Chesapeake, VA homes for sale & real estate

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3D WALKTHROUGH

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or future entertaining. Recent updates provide added value and peace of mind, including a new hot water heater (2026), new air conditioner condenser (2025), new living room carpet (2026), updated downstairs toilet (2026), and new primary bathroom faucets (2026). Outdoor improvements include a back pat

$565,000

4 beds2.5 baths2,414 sq ft

1916 Orangewood Rd, Chesapeake, VA 23323

Sunroom sitting area • New front porch • Large backyard

3D WALKTHROUGH

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
4 bedroom ranch offering an open layout. This home features a converted garage that provides additional living space. Come check this home out, it wont last long!

$277,500

4 beds2 baths1,275 sq ft

3931 Port Rd, Chesapeake, VA 23321

Converted garage • Open layout • 0.25 acre lot

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Low-maintenance living awaits in this rare detached 3 BR, 2.5 BA Greenbrier condo. Enjoy a 2-car garage, fully fenced backyard, & primary en-suite and laundry on the first-floor. The open kitchen to main living area with gas fireplace. Additional flex room great for a home office, or media room. Recent 2025 updates include a new HVAC, granite counters with subway tile backsplash, LED recessed lighting, and more; washer/dryer replaced in 2021. Association handles exterior care; roof, siding, power washing, termite prevention, and front yard maintenance. Conveniently near Town Center, grocery stores, dining, parks, farmer markets & easy interstate access. This home blends convenien

$429,900

3 beds2.5 baths2,225 sq ft

808 Monroe Ct, Chesapeake, VA 23320

Primary en-suite • New hvac • Gas fireplace

3D WALKTHROUGH

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Waterfront opportunity! Well-maintained home situated on a scenic waterfront lot in the desirable Western Branch area of Chesapeake. Enjoy peaceful water views from an enclosed porch, and a spacious backyard ideal for relaxing, entertaining, fishing, kayaking, or simply taking in the surroundings. Walk in basement and Attic with plenty of storage. Recent improvements and updates help make this home move-in ready while still offering buyers the opportunity to add their own personal touches. New Concrete Driveway, New Storage Shed & Dock, Resurfaced Wood Floors, and Remodeled Master Bath. Conveniently located near shopping, dining, bases, major highways, and all that Hampton Roads has t

$489,000

2 beds2 baths1,641 sq ft

3901 Wedgewood Dr, Chesapeake, VA 23321

Spacious backyard • Enclosed porch • Walk in basement

FLOOR PLAN

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
This meticulously maintained home in the sought-after Grassfield area of Chesapeake is waiting for you! Featuring 5 bedrooms and 4 full bathrooms, this spacious home offers plenty of room for everyday living and entertaining. The upstairs primary suite provides a relaxing retreat with two closets, a double vanity, stand-up shower, and garden tub. Three additional bedrooms and two full bathrooms complete the upstairs living space. The downstairs bedroom with an en-suite bathroom offers flexibility for guests, an in-law suite, or home office. The well-appointed kitchen features granite countertops, a breakfast bar, and updated appliances. The spacious living room is warmed by a gas

$595,000

5 beds4 baths3,000 sq ft

705 Creekwood Dr, Chesapeake, VA 23323

Wooded backyard • Gas fireplace • Bright sunroom

Property at 2537 Number Ten Ln, Chesapeake, VA 23323, 6 beds, 4.5 baths

$849,800

6 beds4.5 baths3,251 sq ft

2537 Number Ten Ln, Chesapeake, VA 23323

Property at 4111 Williamson St, Chesapeake, VA 23324, 3 beds, 2 baths

$325,000

3 beds2 baths1,200 sq ft

4111 Williamson St, Chesapeake, VA 23324

Property at 3909 Bruce Rd, Chesapeake, VA 23321, 5 beds, 3 baths

$799,900

5 beds3 baths3,125 sq ft

3909 Bruce Rd, Chesapeake, VA 23321

Property at 458 Blue Beech Way, Chesapeake, VA 23320, 3 beds, 2.5 baths

$424,900

3 beds2.5 baths2,151 sq ft

458 Blue Beech Way, Chesapeake, VA 23320

Property at 1417 Gust Ln, Chesapeake, VA 23323, 5 beds, 3.5 baths

$314,000

5 beds3.5 baths2,354 sq ft

1417 Gust Ln, Chesapeake, VA 23323

Property at 614 Middleton Way, Chesapeake, VA 23322, 4 beds, 2.5 baths

$594,000

4 beds2.5 baths2,456 sq ft

614 Middleton Way, Chesapeake, VA 23322

Property at 420 Dundee Ln, Chesapeake, VA 23322, 3 beds, 2.5 baths

$532,500

3 beds2.5 baths2,526 sq ft

420 Dundee Ln, Chesapeake, VA 23322

Property at 4700 Harlequin Way, Chesapeake, VA 23321, 4 beds, 2.5 baths

$560,000

4 beds2.5 baths2,710 sq ft

4700 Harlequin Way, Chesapeake, VA 23321

Property at 811 Twin Peak Ct Ct, Chesapeake, VA 23320, 4 beds, 3 baths

$620,000

4 beds3 baths2,900 sq ft

811 Twin Peak Ct Ct, Chesapeake, VA 23320

Property at 357 Dexter St E, Chesapeake, VA 23324, 3 beds, 2.5 baths

$409,500

3 beds2.5 baths2,250 sq ft

357 Dexter St E, Chesapeake, VA 23324

Property at 1804 Portlock Rd, Chesapeake, VA 23324, 2 beds, 1.5 baths

$199,900

2 beds1.5 baths792 sq ft

1804 Portlock Rd, Chesapeake, VA 23324

Property at 509 Ballahack Rd, Chesapeake, VA 23322, 5 beds, 3.5 baths

$1,199,000

5 beds3.5 baths3,714 sq ft

509 Ballahack Rd, Chesapeake, VA 23322

Property at 711 Pile Ave, Chesapeake, VA 23320, 3 beds, 2.5 baths

$420,000

3 beds2.5 baths2,058 sq ft

711 Pile Ave, Chesapeake, VA 23320

Property at 4985 Boone Rd, Chesapeake, VA 23321, 2 beds, 2.5 baths

$330,900

2 beds2.5 baths1,464 sq ft

4985 Boone Rd, Chesapeake, VA 23321

Property at 4607 Longleaf Pl, Chesapeake, VA 23321, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths2,557 sq ft

4607 Longleaf Pl, Chesapeake, VA 23321

Property at 825 Waterfall Way, Chesapeake, VA 23322, 4 beds, 3 baths

$829,900

4 beds3 baths3,134 sq ft

825 Waterfall Way, Chesapeake, VA 23322

Property at 4624 Westborough Dr, Chesapeake, VA 23321, 5 beds, 3 baths

$497,500

5 beds3 baths3,590 sq ft

4624 Westborough Dr, Chesapeake, VA 23321

Property at 716 Hillwell Rd Unit B, Chesapeake, VA 23322, 3 beds, 2 baths

$380,000

3 beds2 baths1,356 sq ft

716 Hillwell Rd Unit B, Chesapeake, VA 23322

Property at 1012 Rue Marseille, Chesapeake, VA 23320, 2 beds, 2 baths

$219,900

2 beds2 baths919 sq ft

1012 Rue Marseille, Chesapeake, VA 23320

Property at 1641 Orchard Grove Dr, Chesapeake, VA 23320, 2 beds, 2 baths

$269,900

2 beds2 baths1,383 sq ft

1641 Orchard Grove Dr, Chesapeake, VA 23320

Property at 451 Seahorse Run, Chesapeake, VA 23320, 2 beds, 2 baths

$275,000

2 beds2 baths1,670 sq ft

451 Seahorse Run, Chesapeake, VA 23320

Property at 4 Harbor Watch Dr #520, Chesapeake, VA 23320, 3 beds, 2 baths

$308,500

3 beds2 baths1,668 sq ft

4 Harbor Watch Dr #520, Chesapeake, VA 23320

Property at 1625 Redwing Arc, Chesapeake, VA 23323, 3 beds, 2.5 baths

$419,900

3 beds2.5 baths1,744 sq ft

1625 Redwing Arc, Chesapeake, VA 23323

Property at 145 Hurdle Dr Dr, Chesapeake, VA 23322, 4 beds, 2 baths

$469,900

4 beds2 baths1,852 sq ft

145 Hurdle Dr Dr, Chesapeake, VA 23322

Property at 858 Waters Rd, Chesapeake, VA 23322, 4 beds, 2 baths

$525,000

4 beds2 baths1,736 sq ft

858 Waters Rd, Chesapeake, VA 23322

Property at 1908 Benefit Rd, Chesapeake, VA 23322, 5 beds, 3 baths

$935,000

5 beds3 baths3,252 sq ft

1908 Benefit Rd, Chesapeake, VA 23322

Property at 810 Hedgerow Ct, Chesapeake, VA 23322, 5 beds, 3 baths

$682,500

5 beds3 baths3,200 sq ft

810 Hedgerow Ct, Chesapeake, VA 23322

Property at 4141 3rd St, Chesapeake, VA 23324, 3 beds, 2 baths

$319,700

3 beds2 baths1,154 sq ft

4141 3rd St, Chesapeake, VA 23324

Property at 3248 Battlefield Blvd S, Chesapeake, VA 23322, 3 beds, 2.5 baths

$489,900

3 beds2.5 baths2,020 sq ft

3248 Battlefield Blvd S, Chesapeake, VA 23322

Property at 2505 Sylvia Ct, Chesapeake, VA 23322, 4 beds, 4 baths

$1,750,000

4 beds4 baths5,707 sq ft

2505 Sylvia Ct, Chesapeake, VA 23322

Property at 710 Willow Green Ct, Chesapeake, VA 23320, 2 beds, 2.5 baths

$235,000

2 beds2.5 baths1,180 sq ft

710 Willow Green Ct, Chesapeake, VA 23320

Property at 4004 Oak Dr, Chesapeake, VA 23321, 4 beds, 2 baths

$439,000

4 beds2 baths1,655 sq ft

4004 Oak Dr, Chesapeake, VA 23321

Property at 729 Wood Duck Ln, Chesapeake, VA 23323, 3 beds, 2 baths

$615,000

3 beds2 baths2,016 sq ft

729 Wood Duck Ln, Chesapeake, VA 23323

Property at 4006 Hamilton St, Chesapeake, VA 23324, 3 beds, 2 baths

$295,000

3 beds2 baths968 sq ft

4006 Hamilton St, Chesapeake, VA 23324

Property at 913 Long Ridge Rd, Chesapeake, VA 23322, 4 beds, 2 baths

$599,999

4 beds2 baths2,493 sq ft

913 Long Ridge Rd, Chesapeake, VA 23322

Property at 1928 Centerville Tpke S, Chesapeake, VA 23322, 3 beds, 2 baths

$549,000

3 beds2 baths1,688 sq ft

1928 Centerville Tpke S, Chesapeake, VA 23322

Viewing page 12 of 21

Average home prices near Chesapeake, VA

Cities

Counties

Isle of Wight County homes for sale
$517,450
York County homes for sale
$549,945
Norfolk homes for sale
$340,000

Chesapeake, VA real estate trends

All Home Types trends in Chesapeake, VA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$435,443

+3.1% YoY | Aug 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2026

Growth

% YoY

Chesapeake, VA

$435,443

+3.1%

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10 Redfin agents serving Chesapeake

299

Deals*

4.8

Satisfaction

1470

Homes closed*

* Data from the last year

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