222,000

8 beds3.5 baths3,455 sq ft

9700 Old Cannon Rd, North Chesterfield, VA 23237

Property at 6632 Johnston St, South Chesterfield, VA 23803, 4 beds, 3.5 baths

$299,900

4 beds3.5 baths2,126 sq ft

6632 Johnston St, South Chesterfield, VA 23803

Property at 3510 E River Rd, South Chesterfield, VA 23803, 2 beds, 1 bath

$229,900

2 beds1 bath1,034 sq ft

3510 E River Rd, South Chesterfield, VA 23803

Property at 21407 Perdue Ave, South Chesterfield, VA 23803, 4 beds, 2 baths

$315,000

4 beds2 baths1,396 sq ft

21407 Perdue Ave, South Chesterfield, VA 23803

Property at 307 Roanoke, Colonial Heights, VA 23834, 3 beds, 1 bath

$249,900

3 beds1 bath1,317 sq ft

307 Roanoke, Colonial Heights, VA 23834

Property at 12020 Winfree St, Chester, VA 23831, 7 beds, 4 baths

$640,000

7 beds4 baths2,716 sq ft

12020 Winfree St, Chester, VA 23831

Property at 9934 Friend Ave, North Chesterfield, VA 23237, 4 beds, 1 bath

$275,000

4 beds1 bath1,224 sq ft

9934 Friend Ave, North Chesterfield, VA 23237

Property at 21611 Pannill St, South Chesterfield, VA 23803, 3 beds, 1 bath

$235,000

3 beds1 bath996 sq ft

21611 Pannill St, South Chesterfield, VA 23803

Property at 421 E Hundred Rd, Chester, VA 23836

$349,950

Land0.83 acre (lot)

421 E Hundred Rd, Chester, VA 23836

Property at 8501 Hickory Rd, South Chesterfield, VA 23803, 3 beds, 2 baths

$650,000

Land26.71 acres (lot)

8501 Hickory Rd, South Chesterfield, VA 23803

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Vintage Homes for Sale in Chesterfield County

There are currently 36 vintage homes for sale in Chesterfield County at a median listing price of $450K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chesterfield County stay on the market for 44 days and receive 2 offers. This map is refreshed with the newest listings in Chesterfield County every 15 minutes.

In the past month, 472 homes have been sold in Chesterfield County. In addition to houses in Chesterfield County, there were also 123 condos, 263 townhouses, and 2 multi-family units for sale in Chesterfield County last month. Find your dream home in Chesterfield County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chesterfield County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chesterfield County. If you're looking to sell your home in the Chesterfield County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chesterfield County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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