Chesapeake, VA homes for sale & real estate

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FLOOR PLAN

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you’ll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one

$825,000

4 beds4 baths2,769 sq ft

1837 Benefit Rd, Chesapeake, VA 23322

Two ensuite bedrooms • Custom built retreat • Screened porch

3D WALKTHROUGH

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Say hello to 1810 Martin Avenue!! This cute-as-a-button ranch in Chesapeake's Sheridan Heights is ready for its next chapter. This home was updated in 2024 with a new HVAC system, roof, hot water heater, kitchen counters, appliances, and more! Conveniently located near shopping, dining, and interstates, making for an easy commute. Some photos have been virtually staged to show the homes potential.

$284,900

3 beds2 baths864 sq ft

1810 Martin Ave, Chesapeake, VA 23324

New hot water heater • New kitchen counters • New appliances

NEW CONSTRUCTION

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
The Aspen Barndominium! Customize this 4b/ 2.5b barndo with your style, colors and finishes with the builder. Stunning Covered Front Porch leads to the Open Great Room designed with 18ft vaulted ceiling for the perfect open Living, Dining and Kitchen space. Kitchen with Stainless Steel Appliances, granite counters, tile backsplash, and walk-in pantry. Large Primary with huge walk-in closet and Spa-like Bathroom. Large laundry room, mudroom with lots of storage space and wash area. Bedrooms 2, 3, 4 share a bathroom with rec/bonus space. Best spot may just be the huge covered back porch with lovely nature views and access from the kitchen great room. Pics of previously built Aspen and may sho

$799,900

4 beds2.5 baths2,400 sq ft

2907 Seven Eleven Rd, Chesapeake, VA 23322

Covered front porch • Open great room • Granite counters

3D WALKTHROUGH

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Welcome to this fantastic opportunity in the desirable Norfolk Highlands neighborhood! This versatile property features a spacious 3-bedroom, 2-bath main home plus a detached studio-style in-law suite complete with its own kitchen, full bath, and a new mini split system (2024)for heating and cooling great for multigenerational living, guests, or a private office. Enjoy a fully fenced backyard great for entertaining, pets, or relaxing outdoors. Two powered storage sheds provide ample space for storage, hobbies, or a workshop. Updates include a new HVAC system (2016) and new roofs on both the main home and detached suite (2016), offering added peace of mind. Conveniently located near shoppin

$382,500

4 beds3 baths1,605 sq ft

1415 Willow Ave, Chesapeake, VA 23325

New roofs • New hvac system • 7,492 sq ft lot

ABOUT THIS HOME
Chesapeake, VA Homes for Sale
Move in ready 2 bedroom 1 bath condo in Western Branch. Open layout with spacious living room with vaulted ceiling and skylight. Large utility room with washer and dryer that convey. Renovated in 2025 with new HVAC 2025 and hot water heater 2026. New carpet, LVP, and paint in 2025. Newer appliances to include dryer (2025), dishwasher (2025), and electric range (2026). Exterior storage shed next to front door. One assigned parking spot and plenty of guest parking. Close to interstate and military bases.

$147,900

2 beds1 bath897 sq ft

3331 Clover Meadows Dr, Chesapeake, VA 23321

Renovated • Vaulted ceiling • New hvac

Property at 624 Rock Dr, Chesapeake, VA 23323, 4 beds, 2 baths

$399,700

4 beds2 baths2,460 sq ft

624 Rock Dr, Chesapeake, VA 23323

Property at 1916 Orangewood Rd, Chesapeake, VA 23323, 4 beds, 2.5 baths

$565,000

4 beds2.5 baths2,414 sq ft

1916 Orangewood Rd, 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 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 1540 Eldwick Drive #204, Chesapeake, VA 23320, 2 beds, 2 baths

$290,130

2 beds2 baths1,355 sq ft

1540 Eldwick Drive #204, Chesapeake, VA 23320

Property at 808 Monroe Ct, Chesapeake, VA 23320, 3 beds, 2.5 baths

$429,900

3 beds2.5 baths2,225 sq ft

808 Monroe Ct, Chesapeake, VA 23320

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 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 3931 Port Rd, Chesapeake, VA 23321, 4 beds, 2 baths

$277,500

4 beds2 baths1,275 sq ft

3931 Port Rd, Chesapeake, VA 23321

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 1520 Jimmy Ln, Chesapeake, VA 23322, 5 beds, 3 baths

$699,990

5 beds3 baths3,010 sq ft

1520 Jimmy Ln, 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 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 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 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 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 2704 Faulkner Dr, Chesapeake, VA 23321, 2 beds, 2.5 baths

$278,000

2 beds2.5 baths1,314 sq ft

2704 Faulkner Dr, Chesapeake, VA 23321

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 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 1625 Redwing Arch, Chesapeake, VA 23323, 3 beds, 2.5 baths

$419,900

3 beds2.5 baths1,744 sq ft

1625 Redwing Arch, Chesapeake, VA 23323

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 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 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 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 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 746 Yorkshire Trl, Chesapeake, VA 23322, 4 beds, 2.5 baths

$589,699

4 beds2.5 baths2,612 sq ft

746 Yorkshire Trl, Chesapeake, VA 23322

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 1435 Seaboard Ave, Chesapeake, VA 23324, 3 beds, 2.5 baths

$379,900

3 beds2.5 baths1,530 sq ft

1435 Seaboard Ave, Chesapeake, VA 23324

Property at 901 Railroad Ave, Chesapeake, VA 23324, 5 beds, 2.5 baths

$436,500

5 beds2.5 baths1,862 sq ft

901 Railroad Ave, Chesapeake, VA 23324

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

$429,000

4 beds2 baths1,655 sq ft

4004 Oak Dr, Chesapeake, VA 23321

Viewing page 12 of 21

Average home prices near Chesapeake, VA

Cities

Counties

Isle of Wight County homes for sale
$509,900
York County homes for sale
$544,950
Norfolk homes for sale
$339,500

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

298

Deals*

4.8

Satisfaction

1470

Homes closed*

* Data from the last year

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