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$485,000
4 Beds ⋅ 2.1 Baths ⋅ 10623213 MLS
Beautiful Colonial-style home situated on a spacious 0.41 acre corner lot w/ deep water access, dock and bulkhead. Offering approx. 2100 sq.ft. Of living space, this 4 bed 2.5 bth home blends classic charm w/ comfy living. Enjoy cozy evenings by the fireplace and take advantage of the expansive backyard-perfect for entertaining, outdoor activities, or future enhancements. The large corner lot provides added privacy and curb appeal, while the storage shed and attached garage offers lots of extra space for tools and equipment. A rare opportunity to own a waterfront property w/ room to spread out, both inside and out.

824 Heritage Point, South Chesapeake
$289,900
10620680 MLS
"Turnkey Commercial Property with Income producing opportunity!! Zoned B-3, this versatile property supports a wide range of commercial uses. Currently operating as a fitness studio, the space can easily be adapted to accommodate various business types. Extensively renovated and upgraded in 2024, this property standsout having a valid Certificate of Occupancy and is ADA compliant. Excellent road frontage provides strong visibility and is close to major highways for easy access to all of Hampton Roads. Features include front and rear entrances and ample paved off-street parking in both the front and rear of the building. Detached oversized garage with electricity offers additional storage or workspace. Garage conveys As Is. Month to month tenants in place, Rent rolls available upon request. Shown by appointment only."

4208 Bainbridge Boulevard, Central Chesapeake
$669,900
10621269 MLS
Vacant Land on Shillelagh Rd in a country setting that spans over 97.9 acres. Building on the property is used for the Hunt Club. Great location and School District. Quick access to Dominion Blvd to the I-64 to Downtown Norfolk, NPN, Hampton, and the MM-Tunnel and Military Bases. Go south to Benefit Rd and a short drive to the Outer Banks to NC and Virginia Beach Oceanfront or the Chesapeake Bay. Access to the property through the locked front gate. Call for access.

2237 Shillelagh Road, South Chesapeake
$1,325,000
5 Beds ⋅ 3.1 Baths ⋅ 10620633 MLS
Two homes. Endless possibilities. Tucked away on a 1.5-acre lot in the heart of Great Bridge, this rare property offers 5,633 SF across two beautifully updated homes great for multigenerational living, extended family, a home business, or potential rental income. The main home features 5 bedrooms, 3.5 baths, and a stunning kitchen with GE Café appliances, slate countertops, hand-painted cabinetry, reclaimed wood accents, and a custom bourbon bar great for entertaining. The detached guest house lives like its own residence with 2 bedrooms, 2 baths, an office, and a 2-car garage. Enjoy a backyard retreat with a 35,000-gallon saltwater pool, new decking, screened porch, and lush landscaping. Tankless water heaters and a whole-house generator add peace of mind. Located in the sought-after Great Bridge school district.

1149 Waters Road, South Chesapeake
$750,000
10620473 MLS
SURVEYED, BUILDABLE BOTH PROPERTIES TO BE SOLD TOGETHER, TOTAL 7.4 AC+OR- RECENTLY SURVEYED BUIDABLE LEGAL DESCRIPTION FOR EACH PROPERTY NECK ROAD 4.352 AC, NECK ROAD 2.85 AC CHECK WITH CITY IF THINKING OF HAVING REZONED TO COMMERCIAL, ONE PROPERTY ON NORTH SIDE OF MOSSES GRANDY TRAIL OTHER ON SOUTH SIDE OF MOSES GRANDY TRAIL, BOTH DIRECTLY ACROSS FROM EACH OTHER, SURVEY IN DOCUMENTS. THERE IS A EASEMENT AND A RIGHT-AWAY.

7.4 AC Moses Grandy Trail, South Chesapeake
$434,900
10620048 MLS
Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 27.232 acres of raw farm land is a rare find in southern Chesapeake. The property is not currently leased, but can be an option if desired. This parcel is the largest of four and is Lot D on the plat. Buyer to do their due diligence on well, septic, and building permit. Call the listing agent for a showing today!

Lot D Buskey Road, South Chesapeake
$866,319
54 Beds ⋅ 4.1 Baths ⋅ 10619381 MLS
The Miles offers a layout designed to grow with you—while still feeling intentional and welcoming at every turn. Featuring 4 beds, 4.5 baths, & 3,585 square feet, this thoughtfully designed home delivers space, flexibility, & timeless appeal for modern living. Enter into a grand foyer that immediately sets the tone. To your left, a private home office offers the a retreat for remote work, quiet study, or creative pursuits. To the right, a formal dining room invites everything from holiday gatherings to weeknight dinners filled with conversation & connection. As you move forward, the home opens into a stunning great room, seamlessly flowing into the breakfast area / kitchen—creating the heart of home where life naturally comes together. Kitchen is designed with both beauty & practicality in mind, featuring a generous pantry —ideal for effortless entertaining & everyday organization. Just beyond breakfast area, you’ll find a half bath & direct access to the garage, making comings / goings easy & efficient. Tucked just off the great room, a versatile flex room with adjacent full bath & closet offers endless possibilities—whether you envision a guest suite, playroom, fitness space, or secondary living area. Upstairs continues to impress with spacious loft that serves as a natural gathering space—perfect for movie nights, homework sessions, or a cozy lounge. 3 additional beds provide comfort & privacy for family /guests, with Bed 2 & 3 connected by a Jack-and-Jill bathroom, blending convenience with thoughtful design. Primary suite is a true retreat, offering a peaceful escape complete with luxurious bath & expansive walk-in closet. Just outside the suite, the upstairs laundry room adds everyday ease—no hauling baskets up & down stairs, just smart living done right. Every corner has been carefully considered to support the rhythms of daily life while offering moments of comfort, connection, calm. Flexible living spaces to generous storage & intuitive layout, this home is more than a floorplan—it’s a place where memories are made!

2100 Sanderson Road, South Chesapeake
$349,000
10619323 MLS
COMMERCIAL PROPERTY FOR SALE (FORMER TIRE SHOP) | B-2 ZONING | CORNER LOT | HIGH-VISIBILITY FRONTAGE | FULLY RENOVATED. Freestanding fully renovated commercial building on a high-visibility corner lot at Bainbridge Blvd & Jefferson St in Chesapeake. Zoned B-2 allowing a wide range of retail, office, and service uses. Property has been previously advertised/operated for automotive-related services. Features 825 SF, one-story building on 0.182-acre lot with large paved area (7,041 SF), providing excellent parking and flexibility. Recently REMODELED: New roof, flooring, doors, updated walls, modern kitchen, fully renovated bathroom w/ tankless water heater, new vanities, new recessed lighting, and 2 brand-new high-efficiency split HVAC systems. Buyer shall perform all due diligence and confirm zoning, use approval, and permitting requirements with the City of Chesapeake prior to making an offer.

1234 Bainbridge Boulevard, Central Chesapeake
$639,777
4 Beds ⋅ 3 Baths ⋅ 10618968 MLS
Stunning new construction ranch home by an experienced, award-winning builder! The popular Sandpiper model offers an open-concept main level designed for comfortable living and entertaining. The great room flows into the gourmet kitchen, featuring custom cabinetry, a large granite island, & stainless steel appliances. The primary suite is a private retreat with a generous walk-in closet & spa-inspired bath with LVT flooring, tub, tiled shower, double vanity, and private water closet. Two additional large bedrooms and a full hall bath are conveniently located on the main level. A fourth room situated over the garage includes its own full bath, making it ideal for guests, a home office, or bonus living space. Other features include a large utility room located just off the two-car garage, 9-foot ceilings, upscale LVT and carpet flooring, and an electronic fireplace with mantle. Large 1.7-acre lot close to interstates, schools and shopping.

2500 Deal's Creek Court, South Chesapeake
$95,000
2 Beds ⋅ 1 Baths ⋅ 10616828 MLS
Value is in the land. Property being sold as-is. Home is not in livable condition.

2053 Iowa Street, South Chesapeake
$840,000
10614351 MLS
Property is priced to reflect the updates needed and is being sold as-is, including all buildings. The property features a pond, a dwelling and acreage. Ideal opportunity for investors or developers seeking future upside, potential tax advantages with the City of Chesapeake, or a private estate setting. Conveniently located just minutes from Grassfield High School, shopping, I-64, and easy access to Moyock, NC.

4500 Backwoods Road, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10613272 MLS
Start building your custom dream home today! Exceptional new construction opportunity on a spacious half-acre lot in the heart of Western Branch. Design your own floor plan to match your lifestyle or choose from one of the builder's stunning models. This featured plan offers a modern open-concept layout. The chef's kitchen features granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. A formal dining room can easily serve as a home office. Enjoy luxury vinyl plank flooring throughout the first floor and baths, plus a covered front porch and rear patio for outdoor living. Experience quality craftsmanship, thoughtful design, and the freedom to create the home you've always imagined. Ready in Spring 2026. Contact us today to start designing your custom dream home!

1530 Jolliff Road, West Chesapeake
$1,150,000
6 Beds ⋅ 5 Baths ⋅ 10611669 MLS
Welcome to this stunning 6-bedroom, 5-bath, 4,726 sq ft brick estate set on nearly 6 acres of serene countryside. This two-story residence offers an amazing blend of luxury, comfort, and functionality. Inside, you’ll find expansive living spaces, a well-appointed kitchen, and generously sized bedrooms designed for both privacy and togetherness. The home is ideal for entertaining, featuring an in-ground heated pool for year-round enjoyment. A land-mounted solar system adds modern efficiency, keeping energy costs low while supporting sustainable living. With plenty of room to spread out, both indoors and out, this property is a rare opportunity to enjoy refined living on a private, spacious retreat.

2700 Ballahack Road, South Chesapeake
$938,197
4 Beds ⋅ 3.1 Baths ⋅ 10609126 MLS
Discover just the right blend of comfort & functionality in this exceptional property, featuring two primary bedrooms - one on each level! Situated on a sprawling 3-acre lot, this home offers ample space for a hobby farm & enjoying stunning sunsets. The kitchen boasts a walk-in pantry, extensive cabinetry, as well as an 8ft island. A versatile loft offers storage & flexible living areas for those needing a play room or office space. The formal dining room offers flexibility to suit your needs, whether you prefer an elegant dining space or home office. Outdoor enthusiasts will appreciate the expansive covered rear porch and large front porch, great for relaxation, entertaining, and morning coffee! Trusted lender incentives available! PRESOLD & TO BE BUILT. OTHER HOMESITES AVAILABLE. BUILD TIME 7-10 MONTHS. INCENTIVES AVAILABLE WITH TRUSTED LENDER.

1432 Taft Road, South Chesapeake
$240,000
10608068 MLS
Vacant cleared lot, road access via access easement via lot 1 adjacent to Taft road

B Taft Road, South Chesapeake
$95,000
10607003 MLS
Prime opportunity in Chesapeake’s South Norfolk/Money Point area! This property is zoned M-2 (Heavy Industrial), offering excellent potential for commercial or industrial use. The parcel is approx. 3,572 sq ft and well-situated with convenient access to major thoroughfares, ports, and interstates.Onsite is a 2-bedroom, 1-bath home (approx. 1,016 sq ft) that can provide immediate rental income, office space, or temporary use while future plans are developed. The structure is a bonus, but the true value lies in the land and its versatile zoning, making this a rare find for investors, business owners, or developers seeking expansion opportunities.Capitalize on a location with strong growth, flexible uses, and multiple options for maximizing value.

427 Freeman Avenue, Central Chesapeake
$985,769
4 Beds ⋅ 3.1 Baths ⋅ 10604315 MLS
Discover just the right blend of comfort & functionality in this exceptional property, featuring two primary bedrooms - one on each level! Situated on a sprawling 3-acre lot, this home offers ample space for a hobby farm & enjoying stunning sunsets. The kitchen boasts a walk-in pantry, extensive cabinetry, as well as an 8ft island. A versatile loft offers storage & flexible living areas for those needing a play room or office space. The formal dining room offers flexibility to suit your needs, whether you prefer an elegant dining space or home office. Outdoor enthusiasts will appreciate the expansive covered rear porch and large front porch, great for relaxation, entertaining, and morning coffee! Trusted lender incentives available! PRESOLD & TO BE BUILT. OTHER HOMESITES AVAILABLE. BUILD TIME 7-10 MONTHS. INCENTIVES AVAILABLE WITH TRUSTED LENDER.

1429 Taft Road, South Chesapeake
$435,000
10603705 MLS
Hurry to see a LUCRATIVE Mixed Use Property that is FULLY RENTED and generating exceptional income right now! The very attentive owner of 50 YEARS has skillfully maintained and improved this premium property that features TWO Commercial Spaces + THREE Residential Apartments. The Gross Monthly Rents total $4,250 and there are 5 SEPARATE METERS for the Electricity. The Owner occupies an additional modest office space with half bath and separate entrance. This rare gem is located just off Interstates 464 & 64, and is near the up and coming Poindexter Street corridor of beautiful downtown South Norfolk! The city of Chesapeake's brand new, municipal building and parking garage (under construction) are located just around the corner, and downtown Norfolk is only five minutes away! PRICED TO MOVE, this desirable asset will be a quality addition to any Investor's portfolio! ACT FAST -- Opportunities come and go in life, so COME SEE . . . this one could be YOURS!

1300 Bainbridge Boulevard, Central Chesapeake
$435,000
10603701 MLS
Hurry to see a LUCRATIVE Mixed Use Property that is FULLY RENTED and generating exceptional income right now! The very attentive owner of 50 YEARS has skillfully maintained and improved this premium property that features TWO Commercial Spaces + THREE Residential Apartments. The Gross Monthly Rents total $4,250 and there are 5 SEPARATE METERS for the Electricity. The Owner occupies an additional modest office space with half bath and separate entrance. This rare gem is located just off Interstates 464 & 64, and is near the up and coming Poindexter Street corridor of beautiful downtown South Norfolk! The city of Chesapeake's brand new, municipal building and parking garage (under construction) are located just around the corner, and downtown Norfolk is only five minutes away! PRICED TO MOVE, this desirable asset will be a quality addition to any Investor's portfolio! ACT FAST -- Opportunities come and go in life, so COME SEE . . . this one could be YOURS!

1300 Bainbridge Boulevard, Central Chesapeake
$460,500
4 Beds ⋅ 2 Baths ⋅ 10601728 MLS
Welcome to your new home! This beautifully maintained 4-bedroom, 2-bathroom house offers a perfect blend of comfort and style. This home includes Newly installed Roof and water heater for year-round comfort and efficiency. Kitchen is cozy and Fully equipped with all-new stainless steel appliances, granite counter-tops, stylish fixtures, and ample counter space, great for cooking and entertaining. Enjoy a bright and airy living room featuring large windows and new flooring that enhances the welcoming atmosphere. Bedrooms have fresh paint, new windows and new fixtures. Located in the heart of Great Bridge this home is near school, parks, and shopping

557 Waters Road, South Chesapeake
$2,000,000
10591677 MLS
Discover nearly 168 acres of opportunity in the heart of Chesapeake, just minutes from the popular Edinburgh shopping district. Tucked away off St. Brides Road, this rare piece of land offers a peaceful natural backdrop with a blend of open space, mature woods, and a scenic pond that adds to the charm. Zoned for residential use, the property is great for a custom private estate or thoughtful development with room to spread out and grow. Whether you're envisioning a tranquil retreat or a new residential enclave, this parcel provides the setting to bring that vision to life. Note: This property is to be sold in conjunction with adjacent lot on Taft Rd. (MLS # 10591641)

168 AC St Brides Road W, South Chesapeake
$289,900
10588694 MLS
You finally found a lot for sale in Great Bridge - in a subdivision - in a cul-de-sac-ready for your house to be platted - need a builder - no problem - got it covered yourself - no problem - give us a call - Great Bridge School District at every level -Whether you're an investor, builder, or future homeowner, this is a rare opportunity to secure a premium piece of land in a desirable neighborhood - ready for development—don’t miss out! This lot offers the perfect blend of privacy and community.

904 Brice Court, South Chesapeake
$490,000
3 Beds ⋅ 2.1 Baths ⋅ 10588377 MLS
Beautiful traditional style home. Located on a large lot in the Western Branch area of Chesapeake. Home features include three large bedrooms. Large family room with a fireplace. Eat in kitchen with stainless steel wireless refrigerator, stove, microwave, and washer and dryer, all convey. Dining room leads to the enormous living room. Primary bedroom includes a walk in closet. Huge backyard with a vegetable garden and two storage sheds.

904 Flintfield Crescent, West Chesapeake
$949,000
10571242 MLS
Two parcels of cleared land Zoned A-1 totaling over 37 acres with 604.83 feet on Cedarville Road in the Hickory area of Chesapeake the front lot with 21.67 acres. The back lot with 15.87 acres. Listing Agent is the managing partner of the ownership LLC. Must request appointment to see the property and provide a 24-hour notice. Contact the Listing Agent to schedule your appointment.

3016 Cedarville Road, South Chesapeake
$949,000
3 Beds ⋅ 1 Baths ⋅ 10571232 MLS
Two parcels of cleared land Zoned A-1 totaling over 37 acres with 604.83 feet on Cedarville Road in the Hickory area of Chesapeake. The front lot with 21.67 acres. The back lot with 15.87 acres. Listing Agent is the managing partner of the ownership LLC. Must request appointment to see the property and provide a 24-hour notice. Contact the Listing Agent to schedule your appointment.

3016 Cedarville Road, South Chesapeake
$1,700,000
10569030 MLS
12 ACRES Wooded Area

10+AC Yadkin Property I-64 Express Way Road, South Chesapeake
$1,275,000
10453948 MLS
THIS PARCEL IS A MIX OF ROAD FRONTAGE AND WETLANDS. THE PROPERTY IS LOCATED AT THE INTERSECTION OF CENTERVILLE TURNPIKE AND BUTTS STATION ROAD. THE INTERECTION HAS A TRAFFIC SIGNAL. **SELLER WILL CONSIDER OWNER FINANCING

413 Centerville Turnpike N, South Chesapeake
$3,537,900
10395092 MLS
Parcels B=6.71 acres, C + D=25.5 acres. Parcels B, C & D are all residential acreage with city sewer and water ready for you to build a beautiful new home on or possibly rezone for a different use. Seller may consider selling the parcels separately. Buyer to do due Diligence and Seller has no survey.

Lots Moses Grandy ( Par.B,C,D) Trail, South Chesapeake
$982,800
10395057 MLS
Parcel A- residential lot on the waterway. Condemned home & small cemetery on premises. 12.285 ac in the heart of grassfield, perfect for building a home on a 15,000 sq foot lot and have privacy all around you. Parcels B,C & D are also available

1928 Moses Grandy Trail, South Chesapeake
$200,000
10244776 MLS
Commercial Building Lot in the Deep Creek area of Chesapeake. Located on the Dismal Swamp Canal & George Washington Hwy across the street from a Shopping Center. Property is on the navigable Dismal Swamp Canal. Property Zoning is B-1 with over 250 feet of road frontage.

Par B George Washington Highway S, South Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.