Homes with Pools for Sale in Chesapeake, VA

561 homes

Sort:

Recommended

NEW 7 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Chesapeake, VA:
This home was designed for both connection and comfort. From the inviting foyer, you’ll be drawn into the open great room and chef-inspired kitchen featuring a large island, fantasy brown granite, and a walk-in pantry that makes meal prep a dream. The flexible room is great for a dining space, home office, or play area — whatever fits your lifestyle. Upstairs, you’ll find comfortably-sized guest rooms, a generous loft, and a serene owner’s suite that feels like a true retreat. Details like mudroom cubbies, painted cabinets with an accent island, and luxury vinyl plank flooring make everyday living feel effortlessly elevated. Make your day a short one, and tour this f

$569,000

4 beds2.5 baths2,404 sq ft

1639 Mount Pleasant Rd, Chesapeake, VA 23322

Generous loft • Flexible room • Large island

NEW 1 HR AGO

ABOUT THIS HOME
Home with a Pool for sale in Chesapeake, VA:
Welcome to this beautifully designed END-UNIT townhome offering the perfect blend of comfort, style, and convenience. With a spacious floor plan spread across three levels, there’s plenty of room to relax, entertain, and enjoy! The main living area is bright and inviting, while the kitchen features granite countertops, stainless steel appliances, recessed lighting, upgraded tile, and a large island. Upstairs, you will find generously sized bedrooms that offer comfort and privacy. The lower level adds flexibility for a home office, gym, playroom, or guest suite. The attached 2- car garage adds everyday convenience for parking and extra storage. Conveniently located to shopping, dining,

$389,999

3 beds2.5 baths1,776 sq ft

4235 Meander Way, Chesapeake, VA 23321

End unit townhome • Large island • Recessed lighting

OPEN SAT, 1PM TO 4PM3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Chesapeake, VA:
This amazing floor plan, paired with a top-to-bottom renovation, is sure to captivate! Enjoy fresh interior paint, BRAND-NEW LVP flooring, NEW carpet, NEW windows, and a beautifully renovated kitchen featuring NEW stainless steel appliances and granite countertops. In addition the two bathrooms are high end with modern vanities and mirrors! Updated lighting and a new ceiling fan complete the modern look. Neutral, natural organic tones create a warm, on-trend feel that’s instantly welcoming. Final touch-ups are underway! Outside, you’ll find an extended driveway with RV pad behind the fence, an extra-large fenced backyard, and a storage shed that conveys as-is. The potential of t

$549,900

4 beds2 baths2,137 sq ft

704 Yateley Ct, Chesapeake, VA 23322

High end bathrooms • Modern vanities • Renovated kitchen

NEW 6 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Chesapeake, VA:
UPDATED BRICK RANCH IN ESTABLISHED NEIGHBORHOOD. .. Fresh Paint & New Flooring Throughout, Spacious Kitchen with New Cabinets, Granite Countertops, & Stainless Steel Appliances. Formal Living & Dining Rooms, Family Room with Vaulted Ceiling & Fireplace. Primary Suite with Updated Bathroom & 2 Closets, Inviting Foyer, & Covered Front Porch. OVERSIZED Detached Garage/Workshop with Unfinished 2nd Floor, Deck, & HUGE Backyard. Convenient to Shopping, Dining, & Easy Access to I-64.

$419,900

3 beds2 baths1,939 sq ft

2628 Roundtree Cir, Chesapeake, VA 23323

Vaulted ceiling • Spacious kitchen • New cabinets

NEW 7 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Chesapeake, VA:
Beautifully maintained condo tucked away but convenient to everything. Prime location in Orchard Grove Community in Greenbrier. Come into spacious living area with vaulted ceilings, gas fireplace in family room, wood laminate in downstairs living area. New carpet in downstairs bedroom, stairs to second floor, large loft/office/flex room and Primary Bedroom. Walk-in closets in bedrooms. New Vinyl in upstairs bathroom. Brand new water heater (2025). Kitchen sink has water filtration with separate faucet for filtered water. Freshly painted. Sunroom/enclosed Patio adds to the living space and charm which includes large storage closet with shelving. Two reserved parking spots are directly in fro

$274,900

2 beds2 baths1,383 sq ft

1720 Orchard Way, Chesapeake, VA 23320

Wood laminate • New carpet • Large loft

Property at 604 Caleb Dr, Chesapeake, VA 23322, 5 beds, 3 baths

$475,000

5 beds3 baths2,672 sq ft

604 Caleb Dr, Chesapeake, VA 23322

Property at 11 Penzance Cir, Chesapeake, VA 23320, 3 beds, 1.5 baths

$279,000

3 beds1.5 baths1,300 sq ft

11 Penzance Cir, Chesapeake, VA 23320

Property at 1213 Fentress Rd, Chesapeake, VA 23322, 4 beds, 1 bath

$287,000

4 beds1 bath1,856 sq ft

1213 Fentress Rd, Chesapeake, VA 23322

Property at 1209 Ohio St, Chesapeake, VA 23324, 4 beds, 3 baths

$355,000

4 beds3 baths1,939 sq ft

1209 Ohio St, Chesapeake, VA 23324

Property at 1209 Sparrow Rd, Chesapeake, VA 23325, 4 beds, 2 baths

$319,900

4 beds2 baths1,200 sq ft

1209 Sparrow Rd, Chesapeake, VA 23325

Property at 3201 Jean Ct, Chesapeake, VA 23323, 4 beds, 2.5 baths

$530,000

4 beds2.5 baths2,222 sq ft

3201 Jean Ct, Chesapeake, VA 23323

Property at 1205 Bramblewood Ct, Chesapeake, VA 23323, 5 beds, 3 baths

$360,000

5 beds3 baths1,825 sq ft

1205 Bramblewood Ct, Chesapeake, VA 23323

Property at 2841 Bunch Walnuts Rd, Chesapeake, VA 23322, 4 beds, 2.5 baths

$595,000

4 beds2.5 baths2,016 sq ft

2841 Bunch Walnuts Rd, Chesapeake, VA 23322

Property at 1209 Priscilla Ln, Chesapeake, VA 23322, 4 beds, 3 baths

$530,000

4 beds3 baths2,526 sq ft

1209 Priscilla Ln, Chesapeake, VA 23322

Property at 707 Sailfish Quay, Chesapeake, VA 23320, 3 beds, 2.5 baths

$296,900

3 beds2.5 baths1,639 sq ft

707 Sailfish Quay, Chesapeake, VA 23320

Property at 301 Lincoln Rd, Chesapeake, VA 23320, 4 beds, 2.5 baths

$405,000

4 beds2.5 baths2,120 sq ft

301 Lincoln Rd, Chesapeake, VA 23320

Property at 313 Woodbridge Dr, Chesapeake, VA 23322, 4 beds, 2 baths

$520,000

4 beds2 baths2,582 sq ft

313 Woodbridge Dr, Chesapeake, VA 23322

Property at 4004 River Breeze Cir, Chesapeake, VA 23321, 4 beds, 2.5 baths

$345,000

4 beds2.5 baths2,350 sq ft

4004 River Breeze Cir, Chesapeake, VA 23321

Property at 208 Marsh Quay, Chesapeake, VA 23320, 4 beds, 2.5 baths

$640,000

4 beds2.5 baths3,239 sq ft

208 Marsh Quay, Chesapeake, VA 23320

Property at 704 Southwood Dr, Chesapeake, VA 23322, 4 beds, 2.5 baths

$695,000

4 beds2.5 baths3,700 sq ft

704 Southwood Dr, Chesapeake, VA 23322

Property at 3121 Deans Ct, Chesapeake, VA 23321, 5 beds, 3 baths

$537,500

5 beds3 baths3,347 sq ft

3121 Deans Ct, Chesapeake, VA 23321

Property at 2932 Sunrise Ave, Chesapeake, VA 23324, 4 beds, 2.5 baths

$365,000

4 beds2.5 baths1,940 sq ft

2932 Sunrise Ave, Chesapeake, VA 23324

Property at 1957 Rockwood Dr, Chesapeake, VA 23323, 4 beds, 2.5 baths

$525,000

4 beds2.5 baths2,061 sq ft

1957 Rockwood Dr, Chesapeake, VA 23323

Property at 3017 Guenevere Dr, Chesapeake, VA 23323, 3 beds, 2 baths

$350,000

3 beds2 baths1,790 sq ft

3017 Guenevere Dr, Chesapeake, VA 23323

Property at 2959 Drum Point Cres, Chesapeake, VA 23321, 6 beds, 3.5 baths

$450,000

6 beds3.5 baths2,590 sq ft

2959 Drum Point Cres, Chesapeake, VA 23321

Property at 3501 Old Mill Rd, Chesapeake, VA 23323, 4 beds, 3 baths

$420,000

4 beds3 baths1,820 sq ft

3501 Old Mill Rd, Chesapeake, VA 23323

Property at 1441 Waterlawn Ave, Chesapeake, VA 23323, 3 beds, 2.5 baths

$355,000

3 beds2.5 baths1,700 sq ft

1441 Waterlawn Ave, Chesapeake, VA 23323

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

$275,000

3 beds2 baths1,595 sq ft

1402 Earle Ave, Chesapeake, VA 23324

Property at 1104 Cutspring Rd, Chesapeake, VA 23322, 4 beds, 2.5 baths

$499,000

4 beds2.5 baths2,606 sq ft

1104 Cutspring Rd, Chesapeake, VA 23322

Property at 1513 Percheron Ct, Chesapeake, VA 23322, 4 beds, 2 baths

$450,000

4 beds2 baths1,720 sq ft

1513 Percheron Ct, Chesapeake, VA 23322

Property at 1707 Bancroft Rd, Chesapeake, VA 23320, 4 beds, 3 baths

$717,605

4 beds3 baths3,270 sq ft

1707 Bancroft Rd, Chesapeake, VA 23320

Property at 1712 Ohio St, Chesapeake, VA 23324, 4 beds, 1 bath

$125,000

4 beds1 bath1,216 sq ft

1712 Ohio St, Chesapeake, VA 23324

Property at 517 Seahorse Run, Chesapeake, VA 23320, 3 beds, 2.5 baths

$294,999

3 beds2.5 baths1,670 sq ft

517 Seahorse Run, Chesapeake, VA 23320

Property at 3017 Big Bend Dr, Chesapeake, VA 23321, 3 beds, 2.5 baths

$349,999

3 beds2.5 baths1,786 sq ft

3017 Big Bend Dr, Chesapeake, VA 23321

Property at 4628 Helensburgh Dr, Chesapeake, VA 23321, 4 beds, 2 baths

$375,000

4 beds2 baths1,960 sq ft

4628 Helensburgh Dr, Chesapeake, VA 23321

Property at 732 Finck Ln, Chesapeake, VA 23320, 4 beds, 2 baths

$400,000

4 beds2 baths1,700 sq ft

732 Finck Ln, Chesapeake, VA 23320

Property at 276 Bridgeview Cir, Chesapeake, VA 23322, 3 beds, 2 baths

$460,000

3 beds2 baths1,953 sq ft

276 Bridgeview Cir, Chesapeake, VA 23322

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 1022 Hill St, Chesapeake, VA 23324, 3 beds, 2.5 baths

$330,000

3 beds2.5 baths1,536 sq ft

1022 Hill St, Chesapeake, VA 23324

Property at 509 Graphite Trl, Chesapeake, VA 23320, 5 beds, 4 baths

$679,900

5 beds4 baths2,800 sq ft

509 Graphite Trl, Chesapeake, VA 23320

Property at 416 Blue Beech Way, Chesapeake, VA 23320, 3 beds, 2.5 baths

$429,999

3 beds2.5 baths2,352 sq ft

416 Blue Beech Way, Chesapeake, VA 23320

Viewing page 1 of 9

Homes with Pools for Sale in Chesapeake

There are currently 561 homes with pools for sale in Chesapeake at a median listing price of $450K. 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 52 days and receive 5 offers. This map is refreshed with the newest listings in Chesapeake every 15 minutes.

In the past month, 249 homes have been sold in Chesapeake. In addition to houses in Chesapeake, there were also 204 condos, 55 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.

More real estate resources for Chesapeake, VA

Cities

Nearby Counties

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

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.