Western Branch Homes for Sale in Chesapeake, VA

Western Branch is a residential neighborhood in Chesapeake, Virginia, characterized by tree-lined streets and a mix of single-family homes. The area reflects the broader suburban character of Chesapeake while maintaining its own distinct identity. Established development and mature landscaping contribute to the neighborhood's established feel.

47 homes for sale in Western Branch right now.

47

Active Listings

$525,000

Median List Price

$203

Avg. $ / Sq. Ft.

27

Avg. Days on Market

1d ago

Newest Listing

Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Western Branch.

4249 Taylor RD, CHESAPEAKE VA 23321

$950,000

4249 Taylor RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

1 bd2,272 sqft
3315 Tyre Neck RD, CHESAPEAKE VA 23321

$850,000

3315 Tyre Neck RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3.1 ba3,000 sqft
3932 Colony Pointe DR, CHESAPEAKE VA 23321

$690,000

3932 Colony Pointe DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

5 bd3 ba3,466 sqft
3120 Deans CT, CHESAPEAKE VA 23321

$615,000

3120 Deans CT, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3 ba3,444 sqft
2209 HAMPTON ROADS PW, CHESAPEAKE VA 23321

$609,900

2209 HAMPTON ROADS PW, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

6 bd3 ba2,812 sqft
2223 Hampton Roads PW, CHESAPEAKE VA 23321

$609,900

2223 Hampton Roads PW, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

6 bd3 ba2,812 sqft
MM Myrtle II NONE, CHESAPEAKE VA 23321

$609,900

MM Myrtle II NONE, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

6 bd3 ba2,812 sqft
2307 Tybee LOOP, CHESAPEAKE VA 23321

$600,000

2307 Tybee LOOP, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3 ba2,808 sqft
4513 Overlook PL, CHESAPEAKE VA 23321

$585,000

4513 Overlook PL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3.1 ba2,941 sqft
5112 ANNAPOLIS DR, CHESAPEAKE VA 23321

$578,645

5112 ANNAPOLIS DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,420 sqft
5103 Annapolis DR, CHESAPEAKE VA 23321

$574,900

5103 Annapolis DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3 ba2,515 sqft
2250 Captiva LN, CHESAPEAKE VA 23321

$569,900

2250 Captiva LN, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

5 bd3.1 ba2,801 sqft
2207 Hampton Roads PW, CHESAPEAKE VA 23321

$551,900

2207 Hampton Roads PW, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2 ba2,145 sqft
2211 Hampton Roads PW, CHESAPEAKE VA 23321

$550,900

2211 Hampton Roads PW, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,420 sqft
MM Sycamore NONE, CHESAPEAKE VA 23321

$550,900

MM Sycamore NONE, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,420 sqft
2206 Wilmington AVE, CHESAPEAKE VA 23321

$550,900

2206 Wilmington AVE, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,447 sqft
2205 Hampton RD, CHESAPEAKE VA 23321

$550,900

2205 Hampton RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,447 sqft
5025 Duxbury RD, CHESAPEAKE VA 23321

$545,900

5025 Duxbury RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,194 sqft
MM Myrtle NONE, CHESAPEAKE VA 23321

$539,900

MM Myrtle NONE, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2 ba2,183 sqft
2204 Wilmington AVE, CHESAPEAKE VA 23321

$539,900

2204 Wilmington AVE, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2 ba2,145 sqft
2216 Hampton Roads PW, CHESAPEAKE VA 23321

$539,000

2216 Hampton Roads PW, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,542 sqft
5014 Pearl ST, CHESAPEAKE VA 23321

$535,000

5014 Pearl ST, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

5 bd3.1 ba3,680 sqft
5041 Queen ST, CHESAPEAKE VA 23321

$525,000

5041 Queen ST, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

5 bd3.1 ba2,302 sqft
2900 Tyre Neck RD, CHESAPEAKE VA 23321

$525,000

2900 Tyre Neck RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

6 bd3 ba2,683 sqft
5036 Queen ST, CHESAPEAKE VA 23321

$525,000

5036 Queen ST, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

5 bd3.1 ba2,302 sqft
2871 Lilley Cove DR, CHESAPEAKE VA 23321

$510,000

2871 Lilley Cove DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd1.1 ba2,356 sqft
4000 Wyant CT, CHESAPEAKE VA 23321

$497,000

4000 Wyant CT, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

6 bd4 ba3,789 sqft
4743 Mahogany RN, CHESAPEAKE VA 23321

$489,500

4743 Mahogany RN, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,653 sqft
4609 Longleaf PL, CHESAPEAKE VA 23321

$457,195

4609 Longleaf PL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba2,614 sqft
4245 Taylor RD, CHESAPEAKE VA 23321

$450,000

4245 Taylor RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd1.1 ba1,668 sqft
4605 Longleaf PL, CHESAPEAKE VA 23321

$449,900

4605 Longleaf PL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3 ba2,842 sqft
4603 Longleaf PL, CHESAPEAKE VA 23321

$449,900

4603 Longleaf PL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3 ba2,880 sqft
4620 Longleaf PL, CHESAPEAKE VA 23321

$443,900

4620 Longleaf PL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd3 ba2,842 sqft
2949 Big Bend DR, CHESAPEAKE VA 23321

$355,500

2949 Big Bend DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2.1 ba1,633 sqft
3004 Big Bend DR, CHESAPEAKE VA 23321

$355,000

3004 Big Bend DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2.1 ba1,633 sqft
5213 Winery DR, CHESAPEAKE VA 23321

$349,900

5213 Winery DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2.1 ba1,504 sqft
2409 Leytonstone DR, CHESAPEAKE VA 23321

$320,000

2409 Leytonstone DR, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

2 bd2.1 ba1,870 sqft
4320 Oneford PL, CHESAPEAKE VA 23321

$320,000

4320 Oneford PL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2.1 ba1,952 sqft
4261 Taylor RD, CHESAPEAKE VA 23321

$300,000

4261 Taylor RD, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2 ba2,242 sqft
No photo provided

$285,000

4606 Old Fox TRL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2.1 ba1,703 sqft
2314 Alcott WAY, CHESAPEAKE VA 23321

$285,000

2314 Alcott WAY, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

2 bd2.1 ba1,329 sqft
5001 Clifton ST, CHESAPEAKE VA 23321

$269,900

5001 Clifton ST, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd1 ba960 sqft
4610 Olde Stone WAY, CHESAPEAKE VA 23321

$250,000

4610 Olde Stone WAY, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2.1 ba1,703 sqft
4626 Old Fox TRL, CHESAPEAKE VA 23321

$250,000

4626 Old Fox TRL, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

3 bd2 ba1,245 sqft
4999 Clifton ST, CHESAPEAKE VA 23321

$75,000

4999 Clifton ST, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

2250 Captiva LN, CHESAPEAKE VA 23321

$3,700

2250 Captiva LN, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

5 bd3.1 ba2,801 sqft
4314 Midhurst LN, CHESAPEAKE VA 23321

$2,650

4314 Midhurst LN, CHESAPEAKE VA 23321

Chesapeake, Virginia 23321

4 bd2.1 ba1,940 sqft

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Living in Western Branch

Residents of Western Branch enjoy access to local parks and outdoor recreation typical of the Chesapeake area. The neighborhood supports a quiet, family-oriented atmosphere with convenient access to schools and shopping. Daily life centers around residential stability and community-oriented living in a suburban setting.

Western Branch appeals to buyers seeking established suburban living within Chesapeake's borders. The neighborhood offers a range of home sizes and styles suited to various household needs. This area represents a practical choice for those prioritizing neighborhood stability and residential character.

Listings & market data updated July 2026 · Live REIN MLS data

Western Branch real estate FAQ

Where is Western Branch located within Chesapeake, VA?+

Western Branch is the northernmost borough of Chesapeake, set in the northwestern part of the city and separated from the rest of Chesapeake by the Western Branch of the Elizabeth River, the Great Dismal Swamp, and rail and interstate corridors. It borders Portsmouth to the east and northeast and Suffolk to the west and northwest, with the Bowers Hill area to its south, and Interstate 664 runs through the center of the area. This geography gives Western Branch its own distinct identity within the city.

What kinds of homes are in Western Branch?+

Western Branch is a mature, tree-lined area with a wide mix of housing built over several decades, from brick ranch-style homes dating to the 1960s and traditional two-story houses to newer construction, including some homes near the Elizabeth River. Lots tend to be established with grown trees, and the area includes numerous named subdivisions across the Western Branch North, South, and riverside sections. Inventory ranges from modest single-story homes to larger waterfront properties.

What schools serve Western Branch?+

Western Branch is served by Chesapeake Public Schools, and the area has its own grade-level progression of Western Branch schools: Western Branch Primary (PreK-2), Western Branch Intermediate (grades 3-5), Western Branch Middle (grades 6-8), and Western Branch High (grades 9-12). Western Branch High opened in 1968 and enrolls more than 2,100 students; Jolliff Middle is the other middle school that feeds into it. Exact attendance zones are set by Chesapeake Public Schools, so buyers should confirm the assigned schools for any specific address and review current GreatSchools and Virginia School Quality Profile ratings.

How far is Western Branch from the interstates and military bases?+

Interstate 664, part of the Hampton Roads Beltway, runs through the center of Western Branch and connects to I-64, State Route 164 (the Western Freeway), Route 17, and Portsmouth Boulevard, putting much of the region within reach. The Monitor-Merrimac Memorial Bridge-Tunnel carries I-664 across the harbor at the mouth of the James River toward Newport News and Hampton on the Peninsula. Naval Medical Center Portsmouth and the Norfolk Naval Shipyard are a short drive away, which makes the borough convenient for commuters working across the harbor.

What parks and amenities are in Western Branch?+

Recreation anchors include the roughly 90-acre Western Branch Park (officially Claire R. Askew Western Branch Park) with ball fields, tennis and pickleball courts, walking trails, and a dog park, plus Elizabeth River Park with its boat ramp on the Southern Branch of the Elizabeth River, Dunedin Park, and the smaller Crossings at Western Branch. The Western Branch Community Center adds an indoor gathering space. Everyday shopping, grocery stores, and dining are clustered along Portsmouth Boulevard and Western Branch Boulevard, near the Chesapeake Square retail area, which is undergoing a major redevelopment.

What is it like living in Western Branch compared to the rest of Chesapeake?+

Western Branch reads as a settled, suburban borough with mature streetscapes and its own concentration of schools, parks, and shopping, distinct from the newer-growth areas of southern Chesapeake. Bounded by the Elizabeth River, the Great Dismal Swamp, and the Suffolk and Portsmouth lines, it functions almost as a community of its own while still being part of the City of Chesapeake, with I-664 providing access to jobs across Hampton Roads.

About Chesapeake

Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled every 5 minutes from the REIN feed.

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Schools serving Chesapeake

Browse Chesapeake homes by CPS attendance zone. Zoning is assigned by address and can change — always confirm a specific home’s zoned schools with the school division.

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What residents say about Western Branch

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