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$559,000
5 Beds ⋅ 3 Baths ⋅ 10646652 MLS
This is classic Great Bridge living at it's best! Nestled on a quiet cul-de-sac in the desirable Southern Pines neighborhood, this beautifully maintained 5-bedroom, 3-bath home offers 2,491 square feet of versatile living space on a private, half-acre wooded lot. A standout feature is the in-law suite, complete with its own bedroom, attached sitting/living area, and full bath ideal for multigenerational living or long-term guests. Two bathrooms have been tastefully renovated, while the newer roof and replacement windows provide added peace of mind. The cozy living room features a gas log/wood-burning fireplace, and the finished room over the garage offers endless flexibility as a bedroom, playroom, media room, or home office. Relax on the welcoming front porch or entertain on the spacious rear deck overlooking the peaceful backyard. Complete with a 2-car attached garage, detached storage shed, and no HOA.

529 Wittington Drive, South Chesapeake
$430,000
4 Beds ⋅ 2.1 Baths ⋅ 10646343 MLS
Opportunity awaits at 1929 Shepherds Gate, where spacious living, a large corner lot and a convenient Chesapeake location come together! This 4-bedroom, 2.5-bath home offers classic brick curb appeal and an attached garage. Inside, enjoy a bright, open living and dining area with hardwood flooring and crown molding. The kitchen features abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting and plenty of workspace. A separate family room provides additional living space with a cozy fireplace and direct access to the backyard. Upstairs, the generously sized primary bedroom includes a private bath with a walk-in shower. Three additional bedrooms offer flexibility for guests, a home office or playroom. Outside, the fully fenced backyard features a large patio and storage shed, creating an excellent setting for relaxing, entertaining or outdoor activities. Conveniently located near Greenbrier shopping, restaurants, schools, interstate access and Chesapeake attractions. Bring your personal style and make this wonderful home your own!

1929 Shepherds Gate, South Chesapeake
$519,900
4 Beds ⋅ 2.1 Baths ⋅ 10646160 MLS
This charming brick colonial home is on a corner lot of a cul-de-sac in the desirable Silverwood development. The spacious 20x40 ft. pool boasts of a new liner in 2024, complemented by a brand-new back porch added three years ago and a freshly renovated front porch completed this summer. Inside, the updated kitchen shines with granite countertops, freshly painted cabinets (including upper cabinets repainted this summer), a new sink, and modern cabinet pulls. Beautiful hardwood floors grace the front half of the downstairs (recently refinished) and all of the upstairs, creating a warm and inviting atmosphere. Western Branch High School, middle school, and elementary school all located within the development, along with festive community events like the annual Holiday parade with firetruck and spring egg hunt. Restaurants, shopping all nearby and just a quick trip to downtown Norfolk, this home offers the ideal blend of comfort, updates, and community charm.

3316 Kindlewood Crescent, West Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10646475 MLS
Fantastic opportunity to own this beautifully maintained ranch in the desirable Etheridge Manor neighborhood. Situated on a spacious, deep lot, this single-family home has been meticulously cared for over the years. Inside, you'll find stunning hardwood floors, a welcoming fireplace, and a thoughtfully designed floor plan that's great for everyday living and entertaining. Recent updates include the HVAC system and water heater. The inviting front porch is the perfect place to relax, and the expansive backyard provides plenty of room for gardening, play, or entertaining. Conveniently located near shopping, dining, parks, and schools, this is a wonderful opportunity to own a fantastic home in an established neighborhood.

920 Bellingham Drive, South Chesapeake
$750,000
6 Beds ⋅ 3 Baths ⋅ 10646538 MLS
Spacious House with many gems. Master Bedroom has walk-in tub. Two sunrooms with 5 ft windows.Second level add on has two spacious rooms with extensive closet space and built in storage. Office/study. Family Room 15 x 15 . Two sunrooms. Kitchen has Island that seats six with built in storage beneath Detached garage with Apartment approximately 864 ft ready for occupancy. Carport, Storage barn with electricity 654ft. Hot tub for 6. Lots of space for lighting up the grill. Drive way willaccommodate several vehicles Many updates. Close to interstate 64, Military Bases, Hospital and Shopping.

245 Fernwood Farms Road, South Chesapeake
$510,000
2 Beds ⋅ 2 Baths ⋅ 10646325 MLS
Waterfront opportunity! Well-maintained home situated on a scenic waterfront lot in the desirable Western Branch area of Chesapeake. Enjoy peaceful water views from an enclosed porch, and a spacious backyard ideal for relaxing, entertaining, fishing, kayaking, or simply taking in the surroundings. Walk in basement and Attic with plenty of storage. Recent improvements and updates help make this home move-in ready while still offering buyers the opportunity to add their own personal touches. New Concrete Driveway, New Storage Shed & Dock, Resurfaced Wood Floors, and Remodeled Master Bath. Conveniently located near shopping, dining, bases, major highways, and all that Hampton Roads has to offer.

3901 Wedgewood Drive, West Chesapeake
$609,700
4 Beds ⋅ 2.1 Baths ⋅ 10646302 MLS
Beautifully maintained all-brick transitional corner lot in Great Bridge. 4 bedroom/2 bath. 1st floor MB with en suite. Open floor plan with huge kitchen and stainless steel appliances, breakfast area. Wood-burning fireplace for cozy evenings. Walk out of family room door onto a TREX deck and large backyard. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. Shed sold as-is.

746 Yorkshire Trail, South Chesapeake
$565,000
5 Beds ⋅ 2.1 Baths ⋅ 10646268 MLS
Welcome to this charming 5-bedroom home, perfectly situated in a wonderful, established neighborhood in Chesapeake. If you appreciate a home with character and room to grow, this is the perfect canvas for your vision. The heart of the home features a kitchen designed for those who love to cook, offering an abundance of counter and cabinet space, plus the convenience of a double oven. You’ll love spending quiet evenings by one of the two cozy fireplaces or unwinding on the beautiful, screened-in porch that overlooks a private, tree-lined backyard. With spacious bedrooms throughout, this home offers plenty of room for everyone to enjoy. Bring your personal touch and make this well-loved house your own!

2949 Prince Of Wales Drive, West Chesapeake
$248,500
2 Beds ⋅ 2.1 Baths ⋅ 10646300 MLS
Come see this beautiful 2 bedroom, 2 1/2 bath end-unit condo in Knells Ridge — where style meets easy living! Step inside to a bright, open-concept layout with cozy fireplace that sets the tone for relaxed evenings. The updated kitchen features a pantry, gleaming granite countertops and stainless steel appliances, perfect for whipping up your favorite meals or entertaining guests. The spacious primary suite offers a peaceful retreat, complete with a walk-in closet and an en-suite vanity area for that extra touch. Slide open the glass doors and step out to your own private patio for morning coffee or evening unwinding. With its end-unit privacy, thoughtful updates, and true move-in-ready condition, this Knells Ridge condo checks every box—now it just needs you. Come fall in love, schedule your showing today.

772 Ridge Circle, South Chesapeake
$289,000
3 Beds ⋅ 1 Baths ⋅ 10646147 MLS
Welcome home to this charming ranch that's full of warmth, character, and timeless appeal! Nestled at the end of your street with no through traffic, this adorable home offers the perfect blend of privacy, comfort, and convenience. Enter to discover soaring vaulted ceilings that create an open, airy feel throughout the main living spaces. With two inviting fireplaces and two separate dens, there's plenty of room to gather with family, entertain guests, or simply relax with a good book. The spacious eat-in kitchen is great for casual mornings, while the adjoining dining area is ready for holiday meals and special celebrations. Every room is filled with charm, making this home feel welcoming from the moment you walk through the door. Outside, you'll love the yard, offering endless possibilities for gardening, play, pets, or creating your own backyard oasis. The oversized carport provides excellent covered parking and additional storage space.

1106 Maryview Avenue, Central Chesapeake
$335,000
4 Beds ⋅ 2.1 Baths ⋅ 10646230 MLS
Priced 50k below market, this home features an open and bright floor plan and sits on an amazing lot with a huge fenced backyard. HVAC only a couple years old. Newer Pella windows upstairs. If you are ready to provide a little TLC, this is an amazing opportunity. Located in the beautiful and quiet Spinners Creek section of Deep Creek. Close to shopping, highways, and all bases.

2725 Spinners Way, South Chesapeake
$550,000
3 Beds ⋅ 2.1 Baths ⋅ 10645963 MLS
Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, South Chesapeake
$245,000
2 Beds ⋅ 2 Baths ⋅ 10645622 MLS
Welcome home to this beautifully updated 2 bedroom, 2 bath condo in the desirable Riverwalk community! Featuring fresh paint throughout, newer luxury vinyl plank flooring, stylish new cabinetry, and updated countertops, this home is move-in ready. The kitchen is complete with stainless steel appliances, offering both modern style and functionality. Enjoy low-maintenance living with condo fees that include water, sewer, and access to fantastic community amenities, including a clubhouse, swimming pool, and playgrounds. Conveniently located near shopping, dining, and entertainment, this is an excellent opportunity for first-time buyers, downsizers, or anyone looking for easy, affordable living. Schedule your private showing today!

701 Rapidan River Court Unit A, South Chesapeake
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10645717 MLS
Tucked away on a quiet cul-de-sac in the highly sought-after Great Bridge school district, this move-in-ready waterfront home offers nearly 3,000 square feet of thoughtfully updated living space overlooking peaceful water views. Relax on the screened porch while enjoying the privacy of a fully fenced backyard and the freedom of no HOA. Major updates include HVAC (2023 And Serviced), fresh paint, luxury vinyl plank flooring throughout the first floor (2023), updated lighting, water heater (2022), refinished staircase (2022), and an encapsulated crawlspace for clear Termite and Moisture letter. The washer and dryer convey, making this home truly move-in ready. Offering the perfect blend of everyday comfort and tranquil waterfront living, this is an exceptional opportunity to own a beautifully updated home in one of Chesapeake’s most desirable communities.

705 Turnbuckle Court, South Chesapeake
$675,000
6 Beds ⋅ 2.1 Baths ⋅ 10645171 MLS
Rare opportunity to own over 6 private acres in the heart of Deep Creek! This exceptional property includes two parcels conveying with the sale, creating a combined 6+ acres of wooded privacy at the end of a quiet road. The spacious 6-bedroom home offers endless possibilities for multigenerational living, a home office, hobby space, or guest accommodations. Enjoy the peace and seclusion of country-style living while remaining just minutes from shopping, dining, schools, and major interstates. Come see this one first!

3249 Pioneer Lane, South Chesapeake
$324,900
4 Beds ⋅ 1 Baths ⋅ 10645441 MLS
This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, new flooring throughout, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily serve as a 4th bedroom, home office, playroom, or home workout space to fit your lifestyle. Step outside to your fully fenced backyard retreat, designed for both relaxation and entertaining. Enjoy summer days in the above-ground pool and unwind or host gatherings under the pergola on the patio while appreciating the privacy this backyard provides. Conveniently located near shopping, dining, schools, and major interstates, this move-in-ready home combines thoughtful updates, flexible living space, and exceptional outdoor setting you won't want to miss.

2801 Southport Ave., Central Chesapeake
$315,000
3 Beds ⋅ 1.1 Baths ⋅ 10645375 MLS
This well-maintained home offers peace of mind with numerous updates completed over the years. According to the seller, replacement windows were installed in 2006, followed by a new HVAC system and roof in approximately 2009. The home also features a newer washer and dryer (2016), stove (2020), water heater (2021), and refrigerator (2024). Most recently, the kitchen was refreshed in 2025 with beautiful new cabinets and countertops, creating a bright, modern space that's perfect for everyday living and entertaining. With so many major improvements already completed, this home is ready for its next owner to move in and enjoy.

4213 Valencia Road, West Chesapeake
$579,000
4 Beds ⋅ 2.1 Baths ⋅ 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, South Chesapeake
$765,000
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
$479,000
4 Beds ⋅ 2 Baths ⋅ 10645014 MLS
A dream find for those looking for a one story home. Ranch home in pristine condition ready for you. New soft close solid oak cabinets and laminate in the kitchen featuring all stainless appliances. Located on a .341 acre lot in a one street subdivision home has 4 Bedrooms, 2 baths with frog as 4th bedroom. Baths have been updated with new toilets and vanities. Crawl is encapsulated for low maintenance. HVAC new 2023. Replacement windows. All Hickory schools.

736 Hilda Pine Drive, South Chesapeake
$599,999
4 Beds ⋅ 2 Baths ⋅ 10644979 MLS
Welcome to this beautifully remodeled all-brick ranch tucked into the peaceful Hickory area of Chesapeake, where country charm meets modern comfort on approximately 3 sprawling acres. This 4-bedroom, 2-bath gem has been thoughtfully updated from top to bottom, featuring luxury vinyl plank flooring, tiled showers, granite countertops, and stainless steel appliances throughout a bright, open layout made for both everyday living and easy entertaining. Step outside and fall in love with the lifestyle this property offers: relax on the covered front porch, host gatherings on the expansive rear deck, or unwind on your own private deck just off the primary suite. Dreaming of homegrown eggs? The property includes chicken coops, ready for you to raise your own flock and enjoy farm-fresh living right in your backyard. A newly poured driveway and a 50-AMP power pole with RV hookup round out the practical upgrades, making this move-in-ready retreat as functional as it is charming. With updated finishes, room to roam, and space to grow your own little homestead, this Chesapeake beauty is ready to welcome you home.

913 Long Ridge Road, South Chesapeake
$305,000
2 Beds ⋅ 1 Baths ⋅ 10644942 MLS
Welcome home to this charming all brick ranch nestled in Brentwood Estates neighborhood. This well-maintained home offers the perfect combination of classic charm and thoughtful updates making it truly move-in ready. Inside you will find a beautifully updated bathroom. The kitchen provides abundant cabinetry, and the dining room has been enhanced with new windows, elegant chandelier creating a nice setting for family dinners. All appliances convey. Enjoy peace of mind with updated roof, windows (2017), along with a brand-new sidewalk, garage floor and driveway offering exceptional curb appeal. Step outside to a large, fully fenced backyard complete with a covered deck, an ideal space for relaxing, grilling and entertaining family & friends.

2209 Wildwood Road, South Chesapeake
$312,500
3 Beds ⋅ 1 Baths ⋅ 10644691 MLS
Welcome home to this beautiful, move-in-ready ranch style property in Chesapeake! Featuring a bright and airy open-concept floor plan, this home offers an effortless flow is great for entertaining. The interior boasts 3 bedrooms, 1 full bath and tasteful modern updates throughout. Step outside to your private outdoor retreat, complete with a newer deck that leads to a generously sized backyard, fully enclosed by a privacy fence. Wrapped in newer, low-maintenance vinyl, this home combines classic appeal with easy upkeep. Conveniently located with quick access to local military bases, premier shopping, dining, and major interstates for an easy commute.

1313 Willow Avenue, Central Chesapeake
$499,900
3 Beds ⋅ 2.1 Baths ⋅ 10644718 MLS
Amazing property in the heart of Hickory. Home is dated before 1850, that is when they started record keeping! 3 beds up with 2 baths, and 1/2 bath down. 2 wood burning fireplaces. Owner willing to make minor repairs with acceptable offer. Large barn/garage, that was a former auto-mechanic shop! Large, covered deck with additional open-air deck. All appliances convey. Must see to appreciate the size.

3248 Battlefield Boulevard S, South Chesapeake
$499,890
4 Beds ⋅ 2.1 Baths ⋅ 10644750 MLS
Beautifully renovated and move-in ready, this spacious 4-bedroom, 2.5-bath home offers approximately 2,621 square feet, including an addition that provides extra living space. The open and inviting main level features fresh luxury vinyl plank flooring, updated lighting, and a bright sunroom. The updated kitchen offers granite countertops, stainless steel appliances, and attractive cabinetry. Upstairs, you’ll find four comfortably sized bedrooms with new carpeting and updated bathrooms featuring modern ceramic tile. The home is equipped with gas heat and central air conditioning on the first floor and a heat pump serving the second floor. Additional features include an attached garage, a generous lot, and a roof replaced approximately in 2021. Conveniently located in Western Branch near shopping, dining, schools, and major roadways with access throughout Hampton Roads. Schedule your showing and see all this home has to offer.

4257 Meadow Wood Drive, West Chesapeake
$235,000
2 Beds ⋅ 2 Baths ⋅ 10644371 MLS
Move-in ready condo living at its best, situated in much sought-after the Riverwalk/Queens Gate community. Living level upstairs has open layout for easy living and entertainment + desirable natural light. Primary bedroom w/ensuite, second bedroom w/full bathroom across the hall. Renovated with new LVP flooring throughout condo, carpet on stairway, recently painted interior, remodeled kitchen includes new cabinets, quartz countertop, stainless steel appliances, and recessed lighting. New vanity lights and faucets in both bathrooms. Convenient location near dining, shopping, and entertainment! Must see before its gone!

709 Rapidan River Court Unit D, South Chesapeake
$1,269,997
4 Beds ⋅ 2.1 Baths ⋅ 10644328 MLS
Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10644346 MLS
You will love coming home to this comfortable ranch home with cozy rooms. Located near the intersection of Greenbrier Parkway and Volvo Parkway in Turtle Rock on a cul-de-sac. Enjoy the floor plan which includes living room, dining room, den with fireplace, eat-in kitchen, laundry room, primary bedroom with bathroom, two other bedrooms and hall bathroom. Walking trails & playgrounds nearby. Lots of shopping and dining closeby in Greenbrier area. This home has been well cared for and is ready for you. Welcome home!

1109 Hearthstone Landing, South Chesapeake
$685,000
5 Beds ⋅ 3 Baths ⋅ 10643877 MLS
A Gem! Pristine condition all brick transitional on 1/3 acre cul de sac lot in Great Bridge. 5 bedrooms plus 1st floor 6th bedroom or office with ensuite. Open floor plan with huge updated kitchen (quartz counters), breakfast room and family room overlooking impeccably landscaped and treed backyard. Remodeled primary & hall bathrooms. 2 zone HVAC. Wood burning fireplace also plumbed for gas. Spacious family room, living and dining rooms, bedrooms and FROG. Screened porch with concrete floor. 2 car side loading garage with long driveway. Updates include windows, roof, 1st floor gas pack HVAC, garage door and leaf filter gutters. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. In-ground sprinkler system, appliances, and window treatments convey "as is". Home warranty.

810 Hedgerow Court, South Chesapeake
$549,000
4 Beds ⋅ 2.1 Baths ⋅ 10642714 MLS
Impeccably maintained brick ranch with 4 bedrooms, 2.5 baths, an attached one-car garage, wood-burning fireplace and a spacious backyard. The remodeled kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, under-cabinet lighting, and a movable island. Updated bathrooms, custom wood trim, and closet organization systems add thoughtful touches throughout. Enjoy the 15x40 deck, fenced yard, storage shed, and newly expanded driveway with RV pad, 50-amp hookup, and generator connection. Major improvements over the years include windows, HVAC, 200-amp electrical panel, flooring, garage door, water heater, sprinkler/well system, and more. Convenient to bases, shopping & highways for easy access in Hampton Roads and to NC. Hickory HS district. This home has been diligently cared for inside and out and is truly move-in ready!

1025 Ramsgate Lane, 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.