Vintage homes for sale & real estate in Chesapeake, VA

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OPEN FRI, 3PM TO 6PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Welcome to this beautifully transformed 4-bedroom, 2-bath home in a sought-after Chesapeake neighborhood. Step inside to a bright, modern interior featuring a brand-new kitchen with quartz countertops, new cabinetry and stainless-steel appliances, two beautifully updated full bathrooms, fresh finishes, and a clean contemporary look throughout. You name it and its NEW in 2026! Roof, siding, doors, windows, drywall, flooring, carpet, paint, light fixtures, kitchen, bathrooms, appliances, HVAC, water heater…the list keeps going. And wait until you see the backyard. HUGE, fully fenced, and ready for the pets, cookouts, cornhole or that backyard setup you’ve been saving on Pinterest

$349,999

4 beds2 baths1,310 sq ft

1405 Salton Dr, Chesapeake, VA 23325

Quartz countertops • Brand new kitchen • New cabinetry

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Tucked away on a quiet dead-end street, this beautifully updated 3-bedroom, 2-bath ranch offers peaceful water views and an inviting indoor-outdoor lifestyle. Enjoy an open, flexible floor plan, screened porch, oversized deck, and private fenced backyard great for relaxing, entertaining, kayaking, or simply enjoying the tranquil surroundings. Major updates include a NEW central HVAC system with new ductwork (2025), NEW kitchen appliances (2025), LVP flooring and fresh neutral paint.

$420,000

3 beds2 baths1,500 sq ft

668 Luther St, Chesapeake, VA 23322

Oversized deck • Screened porch • Central hvac system

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Five acres. A powered detached workshop. Room to breathe, space to make your own. This updated Cape Cod offers the flexibility of acreage living in Chesapeake’s Grassfield area. The home features 3 bedrooms, 2 full baths and a first-floor bedroom and full bath. MLS square footage reflects 1,869 sq. ft. per tax records; a recent appraisal measured approximately 2,067 sq. ft. Updates include a renovated kitchen and baths, replacement windows, updated electrical and plumbing, a 2023 heat pump, 2024 whole-house paint and newer flooring. Beautiful hardwood floors, a fireplace, and generous mud/laundry space add function and character. The approx. 736 sq. ft. powered detached garage/worksho

$524,900

3 beds2 baths1,869 sq ft

317 George Washington Hwy S, Chesapeake, VA 23323

Updated electrical • Heat pump • Renovated kitchen

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Completely remodeled three bedroom, two bath with new LVP flooring, new carpet, a brand new kitchen, and updated bathrooms. One bedroom and a full bath are downstairs, which works well for guests, an office, or anyone who would rather skip the stairs. There's a front porch out front, and the backyard is large, with plenty of off street parking. Lakeside Park sits right around the corner, with a lake you can fish, two playgrounds, covered pavilions, and a walking path through the trees. Elizabeth River Park is about a mile up the road and has a dog park, a fishing pier, a boat ramp, and a paved path along the water. I-464 puts you in downtown Norfolk in about ten minutes. Updated and ready f

$267,700

3 beds2 baths1,336 sq ft

1318 18th St, Chesapeake, VA 23324

New kitchen • Off street parking • Front porch

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Welcome home to this inviting 3 bdrm, 2 full bath plus a bonus room that can be used as an office, nursery, craft room or guest room. This ranch offers comfortable and spacious one-level living. Beautiful wood floors add warmth and character throughout the home. The kitchen features attractive granite countertops with a large breakfast bar, providing both style and functionality for everyday living and entertaining. The thoughtfully designed floor plan offers comfortable living spaces, well-proportioned bedrooms, extra large primary bedroom and the convenience of single story living. Enjoy the large yard and detached garage with carport. Whether you are a first-time homebuyer, downsizing, o

$350,000

3 beds2 baths2,000 sq ft

3210 Indigo Rd, Chesapeake, VA 23325

Large breakfast bar • Large yard • Carport

Property at 111 Goldcrest Drive Dr, Chesapeake, VA 23325, 3 beds, 2 baths

$465,000

3 beds2 baths1,857 sq ft

111 Goldcrest Drive Dr, Chesapeake, VA 23325

Property at 109 Causeway Dr, Chesapeake, VA 23322, 3 beds, 2 baths

$429,900

3 beds2 baths1,500 sq ft

109 Causeway Dr, Chesapeake, VA 23322

Property at 2025 Battery Park Rd, Chesapeake, VA 23323, 3 beds, 2 baths

$280,000

3 beds2 baths1,791 sq ft

2025 Battery Park Rd, Chesapeake, VA 23323

Property at 224 Northview Dr, Chesapeake, VA 23322, 3 beds, 2.5 baths

$485,000

3 beds2.5 baths1,854 sq ft

224 Northview Dr, Chesapeake, VA 23322

Property at 1601 Lilac Ave, Chesapeake, VA 23325, 4 beds, 2 baths

$419,000

4 beds2 baths1,853 sq ft

1601 Lilac Ave, Chesapeake, VA 23325

Property at 1225 Jackson Ave, Chesapeake, VA 23324, 3 beds, 1 bath

$225,000

3 beds1 bath996 sq ft

1225 Jackson Ave, Chesapeake, VA 23324

Property at 1321 Seaboard Ave, Chesapeake, VA 23324, 4 beds, 2 baths

$275,000

4 beds2 baths1,550 sq ft

1321 Seaboard Ave, Chesapeake, VA 23324

Property at 101 Stadium Dr, Chesapeake, VA 23322, 4 beds, 3.5 baths

$649,900

4 beds3.5 baths3,458 sq ft

101 Stadium Dr, Chesapeake, VA 23322

Property at 944 Bells Mill Rd, Chesapeake, VA 23322, 3 beds, 1 bath

$347,500

3 beds1 bath1,330 sq ft

944 Bells Mill Rd, Chesapeake, VA 23322

Property at 1308 Sunnybrook Ter, Chesapeake, VA 23321, 4 beds, 3 baths

$365,000

4 beds3 baths2,200 sq ft

1308 Sunnybrook Ter, Chesapeake, VA 23321

Property at 3433 Martin Johnson Rd, Chesapeake, VA 23323, 3 beds, 2 baths

$394,990

3 beds2 baths1,607 sq ft

3433 Martin Johnson Rd, Chesapeake, VA 23323

Property at 1085 Cascade Blvd, Chesapeake, VA 23324, 3 beds, 2.5 baths

$324,900

3 beds2.5 baths1,250 sq ft

1085 Cascade Blvd, Chesapeake, VA 23324

Property at 1307 Perry St, Chesapeake, VA 23324, 4 beds, 2 baths

$252,000

4 beds2 baths1,659 sq ft

1307 Perry St, Chesapeake, VA 23324

Property at 2410 Centerville Tpke, Chesapeake, VA 23322, 3 beds, 2 baths

$879,000

3 beds2 baths2,863 sq ft

2410 Centerville Tpke, Chesapeake, VA 23322

Property at 2204 Ardmore Ave Ave, Chesapeake, VA 23324, 4 beds, 2 baths

$354,999

4 beds2 baths1,399 sq ft

2204 Ardmore Ave Ave, Chesapeake, VA 23324

Property at 5144 Ballahack Rd, Chesapeake, VA 23322, 4 beds, 2 baths

$415,000

4 beds2 baths1,470 sq ft

5144 Ballahack Rd, Chesapeake, VA 23322

Property at 245 Old Dr, Chesapeake, VA 23322, 3 beds, 1.5 baths

$410,000

3 beds1.5 baths1,629 sq ft

245 Old Dr, Chesapeake, VA 23322

Property at 4212 Bainbridge Blvd, Chesapeake, VA 23324, 4 beds, 3 baths

$349,900

4 beds3 baths1,588 sq ft

4212 Bainbridge Blvd, Chesapeake, VA 23324

Property at 1513 Wingfield Ave, Chesapeake, VA 23325, 3 beds, 2 baths

$324,900

3 beds2 baths1,361 sq ft

1513 Wingfield Ave, Chesapeake, VA 23325

Property at 1441 Whittamore Rd, Chesapeake, VA 23322, 5 beds, 2 baths

$469,900

5 beds2 baths1,800 sq ft

1441 Whittamore Rd, Chesapeake, VA 23322

Property at 1514 Myrtle Ave, Chesapeake, VA 23325, 3 beds, 2 baths

$339,900

3 beds2 baths1,508 sq ft

1514 Myrtle Ave, Chesapeake, VA 23325

Property at 100 Alice St, Chesapeake, VA 23323, 4 beds, 2.5 baths

$369,000

4 beds2.5 baths1,428 sq ft

100 Alice St, Chesapeake, VA 23323

Property at 28 Hinton Ave, Chesapeake, VA 23323, 4 beds, 2 baths

$345,900

4 beds2 baths1,500 sq ft

28 Hinton Ave, Chesapeake, VA 23323

Property at 405 Tekoa Rd, Chesapeake, VA 23325, 3 beds, 2 baths

$325,000

3 beds2 baths1,330 sq ft

405 Tekoa Rd, Chesapeake, VA 23325

Property at 1028 Livingston Ave Ave, Chesapeake, VA 23324, 2 beds, 2 baths

$294,500

2 beds2 baths1,153 sq ft

1028 Livingston Ave Ave, Chesapeake, VA 23324

Property at 901 Stewart St, Chesapeake, VA 23324, 2 beds, 1 bath

$220,000

2 beds1 bath825 sq ft

901 Stewart St, Chesapeake, VA 23324

Property at 605 Wingfield Ave, Chesapeake, VA 23325, 4 beds, 1 bath

$279,900

4 beds1 bath1,484 sq ft

605 Wingfield Ave, Chesapeake, VA 23325

Property at 1202 Berkley Ave, Norfolk, VA 23523, 2 beds, 1 bath

$195,000

2 beds1 bath963 sq ft

1202 Berkley Ave, Norfolk, VA 23523

Property at 916 Redstart Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$360,000

3 beds2 baths1,744 sq ft

916 Redstart Ave, Chesapeake, VA 23324

Property at 1207 Kay Ave, Chesapeake, VA 23324, 3 beds, 1 bath

$282,500

3 beds1 bath912 sq ft

1207 Kay Ave, Chesapeake, VA 23324

Property at 1129 Hazel Ave, Chesapeake, VA 23325, 4 beds, 3.5 baths

$394,999

4 beds3.5 baths2,000 sq ft

1129 Hazel Ave, Chesapeake, VA 23325

Property at 2502 Livesay Rd, Chesapeake, VA 23323, 3 beds, 2 baths

$290,000

3 beds2 baths1,221 sq ft

2502 Livesay Rd, Chesapeake, VA 23323

Property at 4210 Bainbridge Blvd, Chesapeake, VA 23324, 3 beds, 2 baths

$284,900

3 beds2 baths900 sq ft

4210 Bainbridge Blvd, Chesapeake, VA 23324

Property at 3861 Ahoy Dr Unit Dr, Chesapeake, VA 23321, 5 beds, 2 baths

$395,000

5 beds2 baths3,333 sq ft

3861 Ahoy Dr Unit Dr, Chesapeake, VA 23321

Property at 708 B St, Chesapeake, VA 23324, 4 beds, 1.5 baths

$275,000

4 beds1.5 baths1,624 sq ft

708 B St, Chesapeake, VA 23324

Property at 2213 Wildwood Rd, Chesapeake, VA 23323, 4 beds, 2 baths

$429,900

4 beds2 baths2,188 sq ft

2213 Wildwood Rd, Chesapeake, VA 23323

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Vintage Homes for Sale in Chesapeake

There are currently 88 vintage homes for sale in Chesapeake at a median listing price of $459K. 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 49 days and receive 3 offers. This map is refreshed with the newest listings in Chesapeake every 15 minutes.

In the past month, 282 homes have been sold in Chesapeake. In addition to houses in Chesapeake, there were also 237 condos, 67 townhouses, and 2 multi-family units for sale in Chesapeake last month. 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. 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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