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$250,000
2 Beds ⋅ 2.1 Baths ⋅ 10646776 MLS
This beautifully updated home features an open floor plan with durable luxury vinyl plank (LVP) flooring throughout the main level. Enjoy the community's beautiful pool and clubhouse, perfect for relaxing and socializing. Conveniently located near shopping, the mall, and major interstates, this move-in-ready home offers both comfort and convenience!

3613 Cinnamon Court, West Chesapeake
$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 4-bedroom, 2.5-bath 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 ideal 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
3 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
$299,000
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
$350,000
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
$449,900
5 Beds ⋅ 2 Baths ⋅ 10646209 MLS
Spacious all-brick ranch offering 5 bedrooms in a highly desirable school district! Nice home features new flooring and a flexible floor plan designed for comfortable living. Enjoy a formal living room, formal dining room, and a cozy den with a wood fireplace. The eat-in kitchen offers plenty of cabinet space and includes a pantry for additional storage. The converted garage provides a versatile bonus space perfect for a home office, playroom, or hobby area. The first-floor primary bedroom adds convenience, while the room over the garage offers even more living space. Step outside to a privacy-fenced, spacious backyard complete with a deck, ideal for entertaining, relaxing, or enjoying outdoor activities. A rare opportunity to own a home with space, functionality, and an excellent location!

1024 Weeping Willow Drive, South Chesapeake
$350,000
3 Beds ⋅ 2 Baths ⋅ 10646152 MLS
Welcome Home! Just bring your furniture because this beautifully updated 3-bedroom, 2-bath home is truly move-in ready! Enjoy peace of mind with a new roof, water heater, LVP flooring, new carpet, fresh paint, updated fixtures, kitchen cabinets, granite countertops, and new stainless steel appliances including the stove, microwave, refrigerator, and dishwasher. The open-concept kitchen overlooks the spacious living room with a cozy fireplace, making it optional for everyday living and entertaining. The primary suite features a beautifully renovated bath with a custom tile surround shower. Neutral colors throughout make it easy to add your personal style. Step outside to a fully fenced backyard with a deck for relaxing or grilling and a storage shed for extra storage. This home has all the updates you've been looking for and is ready for you to move right in!

1451 Glendale Avenue, South Chesapeake
$300,000
3 Beds ⋅ 1.1 Baths ⋅ 10646018 MLS
Ideally located in the heart of Greenbrier, this move-in-ready three-bedroom townhouse is the perfect find! Recently refreshed with updated flooring and renovated bathrooms, this home is ready for its new owners. Features include a spacious kitchen with plenty of counter space, a convenient laundry area, and roomy, comfortable bedrooms. Complete with a private, fenced-in backyard and patio, this home offers everything you need. Schedule your showing today!

1204 Cedar Mill Square, 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
$435,000
4 Beds ⋅ 2 Baths ⋅ 10645687 MLS
Welcome to this inviting 4-bedroom ranch in the sought after Mill Creek neighborhood. Freshly painted throughout with brand new carpet and a new roof, this home is truly move-in ready. Enter into a bright living room featuring vaulted ceilings and a cozy wood-burning fireplace, seamlessly opening to the fully remodeled kitchen. The kitchen shines with white shaker soft-close cabinets, quartz countertops, and stainless steel appliances. Two bedrooms sit just off the living room, accompanied by a beautifully updated hall bathroom and laundry room. The spacious primary bedroom offers a remodeled en-suite bathroom and a generous walk-in closet. The FROG provides flexibility as a 4th bedroom, guest space, or bonus room. Out back, enjoy a wood deck overlooking an above-ground pool and a peaceful backyard with views of the wooded area maintained by the Army Corps of Engineers along the Dismal Swamp Canal. The property extends about 10 ft beyond the back fence line. Don't miss this one.

500 Willow Bend Drive, 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
OPEN HOUSE Fri 7/31 from 4-6 PM Sat Sun 8/1-2 from 12-2 PM ~ 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
$335,000
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
$440,000
4 Beds ⋅ 2 Baths ⋅ 10645311 MLS
Beautiful 4-bedroom, 2-bath ranch offering comfortable one-level living with a spacious FROG and attic storage. Inviting family room features a cozy wood-burning stove, while the eat-in kitchen is equipped with stainless steel appliances and a pantry. The generous primary suite boasts a walk-in closet, double vanity, separate shower, and relaxing garden tub. Spacious secondary bedrooms provide plenty of room for family or guests. Recent updates include new LVP flooring, new carpet, and a new roof, making this home truly move-in ready. Enjoy a large, fully fenced backyard with a brand-new deck perfect for entertaining, grilling, or relaxing. Don't miss this one!

317 Spurlane Circle, South 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
$585,000
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
$285,000
3 Beds ⋅ 1.1 Baths ⋅ 10645022 MLS
Be settled before summer ends! Townhome offers a modern/functional layout. First floor features a light & bright eat-in kitchen, SS appliances, ample counter space & vintage cabinets. Living room boasts an attractive wood burning fireplace, you'll finally have that mantle for holiday decorating! Three bedrooms up with a full bath, new carpet, fresh paint throughout. Enjoy direct access to the fully fenced back yard from the dining area. Back yard provides the perfect space for entertaining, relaxing or allowing pets to roam. Take advantage of the path that runs along the lake, just outside the rear gate.

939 Still Harbor Circle, South Chesapeake
$1,195,000
4 Beds ⋅ 4.1 Baths ⋅ 10644941 MLS
Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

377 Homestead Road, West 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 fully remodeled all-brick ranch located in the Hickory area of Chesapeake. Offering 4 bedrooms, 2 updated bathrooms, and situated on approximately 3 acres, this property provides generous indoor and outdoor living space. Interior updates include luxury vinyl plank flooring, tiled showers, granite countertops, stainless steel appliances, and an open, light-filled layout designed for everyday living and entertaining. Outdoor features include a covered front porch, an expansive rear deck, and a private deck accessible from the primary suite. Additional improvements include a newly poured driveway and a 50-AMP power pole ready for RV hookup. This move-in-ready home combines updated finishes with functional living space in a convenient Chesapeake location.

913 Long Ridge Road, South Chesapeake
$275,000
2 Beds ⋅ 2 Baths ⋅ 10644809 MLS
Welcome to easy, low-maintenance living in the desirable Riverwalk community! This charming one-story, 2-bedroom, 2-bath condo features an inviting open floor plan with vaulted ceilings, a cozy wood-burning fireplace, and an attached one-car garage. The comfortable layout offers plenty of natural light and space to relax or entertain. Conveniently located in the heart of Chesapeake near shopping, dining, parks, and major roadways, this home combines comfort, convenience, and a wonderful community setting.

800 Shenandoah River 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.