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$420,000
3 Beds ⋅ 2.1 Baths ⋅ 10649201 MLS
Like New Construction! Nestled in the highly sought-after Grassfield area of Chesapeake. Welcome home to this stunning two-story townhome featuring modern finishes and a functional open layout. The kitchen features white shaker cabinets, quartz countertops, and a generous island. Upstairs, you’ll find the primary suite includes 2 spacious closets and a private en-suite bathroom. Additional bedrooms offer flexibility for guests, a home office, playroom, etc. Come home to a neighborhood with top-rated schools, parks, walking trails, and easy access to shopping, dining, and major highways.

1605 Redwing Arch, South Chesapeake
$789,900
5 Beds ⋅ 3 Baths ⋅ 10648928 MLS
NEW PRICE—NOW $789,900! $25K+ REDUCTION. Located in a welcoming, highly desirable community with NO HOA, this meticulously maintained home offers the feel of new construction with over $75,000 in thoughtful upgrades. The customized gourmet kitchen features double ovens, a built-in microwave drawer, designer finishes, and a dry bar with beverage refrigerator—great for gathering and entertaining. Custom window treatments, upgraded lighting, smart-home features, a reverse-osmosis water system, and more elevate everyday living. A first-floor bedroom and full bath offer flexibility. Relax on the inviting front porch, enjoy the screened-in porch, expansive patio, fully fenced yard, and peaceful wooded backdrop. Close to shopping, dining, and everyday conveniences, this truly move-in-ready home delivers the best of both worlds: a strong sense of community with privacy in your own backyard. Luxury country living at its finest!

633 Ambrose Street, South Chesapeake
$750,000
10648883 MLS
AMAZING OPPORTUNITY TO BUILD NEW CONSTRUCTION HOMES IN A PEACEFUL SETTING, YET CONVENIENTLY LOCATED AND CLOSE TO SHOPPING, SCHOOLS AND INTERSTATE. TO BE SOLD TOGETHER WITH 1136 SUNLIGHT DR, THIS ALLOWS FOR 3 BUILDABLE LOTS AT 0.64 AC EACH. ALL THE WORK IS DONE, YOU JUST NEED TO BUILD!

1148 Sunlight Drive, South Chesapeake
$150,000
10648880 MLS
AMAZING OPPORTUNITY TO BUILD NEW CONSTRUCTION HOMES IN A PEACEFUL SETTING, YET CONVENIENTLY LOCATED AND CLOSE TO SHOPPING, SCHOOLS AND INTERSTATE. TO BE SOLD TOGETHER WITH 1148 SUNLIGHT DR, THIS ALLOWS FOR 3 BUILDABLE LOTS AT 0.64 AC EACH. ALL THE WORK IS DONE, YOU JUST NEED TO BUILD!

1136 Sunlight Drive, South Chesapeake
$750,000
10648561 MLS
Stunning property with mature trees and a lake. Pole barn as is. Survey available upon request.

2650 Benefit Road, South Chesapeake
$849,800
6 Beds ⋅ 4.1 Baths ⋅ 10648478 MLS
RARE FIND IN CHESAPEAKE! Nearly 3 acres of space, privacy, and endless possibilities surround this stunning home. Inside, a bright open layout and show-stopping kitchen with an oversized island, granite countertops, stainless steel appliances, and double ovens create the perfect setting for everyday living and entertaining. Step outside to a screened porch, above-ground pool, and expansive property with room to truly spread out. Privacy, space, and modern living—this is more than a home, it’s a lifestyle!

2537 Number Ten Lane, South Chesapeake
$825,000
4 Beds ⋅ 3.1 Baths ⋅ 10648270 MLS
Beautiful custom home on 3 Acres that backs up to woods! Two Primary Suites, one downstairs and one upstairs each with their own full bath! Amazing custom Kitchen with loads of storage, Pantry, plenty of counter space, center island, brand new cabinets, granite and Stainless Steel Appliances! Dual zoned central Heat/AC. Move in ready! Located in the Grassfield School district! Completely remodeled and waiting for you, be sure to come check this one out first! No HOA, bring your horses, chickens and goats!

2239 Benefit Road, South Chesapeake
$935,000
5 Beds ⋅ 3 Baths ⋅ 10648261 MLS
Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, South Chesapeake
$13,500
10648037 MLS
Vacant lot currently being used as Camp site.

.229AC Trinkle Street, South Chesapeake
$645,000
4 Beds ⋅ 2.1 Baths ⋅ 10647705 MLS
Experience the perfect blend of quality, comfort, and outdoor living at 1928 Rockwood Drive in the highly sought-after Grassfield School District! Originally built by Stephen Alexander Homes, this beautifully maintained home is tucked away in a quiet neighborhood and features a dedicated office/study, second-floor laundry, and a spacious primary suite with soaring cathedral ceilings. The inviting living room showcases a gas fireplace flanked by custom built-ins. Outside, enjoy a private backyard oasis with an in-ground pool and TREX decking, installed in 2020. Additional updates include new windows and doors, installed in 2021. Complete with a two-car attached garage and driveway parking for four vehicles, this home truly has it all!

1928 Rockwood Drive, South Chesapeake
$535,000
5 Beds ⋅ 3.1 Baths ⋅ 10647572 MLS
Welcome home to this beautifully updated 5-bedroom home, where thoughtful upgrades and spacious living come together perfectly. The heart of the home is the stunning kitchen featuring quartzite countertops, a Sub-Zero refrigerator, butler's pantry, and an open layout overlooking the dining area and expansive family room—great for entertaining and everyday living. A first-floor bedroom with its own private en-suite bath offers the perfect space for guests or multi-generational living. Upstairs, retreat to the impressive primary suite with vaulted ceilings, a generous sitting area, and a walk-in closet. Convenient second-floor laundry includes a granite folding counter for added functionality. Enjoy abundant parking with a half-moon driveway plus additional gravel parking. Generator conveys as-is; sellers have never used it. 1.5% closing cost assistance with a full priced offer!

514 Waters Road, South Chesapeake
$674,500
5 Beds ⋅ 3 Baths ⋅ 10647461 MLS
Qualified buyers may be able to assume the Seller's existing VA Loan - Grassfield High School Zone | Outdoor Oasis with In-Ground Pool | Renovated Kitchen & 1st Floor Bedroom Welcome to 1076 Scenic Blvd, located on nearly half an acre with NO HOA! This spacious 5 bedroom home features a main-floor bedroom with a full bath, new LVP flooring, fresh Paint, and a fully remodeled 2026 kitchen with smart Appliances. Step into your private outdoor oasis complete with an in-ground pool surrounded by an extended concrete deck, plus a cozy fire pit for entertaining. Convenient to local bases, shopping, and dining. Schedule your tour today!

1076 Scenic Boulevard, South Chesapeake
$7,900
10647463 MLS
Vacant Land in Hillcrest subdivision. Zoned for great schools! Drive by anytime. Seller has never occupied the land, has no information to share. Buyer to perform all due diligence.

14 Blk Tuck Street, South Chesapeake
$825,000
4 Beds ⋅ 4 Baths ⋅ 10647485 MLS
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-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today’s buyers are looking for.

1837 Benefit Road, South Chesapeake
$614,900
4 Beds ⋅ 3.1 Baths ⋅ 10646890 MLS
Beautifully maintained 4 Br 3.5 bath home on 1/2 acre lot located in the Grassfield area of Chesapeake. 2 large primary suites 1 upstairs and 1 downstairs. 2 additional bedrooms upstairs that share a Jack n Jill. Theater room located downstairs that you will absolutely love. Some other upgrades include gourmet kitchen, granite countertops, stainless steel appliances, hard wood/LVP flooring, full privacy fence and beautifully maintained landscaping. The roof was replaced 2018.

2308 Angler Lane, South Chesapeake
$599,900
5 Beds ⋅ 3 Baths ⋅ 10646979 MLS
Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

789 Caddie Street, South Chesapeake
$519,998
4 Beds ⋅ 3.1 Baths ⋅ 10646463 MLS
BACK ON MARKET DUE TO NO FAULT OF THE SELLER! If you’ve been searching for true peace and privacy without sacrificing convenience, this Grassfield gem is an absolute must-see. Set back from the street on a private driveway, the property opens up to nearly an acre of total solitude, completely enveloped by woods and lush mature greenery. Inside, fresh paint brings a bright, inviting energy to a floor plan built for real life. The layout is a rare find for multi-generational living, featuring two distinct main-level suites. The in-law wing includes its own living room, making it easy to use as a private apartment, a 5th bedroom, or a home office. The primary suite feels like a custom getaway with live-edge wood countertops, dual shower heads, and a custom walk-in closet system. Out back, the property turns into a full outdoor retreat featuring a storage shed, a chicken coop, separate hookups ready for a pool and hot tub, and a massive detached two-car workshop/garage complete with a carport and RV hookup. Welcome home!

891 Bells Mill Road, South Chesapeake
$500,000
4 Beds ⋅ 2 Baths ⋅ 10646286 MLS
Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, South Chesapeake
$849,900
5 Beds ⋅ 4.1 Baths ⋅ 10646141 MLS
Under Construction – Luxury New Construction with Timeless Coastal Farmhouse Style! This stunning 3-level home blends classic board-and-batten architecture, clean lines, black-framed windows, and thougthful accents to create exceptional appeal. Inside, an open-concept first floor is designed for modern living, featuring a spacious family room, dining area, and a designer kitchen with a large center island, custom cabinetry, and premium finishes. The second level offers four generously sized bedrooms, including an impressive owner's suite with a spa-inspired bath, plus two full bathrooms to comfortably accommodate family and guests. The third floor provides incredible flexibility with a spacious bonus room or fifth bedroom, a full bath, and convenient walk-in attic storage. With 5 bedrooms, 4.5 baths, thoughtful craftsmanship, and stylish finishes throughout, this exceptional new home offers the perfect blend of luxury, comfort, and functionality for today's lifestyle.

1833 Shillelagh Road, South Chesapeake
$355,000
3 Beds ⋅ 1 Baths ⋅ 10645994 MLS
Welcome to 944 Bells Mill Road, a beautifully updated Craftsman-style bungalow in the highly desirable Great Bridge area of Chesapeake. This home blends timeless character with modern updates, featuring fresh paint throughout, brand-new kitchen countertops, new luxury vinyl plank flooring in the kitchen and laundry room, and a refreshed bathroom. Situated on a spacious 0.36-acre lot, the property offers a detached garage/workshop, a welcoming front porch, a newer HVAC system, energy-efficient windows, and a durable metal roof. This charming home is just minutes from shopping, dining, parks, and major commuter routes. If you're looking for character, thoughtful updates, and an unbeatable location, 944 Bells Mill Road is ready to welcome you home.

944 Bells Mill Road, South Chesapeake
$525,000
4 Beds ⋅ 2.1 Baths ⋅ 10645295 MLS
Located in the highly sought-after Grassfield High School district, this home offers an incredible opportunity to make a home of your own in one of Chesapeake's most desirable areas. Inside features a spacious, functional floor plan boasting nearly 2700 square feet of living space. The living areas are generous with comfortable bedrooms and plenty of room to personalize. Head outside to the home's standout feature -- an expansive backyard and large deck with endless possibilities for entertaining or creating a private outdoor retreat. Conveniently located near shopping, dining, parks, and major interstates!

963 Speight Lyons Loop, South Chesapeake
$230,000
10645662 MLS
This is a wooded 1.38 acre lot along a lightly traveled road that's being gradually redeveloped. Survey in hand as well as a wetlands delineation report done in 2025 showing about 0.88 Acre of wetlands and about 0.50 Acre of non-wetlands towards the back of the lot. Seller has already done soil test and the property can accommodate a single-family home. Soil analysis and location of septic field has been approved. Site plan is being drawn up. Construction entrance installed and lot underbrush cleared to allow walking access to the construction site. Buy now to build your custom dream home before the current owner builds on it.

2701 Seven Eleven Road, South Chesapeake
$16,700
10645394 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1536 Tuck Street, South Chesapeake
$16,700
10645392 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1534 Tuck Street, South Chesapeake
$16,700
10645395 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. Offered at $16,700 per lot. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1538 Tuck Street, South Chesapeake
$735,000
5 Beds ⋅ 2.1 Baths ⋅ 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake
$16,500
10645088 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 9 Tuck Street, South Chesapeake
$16,500
10645087 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 8 Tuck Street, South Chesapeake
$16,500
10645086 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 7 Tuck Street, South Chesapeake
$16,500
10645083 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 6 Tuck Street, 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.