Vintage homes for sale & real estate in Chesapeake, VA

68 homes

Sort:

Recommended

NEW 17 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
This 3 Bedroom home located in the heart of Brentwood offers comfort, convenience, and a spacious layout perfect for first-time buyers, downsizers, or anyone looking for single-level living. Step inside to find a warm and inviting living space with plenty of natural light. The functional floor plan includes three comfortable bedrooms, a full bath, & an additional half bath for added convenience. The kitchen & dining area provide plenty of room for gatherings and daily living. Outside, enjoy a large yard ideal for gardening, outdoor entertaining, pets, or play. Relax on the covered front porch, perfect for your morning coffee or evening unwinding. With two driveways, parking is ne

$299,900

3 beds1.5 baths1,400 sq ft

2029 Battery Park Rd, Chesapeake, VA 23323

Covered front porch • Near schools • Two driveways

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Wonderful three bedroom, two bathroom house has an eat-in-kitchen, bonus space upstairs that is great for working from home, game room, or a workout space. This house has some unique features like large baseboards, door trim and curved doorways. Back deck recently painted, new flooring installed, and bathtub has been re-glazed. This home is near 464, 264, and 64 which makes it easy to get to just about anywhere on the southside of Hampton Roads.

$310,000

3 beds2 baths1,541 sq ft

1208 Edgewood Ave, Chesapeake, VA 23324

Eat-in-kitchen • Curved doorways • Large baseboards

NEW 24 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
This cream puff of a home is truly move-in ready! Completely renovated with a brand-new kitchen featuring new cabinets, granite countertops, new electric range, new hood vent and flooring. Beautifully refinished hardwood floors, and updated paint inside and out. Upgraded electrical, new plumbing and new light fixtures. Enter into the spacious family room with wood fireplace and built-in shelving all open to the dining area and kitchen. Two bedrooms on first floor with a full bathroom with new wainscotting, new flooring and new vanity. Spacious bedroom upstairs with new carpet and new Mistsubishi split unit to ensure modern comfort and efficiency. Spend mornings enjoy a cup of coffee in the

$348,000

3 beds1 bath1,973 sq ft

2320 Battery Park Rd, Chesapeake, VA 23323

New kitchen • Wood fireplace • Sunroom

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Experience peaceful country living with thoughtful upgrades throughout this beautifully maintained home. The main level features 9' ceilings, an updated kitchen with newer appliances, quartz countertops, and a reverse osmosis water filtration system. Additional improvements include an upgraded well pump, septic pumped in 2023, new flooring, a newly installed shower door in the larger shower, and a new garbage disposal. Both heat pumps were replaced in 2019, and the attic access has been relocated for improved convenience. This property offers the best of both worlds—quiet country living with the convenience of popular stores and restaurants just 15 minutes away. The outdoor spaces pro

$415,000

3 beds2.5 baths1,700 sq ft

2816 Benefit Rd, Chesapeake, VA 23322

Quartz countertops • Upgraded well pump • New garbage disposal

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Welcome home to this charming Chesapeake house featuring 3 bedrooms and 2 bathrooms and PAID OFF Solar Panels! Enter your newly renovated dining room and kitchen that lead to the living room with fireplace and out to the fully fenced backyard. To the right, you will find 2 additional bedrooms, a full bathroom and spacious primary bedroom featuring an ensuite bathroom and walk in closet. The home features ample room for parking and a detached garage as well as new paint & flooring throughout, walk-in closets, ceiling fans, updated lighting, and an indoor laundry closet. Don’t miss the chance to experience this home's comfort and style! Schedule your showing today! Property has so

$290,000

3 beds2 baths1,216 sq ft

606 Bethel Rd, Chesapeake, VA 23325

Walk in closet • Ensuite bathroom • 6,926 sq ft lot

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 2221 Decatur St, Chesapeake, VA 23324, 5 beds, 4 baths

$384,000

5 beds4 baths2,356 sq ft

2221 Decatur St, Chesapeake, VA 23324

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 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 1624 Battlefield Blvd S, Chesapeake, VA 23322, 3 beds, 2 baths

$349,900

3 beds2 baths1,000 sq ft

1624 Battlefield Blvd S, Chesapeake, VA 23322

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

$327,500

3 beds2 baths1,600 sq ft

3009 Mattox Dr, Chesapeake, VA 23325

Property at 1000 Towanda Rd, Virginia Beach, VA 23464, 4 beds, 2 baths

$320,000

4 beds2 baths1,184 sq ft

1000 Towanda Rd, Virginia Beach, VA 23464

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 1530 Atlantic Ave, Chesapeake, VA 23324, 3 beds, 1.5 baths

$160,000

3 beds1.5 baths1,368 sq ft

1530 Atlantic Ave, 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 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 811 Wright Ave, Chesapeake, VA 23324, 3 beds, 1.5 baths

$254,900

3 beds1.5 baths1,303 sq ft

811 Wright 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 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 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 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 1308 Chesapeake Ave, Chesapeake, VA 23324, 4 beds, 2 baths

$290,000

4 beds2 baths1,868 sq ft

1308 Chesapeake Ave, 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 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 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 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 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

Property at 611 Lafayette Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$259,000

3 beds2 baths1,456 sq ft

611 Lafayette Ave, Chesapeake, VA 23324

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 4121 Everett St, Chesapeake, VA 23324, 4 beds, 2 baths

$324,999

4 beds2 baths1,809 sq ft

4121 Everett St, Chesapeake, VA 23324

Property at 814 Hughes Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$269,900

3 beds2 baths1,122 sq ft

814 Hughes Ave, Chesapeake, VA 23324

Property at 714 B St, Chesapeake, VA 23324, 3 beds, 2 baths

$245,000

3 beds2 baths1,372 sq ft

714 B St, Chesapeake, VA 23324

Property at 1848 Ballahack Rd, Chesapeake, VA 23322, 4 beds, 2.5 baths

$579,000

4 beds2.5 baths2,600 sq ft

1848 Ballahack Rd, Chesapeake, VA 23322

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 2761 Cedar Rd, Chesapeake, VA 23323, 3 beds, 2 baths

$370,000

3 beds2 baths1,590 sq ft

2761 Cedar Rd, Chesapeake, VA 23323

Property at 2702 Cayce Dr, Chesapeake, VA 23324, 3 beds, 1 bath

$160,000

3 beds1 bath1,500 sq ft

2702 Cayce Dr, Chesapeake, VA 23324

Property at 4102 1st St, Chesapeake, VA 23324, 3 beds, 2 baths

$350,000

3 beds2 baths1,124 sq ft

4102 1st St, Chesapeake, VA 23324

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

$379,000

4 beds2 baths1,785 sq ft

123 Ridgewood Rd, Chesapeake, VA 23325

Property at 1755 Oliver Ave, Chesapeake, VA 23324, 3 beds, 2 baths

$235,000

3 beds2 baths1,526 sq ft

1755 Oliver Ave, Chesapeake, VA 23324

Property at 708 Stalham Rd, Chesapeake, VA 23325, 3 beds, 1 bath

$275,000

3 beds1 bath1,309 sq ft

708 Stalham Rd, Chesapeake, VA 23325

Viewing page 1 of 2

Vintage Homes for Sale in Chesapeake

There are currently 68 vintage homes for sale in Chesapeake at a median listing price of $445K. 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 46 days and receive 3 offers. This map is refreshed with the newest listings in Chesapeake every 15 minutes.

In the past month, 300 homes have been sold in Chesapeake. In addition to houses in Chesapeake, there were also 240 condos, 69 townhouses, and 6 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.

More real estate resources for Chesapeake, VA

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Chesapeake, VA

How to buy a house in Chesapeake, VA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Virginia

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.