Vintage homes for sale & real estate in Chesapeake, VA

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NEW 20 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Welcome home to the heart of Hickory! This stunning, fully remodeled home perfectly blends country charm with modern elegance. Featuring 4 spacious bedrooms, 3 beautifully updated bathrooms, and sitting on 1.5 serene acres, this home offers the ideal balance of privacy and convenience. Inside, you’ll love the brand-new LVP flooring, stylish tile showers, granite countertops, and wet bar—all thoughtfully chosen to complement the open, inviting layout. Step outside to enjoy the peaceful surroundings from the wide front porch, host gatherings on the large back deck, or savor quiet mornings on the private deck. Move-in ready and designed for everyday comfort, this home is a rare fin

$579,000

4 beds3 baths1,711 sq ft

509 Head Of River Rd, Chesapeake, VA 23322

Fully remodeled home • Stylish tile showers • Wet bar

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Built in 1940, once known as Parsons General Store, it proudly served as a gathering place for the Chesapeake community for many years. Rich with memories, this home blends historical character with modern updates, creating the perfect balance of nostalgia and comfort. Step inside to find a beautifully refreshed interior that honors the home’s heritage while offering all the conveniences for today’s lifestyle. Discover the recent upgrades including a brand-new kitchen featuring granite countertops, new cabinetry, stainless steel appliances and a convenient walk-in pantry. New LVP flooring throughout. It offers two primary bedrooms, both with en-suite bathrooms and spacious walk-

$569,000

4 beds2.5 baths2,600 sq ft

1848 Ballahack Rd, Chesapeake, VA 23322

Brand new kitchen • New cabinetry • New lvp flooring

NEW 19 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Fantastic opportunity to own this duplex with large first floor living area with 3 bedrooms and 1 full bath family room and dining room and eat-in kitchen. First floor unit A is a ranch on one level. Upstairs unit B is a one bedroom + 1 bath with a kitchen and living room. Access to unit B has wooden stairs on the exterior and a back door with stairs. Newer 30 yr arch roof + vinyl insulated windows. Huge corner lot. Property to be sold in " as-is" condition. Seller will not make any repairs. Rehab loan or cash needed to buy this property. Driveway space for the upstairs unit in the back. Storage shed to convey + dog run fenced area. Some wood flooring in Unit A. Utility room on th

$275,000

4 beds2 baths1,878 sq ft

701 Wingfield Ave, Chesapeake, VA 23325

Huge corner lot • Wooden stairs • Eat-in kitchen

NEW 21 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Rancher with covered front porch. Great room, three bedrooms, one full bath. Kitchen appliances include stove, refrigerator, and dishwasher. Shed with washer and dryer hook ups. Fenced backyard. Driveway and street parking. Vinyl siding, insulated windows, gutters and downspouts. Updated bath and kitchen. Central heat and air. This will be an "as is" sale.

$185,000

3 beds1 bath1,144 sq ft

6 Worden Pl, Portsmouth, VA 23702

Covered front porch • Updated bath • Insulated windows

NEW 23 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Come see this recently renovated 3-bedroom, 2-full bath brick ranch with an open floor plan and fully updated interior! This home features a beautifully updated eat-in kitchen with all new stainless-steel appliances, new quartz countertops, glass backsplash, new two-tone cabinets and recessed lighting! Primary bedroom with primary bath with new marble shower floor and ceramic tile shower surround!! New laminate flooring throughout! Fresh paint! Updated fixtures! Updated baths! New roof! New HVAC! 2 storage sheds (as-is)! Don't miss this one! Property has been staged and staging items do not convey.

$295,000

3 beds2 baths950 sq ft

3005 Scotia Dr, Chesapeake, VA 23325

Glass backsplash • Quartz countertops • Renovated

Property at 501 Fernwood Farms Rd, Chesapeake, VA 23320, 4 beds, 2 baths

$485,000

4 beds2 baths1,873 sq ft

501 Fernwood Farms Rd, Chesapeake, VA 23320

Property at 120 Causeway Dr, Chesapeake, VA 23322, 2 beds, 1.5 baths

$299,500

2 beds1.5 baths1,100 sq ft

120 Causeway Dr, Chesapeake, VA 23322

Property at 1998 Angora Dr, Chesapeake, VA 23325, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths2,786 sq ft

1998 Angora Dr, Chesapeake, VA 23325

Property at 123 Ridgewood Rd, Chesapeake, VA 23325, 4 beds, 2 baths

$374,900

4 beds2 baths1,785 sq ft

123 Ridgewood Rd, Chesapeake, VA 23325

Property at 1402 Earle Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$285,000

3 beds2 baths1,595 sq ft

1402 Earle Ave, Chesapeake, VA 23324

Property at 2029 Battery Park Rd, Chesapeake, VA 23323, 3 beds, 1.5 baths

$299,900

3 beds1.5 baths1,400 sq ft

2029 Battery Park Rd, Chesapeake, VA 23323

Property at 3106 Joseph Ave, Chesapeake, VA 23324, 2 beds, 2 baths

$299,900

2 beds2 baths1,153 sq ft

3106 Joseph Ave, Chesapeake, VA 23324

Property at 308 Taft Dr, Portsmouth, VA 23701, 3 beds, 2 baths

$259,900

3 beds2 baths1,235 sq ft

308 Taft Dr, Portsmouth, VA 23701

Property at 2609 Harling Dr, Chesapeake, VA 23325, 2 beds, 1 bath

$199,000

2 beds1 bath1,230 sq ft

2609 Harling Dr, Chesapeake, VA 23325

Property at 2900 Mayon Dr, Chesapeake, VA 23325, 3 beds, 1 bath

$210,000

3 beds1 bath950 sq ft

2900 Mayon Dr, Chesapeake, VA 23325

Property at 3317 Hornsea Rd, Chesapeake, VA 23325, 5 beds, 3.5 baths

$420,000

5 beds3.5 baths2,600 sq ft

3317 Hornsea Rd, Chesapeake, VA 23325

Property at 2816 Benefit Rd, Chesapeake, VA 23322, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,700 sq ft

2816 Benefit Rd, Chesapeake, VA 23322

Property at 1208 Edgewood Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$310,000

3 beds2 baths1,541 sq ft

1208 Edgewood Ave, Chesapeake, VA 23324

Property at 1234 Kay Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$300,000

3 beds2 baths1,682 sq ft

1234 Kay Ave, Chesapeake, VA 23324

Property at 606 Bethel Rd, Chesapeake, VA 23325, 3 beds, 2 baths

$290,000

3 beds2 baths1,216 sq ft

606 Bethel Rd, Chesapeake, VA 23325

Property at 4032 Georgia Rd, Chesapeake, VA 23321, 5 beds, 3 baths

$500,000

5 beds3 baths3,119 sq ft

4032 Georgia Rd, Chesapeake, VA 23321

Property at 3009 Mattox Dr, Chesapeake, VA 23325, 3 beds, 2 baths

$325,000

3 beds2 baths1,500 sq ft

3009 Mattox Dr, Chesapeake, VA 23325

Property at 1119 Decatur St, Chesapeake, VA 23324, 2 beds, 1 bath

$179,000

2 beds1 bath818 sq ft

1119 Decatur St, Chesapeake, VA 23324

Property at 2320 Battery Park Rd, Chesapeake, VA 23323, 3 beds, 1 bath

$348,000

3 beds1 bath1,973 sq ft

2320 Battery Park Rd, Chesapeake, VA 23323

Property at 700 Stewart St, Chesapeake, VA 23324, 3 beds, 2 baths

$279,990

3 beds2 baths1,966 sq ft

700 Stewart St, Chesapeake, VA 23324

Property at 708 Sparrow Rd, Chesapeake, VA 23325, 2 beds, 1 bath

$290,000

2 beds1 bath834 sq ft

708 Sparrow Rd, Chesapeake, VA 23325

Property at 1441 Boxwood Dr, Chesapeake, VA 23323, 3 beds, 2 baths

$365,000

3 beds2 baths1,739 sq ft

1441 Boxwood Dr, Chesapeake, VA 23323

Property at 1151 Virginia Ave, Chesapeake, VA 23324, 3 beds, 1.5 baths

$190,000

3 beds1.5 baths1,154 sq ft

1151 Virginia Ave, Chesapeake, VA 23324

Property at 1513 Manson St, Norfolk, VA 23523, 3 beds, 2 baths

$195,000

3 beds2 baths1,350 sq ft

1513 Manson St, Norfolk, VA 23523

Property at 1007 Holly Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$282,000

3 beds2 baths1,586 sq ft

1007 Holly Ave, Chesapeake, VA 23324

Property at 1004 Mayfield Ave, Chesapeake, VA 23324, 3 beds, 1 bath

$275,000

3 beds1 bath1,005 sq ft

1004 Mayfield Ave, Chesapeake, VA 23324

Property at 413 George Washington Hwy N, Chesapeake, VA 23323, 2 beds, 2 baths

$214,900

2 beds2 baths1,356 sq ft

413 George Washington Hwy N, Chesapeake, VA 23323

Property at 1217 Cleona Dr, Chesapeake, VA 23324, 3 beds, 1 bath

$260,000

3 beds1 bath1,014 sq ft

1217 Cleona Dr, Chesapeake, VA 23324

Property at 802 Decatur St, Chesapeake, VA 23324, 6 beds, 2.5 baths

$550,000

6 beds2.5 baths4,056 sq ft

802 Decatur St, Chesapeake, VA 23324

Property at 4707 Dermott St, Chesapeake, VA 23320, 3 beds, 1.5 baths

$345,000

3 beds1.5 baths1,360 sq ft

4707 Dermott St, Chesapeake, VA 23320

Property at 1204 Myrtle Ave, Chesapeake, VA 23325, 4 beds, 1 bath

$330,000

4 beds1 bath1,208 sq ft

1204 Myrtle Ave, Chesapeake, VA 23325

Property at 212 George Washington Hwy N, Chesapeake, VA 23323, 3 beds, 2 baths

$329,900

3 beds2 baths1,875 sq ft

212 George Washington Hwy N, Chesapeake, VA 23323

Property at 1105 Kay Ave, Chesapeake, VA 23324, 3 beds, 1 bath

$230,000

3 beds1 bath912 sq ft

1105 Kay Ave, Chesapeake, VA 23324

Property at 87 Dahlgren Ave, Portsmouth, VA 23702, 3 beds, 1.5 baths

$263,000

3 beds1.5 baths1,633 sq ft

87 Dahlgren Ave, Portsmouth, VA 23702

Property at 727 Sparrow Rd, Chesapeake, VA 23325, 3 beds, 1 bath

$345,000

3 beds1 bath1,491 sq ft

727 Sparrow Rd, Chesapeake, VA 23325

Property at 612 River Creek Rd, Chesapeake, VA 23320, 3 beds, 2 baths

$287,000

3 beds2 baths1,157 sq ft

612 River Creek Rd, Chesapeake, VA 23320

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Vintage Homes for Sale in Chesapeake

There are currently 82 vintage homes for sale in Chesapeake at a median listing price of $447K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chesapeake stay on the market for 51 days and receive 5 offers. Popular neighborhoods include Ghent, Western Branch, Great Bridge, West Ghent, and Pungo-Blackwater. This map is refreshed with the newest listings in Chesapeake every 15 minutes.

In the past month, 236 homes have been sold in Chesapeake. In addition to houses in Chesapeake, there were also 199 condos, 52 townhouses, and 1 multi-family unit for sale in Chesapeake last month. Chesapeake is a not walkable city in Virginia with a Walk Score of 21. Chesapeake is home to approximately 222,581 people and 98,255 jobs. Find your dream home in Chesapeake 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 Chesapeake are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chesapeake. Our Chesapeake real estate stats and trends will give you more information about home buying and selling trends in Chesapeake. If you're looking to sell your home in the Chesapeake area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chesapeake with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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