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$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
$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
$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
$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
$600,000
4 Beds ⋅ 2.1 Baths ⋅ 10645717 MLS
OPEN HOUSE Aug 22 & 23 Sat & Sun 1 to 3 PM ~ NEW PRICE — $600,000 | WATERFRONT LIVING IN GREAT BRIDGE! Welcome to your own Chesapeake waterfront retreat, tucked away on a quiet cul-de-sac in the sought-after Great Bridge school district. This beautifully updated 4-bedroom, 2.5-bath home offers nearly 3,000 square feet of living space with peaceful water views and no HOA. Step outside to a fully fenced backyard overlooking the water or unwind on the screened porch and enjoy the setting that makes this home truly special. Inside, fresh paint, LVP flooring throughout the first floor, updated lighting and a refinished staircase create a move-in-ready feel. Major improvements include HVAC (2023), water heater (2022) and an encapsulated crawlspace. Washer and dryer convey. Nearly 3,000 square feet, waterfront, Great Bridge and now $600,000 — come experience “The Lake House” for yourself.

705 Turnbuckle Court, South 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
$750,000
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
$469,000
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
$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
$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
$1,259,997
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
$325,000
3 Beds ⋅ 2.1 Baths ⋅ 10643661 MLS
Welcome home to this well-maintained End unit 3-bedroom, 2.5-bath townhome located in the Riverwalk community. The inviting open floor plan provides a comfortable flow between the living, dining, and kitchen areas, making it ideal for everyday living and entertaining. Step outside to enjoy the private rear patio, complete with a storage shed for added convenience. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with an en-suite bath and ample closet space.

719 Creekside Crescent, South Chesapeake
$440,000
6 Beds ⋅ 3 Baths ⋅ 10643653 MLS
15K INSTANT EQUITY!!!!!!! A peaceful neighborhood in the Deep Creek area of Chesapeake with close water views and wooded scenery. This home is one of the largest homes, in the neighborhood, spacious bedrooms 6 & 3 full bathrooms. This home features a modern open layout with generous living areas and a well-appointed kitchen open for entertaining. 3 first-floor bedrooms and 1 full bath provide ideal flexibility for guests or multi-generational living while the other 3 to include the Primary bedroom on the second floor. The home has a new LVP life proof floors, New paint, New carpet, New two car driveway with a wrap around sidewalk and a generous size yard for gathering a outdoor activities. Flood Insurance of 880 yearly (Never floods) SOME CLOSING COST ASSISTANCE AVAILABLE.

421 Plummer Drive, South Chesapeake
$235,000
2 Beds ⋅ 1.1 Baths ⋅ 10643623 MLS
**OWNER FINANCE ONLY, NO BANK FINANCING. Property has new flooring, new fixtures, new toilets, and fresh paint! Property is being sold as is. No credit check, no bank approval needed. Seller financing available with $10,000 down payment, and $2000/mo payment. Proof of funds required for showing. Email or text POF to Listing Agent. Owner is a licensed Real Estate Agent in the state of Virginia.

824 Nottaway Drive, South Chesapeake
$295,000
2 Beds ⋅ 1.1 Baths ⋅ 10642955 MLS
Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in desirable Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace, fresh finishes, and an inviting layout perfect for everyday living or entertaining. Recent improvements include fresh paint, new flooring, new carpet, an updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry bath, and a large hall closet for extra storage. Enjoy a private fenced backyard with a new deck, ideal for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major interstates, Chesapeake City Hall, and award-winning Grassfield schools, this move-in ready home is ready for its new owner.

300 San Roman Drive, South Chesapeake
$890,000
7 Beds ⋅ 4 Baths ⋅ 10643086 MLS
Welcome home! This beautifully updated 7 bedroom and 4 full bath property offers over 3 acres of land and ample parking. First floor primary suite features a fireplace and upgraded bathroom with sleek tile. The kitchen boasts a large island, all new countertops, stainless steel appliances, and tile backsplash. Two upstairs bedrooms include full baths and walk-in closets. Open layout with recessed ceiling lighting, two fireplaces, and two sets of sliding glass doors lead to a spacious backyard. Schedule your showing today!

537 Margaret Drive, South Chesapeake
$775,000
5 Beds ⋅ 2.1 Baths ⋅ 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake
$879,000
3 Beds ⋅ 2 Baths ⋅ 10642255 MLS
If these walls could talk, they would tell you 175 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake
$487,500
5 Beds ⋅ 2.1 Baths ⋅ 10642464 MLS
Lakefront 5 bedroom home in Grassfield High and Middle School District! Fully updated $60k of premium upgrades intended for a forever home! Quiet, sought-after neighborhood. Just minutes from shopping and interstate. Large property features a 30-yrnew architectural roof, all-new hardwood floors, and a new driveway. Interior boasts an office, formal dining, eat-in-kitchen with a new refrigerator, and a family room with a fireplace. Enjoy a Master bath upgrade ($30k) and pristine Trex deck in the large, fenced-in backyard.

517 Whisper Walk, South Chesapeake
$288,500
3 Beds ⋅ 1 Baths ⋅ 10642393 MLS
Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character. The property is zoned Industrial and the current legal use is residential (nonconforming-grandfathered) Buyers should independently verify requirements with the City of Chesapeake, for any plans for additions or redevelopment or converting to an Airbnb STR.

106 Greenbrier Road, South Chesapeake
$440,000
4 Beds ⋅ 2.1 Baths ⋅ 10641959 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake
$635,000
4 Beds ⋅ 2 Baths ⋅ 10641777 MLS
Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home! You won't want to miss this one!

1345 Oak Ridge Drive, South Chesapeake
$624,900
4 Beds ⋅ 2 Baths ⋅ 10641403 MLS
Enjoy the tranquility of this charming ranch nestled on a private lot spanning nearly 3 acres. The inviting floor plan welcomes you with a cozy living room featuring a fireplace and wet bar, creating a great space to relax or entertain. At the heart of the home, the kitchen is filled with natural light from two large windows and offers ample cabinet and counter space, along with stainless steel appliances. Just off the kitchen, the dining area allows for effortless gatherings and everyday living. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private ensuite bathroom. The additional bedrooms are generously sized, offering flexibility for family, guests, or a home office. Outside, the expansive backyard and screened porch provide endless opportunities to enjoy the surrounding natural beauty and peaceful setting. Experience the best of country living with the convenience of a short commute to shopping, dining, and everyday amenities.

2448 Johnstown Road, South Chesapeake
$599,000
4 Beds ⋅ 2.1 Baths ⋅ 10641342 MLS
Spacious Riverwalk home offering over 3,372 sq. ft. with 4 bedrooms, 2.5 baths, a two-car garage, 2 decks with private views of the lake. Recent improvements include gas HVAC in 2022, roof approximate 6 years old, encapsulated crawl space, Anderson windows with warranty, and new kitchen appliances. Large family room and kitchen - great for everyday life and easy hosting. Enjoy Riverwalk amenities including clubhouse, pool, playgrounds, and tennis courts. A wonderful opportunity to personalize a spacious home in a sought-after Chesapeake community. Close to the Hospital, Dining, Shopping and Interstates.

220 Marsh Island Drive, South Chesapeake
$334,900
2 Beds ⋅ 2.1 Baths ⋅ 10639821 MLS
MOVE-IN READY! Desirable END UNIT townhome in sought after Greenbrier. Fresh paint and new carpet throughout make this beautifully updated home shine. The bright eat-in kitchen features stainless steel appliances and granite countertops. The spacious great room offers a dining area, cozy fireplace, and access to the large, fenced backyard with utility room and storage shed (shed conveys As-Is). A half bath and laundry room complete the first floor. Upstairs, you'll find two generous EN-SUITE bedrooms filled with natural light. The third-floor loft provides flexible space perfect for a home office, study area, media room, playroom, or guest retreat. Conveniently located near shopping, dining, parks, and major highways, this low-maintenance home offers comfort, style, and an easy commute. Schedule your private showing today!

1213 Killington Square, 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.