Fixer Upper homes for sale & real estate in Chesapeake, VA

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ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
Welcome home to Cypress Place! Nestled in the heart of Chesapeake, this home offers endless possibilities and convenience all around. With a little vision and TLC, you can transform this property into your dream home while possibly creating an opportunity to build valuable sweat equity along the way. Don't miss the chance to make this home truly yours and enjoy everything this vibrant community has to offer.

$385,000

4 beds3 baths2,054 sq ft

1363 Cypress Pl, Chesapeake, VA 23320

7,840 sq ft lot • Built 1978

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
PROPERTY BEING SOLD AS IS WHERE IS -- SELLER TO MAKE NO REPAIRS.

$179,600

3 beds1 bath1,182 sq ft

4111 Williamson St, Chesapeake, VA 23324

5,662 sq ft lot • Built 1962 • Listed 20 days

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
This home has great potential! Needs updating! Enjoy sweat equity on large corner lot. Property being sold "as-is, where-is".

$250,000

4 beds2 baths1,600 sq ft

3144 Gaston Dr, Chesapeake, VA 23323

0.23 acre lot • 2 parking spots • Pool

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
Charming townhome in the desirable Middle Oaks community, located in the highly sought-after Great Bridge school district! This home features 2 spacious bedrooms and 2.5 baths, offering plenty of room to relax or entertain. Recent updates include a new HVAC system (indoor and outdoor units replaced in 2021) and a fully replaced privacy fence in 2022. With just a little TLC, this home is ready to truly shine—perfect for buyers looking to add their own personal touch and make it their own. Enjoy a bright layout, low-maintenance living, and a peaceful cul-de-sac location close to shopping, restaurants, and easy interstate access. A fantastic opportunity in one of Chesapeake’s most

$275,000

2 beds2.5 baths1,278 sq ft

418 Middle Oaks Dr, Chesapeake, VA 23322

Close to shopping • New hvac system • 2 parking spots

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
Priced To Sell Fast! Renovate & Resell, Buy & Hold, or Move-In and Build Some Sweat Equity. Charming 2 Level Bungalow with Detached 2 Car Garage, Spacious Kitchen with Stainless Steel Appliances, Spacious Bedrooms, Attic Can Be Finished For a 3rd Bedroom, Walk in Closet, Covered Front Porch, Fenced Backyard, Storage Sheds, Much More!! Just Waiting For Your Personal Cosmetics and Updates to Make it Shine. Shopping and Commuter Routes nearby. This Will Not Last! Sold As-Is.

$249,895

2 beds2 baths1,304 sq ft

1114 Willow Ave, Chesapeake, VA 23325

Covered front porch • Spacious kitchen • Walk in closet

Property at 4130 Everett St, Chesapeake, VA 23324, 3 beds, 1 bath

$142,000

3 beds1 bath875 sq ft

4130 Everett St, Chesapeake, VA 23324

Property at 317 Shadowlake Dr, Chesapeake, VA 23320, 4 beds, 2.5 baths

$404,900

4 beds2.5 baths2,528 sq ft

317 Shadowlake Dr, Chesapeake, VA 23320

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

$285,000

3 beds2 baths1,526 sq ft

1755 Oliver Ave, Chesapeake, VA 23324

Property at 901 Washington Dr, Chesapeake, VA 23322, 3 beds, 1 bath

$260,000

3 beds1 bath900 sq ft

901 Washington Dr, Chesapeake, VA 23322

Property at 5533 Willow Lake Rd, Chesapeake, VA 23321, 3 beds, 2 baths

$425,000

3 beds2 baths1,728 sq ft

5533 Willow Lake Rd, Chesapeake, VA 23321

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ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
This is the home you've been looking for! Custom built beautiful one of a kind 2 story. Has 4 large bedrooms, 2.5 bath set on 3+ acres. Large open kitchen with granite countertops, breakfast bar and dining room. Large family room with fireplace that looks out onto the deck of your own backyard oasis with a sparkling inground pool. Plenty of room for relaxing or hosting friends and family get-togethers. The backyard is set up for your homesteading with chicken coops, a fenced in pasture for the horses. Large, detached garage has 3 small stalls inside. Oversized 2 car attached garage plus a 2400 sq. ft detached garage / workshop complete with electricity, half bath and det. compressor air lin

$795,000

4 beds2.5 baths3,016 sq ft

3337 Old Carolina Rd. Rd, Virginia Beach, VA 23457

3.4 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
INVESTOR SPECIAL! STRICTLY SOLD AS IS, SELLER TO MAKE NO REPAIRS! CASH OR CONVENTIONAL LOANS ONLY! NEWER WINDOWS, ROOF, AND MORE. UTILITIES ARE OFF! LOTS OF POTENTIAL, BRING ALL OFFERS!

$199,900

3 beds2 baths1,894 sq ft

17 Davis St, Portsmouth, VA 23702

6,098 sq ft lot • Very walkable

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
Spacious 3-bedroom, 2-bath home located on a quiet cul-de-sac. Features include a large family room, separate living room, and an eat-in kitchen. Enjoy three levels of living space with plenty of room to spread out. Kitchen appliances convey. Large backyard with storage shed (sold as-is). Home needs a little TLC but offers great potential. Conveniently located near shopping, hospitals, and the interstate for easy access to everything Norfolk has to offer.

$290,000

3 beds2 baths1,416 sq ft

5976 Monaco Ct, Norfolk, VA 23502

Garage • Car-dependent

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
A great project for an income property or to convert back into a single family. Home's sq footage by tax records. Units sq footage is not measured, the building is 1948 sq ft by the tax records. Present your highest and best offer before November 14th. More consideration given to offers that include other properties MLS #s 10609080 & 10609081. Keep in mind owner may accept an offer prior to that date, so do not delay. Do your due diligence and submit a non-contingent offer above asking only as offers are already on the table.

$75,000

3 beds2 baths1,948 sq ft

833 Fremont St, Norfolk, VA 23504

Somewhat walkable

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
Corner lot property with off street parking. This historic district duplex provides a great chance to rehab into an income producing property, or convert into single family usage. Most lots in the neighborhood do not have off-street parking in the neighborhood, but this one does increasing it's desirability once renovated. Units' sq footage is not measured, the building is 2320 sq ft by the tax records. Selling as-is, where-is. Seller to make no repairs. Offers including other properties will be considered first. MLS # 10609052 & 1069081

$80,000

3 beds2 baths2,320 sq ft

803 A Ave, Norfolk, VA 23504

3,074 sq ft lot • Somewhat walkable

ABOUT THIS HOME
Fixer Upper for sale in Chesapeake, VA:
Don't miss the opportunity to make a great investment decision. Put in the sweat and live with equity, or use this as a value-added investment property. Noticeable slant in floor. Do your due diligence and make your highest and best offer before 11/14/25 at 12pm. Owner may take accept an offer prior to that date so do not delay. Higher consideration if purchased with MLS #s 10609052 & 10609080

$80,000

3 beds1.5 baths1,470 sq ft

2603 Middle Ave, Norfolk, VA 23504

2,613 sq ft lot • Somewhat walkable

Property at 215 Maryland Ave, Portsmouth, VA 23707, 4 beds, 2 baths

$125,000

4 beds2 baths1,784 sq ft

215 Maryland Ave, Portsmouth, VA 23707

Property at 232 Maryland Ave, Portsmouth, VA 23707, 3 beds, 1 bath

$100,000

3 beds1 bath1,416 sq ft

232 Maryland Ave, Portsmouth, VA 23707

Property at 682 Princess Anne Rd, Virginia Beach, VA 23457, 5 beds, 3 baths

$1,200,000

5 beds3 baths2,529 sq ft

682 Princess Anne Rd, Virginia Beach, VA 23457

Property at 240 Driftwood Rd, Virginia Beach, VA 23452, 5 beds, 2.5 baths

$344,000

5 beds2.5 baths2,000 sq ft

240 Driftwood Rd, Virginia Beach, VA 23452

Property at 512 Gladstone Rd, Norfolk, VA 23505, 2 beds, 1 bath

$200,000

2 beds1 bath911 sq ft

512 Gladstone Rd, Norfolk, VA 23505

Property at 2569 Springhaven Dr, Virginia Beach, VA 23456, 5 beds, 3.5 baths

$639,000

5 beds3.5 baths3,469 sq ft

2569 Springhaven Dr, Virginia Beach, VA 23456

$270,000

4 beds2.5 baths1,660 sq ft

974 Philpotts Rd, Norfolk, VA 23513

Property at 4316 Portsmouth Blvd, Portsmouth, VA 23701, 4 beds, 2 baths

$225,000

4 beds2 baths1,953 sq ft

4316 Portsmouth Blvd, Portsmouth, VA 23701

Property at 521 Mahone Ave, Norfolk, VA 23523, 3 beds, 1 bath

$100,000

3 beds1 bath1,112 sq ft

521 Mahone Ave, Norfolk, VA 23523

Property at 5328 Hanyen Dr, Norfolk, VA 23502, 3 beds, 1 bath

$200,000

3 beds1 bath1,000 sq ft

5328 Hanyen Dr, Norfolk, VA 23502

Property at 3791 Towne Point Rd, Portsmouth, VA 23703, 3 beds, 2.5 baths

$245,000

3 beds2.5 baths1,385 sq ft

3791 Towne Point Rd, Portsmouth, VA 23703

Property at 3417 Silina Dr, Virginia Beach, VA 23452, 3 beds, 1 bath

$245,000

3 beds1 bath1,118 sq ft

3417 Silina Dr, Virginia Beach, VA 23452

Property at 617 Westcove Ct, Norfolk, VA 23502, 3 beds, 2 baths

$379,000

3 beds2 baths1,649 sq ft

617 Westcove Ct, Norfolk, VA 23502

Property at 50 Centre Port Cir, Portsmouth, VA 23703, 3 beds, 2.5 baths

$200,000

3 beds2.5 baths1,760 sq ft

50 Centre Port Cir, Portsmouth, VA 23703

Fixer Upper Homes for Sale in Chesapeake

There are currently 10 fixer upper homes for sale in Chesapeake at a median listing price of $446K. 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 45 days and receive 3 offers. This map is refreshed with the newest listings in Chesapeake every 15 minutes.

In the past month, 296 homes have been sold in Chesapeake. In addition to houses in Chesapeake, there were also 235 condos, 67 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.

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