Culpepper Landing Homes for Sale in Chesapeake, VA
Culpepper Landing is a master-planned community in the Deep Creek section of Chesapeake, set just off Dominion Boulevard (U.S. Route 17) and framed by the historic Great Dismal Swamp Canal. Developed beginning in 2007 across roughly 490 acres, it pairs newer construction with a layout that wraps homes around a central amenity core, public squares, pocket parks, and a wide band of preserved woodland. The architecture draws on classic Coastal Virginia styles, including Colonial, Victorian, Craftsman, cottage, and villa designs across single-family homes, townhomes, and condominiums. With roughly 150 acres of conserved green space, the community combines an amenity-rich core with an outdoor, nature-forward setting. Its position near the Veterans Bridge gives it quick reach to the rest of Chesapeake and the wider Hampton Roads region.
7 homes for sale in Culpepper Landing right now.
7
Active Listings
$510,000
Median List Price
$208
Avg. $ / Sq. Ft.
29
Avg. Days on Market
1d ago
Newest Listing
Live from the REIN MLS, refreshed continuously. Stats reflect active for-sale inventory in Culpepper Landing.
$669,000
3307 Dodd DR, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$629,900
781 Big Bear LN, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$590,000
776 Big Bear LN, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$510,000
513 Simpson LN, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$394,900
655 Mill Creek PW, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$295,000
503 Nesbit DR, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$272,500
523 Nesbit DR #101, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
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Living in Culpepper Landing
Daily life in Culpepper Landing centers on its amenity hub, which includes a clubhouse with a fitness center, an outdoor pool and water-play area, a dog park, children's play areas, a community garden, and campsites. Walking and biking paths thread through the neighborhood and the surrounding conservation land, and the nearby Great Dismal Swamp National Wildlife Refuge offers trails, paddling on Lake Drummond, and wildlife watching for time outdoors. For errands and dining, the Greenbrier shopping district, Chesapeake Regional Medical Center, and Greenbrier Mall sit within roughly ten miles, putting stores, restaurants, and services a short drive away. Housing options range from low-maintenance townhomes and condominiums to detached single-family homes with a variety of yard sizes, giving several footprints to choose from. The location off Dominion Boulevard and the Veterans Bridge offers connections to I-64, I-464, and U.S. 17, with downtown Norfolk and Naval Station Norfolk both reachable in roughly half an hour depending on traffic.
Culpepper Landing is a relatively young community, with most homes dating from 2007 onward and newer phases still adding inventory, so the housing stock skews modern compared with much of surrounding Deep Creek. The mix of single-family detached homes, townhomes, condominiums, and villa-style residences gives the neighborhood a range of home sizes, footprints, and maintenance levels under one master plan. Demand is supported by the combination of newer construction, an amenity-rich core, and a setting wrapped in conserved green space, plus a Chesapeake location with strong highway access toward Norfolk and the region's military installations. The planned 2027 opening of the new Culpepper Landing Elementary School within Chesapeake Public Schools has also drawn attention to the area. As a REIN MLS subdivision matching "culpepper landing," active listings tend to be limited at any given time, so inventory can move when homes come to market.
Culpepper Landing real estate FAQ
What is Culpepper Landing in Chesapeake, VA?+
Culpepper Landing is a master-planned community in the Deep Creek section of Chesapeake, developed beginning in 2007 across roughly 490 acres with about 150 acres of conserved green space framed by the historic Great Dismal Swamp Canal. It offers an amenity core that includes a clubhouse, fitness center, outdoor pool, dog park, and walking trails, along with highway connections to the rest of Hampton Roads via Dominion Boulevard and the Veterans Bridge. Touring the community and reviewing current listings is the best way to see whether it fits your needs.
What kinds of homes are in Culpepper Landing?+
The neighborhood offers a mix of single-family detached homes, townhomes, condominiums, and villa-style residences, most built from 2007 onward. Architecture draws on classic Coastal Virginia styles such as Colonial, Victorian, Craftsman, cottage, and villa designs, with single-family homes available in a range of yard sizes. This variety provides several home footprints and maintenance levels within one community.
What schools serve Culpepper Landing?+
Culpepper Landing is part of Chesapeake Public Schools, with students currently zoned to schools serving the Deep Creek area. A new Culpepper Landing Elementary School is scheduled to open in fall 2027, and the school board approved updated elementary attendance zones in March 2026 that take effect in September 2027, while middle and high school assignments remain unchanged. Because zoning can change, confirm the current assigned schools and any GreatSchools ratings directly with Chesapeake Public Schools for a specific address.
How far is Culpepper Landing from the interstates and military bases?+
The community sits just off Dominion Boulevard (U.S. Route 17) near the Veterans Bridge, with connections to I-64 and I-464. Downtown Norfolk and Naval Station Norfolk are typically reachable in about 30 minutes depending on traffic. Its central Chesapeake position also makes other Hampton Roads destinations accessible via the regional highway network.
What amenities does Culpepper Landing offer?+
Culpepper Landing features a clubhouse with a fitness center, an outdoor pool and water-play area, a dog park, children's play areas, a community garden, and campsites. Walking and biking paths run through the neighborhood and the surrounding conservation land. Roughly 150 acres of preserved green space sit within the community, and the nearby Great Dismal Swamp National Wildlife Refuge adds trails, paddling, and outdoor recreation.
Is Culpepper Landing near the water?+
The community is framed by the historic Great Dismal Swamp Canal, which connects to the Southern Branch of the Elizabeth River nearby, giving it a waterway-oriented setting at the edge of central Chesapeake. The surrounding conservation land and the nearby Great Dismal Swamp National Wildlife Refuge, including paddling on Lake Drummond, add to its natural water-and-woodland backdrop. Note that the neighborhood is set in Deep Creek woodland rather than directly on river frontage, so confirm any specific waterway access for an individual property.
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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