Vintage homes for sale & real estate in Chesapeake, VA

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NEW 36 MINS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Welcome home to this beautifully maintained property! The renovated floor plan includes an open living area, large primary bedroom with private bathroom, newly installed HVAC (2025) and water heater (2024). Enjoy a private, fenced backyard along with a detached garage that includes an insulated office space—great for work, hobbies, or extra storage. Move-in ready and full of modern updates!

$299,900

2 beds2 baths1,153 sq ft

3106 Joseph Ave Ave, Chesapeake, VA 23324

Renovated floor plan • Private bathroom • Fenced backyard

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Fantastic, fully renovated 4 bed 2 bath, Ranch! Gleaming Kitchen with Island, Subway tiled Backsplash & ceramic flooring, Gas Oven, SS appliances, Granite counters & newer adjustable Cabinets. This open floorplan is complimented by NEW: wideplank LVP flooring, fresh Wall Color, & bedroom Carpet. Two updated full bathrooms & spacious Bedrooms, each with sizable closets. The backyard is sure to please, with existing raised bed garden, large storage shed, fire pit, & fully fenced. Roof & Siding: 2016. Perfect quiet neighborhood surrounded by the Elizabeth River.

$374,900

4 beds2 baths1,785 sq ft

123 Ridgewood Rd, Chesapeake, VA 23325

Ceramic flooring • Fully renovated • Gas oven

ABOUT THIS HOME
Vintage Home for sale in Chesapeake, VA:
Perfect opportunity for an Investor Flip or a 203K Renovation Loan. Will not qualify for regular financing. Comps within a 1/2 Mile radius are $365,000.00 to $390.000.00. Huge Great room with fireplace, screened in back porch and a 2 car garage!!! To be sold "As-IS, Where IS" any contents not removed will convey.

$285,000

3 beds2 baths1,595 sq ft

1402 Earle Ave, Chesapeake, VA 23324

7,405 sq ft lot • 2 garage spots • Built 1942

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:
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

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 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 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 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 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 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

$326,500

3 beds2 baths1,500 sq ft

3009 Mattox Dr, Chesapeake, VA 23325

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 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 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 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 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 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 1513 Manson St, Norfolk, VA 23523, 4 beds, 2 baths

$195,000

4 beds2 baths1,350 sq ft

1513 Manson St, Norfolk, VA 23523

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 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 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 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 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 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 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 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 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 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 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 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 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 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 41 Irwin St, Portsmouth, VA 23702, 3 beds, 1 bath

$215,000

3 beds1 bath900 sq ft

41 Irwin St, Portsmouth, VA 23702

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Vintage Homes for Sale in Chesapeake

There are currently 75 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 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, 231 homes have been sold in Chesapeake. In addition to houses in Chesapeake, there were also 197 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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