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329 Old Drive, South Chesapeake
$551,000
4 Beds ⋅ 2.1 Baths ⋅ 10630911 MLS
A rare blend of classic charm and resort-style outdoor living awaits in this beautifully updated brick ranch. With 4 bedrooms and 2.5 baths on a spacious lot in an established neighborhood, this home invites you to entertain and unwind outdoors all summer long. The backyard is a true oasis: a saltwater pool, oversized covered deck with a sink and mini-fridge, two sheds (one with power and climate control), and a fenced garden. An automatic pool robot keeps the pool sparkling while you kick back with your favorite beverage. The expansive driveway offers ample parking for family and guests. Inside, the expansive kitchen shines with abundant cabinetry, a large peninsula, granite countertops and backsplash, and new LVP flooring. Modern conveniences include reverse osmosis water filtration and lifetime warranty leaf-guard gutters. HVAC 2021. Water heater 2022. Roof 2022. New fixtures and new paint. Hardwood floors throughout.

329 Old Drive, South Chesapeake
2325 Delwood Road, South Chesapeake
$419,900
3 Beds ⋅ 2.1 Baths ⋅ 10631308 MLS
Fully renovated brick ranch on a quiet, tree-lined street—this is the one you have been waiting for! Every major upgrade has been completed, offering true move-in ready living. The show-stopping kitchen features abundant soft-close cabinetry, a large island, farmhouse sink, and designer finishes that make this space the heart of the home. The spacious primary suite includes a private full bath and overlooks your backyard retreat with an in-ground pool featuring a brand new liner—perfect for summer entertaining. Two additional generously sized bedrooms, including one with its own half bath, offer ideal flexibility for guests or multi-generational living. Enjoy all new flooring, fresh paint, updated fixtures, and beautifully renovated bathrooms with custom tile. Big-ticket updates include upgraded plumbing and electrical, newer roof and windows, and a 2-year-old HVAC. Detached garage with workshop. Convenient to interstates, bases, and Greenbrier.shopping and dining!

2325 Delwood Road, South Chesapeake
1112 Marston Drive, South Chesapeake
$630,000
4 Beds ⋅ 3 Baths ⋅ 10623592 MLS
Welcome to your dream home! This darling, fully renovated property sits on a massive cul-de-sac lot offering privacy and room to roam. Inside, you’ll find fresh, stylish updates, a gorgeous kitchen, and a stunning primary suite featuring an oversized, spa-inspired bathroom designed for relaxation. The expansive backyard is ideal for entertaining, play, or future possibilities. Shed is as-is. Truly a rare find!

1112 Marston Drive, South Chesapeake
10 AC Millville Road, South Chesapeake
$355,000
10574904 MLS

10 AC Millville Road, South Chesapeake
1901 Shady Cove Court, South Chesapeake
$495,000
4 Beds ⋅ 2.1 Baths ⋅ 10633386 MLS
Family Home in sought after Greenbrier area of Chesapeake. Super central location. Near to shopping, restaurants, interstate 64 and 25 min. drive to Virginia Beach Ocean front. 30 years of gardening and planting, something new blooms in back yard every month. If you are looking nature in your back yard. Its here. Large deck and gazabo. Loads of storage and cabinet space.

1901 Shady Cove Court, South Chesapeake
933 Michael Drive, South Chesapeake
$265,000
3 Beds ⋅ 2 Baths ⋅ 10633859 MLS
Welcome home to this,updated ranch in the desirable Deep Creek area of Chesapeake! This move-in ready home features fresh updates throughout, including new flooring, fresh paint, and stylish new light fixtures that give the home a modern , inviting feel. The spacious floor plan offers comfortable one-level living with a large primary ensuite providing the perfect private retreat. Buyers will appreciate the peace of mind of a roof that is only 5 years old, along with the opportunity to personalize and make this home their own. Even better, closing cost assistance is available with a full-price offer, making this an excellent opportunity for first-time buyers or anyone looking to maximize affordability. Furniture is virtually staged by AI.

933 Michael Drive, South Chesapeake
2205 Wildwood Road, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10632858 MLS
Welcome to your new home in Chesapeake, beautifully updated on a quiet, tree-lined street. This move-in-ready property features 3 bedrooms and 2 full baths, including a spacious primary suite with en suite bath, walk-in closet, and direct access to a large, fenced backyard—perfect for relaxing or entertaining. Enjoy an open-concept layout with seamless flow between living spaces. Recent updates include brand-new LVP flooring, new carpet in bedrooms, and fresh paint throughout. Major systems have been updated with a newer roof, windows, HVAC, and water heater (all 2016). Just minutes from the Shipyard and bases, making for an easy, hassle-free commute. A perfect blend of comfort, style, and peace of mind—don’t miss this one!

2205 Wildwood Road, South Chesapeake
208 Terwillinger Road, South Chesapeake
$405,000
3 Beds ⋅ 2 Baths ⋅ 10633474 MLS
Beautiful 3 bedroom 2 bath home with a large 2 car garage/workshop. This home sits on a quiet dead end street on .63 Acres. Across the street is a park and playground. Cozy living room with a wood burning fireplace, large bonus room/office. Huge back deck overlooks the extremely private back yard. This is a rare find! See the attached 3D virtual tour.

208 Terwillinger Road, South Chesapeake
724 Bells Mill Road, South Chesapeake
$525,000
4 Beds ⋅ 2 Baths ⋅ 10633048 MLS
Welcome to your private nature escape at 724 Bells Mill Rd, set on 4.5 acres of stunning waterfront property with deepwater access to the Elizabeth River and beyond—great for boating, kayaking, fishing, or peaceful sunset views. This 4-bedroom, 2-bath home offers the ideal blend of comfort and outdoor living, surrounded by abundant wildlife, mature trees, and a thriving garden. Recent updates include the roof, HVAC, water heater, windows, carpet, flooring, interior paint, plus a remodeled 4th bedroom and laundry room. The expansive property provides privacy, room to explore, and endless opportunities to enjoy nature right from your backyard. A survey is available. Located in the Grassfield High School District, this rare waterfront retreat is waiting on you.

724 Bells Mill Road, South Chesapeake
3201 Hearring Way, South Chesapeake
$610,000
5 Beds ⋅ 2.1 Baths ⋅ 10632678 MLS
Welcome! Check out this 5 bed, 2.5 bath home in Olde Mill community! Some highlights include custom flooring, custom blinds, recessed lighting, spacious family room with natural gas fireplace. The eat-in kitchen features ss appliances, JennAir induction oven, granite counter tops, thoughtful layout with large center island and dedicated coffee nook. First floor offers a private bedroom with adjacent 1/2 bath, ideal for guests, mulit-gen living, home office, sunroom, etc. Owner's suite with double-door entry includes custom closet system with his and hers entry. Ensuite features jetted tub, dual vanities, and separate shower with custom stone backsplash & linen closet. Don't miss the true entertainment space paved patio w/ covered outdoor kitchen pavilion. This includes cooktop w/ burners, water/power connection, recessed lighting, and more! Conveniently located near Black Bear Trails, Olde Mill Run Park, interstates I64, 644, 17, 265, 168, schools, shopping, and entertainment!

3201 Hearring Way, South Chesapeake
1022 Bowling Green Trail, South Chesapeake
$417,513
4 Beds ⋅ 2.1 Baths ⋅ 10632325 MLS
Beautiful 4 BR 2.5 bath home meticulously maintained by loving owners located in Chesapeake. This tri-level style single family home boasts a gorgeous kitchen updated w/ newer appliances and open to the dining room/breakfast area, spacious family room, gleaming flooring throughout, 3 bedrooms on the 2nd floor including primary bedroom w/ beautiful full bath and hall full bath. Downstairs you will find the in-law suite, half bath, laundry room, and converted garage that’s great for a gym or office. Amazing backyard with large screened in porch, newer fencing, and detached garage great for storage or workshop. Fabulous location in a fabulous neighborhood! Deck to be painted prior to closing!

1022 Bowling Green Trail, South Chesapeake
1892 Bancroft Road, South Chesapeake
$750,000
6 Beds ⋅ 4 Baths ⋅ 10631946 MLS
Life feels elevated in the Roseleigh model, offering a thoughtfully designed open layout perfect for everyday living and entertaining. The main level features formal living and dining rooms, a drop zone off the three-car garage entry, and a first-floor suite ideal for in-laws or guests with a full bath. The family room showcases an electric fireplace with custom tile and built-ins, all seamlessly connected. The kitchen is a showpiece with soft-close cabinetry, quartz countertops, stylish backsplash, wall oven, and new stainless steel appliances. Butler-style cabinetry, a walk-in pantry, and generous bar seating make it both functional and inviting. Upstairs, the true Owner’s Suite offers dual closets and a spa-inspired bath. Spacious bedrooms share a Jack-and-Jill bath, plus a media room and laundry with cabinets. In the heart of Greenbrier near Summit Pointe—close to shopping and conveniences—this is new without the wait.

1892 Bancroft Road, South Chesapeake
605 Big Bear Lane, South Chesapeake
$613,500
5 Beds ⋅ 3.1 Baths ⋅ 10631084 MLS
5 Bedroom, 3.5 bath beauty with two en-suites. Seller has put so much thought, love and upgrades into this home. Fabulous layout designed for comfort, privacy and entertaining. Gourmet kitchen with double ovens, massive island with stunning quartz countertops flows seamlessly into the dining room and spacious living area where Seller had exquisitely designed built -ins adding to the elegance and custom feel. The FROG with its own en-suite is ideal for guests or as a playroom/private office. The primary bedroom has two walk-in closets with custom cabinetry. Low maintenance gorgeous landscape by Dreamscapes features beautiful fenced outdoor entertaining space or retreat with pavers and lush lawn; Extra driveway pad, Seller had well installed for gardening. The Culpepper landing community offers fun events and the best in amenities, resort style living with pool, clubhouse, exercise room and more! You will love it!

605 Big Bear Lane, South Chesapeake
2315 Cross Street, South Chesapeake
$389,500
4 Beds ⋅ 2 Baths ⋅ 10630537 MLS
Welcome home to this charming ranch in a sought-after school district! Offering 3 spacious bedrooms plus a versatile FROG, this home easily adapts to your needs—home office, playroom, guest space, or workout area. Inside, enjoy a comfortable layout and a fantastic kitchen with plenty of room to cook and gather. All-electric systems make for efficient living. Major updates include a brand-new roof (2026) and HVAC (2025), water heater (2022), and newer fridge. The crawl space has a vapor barrier, and newer fencing adds value as well. Outside, the huge backyard is great for entertaining, pets, gardening, or relaxing evenings at home. Don’t miss your chance to make this home yours—schedule your showing today!

2315 Cross Street, South Chesapeake
1549 Forest Cove Drive, South Chesapeake
$335,000
4 Beds ⋅ 2 Baths ⋅ 10630286 MLS
4 bedroom home in Forest Cove, one of Chesapeake’s most established neighborhoods where homes are held onto, not turned over, where neighbors know each other, evening walks are part of the routine, and trick-or-treating is still a neighborhood tradition. Offering 4 bedrooms and 2 full baths, the layout includes a true primary suite with walk-in closet and en suite, along with space to grow, settle in, and make your own memories. Major updates include roof replaced 2023, leaf-guard gutters installed 2024, new concrete driveway, and professionally maintained HVAC. The remodeled wet-style bathroom features a large jacuzzi tub and heat fan, creating a spa-like retreat. Out back, enjoy a screened porch, detached 12x20 garage, shed and chicken coop with power, outdoor outlets with timers, and established plum, fig, and apple trees. No flood insurance required. If you have been looking for space, location, and a home you can truly make your own, this one is worth seeing.

1549 Forest Cove Drive, South Chesapeake
1258 Mill Lake Quarter, South Chesapeake
$294,000
2 Beds ⋅ 1.1 Baths ⋅ 10628491 MLS
Beautifully maintained LAKE FRONT townhome located in the highly sought-after Greenbrier neighborhood. The main level offers a bright eat-in kitchen with stainless steel appliances and granite countertops, a spacious great room with a cozy fireplace, French doors opening to a private, fenced backyard with wood patio, storage shed, and BEAUTIFUL LAKE VIEW - great for relaxing or entertaining. A convenient half bath and large walk-in hall closet complete the first floor. Upstairs features two generous, light-filled bedrooms, each with walk-in closets, and double-entry bath with two sinks. Enjoy community amenities such as lakefront walking trails, playground, and a fishing dock. Conveniently located near shopping, dining, parks, and with quick access to I-64 and major highways.

1258 Mill Lake Quarter, South Chesapeake
2736 Benefit Road, South Chesapeake
$419,900
4 Beds ⋅ 2 Baths ⋅ 10629260 MLS
Built in 1933 and maintained by only 2 owners, this 4-bedroom, 2-bath home offers timeless character and flexible living space on nearly 2 acres of fully usable land. The 1st floor features 3 bedrooms 2 full baths, including a spacious primary suite with a walk-in closet. A traditional layout includes a living room, dining room, and a spacious kitchen with separate pantry, plus an enclosed porch/utility room for added convenience. Recent updates include fresh interior paint, refinished hardwood floors, and durable waterproof laminate flooring. Upstairs offers a bedroom, flexible living space, and a bonus nook good for an office or reading area, along with a large walk-in attic for storage or future expansion. Enjoy the fully cleared 1.9-acre lot with mature landscaping, room for outdoor activities, and a rear patio for relaxing or entertaining. Conveniently located near interstates, shopping, and amenities while offering a private, country-style setting.

2736 Benefit Road, South Chesapeake
812 Hardwood Drive, South Chesapeake
$440,000
4 Beds ⋅ 3 Baths ⋅ 10628540 MLS
Welcome to this beautifully maintained 4-bedroom, 3 full bath ranch in the highly desirable Riverwalk community! Nestled on a quiet, tree-lined street, this home offers the ease of single-level living with thoughtful updates throughout. The spacious primary suite features dual sinks, a large jetted tub, and a separate shower for a true retreat experience. Enjoy high ceilings, abundant natural light from skylights, and charming plant ledges that add character to the living space. The updated kitchen boasts granite countertops and modern finishes, perfect for everyday living or entertaining. Step outside to a screened porch off the living room overlooking a large, fenced backyard—ideal for relaxing or hosting guests. Additional highlights include new carpet and a one-car garage. This home combines comfort, style, and location—don’t miss it!

812 Hardwood Drive, South Chesapeake
1601 Stone Moss Reach Unit C, South Chesapeake
$204,000
2 Beds ⋅ 1 Baths ⋅ 10627748 MLS
This is it! Move-in ready at a phenomenal price! Step into this second-level condo that features an open concept floorplan w/vaulted ceiling and a wood-burning fireplace. Kitchen has modern shaker cabinetry and stainless-steel appliances. Primary bedroom w/ample closet space and direct access to upgraded bath. Spare bedroom w/great closet space as well. All that's left to do is move in as everything has been renovated, including the HVAC system, in 2025. Condo association covers the exterior maintenance (association recently replaced the roof!), landscaping, and private trash collection. Located conveniently to shopping, major workplaces, and interstates. This one is ready for you to call home or add to your portfolio!

1601 Stone Moss Reach Unit C, South Chesapeake
617 Prince Andrew Court, South Chesapeake
$433,000
3 Beds ⋅ 2.1 Baths ⋅ 10626902 MLS
Meticulously cared for by its original owner, this 3-bed, 2.5 bedroom split-level home offers 2170 sq feet and thoughtful updates throughout. Major improvements within the past 2 years include new HVAC, carpeting, and epoxy garage flooring. Downstairs is beautifully refreshed with new LVP, updated stairs, and fully remodeled bathroom last year. Detached workshop out back, complete with solar panels. Truly a move-in ready home!

617 Prince Andrew Court, South Chesapeake
1316 Head Of River Road, South Chesapeake
$580,000
3 Beds ⋅ 2 Baths ⋅ 10626572 MLS
You must see this lovely all brick well maintained/updated home in the well-established Hickory area of Chesapeake. Step into a spacious floorplan with 3 bedrooms, 2 full baths. Dream kitchen with huge center island, two ovens and an extra-large eating area. Great space for family dinners/entertaining. Family room with separate outside entry and fireplace. Formal living and dining rooms as well. Home office centrally located for convenience. All situated on a 1-acre private parcel with inground pool making the generous backyard a private oasis for outdoor activities. Wooded view behind the property really adds to the private setting. This is a versatile single story family home in the much-desired Hickory school district. Large utility room and fabulous attached garage. New HVAC system installed March 2026. Stop the car and view this one right away!

1316 Head Of River Road, South Chesapeake
213 Cedar Creek Terrace, South Chesapeake
$285,000
2 Beds ⋅ 1.1 Baths ⋅ 10624196 MLS
SOLAR PANEL LOAN TO BE PAID AT SETTLEMENT!!!Townhouse in the heart of Great Bridge with many new updates to include, updated bathrooms, upstairs carpet, downstairs stamped concrete, hot water heater, asphalt roof, doors, ceiling fans, attic insulation, HVAC in 2021 and a new sewer line. Conveniently located to shopping, and sought after Great Bridge school district. Appliances work but convey as is. SOLAR PANEL LOAN TO BE PAID AT SETTLEMENT!!!

213 Cedar Creek Terrace, South Chesapeake
270 Carawan Lane, South Chesapeake
$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10624855 MLS
Step into modern luxury in this stunning 4-bedroom, 2.5-bathroom home, where 2007 architecture meets a complete, top-to-bottom renovation. No detail was spared in this transformation, offering the perfect blend of established structure and high-end finishes. At the heart of the home, a gourmet chef’s kitchen shines with premium Cafe appliances, custom cabinetry, and sleek stone countertops.The spacious primary suite serves as a private sanctuary, featuring a spa-inspired ensuite with slate tiling and contemporary fixtures.From the Trex decking to the electric car charger, every inch of this residence has been reimagined for the sophisticated buyer. Move-in ready with new paint & carpet, on a quiet street, this better than new home delivers the ultimate turn-key lifestyle in a prime location. All Great Bridge Schools and quick access to the 168 bypass, this well priced home won't last!

270 Carawan Lane, South Chesapeake
421 Blue Beech Way, South Chesapeake
$397,900
3 Beds ⋅ 2.1 Baths ⋅ 10623035 MLS
Condo amenities include ground maintenance, clubhouse, in-ground swimming pool, sewer, water and trash pickup. This is a one-owner home which displays great pride in meticulous upkeep and cleanliness. LVP flooring was installed two years ago, microwave and water heater were installed in the past year. Neighborhood has a convenient layout for outdoor exercising. The annual Chesapeake Jubilee fireworks feel as though they are put on just for you!

421 Blue Beech Way, South Chesapeake
1321 Sebastian Court, South Chesapeake
$723,243
5 Beds ⋅ 3 Baths ⋅ 10616240 MLS
Bellhaven by Wetherington Homes. Features traditional elevation with open concept floor plan and Deluxe Chef's kitchen with large island. Offer's breakfast nook, Butler's pantry and rear covered porch. Kitchen overlooks the Great Room with easy access to your outdoor space. 5 bedrooms, spacious loft that provides a functional space for today's lifestyle. The 2nd floor Owner's Suite boasts tray ceiling, large walk-in closet and spacious luxury spa bath. Stoney Creek is Southern Chesapeake's newest community zoned for desirable schools and conveniently located near shopping, dining, and interstate.

1321 Sebastian Court, South Chesapeake
1239 Kidbrooke Street, South Chesapeake
$751,040
5 Beds ⋅ 4 Baths ⋅ 10588078 MLS
Welcome to The Summit at Riverview Landing, where you’ll discover thoughtfully designed living space across 2 luxurious floors-perfect for families of every size. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the gourmet kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. Enjoy a vibrant, amenity-rich community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches.

1239 Kidbrooke Street, South Chesapeake
125 Millwood Avenue, South Chesapeake
$452,555
4 Beds ⋅ 2 Baths ⋅ 10634335 MLS
Beautifully maintained 4 bed, 2 bath home in Chesapeake featuring a spacious backyard, attached garage, detached garage, and greenhouse. Interior improvements include an updated kitchen, fresh paint, updated flooring, and new carpet throughout. Functional layout offers flexible living space with ample storage and outdoor possibilities. Conveniently located near shopping, dining, parks, and major commuter routes. Move in ready with a combination of indoor comfort and outdoor versatility. Some photos are AI generated to properties full potential.

125 Millwood Avenue, South Chesapeake
820 Henry Avenue, South Chesapeake
$300,000
3 Beds ⋅ 1.1 Baths ⋅ 10633127 MLS
Freshly updated and move-in ready! This home features a freshly painted exterior along with brand new LVP flooring, fresh interior paint, and updated fixtures throughout. The kitchen includes a new dishwasher, and the washer and dryer convey in a separate laundry room. The full bath was completely renovated in 2024, with additional updates to the half bath in 2025. Major systems include HVAC (2022), water heater (2024), architectural roof (2012), and added R30 attic insulation (2025). Situated on a large fenced corner lot with a spacious deck for entertaining or relaxing. Detached garage with 220V and well pump. Conveniently located near shopping, dining, and interstate access.

820 Henry Avenue, South Chesapeake
312 Gallenway Terrace, South Chesapeake
$470,000
4 Beds ⋅ 2 Baths ⋅ 10632407 MLS
Experience refined living in this meticulously maintained, move-in ready ranch. Nestled on a private cul-de-sac in the highly desirable Great Bridge area, this home offers both privacy and convenience. Upon entry you're welcomed by a bright foyer that opens into a stunning living room with soaring vaulted ceilings & a warm, inviting fireplace. The thoughtfully designed kitchen features premium stainless-steel appliances, sleek granite countertops, and a modern backsplash perfectly suited for both everyday living and entertaining. The spacious primary suite includes an updated bathroom designed with comfort and style in mind. Step outside to your expansive, fully fenced backyard an ideal setting for private outdoor gatherings or peaceful evenings at home. Make it easy for yourself and preview this one first and call it home sweet home. Recent updates washer and dryer 2019, Stove 2022, Microwave 2022, Refrigerator 2025, Fireplace 2021, Hallway Bathroom 2020. Crawlspace dehumidifier 2026

312 Gallenway Terrace, South Chesapeake
1972 Beechwood Road, South Chesapeake
$690,000
4 Beds ⋅ 2.1 Baths ⋅ 10632455 MLS
This charming four-bedroom Stephen Alexander Walnut model in the desirable Summer Park community offers 3,100 sq ft of comfortable living with 10-foot ceilings, wood floors, crown molding, and an open floor plan. Located in the highly sought-after Grassfield school district, this home combines quality construction with everyday convenience. The Great Room serves as the heart of the home, perfect for daily living and entertaining. The gourmet kitchen was completely remodeled in 2023 and features stainless steel appliances, granite countertops, a large island with sink. The private primary suite includes walk-in closet, and double vanity. Recent updates include new LVP flooring (2023) and HVAC (2024). Enjoy outdoor living with a screened porch, large deck, saltwater pool with heater, covered pavilion patio, 4 person outdoor barrel sauna, shed, and fenced backyard. Convenient to shopping, highways, and military bases.

1972 Beechwood Road, 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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