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$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
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10645160 MLS
Stunning 4 bed 2 and a half bath custom-built home. Spacious bedrooms, upgraded kitchen with dual ovens and all newer appliances. Surround sound in the large family room. Newer flooring throughout. Custom built screened in back porch with a beautiful large yard. Relax on the front porch swing while overlooking the quiet cul de sac. Sought after neighborhood with the benefit of accessing major highways, bases & stores in minutes. Seller also providing a one year home warranty. Look at this one first!

1237 Spruce Lane, South Chesapeake
$300,000
3 Beds ⋅ 1.1 Baths ⋅ 10645067 MLS
This property is a diamond just waiting to be found. With a little less than 3/4 of an acre, this home offers the country feeling right outside your back door, surrounded by corn fields and plenty of land to spread out on. Plenty of off-street parking, and 1 car attached garage space. Inside, you will find 3 rooms at 1 end of the home, with 1.5 baths spread across a 1,254 sq. ft. home. A fireplace built with craftsmanship and surely a conversation piece. This home is just looking for a little tlc to get it back to prime condition. The dining room is big enough to hold a large table, with an additional space to hold a small table in the kitchen. The garage has an enclosed additional room built to be a workshop with a door and potential for storage as well. Newer septic and newer roof. Sellers are listing well under market value to offset any and all repairs needed. All appliances are as-is, where is.

2423 Herring Ditch Road, South Chesapeake
$629,900
4 Beds ⋅ 2.1 Baths ⋅ 10645157 MLS
BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities are just steps away, while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, South Chesapeake
$575,000
4 Beds ⋅ 2.1 Baths ⋅ 10645016 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, 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
$500,000
4 Beds ⋅ 2 Baths ⋅ 10644991 MLS
Beautifully updated 4 bedroom, 2 bath ranch home in the sought-after Hickory School District! Move-in ready with big-ticket updates. Enjoy easy, single-level living with great natural light, neutral finishes, and smart storage. Outside, relax on the deck in the fenced backyard—perfect for entertaining, pets, and play. Convenient driveway parking and a low-maintenance exterior provide peace of mind. Centrally located near schools, parks, shopping, bases, and the oceanfront, with quick access to major routes.

808 Rutherford Drive, South Chesapeake
$689,900
5 Beds ⋅ 3 Baths ⋅ 10644830 MLS
SPACIOUS 5 BEDRM, 3 BATH ALL BRICK HOME NESTLED IN 1 OF GREAT BRIDGE'S MOST DESIRABLE COMMUNITIES. OVER 3,000 SQ FT OF SPACE. FEATURES VERSATILE FLOOR PLAN W/ GENEROUS ROOMS, HIGH CEILINGS, HARWOOD FLOORS & OVERSIZED GARAGES W/BUILT IN STORAGE & WORKSPACE. REAR DECK PROVIDES PRIVATE & RELAXING OUTDOOR AREA. EXCELLENT OPPORTUNITY FOR NEW OWNER TO PERSONALIZE THE INTERIOR & CREATE THEIR DREAM HOME WHILE BUILDING INSTANT EQUITY. CONVENIENTLY LOCATED NEAR TOP RATED SCHOOLS, INTERSTATE MUNICIPAL CTR

806 Falls Creek Drive, 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
$452,000
4 Beds ⋅ 3 Baths ⋅ 10645004 MLS
Welcome home to this beautiful property ideally situated on corner lot. 4 spacious bdrms with one downstairs bedroom w/ large walk-in closet and full bath access perfect for in-law or guest suite. Primary suite offers walk-in closet, jetted tub and double vanity. Upstairs laundry with cabinetry and laundry workspace. Kitchen with breakfast bar, pantry, double oven, and newer refrigerator, microwave and dishwasher. Go outside onto the lanai w/ceiling and beautiful maturing landscaping. Low maintenance exterior with all wrapped exterior and gutter guards. The standout feature is the detached garage w/ recently installed attached 16x20 carport and expanded driveway-A true hobbyist or RV owners dream. Garage is wired with its own 100amp panel accommodating both 30 and 50 amp connections. Garage is heated and cooled by an installed window unit and pull down access to extra attic storage. A true must see.

1332 Hazel Avenue, Central Chesapeake
$399,900
3 Beds ⋅ 2 Baths ⋅ 10645064 MLS
All brick ranch on expansive 1/2 acre lot with views of the river! 3 bedrooms with hardwood floors in most of the living areas. Impressive Sunroom addition allows for great family gatherings. Kitchen with gas cooktop. Covered carport and detached garage with lots of potential. Roof appx 5 yrs old.

2749 E Meadow Drive, West Chesapeake
$325,000
3 Beds ⋅ 2 Baths ⋅ 10644838 MLS
Discover single-level living at its finest in this charming Chesapeake ranch! Perfectly positioned on a generous corner lot, this 3-bedroom, 2-bath home boasts a bright and open atmosphere. The spacious living area flows seamlessly into a fully updated kitchen featuring modern appliances, a moveable island, and a cheerful breakfast nook. Down the hall, the primary suite offers a peaceful everyday escape, highlighting a beautifully updated closet and an inviting en-suite bathroom. The two additional bedrooms provide endless flexibility to suit your lifestyle. The outdoor space is a true highlight, featuring a brand-new deck that overlooks a spacious yard with endless possibilities for gardening or relaxing. With a new water heater already installed and a prime location near local parks, top-rated schools, and vibrant shopping, this home is completely turnkey!

1553 Forest Cove Drive, 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
$345,000
3 Beds ⋅ 1.1 Baths ⋅ 10644853 MLS
Nestled in the highly desirable Norfolk Highlands neighborhood of Chesapeake, this home built in 2000, offers the perfect combination of modern construction, generous outdoor space, and a location that's hard to beat. Situated on a spacious lot, with no immediate neighbor to the right, you'll enjoy plenty of room for entertaining, gardening, play, or future outdoor enhancements. Conveniently located near Greenbrier, major highways, military bases, shopping, dining, parks, and Chesapeake schools, this home is a must see!

1323 Oleander Avenue, Central Chesapeake
$400,000
4 Beds ⋅ 2.1 Baths ⋅ 10644987 MLS
Welcome home to 4320 Schooner Trail! This beautifully maintained 4 -bedroom, 2.5 bathroom home in the sought- after Western Branch area of Chesapeake. This home offers an ideal blend of space, comfort, tons of storage and modern convenience. The downstairs features an open- concept floor plan seamlessly connecting the living room, dining area and kitchen area that has stainless steel appliances and a private office with French doors. Upstairs features a huge master bedroom with walk in closets and a massive attached bathroom. Enjoy the private, fully fenced in backyard that is perfect for relaxing and entertaining guests. The HVAC system was replaced in 2024 and the fireplace has never been used by the owner. The fireplace sold as-is. Call today for your private showing of your new home!

4320 Schooner Trail, West Chesapeake
$370,000
4 Beds ⋅ 2 Baths ⋅ 10644985 MLS
This beautiful modern ranch has been completely renovated. New Roof, windows, siding, water heater, kitchen, baths, flooring, and fixtures. Updated plumbing and electrical. Hvac is a couple years old. This home features an open layout concept with a huge living area. The backyard is generous in size and has tons of potential for a pool and more. Four bedrooms all with lvp throughout. This home checks all the boxes, come see it today!

3512 Maori Drive, West 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
$190,000
3 Beds ⋅ 1 Baths ⋅ 10644947 MLS
ATTN INVESTORS! SOLD AS IS, CASH OR REHAB LOAN REQUIRED. No utilities on at property, owner not open to connecting utilities. Owner has no knowledge with regard to age of any systems. Subject to court approval (usually only adds a week or so to process). Needs renovation.

341 Keith Court, Central Chesapeake
$359,900
4 Beds ⋅ 2 Baths ⋅ 10643890 MLS
The Ultimate Chef's Kitchen: Equipped with a professional-grade gas stove & griddle, a rustic tile backsplash, granite countertops, a farmhouse sink, a pot filler, and stainless steel appliances. Fresh & Modern Upgrades: Brand-new paint, stunning flooring, carpet, and stylish finishes elevate every room while preserving the home's historic soul. Space to Live & Play: Featuring a spacious formal dining room, a bright and airy sunroom, a huge primary suite drenched in natural light, and a massive stand-in attic for ultimate storage. Outdoor Oasis: Step outside to a fully fenced backyard complete with an expansive deck—great for weekend BBQs and entertaining. Prepare to fall in love! This gorgeous home with upgrades in the Historic District of Chesapeake is a wounderful mix of historic curb appeal and sleek, modern living.

1006 Butt Street, Central Chesapeake
$355,000
3 Beds ⋅ 1 Baths ⋅ 10644878 MLS
.25 acre Corner Lot 3-4 bedroom home featuring a convenient horseshoe driveway plus a paved driveway leading to the detached garage. Flexible bonus room works perfectly as an office, playroom, or guest space. Recent improvements include newer windows, **2025 roof**, **2024 flooring**, & **2025 HVAC service & cleaning**. The open floor plan connects the kitchen, dining area, and living room, with a dedicated large laundry room just off the kitchen. Enjoy outdoor living on both the welcoming front porch and the private back patio. The oversized **696 sq. ft. detached garage** provides exceptional parking, workshop space, and storage. Move-in ready — schedule your showing today. (Some photos virtually staged.)

1505 Sparrow Road, Central Chesapeake
$360,000
3 Beds ⋅ 2 Baths ⋅ 10644772 MLS
Well-maintained ranch in the established Strawberry Acres neighborhood featuring a bright, open floor plan with wood laminate flooring throughout the main living areas. The updated kitchen offers ample cabinetry, granite countertops, stainless steel appliances and ceramic tile flooring. The primary suite includes an updated en-suite bath, while two additional bedrooms share a renovated full hall bath. The rear portion of the garage has been thoughtfully converted into a dedicated laundry room, adding convenience and functionality. Situated on a spacious 0.27-acre lot, the fully fenced backyard features a paver patio with plenty of room for relaxing, gardening, play and entertaining. Conveniently located just minutes from shopping, dining, schools and interstate access. Hot Water Heater - 2021, Roof - 2016, HVAC - 2016.

3204 Hancock Drive, South Chesapeake
$550,000
4 Beds ⋅ 3 Baths ⋅ 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, South Chesapeake
$314,900
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
$335,000
4 Beds ⋅ 1.1 Baths ⋅ 10644626 MLS
Don't miss the opportunity of this beautiful well-maintained home in a tucked off quarter of Chesapeake. This brick ranch with a large back yard and beautiful hardwood floors has been freshly painted. The large front porch offers opportunity for relaxation. The location near the new Blue Heron Landing Park and a central drive to bases, interstates, beaches, and shopping provides convenience and possibility.

1217 Oleander Avenue, Central Chesapeake
$542,000
5 Beds ⋅ 2.1 Baths ⋅ 10644796 MLS
Large Home 3300 sq ft in Western Branch area of Chesapeake 5 Bedrooms, Large Family room with wood burning fireplace. Gas Water Heater & Gas Heat, Large Fenced Yard w/10X10 Shed; Roof 2014 (50 year architectural) Well, Sprinkler System Front Yard. Large Kitchen with Island & Walk in pantry. Large Primary Ensuite with walk in Closets; Dual sinks. Seller Offering CCA or Rate Buy Down with Full Price offer

3025 Crossings Drive, West Chesapeake
$539,900
4 Beds ⋅ 2.1 Baths ⋅ 10644845 MLS
Come Home SWEET Home to beautiful Chapel Hill Estates. This is an opportunity to live in this highly desirable location in the Hickory School District at an Affordable price... Four Bedrooms, 2 1/2 Baths exist in this 2,000+ square feet of Open Concept floor plan with 2-car garage. “Make it Your Own!” Generous Sellers offering $5,000 Decorator's Allowance to boot! Act fast, won't last!

1221 Rosebud Lane, South 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
$325,000
3 Beds ⋅ 1.1 Baths ⋅ 10644798 MLS
Own A Piece Of "Country Living" In "The City!" Original Farmhouse Type Home Situated On Approx. 2 Acres - Very Unusual Lot! Really Private Setting! Home Needs Renovating...Has Lots Of Potential! Located Off Shell Rd. (Firman St) With Flag Driveway To Back Of Properties. HVAC System 2 Years Old, Roof Approx 16 Years Old, 3 Bedrooms, 1 Bathroom Upstairs, Half Bath Downstairs. Good Sized Kitchen With Real Knotty Pine Cedar Cabinets! Laundry Room Off Kitchen. French Doors Into Living Room And Columns Into Dining Room. Original Hardwood Floors Downstairs. Just A Charming House...Needs Renovation! Huge "Pie Shape" Additional Lot...All On One Deed. Interested In Building Another Dwelling? Look Up The New Senate Bill 531 Which Requires All Localities To Allow Assessory Dwelling Units (ADVs) "By Right" In Single Family Residential Zones...It Might Apply! Buyer Would Do Their Own Due Diligence On This Property.

772 Shell Road, South Chesapeake
$231,900
3 Beds ⋅ 2 Baths ⋅ 10644864 MLS
Welcome home to this charming 3 bedroom, 2 full bath single-family home! It offers over 1,000 square feet of comfortable living space. Situated on a 0.12-acre lot, this home features a functional floor plan. Conveniently located with quick access to major highways, military bases, shopping, dining, and entertainment, you'll enjoy an easy commute and all the conveniences of the area. Whether you're a first-time homebuyer, downsizing, or looking to add to your investment portfolio, this home is full of potential and ready for its next owner. Don't miss this fantastic opportunity! Call today for more information and to schedule your tour!

919 Decatur Street, Central 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.