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1674 Benefit Road, South Chesapeake
$425,000
3 Beds ⋅ 1.1 Baths ⋅ 10659765 MLS
Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. So bring your vision and schedule your showing today!

1674 Benefit Road, South Chesapeake

1672 Benefit Road, South Chesapeake
$225,000
3 Beds ⋅ 2 Baths ⋅ 10659764 MLS
Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. Properties must be purchased together, so bring your vision and schedule your showing today!

1672 Benefit Road, South Chesapeake

314 Sussex Court, South Chesapeake
$310,000
2 Beds ⋅ 2.1 Baths ⋅ 10659701 MLS
Rare opportunity to own a well-maintained brick end unit townhome nestled on a quiet cul-de-sac with nearly an acre of land, no HOA fees, private dock and water access rights. This home features new roof, fresh paint, new gas logs, and countertops. New AC unit with 10 year warranty and updated furnace. This newly fenced back yard has a small shed and larger detached workshop with power! This private yard and large deck are great for relaxing and entertaining. Inside, you'll find 2 spacious bedrooms with ensuite bathrooms making it great for comfort and privacy. Large walk-in attic and utility closet with storage. With no HOA fees and a rare setting that allows for waterfront enjoyment and lots of outdoor space, you won't want to miss this one-of-a-kind opportunity! Inground sprinkler, shed, dock, Primary decorative fireplace, and well-As is! Schedule your showing today! Can close quickly.

314 Sussex Court, South Chesapeake

723 Morely Lane, South Chesapeake
$770,155
4 Beds ⋅ 3.1 Baths ⋅ 10659157 MLS
Somerset ranch with FROG. Experience the perfect blend of modern design & customizable luxury. The Owner’s Retreat is a sanctuary at the rear of the home featuring a massive walk-in closet & a spa-inspired bath with a soaking tub & separate shower. The heart of the home boasts a chef-inspired kitchen with a generous island, and butler's pantry, flowing seamlessly into the main living areas. A front-of-house flex room serves as a formal dining room or a home office. Buyer must register agent on or before 1st visit or 1st substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & video are of a completed home, finishes, elevation & upgrades may vary.

723 Morely Lane, South Chesapeake

1103 Old Vintage Road, South Chesapeake
$684,900
4 Beds ⋅ 2.1 Baths ⋅ 10658371 MLS
Elegant, all brick Transitional Ranch tucked away in the small neighborhood of Vintage Estates in the heart of Great Bridge. Well maintained and lovingly cared for by the original owner and situated on a large .80 acre wooded lot where you can enjoy the tranquil setting from the Screened Porch and the maintenance free deck. This Gem boasts many details including a stunning vaulted Great Room with doublesided gas fireplace that opens to the updated Eat in Kitchen with quartz counters and new stainless appliances. Add'l Features: Owner’s Suite with deep tray ceiling and large walk in closet and full bath, Formal Dining Room, nice sized secondary bedrooms, updated Hall and Half Baths, blinds throughout, 2 car garage with opener, and new wrought iron fencing. Finished Room over the Garage is 4th Bedroom or could be used as flex space such as an office, media room, or playroom! Conveniently located to interstate access, shopping, and dining. Attends Great Bridge schools.

1103 Old Vintage Road, South Chesapeake

308 Riverview Road, South Chesapeake
$765,682
5 Beds ⋅ 4 Baths ⋅ 10658443 MLS
The Macon Model at Riverview Landing by Wetherington Homes. Buyers may select their lot and personalize available design options. The community offers eight thoughtfully designed floor plans along with multiple exterior elevations that highlight architectural detail and curb appeal. This plan features five bedrooms, four bathrooms, a loft, and a first-floor bedroom with a full bath. The chef-inspired kitchen includes upscale finishes, a large island, and a Butler's pantry. Designed to balance functionality and craftsmanship, this home offers modern conveniences with thoughtful design throughout. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this new community with convenient access to everyday amenities!

308 Riverview Road, South Chesapeake

700 Old Fields Arch, South Chesapeake
$729,000
4 Beds ⋅ 4 Baths ⋅ 10658359 MLS
PRICED TO SELL WITH SELLER CLOSING COST ASSISTANCE! An incredible opportunity to own a one-of-a-kind, all-brick former Homearama showcase home, recognized with the prestigious Best Kitchen Award! From the grand marble foyer and soaring ceilings to the expansive living spaces, this home offers timeless character, impressive craftsmanship, and exceptional potential. The chef's kitchen features two oversized granite islands, abundant cabinetry, and a nearby wine station, while the media room with wet bar, sunroom, and glass-enclosed porch provide wonderful spaces for entertaining. A first-floor office with custom built-ins offers added flexibility, while two ensuite bedrooms, including a spacious primary retreat with a wraparound walk-in closet and luxurious marble bath, add to the home's appeal. Additional highlights include newer HVAC systems and fantastic community amenities featuring a clubhouse, swimming pool, and parks. Conveniently located near shopping, dining, and interstate access. With its impressive architecture, generous living spaces, and opportunity to customize to your taste, this home offers tremendous potential at an attractive price. Bring your vision, add your finishing touches, and make this one-of-a-kind property your own!

700 Old Fields Arch, South Chesapeake

4337 Sunray Avenue, West Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10658246 MLS
Set in a peaceful, rural-feeling setting while still centrally located in Chesapeake, this home has been restored from top to bottom, keeping its character while nearly everything around it has been thoughtfully updated. The result is a house that feels established without feeling dated, with two fireplaces, generous living spaces and updates that go well beyond what you can see. LVP carries through the main level, new carpet finishes the upstairs, and the two fireplaces give the home completely different personalities: one wood-burning, one with gas logs. The kitchen has its own presence with cream cabinetry extending to the ceiling, granite countertops and GE appliances, while the bathrooms have also been updated to continue the refreshed finish throughout the house. Behind the cosmetic work is an equally strong list of improvements. All-new windows, a new dual-zone HVAC system, a new water heater and an updated electrical panel have already been handled, while the roof is approximately five years old. Outside, the newly extended concrete driveway and patio create even more usable space. And then this property gets fun. There is an attached garage, a separate detached garage, an oversized workshop/shed, another storage shed and a treehouse/playhouse tucked into the property. Add the neighboring horses, chickens and goats, and the setting has a little unexpected country character without leaving Chesapeake. It is the combination that makes this one memorable: a peaceful setting with convenient access, two fireplaces, multiple garages and outbuildings, substantial system updates, refreshed interiors and outdoor space with personality. A house with some history left in it, but very little left untouched.

4337 Sunray Avenue, West Chesapeake

4141 3rd Street, Central Chesapeake
$319,500
3 Beds ⋅ 2 Baths ⋅ 10658174 MLS
Beautifully renovated 3-bedroom, 2-bath contemporary ranch with 1,200 sq. ft. of comfortable living space. The interior features LVP flooring throughout the main living areas and plush carpet in the bedrooms. Recent updates include a new roof, kitchen, and baths. Newer water heater and and HVAC (5 years). The kitchen combines style and function with quartz countertops, stainless steel appliances, and white shaker soft-close cabinets and drawers. Both full bathrooms feature elegant tile and quartz-top vanities for a clean, modern look. The primary suite, complete with a private en-suite bathroom. A large backyard with room to back your boat or RV into, spacious workshop/shed with power and two utility sheds ( both conveys as-is). With its blend of charm, modern updates, and practical space, this home is a standout opportunity for a growing family. CLOSING COST/BUY DOWN ASSISTANCE AVAILABLE!

4141 3rd Street, Central Chesapeake

603 Oxbow Court, South Chesapeake
$850,000
5 Beds ⋅ 3 Baths ⋅ 10657808 MLS
This is the kind of Chesapeake home that feels substantial the second you walk in. Restored inside and out, it carries the scale and character of an established traditional home, with beautiful arched doorways, refinished hardwoods, fresh paint, new carpet, and thoughtful updates that make the entire house feel fresh again. The main level is generous without feeling disconnected. The kitchen sits between the formal dining room, the vast open living space, and the screened porch, making it the natural link between everyday living and entertaining. Ample white cabinetry wraps the room, while an oversized island, thick warm granite countertops, a ceramic Kohler sink, and new appliances give it both presence and function. From there, the screened porch opens to the rear deck and draws you straight out toward the pool. That backyard deserves its own moment. The in-ground pool sits within a wide paver surround and includes a diving board and built-in sitting ledge, all framed by decorative iron fencing. But the fence is not the end of the yard. The property continues beyond it with additional lawn space and an in-ground fire pit, giving the outdoor space far more depth than the pool area first reveals. Inside, nearly every turn brings another room with a purpose. A dedicated library adds character to the main level, while the separate billiard room creates another substantial place to gather. A first-floor bedroom sits near a modern updated full bath, and upstairs, a finished attic adds even more usable space with room for movies, games, hobbies, or whatever comes next. Then there is the primary suite, and it is genuinely oversized. Beyond the sleeping area is a separate sitting room, an enormous walk-in closet, and an ensuite with a jetted soaking tub and separate stand-up shower. Set in Carriage House Estates in Chesapeake’s 23322 with Hickory schools and a central location, this is a home where the size, flow, and character show up in all the right places—inside, outside, and in the spaces you do not expect until you are standing in them.

603 Oxbow Court, South Chesapeake

908 Levee Court, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10657748 MLS
Welcome home to this charming, well-maintained ranch-style home in Chesapeake, VA! Offering move-in-ready, one-level living, this home features 3 spacious bedrooms, 2 full updated bathrooms, an updated eat-in kitchen with new appliances, and washer and dryer. The roof was replaced in 2021, providing added peace of mind. Outside, enjoy a large backyard with plenty of space for entertaining, pets, gardening, or relaxing. A detached garage provides additional storage or workshop space. Conveniently located near shopping, dining, everyday amenities, and major Hampton Roads interstates. If you're looking for a 3-bedroom ranch-style home for sale in Chesapeake, Virginia with an updated kitchen, detached garage, and spacious backyard, this home is a must-see. Schedule your private showing today!

908 Levee Court, South Chesapeake

506 Sloane Street Unit D, Central Chesapeake
$309,900
2 Beds ⋅ 2.1 Baths ⋅ 10657334 MLS
Beautiful 3 story, end unit townhome with a garage. Many, new upgrades! New gas stove 2026, new Bosch quiet dishwasher 2025, new HVAC including a new furnace 2024. There is an office on the lower level with engineered hardwood floors that are also in the kitchen and living room. Kitchen has a beautiful backsplash and is open to the light and bright living room. Enjoy the sunshine on your balcony off of the kitchen. Upper level has a large primary suite with ample closet space, double sinks, and a tiled shower. Convenient to both upstairs bedrooms is a stackable washer and dryer in the hallway, as well as a second full bath. The community has a pool, playground, and clubhouse. Close to the shipyard, within 10 minutes of Waterside, and close to military bases and the highway. Don't miss this beauty!The listing agent is also the property owner.

506 Sloane Street Unit D, Central Chesapeake

176 Driftwood Drive, South Chesapeake
$470,000
4 Beds ⋅ 2.1 Baths ⋅ 10657309 MLS
Welcome home to this desirable Driftwood Meadows property! Step inside to a spacious living room featuring a cozy gas fireplace and abundant natural light. The updated kitchen offers quartz countertops, stainless steel appliances, a pantry, and a charming eat-in breakfast area with built-in bench seating and wraparound windows overlooking the expansive backyard. The primary bathroom features updated flooring and a new tub/shower (2025), while the upstairs guest bathroom offers updated flooring and a new toilet. Step outside to the freshly painted back porch, perfect for relaxing or entertaining. Additional highlights include all-new plumbing throughout the home (December 2022), a spacious two-car driveway, and a private setting tucked away toward the back of the neighborhood. Conveniently located near shopping, dining, entertainment, and easy access to Interstate 64. Don't miss the opportunity to make this home yours!

176 Driftwood Drive, South Chesapeake

302 Gale Ave Avenue, South Chesapeake
$389,900
3 Beds ⋅ 2.1 Baths ⋅ 10657174 MLS
Priced to Sale! Welcome home to this stunning NEW CONSTRUCTION offering modern design, comfort and versatility! This beautifully designed home features 3-bedroom, 2.5 bath, including a spacious primary suite with a spa-inspired bath. A versatile upstairs loft provides the ideal space for a home office, media room, or lounge. The sleek kitchen features stainless steal appliances, including a built-in oven/microwave and dishwasher. The open family room is designed for everyday living and entertaining. Stylish finishes and recessed lighting add to home's contemporary appeal. Conveniently located near shopping, dining and easy access to the highway. Brand new, move-in ready, and waiting for its first owner. Schedule a showing today!

302 Gale Ave Avenue, South Chesapeake

937 Mount Pleasant Road, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10657273 MLS
Welcome home to this move in ready, updated brick ranch situated on a spacious 2/3-acre lot in the heart of Chesapeake. Offering classic curb appeal and room to breathe, this home also boasts new paint & flooring throughout, all new kitchen cabinets, granite & appliances with breakfast bar. Large family room w loads of natural sunlight add to the functional, single-level layout designed for comfortable everyday living. The generous yard provides endless possibilities—perfect for outdoor entertaining, gardening, play, or future expansion. All new windows & garage door. Mature surroundings and ample space create a peaceful setting while still being just minutes from shopping, dining, schools, and major roadways.This home offers a rare opportunity to enjoy privacy, space, and convenience all in one. Properties with this much land in such a desirable location don’t come along often—don’t miss it.

937 Mount Pleasant Road, South Chesapeake

2400 Amie Drive, South Chesapeake
$624,900
4 Beds ⋅ 3 Baths ⋅ 10656439 MLS
$5K SELLER CREDIT toward closing costs/rate buy down on full price offer. VA buyers can take advantage of a VA ASSUMABLE LOAN at 5.625%! Beautiful 4 BR, 3 BA home on 3 private acres with a detached 2-car garage! Renovated in 2025, the home has a spacious family room w/fireplace, eat-in kitchen w/stainless steel appliances, and flex space for a home office, fitness, media or den. The first floor also features two bedrooms, a full bath and utility room. Upstairs, the spacious primary suite includes 3 closets and an ensuite bath with walk-in tiled shower, along with a fourth bedroom and additional full bath. The back deck offers views of a quiet nature retreat. Major updates include HVAC, water heater, water softener/purification system, updated septic system & drain field, 2020 roof and sodded fenced backyard. The detached garage has a workshop area and large walk-in attic w/potential for more finished space. Private setting yet minutes from shopping, dining and the bypass for easy Hampton Roads & NC commutes. Hickory Schools!

2400 Amie Drive, South Chesapeake

708 Nottaway Drive, South Chesapeake
$289,900
2 Beds ⋅ 2.1 Baths ⋅ 10657099 MLS
Welcome to this spacious townhouse in Chesapeake in a great location with NO HOA!! The bright kitchen features a butler's window to provide a convenient pass-through for serving between the kitchen and dining area. The living room opens from the dining room and features a wood-burning fireplace as a centerpiece. Sliding glass doors lead from the living room to the back patio and fenced yard. Upstairs, you'll find two large bedrooms, each with its own ensuite bathroom and plenty of closet space. The primary bedroom also features a second wood-burning fireplace, creating a comfortable space to relax. Conveniently located near shopping, dining, schools, and major roadways. Property updates include a new tank water heater (2022), downstairs flooring (2022), fresh carpet and paint (2026), updated kitchen and bathroom faucets (2026), and a new backyard fence (2026). Water heater warranty may convey.

708 Nottaway Drive, South Chesapeake

521 Hatteras Crescent, South Chesapeake
$450,000
4 Beds ⋅ 2 Baths ⋅ 10656719 MLS
Welcome to your new Home! This well-loved 4-bedroom, 2-bath home that has been meticulously maintained by its original owners and is ready for its next chapter. Located in an established neighborhood within the sought-after Hickory school district, this home offers solid bones and peace of mind with many of the major systems already updated—including a new roof in 2025 with a transferable 50-year warranty and water heater replaced in 2025, extra interior-wall insulation, whole-house generator, and much more! Enjoy the above-ground pool, perfect for making the most of warm Virginia days. Pool liner replaced 2025; pool professionally winterized by East Coast Leisure & all pool accessories convey. While the home may not have all of today’s cosmetic trends, you get to move into a well-cared-for home with newer major components and create the look you love at your own pace. A true blank canvas to create your personalized home sweet home in!

521 Hatteras Crescent, South Chesapeake

639 Appalachian Court, South Chesapeake
$649,920
4 Beds ⋅ 2.1 Baths ⋅ 10656977 MLS
Stunning 4-BR Home on Large Lake View Lot – No HOA! Experience modern living in this 4-bedroom, 2.5-bathroom gem located in the highly desirable Centerville Commons neighborhood. Combining exceptional curb appeal with an expansive layout, this property sits on an oversized lot offering rare privacy free of HOA rules. Main Level: A welcoming foyer leads to an elegant formal dining room features a sophisticated tray ceiling. Open-Concept Great Room: Bright and airy with massive windows, Luxury Vinyl Plank flooring, and a cozy gas fireplace. Chef’s Kitchen features crisp white cabinetry, stainless steel appliances, a pantry, an enormous quartz island over contrasting gray accent cabinets, sunlit in eat-in area with large windows overlooking the sweeping fenced backyard.2nd floor has a gorgeous staircase w/black spindles to the second floor. Spacious primary bedroom, ensuite has dual sinks, tile shower.3 other br's plus hall bath & Laundry room. New carpet.

639 Appalachian Court, South Chesapeake

1629 Shillelagh Road, South Chesapeake
$735,000
5 Beds ⋅ 2.1 Baths ⋅ 10656950 MLS
Why wait on new construction when so much of the work here is already done? Set on three private acres in Grassfield, this modern farmhouse has been completely reworked inside and out, and a detached garage plus whole-house filtration system will both be installed prior to closing. The kitchen centers the main living space with an oversized island and bar, white cabinetry, and a clean, current finish. The renovation continues throughout with new windows, upgraded Hardie Plank siding, a new roof, new water heater, and two new heat pumps with dual-zone HVAC. The primary suite features private porch access, dual closets, and a spa-style bath with a floor-to-ceiling marble-tiled shower. Mature trees and a classic brick fireplace add character against the newer finishes and major system updates. With three acres, a full renovation, major systems already replaced, and a detached garage being completed before closing, this is the kind of property that gives you the space, finish, and function buyers rarely find all in one place.

1629 Shillelagh Road, South Chesapeake

3629 Kathys Way, South Chesapeake
$599,000
5 Beds ⋅ 2.1 Baths ⋅ 10655447 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home with TWO additional flex rooms, offering 2,731 square feet of living space in the sought-after Brooks Run community! Featuring a timeless combination of brick and vinyl siding, this meticulously maintained home delivers exceptional curb appeal with professionally landscaped grounds and a host of impressive upgrades. Come tour the inside and discover fresh paint, new carpeting, and luxury vinyl plank flooring throughout the first floor. The spacious kitchen features a gas cooktop, upgraded appliances, tile backsplash, and abundant natural light. An extensive trim package adds architectural character throughout the home. Upstairs, the oversized primary suite offers a custom tile shower and luxurious soaking tub. Two versatile flex rooms provide endless possibilities for a home office, media room, playroom, or additional living space. Outside, enjoy beautifully maintained landscaping, added concrete, and a spacious backyard complete with a hot tub. The attractive brick-front exterior and attached 3-car garage complete this exceptional property. Outdoor enthusiasts will appreciate the remarkable location through your backyard gate and access the Great Dismal Swamp trail system, including the Portsmouth Trailhead and Black Bear Trail! Enjoy nature hiking, wildlife viewing, and seasonal hunting where permitted and subject to applicable regulations. A rare opportunity to enjoy a beautifully upgraded home with the natural beauty of the Great Dismal Swamp practically in your backyard. Appliance package conveys!

3629 Kathys Way, 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.

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