Refine Search
Sort by
$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

$524,900
3 Beds 2 Baths 10642197 MLS
Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, 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

$349,900
4 Beds 2.1 Baths 10641818 MLS
Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car garage. Situated in a prime location just minutes from shopping, local dining, entertainment, major interstates, and area bases. This property is a wonderful opportunity to bring a little elbow grease, add your personal touches, and truly make it your own. Call today to schedule your private showing! Some virtual staging utilized in pictures.

844 Parapet Road, South Chesapeake

$850,000
6 Beds 3.1 Baths 10641499 MLS
Welcome to your own private retreat in the heart of Grassfield! Nestled on approximately 5 acres, this beautifully maintained 6-bedroom, 3.5-bath home offers more than 4,200 square feet of space designed for both everyday living and unforgettable entertaining. Inside, you'll find generous living areas with room for everyone—whether you're hosting holiday gatherings, working from home, or simply enjoying quiet evenings with family. Go outside to enjoy the peaceful surroundings, then unwind in the hot tub, which conveys with the home, making it easy to relax under the stars after a long day. Now offered at an improved price, this exceptional property also includes a seller-paid carpet allowance with an acceptable offer, giving you the opportunity to add your own personal style before moving in. If you've been dreaming of acreage, privacy, and a home that offers the perfect blend of comfort, flexibility, and room to grow, this Grassfield gem is ready to welcome you home. Schedule your private tour today and experience everything this incredible property has to offer.

2536 Seven Eleven Road, South Chesapeake

$494,900
4 Beds 2.1 Baths 10641167 MLS
Welcome home to Wellington! This spacious 4-bedroom, 2.5-bath traditional home offers over 2,300 square feet of comfortable living space with room to spread out. The inviting family room features a gas fireplace, while the kitchen boasts newer appliances, abundant cabinet space, an open pantry, and a separate pantry closet for exceptional storage. Upstairs, the large primary suite includes two walk-in closets. Flooring throughout includes luxury vinyl plank, ceramic tile, and carpet.Enjoy outdoor living on the large deck overlooking the fully privacy-fenced backyard. An oversized 2-car garage and generous driveway provide plenty of parking and storage. Major updates have already been completed for added peace of mind, including a roof with covered gutters installed in 2020 and several recently replaced windows. Conveniently located in the desirable Wellington neighborhood of Chesapeake, this home is ready for its next owner.

3614 Elkton Drive, West Chesapeake

$385,000
3 Beds 2.1 Baths 10641471 MLS
Welcome home to this beautiful detached condo featuring an open and inviting floor plan designed for comfortable living and entertaining. The two-story living room fills the home with natural light and creates a spacious airy feel. The first-floor primary suite offers convenience and privacy complete with dual walk-in closets and an en-suite bath featuring dual vanity sinks. The kitchen boasts granite countertops, stainless steel appliances and a breakfast bar with counter seating, perfect for dining and gathering with guests. Upstairs you will find 2 additional bedrooms, a full bath and a loft overlooking the living room. This move-in ready home combines style, functionality and low maintenance living in the Greenbrier area. Don't miss this exceptional opportunity!

1519 Tallwood Circle, South Chesapeake

$419,900
3 Beds 2.1 Baths 10641328 MLS
This end unit townhome has been meticulously cared for by the original owners since purchasing it new in 2023. From the welcoming foyer, LVP flooring throughout the 1st floor leads to a stunning great room, which flows nicely into the dinette and gourmet kitchen that provides abundant counter space for all your kitchen storage needs. Upstairs, 3 spacious bedrooms and 2 full bathrooms provide privacy and comfort. Your luxurious owner’s suite includes tray ceilings, a generous sized walk-in closet, a double vanity sink and large stand up shower. When you live in Cardinal Meadows, you’ll love the easy access to Route 17, Cedar Road, I-64 and I-464, not to mention being located right off Cahoon Parkway puts you just minutes away from all your shopping needs at Cahoon Commons.

1607 Songbird Lane, South Chesapeake

$550,900
4 Beds 2.1 Baths 10641029 MLS
This traditional floor plan offers 4 Bedrooms, 2.5 Baths, and 2420 sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2206 Wilmington Avenue, West Chesapeake

$553,900
3 Beds 3 Baths 10641052 MLS
Enjoy peaceful country living on 1.77 acres in the highly sought-after Hickory School District! This charming 3-bedroom, 3-full-bath home offers plenty of space both inside and out, making it perfect for those seeking privacy, comfort, and room to roam.Step inside and discover a welcoming open layout designed for everyday living and entertaining. The spacious heated sunroom deck provides the perfect spot to relax year-round. Huge pantry storage room off kitchen to keep those grocerie store runs to a minimum. The expansive 1.77-acre lot includes a chicken coop, large detach garage, fenced area, carport, and open fields making this property ideal for hobby farmers, homesteaders, or anyone looking to embrace a more self-sufficient lifestyle. With plenty of room for gardening, recreation, and outdoor activities, the possibilities are endless. The back half of detached garage needs work, but has lots of potential for a nice workshop, game room, mancave, apartment, etc.

2420 Mount Pleasant Road, South Chesapeake

$280,000
2 Beds 2 Baths 10641020 MLS
Welcome to 1713 Orchard Way—an inviting home offering comfort, style and versatility. Enjoy 2 dedicated parking spaces + ample guest parking & a charming covered front porch. 1st floor features incl BR with attached bath, soaring vaulted ceilings, new LVP flooring, fresh paint and cozy gas log FP, creating a bright, welcoming living space. Updated kitchen with new counters & SS appliances. Spacious primary BR offers large walk-in closet (easy attic access) & bath with relaxing Jacuzzi tub. Upstairs, HUGE loft/flex area ideal for office, gym or 3rd BR. Add’l highlights: new carpet, generous interior storage, ext storage & screened porch for seamless indoor/outdoor living. Community amenities incl pool. Conveniently located just minutes to bases, interstates, dining, shopping & all of Hampton Roads.

1713 Orchard Way, South Chesapeake

$699,900
5 Beds 3 Baths 10639822 MLS
3% Builder-paid Buyer Incentive to be used at Buyer's discretion with Builder's preferred lender. Welcome to this fantastic 5-BR, 3-full bath, New Construction home on 1+Acre lot that feeds into the Hickory Schools! Boasting 2660SF of modern living with 9' ceilings on the first floor, and a first-floor carpeted bedroom & ensuite! This beautifully designed 2-story home features a gourmet kitchen with granite counters, 42" raised-panel wall cabinets and stainless steel appliances, soft-close drawers, huge island! LVP flooring throughout downstairs and carpeting upstairs! Spacious second-floor Primary suite with tray ceiling and large ensuite! Check out these features: 75 gallon water heater, 60" LED fireplace, 2-zone HVAC, garage prewired for E-car Charger, programmable theremostat. Don't miss this one!

1453 Whittamore Road, South Chesapeake

$734,900
5 Beds 3 Baths 10639162 MLS
Proudly offered by its original owner, this beautifully maintained 5-bedroom, 3 bathroom home is a rare opportunity in one of the area's most desired neighborhoods. The thoughtfully designed floor plan features a spacious downstairs bedroom and full bath, ideal for guest or multi-generational living along with a Great room, well-appointed kitchen, dining room, and flex room. Upstairs you will find 4 additional generous sized bedrooms, including the primary suite with a beautifully updated bathroom and large closet. Enjoy gathering with family and friends in the inviting family room complete with a built-in bar. Start your mornings on the welcoming front porch and unwind in the evenings on the spacious back patio, perfect for outdoor dining, entertaining, or simply relaxing. Find out why Warrington Hall is one of the most desired communities with all of its amenities including: pool, playgrounds, ball fields, and tennis courts.

816 Poquoson Crossing, South Chesapeake

$629,900
4 Beds 3 Baths 10639144 MLS
WATERFRONT LIVING IN SOUGHT-AFTER HUNNINGDON LAKES! THIS BEAUTIFULLY MAINTAINED RANCH OFFERS 4 BEDROOMS, 3 FULL BATHS, FORMAL LIVING AND DINING ROOMS, A SPACIOUS FAMILY ROOM, 2 FIREPLACES, CATHEDRAL CEILINGS, AND 3 SKYLIGHTS THAT FILL THE HOME WITH NATURAL LIGHT. THE UPDATED INTERIOR FEATURES NEW FLOORING, REPLACEMENT WINDOWS, CUSTOM MOSAIC-STYLE KITCHEN CABINET DOORS, AND AN ENCAPSULATED CRAWL SPACE. THE FIRST FLOOR PRIMARY SUITE PROVIDE COMFORT AND CONVENIENCE. ENJOY YEAR-ROUND COMFORT, WITH 4 SEPARATE HVAC ZONES. STEP OUTSIDE TO YOUR PRIVATE LAKESIDE RETREAT WITH A LARGE DECK, PATIO, TRANQUIL 2-TIER WATERFALL KOI POND WITH KOI FISH, AND PEACEFUL WATER VIEWS. YOU CAN EVEN FISH FROM YOUR OWN YARD! A BRAND-NEW EMBANKMENT OFFERS LASTING SHORELINE PROTECTION. ADDITIONAL FEATURES INCLUDE 2 STORAGE SHEDS AND A TRANSFERABLE TERMINIX WARRANTY. PERFECT HOME TO LIVE, ENTERTAIN, UNWIND, AND ENJOY THE WATERFRONT LIFESTYLE RIGHT FROM YOUR BACKYARD!

1104 Copper Stone Circle, South Chesapeake

$443,900
4 Beds 3 Baths 10638879 MLS
Prepare to fall in love with this Beauty in the 55+ community of Retreat at Western Branch. You will be impressed as you move through the Entry Way and into the spacious and flowing Lafayette Floorplan that boasts a vaulted Great Room with gas fireplace that opens to the Dining Room and quartz Kitchen with large center island and upgraded appliances including gas range. You will find a 1st flr Owner's Suite, another 1st flr bedroom ensuite, and a 2nd flr with a Loft and two more bedrooms with direct access to a full bath. Additional Details: Great Room with custom built lighted display cabinets and gas fireplace with heatilator, two Kitchen pantries including large walk in pantry, 1st flr Laundry Room, LVP on 1st flr, whole house water filtration system, lots of storage space, custom blinds, zoned HVAC, covered porch with fan, fenced backyard, 2 car garage with opener, & more! Amenities: pool, fitness center, dog park, walking paths, fire pits, grilling area, garden, and clubhouse.

4620 Longleaf Place, West Chesapeake

$699,000
5 Beds 2.1 Baths 10638474 MLS
Welcome home to 2209 Beeblossom Lane located in the sought-after Grassfield High School well-known for its STEM Academy! Built in 2016, this move-in ready 5-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and energy efficiency. Inside, you’ll find wood flooring, a kitchen with sunny eat in nook open to a den w/ cozy gas fireplace ready for the Fall& Winter holidays. Enjoy living , dining & extra office flex space room , ideal for entertaining or everyday living. The expansive primary suite is a true retreat, featuring a dual-entry oversized walk-in closet and a private en suite bath complete with a soaking tub and separate shower. Upstairs, the dedicated theater room with a big-screen setup is ready for unforgettable movie nights, game days, or family gatherings. Step outside to your own backyard oasis! Relax or entertain around the inground saltwater pool, all within a fully fenced backyard designed for privacy and fun. Additional highlights include a Rinnai tankless water heater and paid-off solar panels, providing energy savings and peace of mind. Dominion Meadows offers planned community events throughout the year, scenic sidewalks, & beautiful fountains that make every stroll through the neighborhood enjoyable. Convenient to interstates to bases, shopping , dining & more. Schedule a showing today & start making new memories in your new home!

2209 Beeblossom Lane, South Chesapeake

$580,000
4 Beds 3.1 Baths 10638478 MLS
Spacious Huntington Woods Home with Pool! Located in the desirable Huntington Woods neighborhood, this expansive home offers over 3,500 square feet of living space and endless potential. Featuring vaulted ceilings, generous living areas, and a two-car garage, there is plenty of room to spread out and make this home your own.Step outside to enjoy the large in-ground pool, perfect for relaxing, entertaining, and making the most of warm summer days. Conveniently situated just minutes from Greenbrier Country Club, you'll enjoy easy access to golf, dining, shopping, and more. With its spacious layout, sought-after location, and opportunity to add your personal touch, this Huntington Woods property is ready for its next owner. Don't miss your chance to call it home!

1340 Danielle Court, South Chesapeake

$489,900
4 Beds 2 Baths 10638400 MLS
WELCOME HOME! to this 1.5 story waterfront home on corner lot with 1st floor master bedroom with tray ceiling & 2 closets/master bath. Former model with converted garage-unlimited possibilities: he/she cave, office, daycare, home school, playroom, sewing/craft room, media room, bedroom, in-law apartment with separate entrance. Updates: new roof, new fence,freshly painted interior & beautiful! New carpet upstairs BR, new gas fireplace igniter & cleaned, large loft, new sink/vanity/floor-master bath w/jetted tub/separate shower. Kit with open bar to dining area, open dining area with pantry and mirrored accent wall, open family room with cathedral ceiling & sliding doors overlooking deck and water with nice shade tree & storage shed. Neighborhood park, clubhouse & pool for summer fun. Dog park and soccer park nearby as well as golf driving range, campground and shopping/dining. Hurry before it is gone!

2705 Sawyers Arch, South Chesapeake

$479,900
4 Beds 3.1 Baths 10637985 MLS
Ready NOW-Model Home for sale!! Luxury End Unit townhome condo w/rear load 2 car garage. covered front deck and entry.Luxury LVP, 2nd Floor:Kitchen GE stainless appliances including refrigerator, pantry,center island w/shiplap, living area linear fireplace w/shiplap and built ins,office/flex room,dining area.1st floor: br/ flex room,hall bath,mudroom. 3rd floor: Primary bedroom,ceramic shower-2 shower heads, dual sinks, linen closet, laundry. Quartz tops kitch, all baths, covered entry, fenced front yard w/gate to multi trail,2nd flr front covered deck. Wood shelving all closets. Pet Friendly. Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board. Builder 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, multipurpose trails with lake and fountain. Only 56 homes. Central Greenbrier location.

1060 Butte Lane, South Chesapeake

$545,000
5 Beds 2.1 Baths 10638238 MLS
Welcome to your ultimate retreat in the heart of Grassfield! Situated in a cul-de-sac in the highly sought-after Sawyers Mill community, this expansive 5-bedroom, 2.5-bath home features vaulted ceilings with a bright open floor plan. The large open kitchen is equipped with granite countertops, white shaker soft-close cabinets and drawers, stainless steel appliances, kitchen island and tile backsplash. Step through the relaxing sunroom onto a sprawling backyard deck serving as an outdoor oasis designed for grand-scale entertaining, summer barbecues, or peaceful evenings under the stars. The bedrooms are spacious, while the primary bedroom features tray ceilings, big walk-in closet, a large & elegantly designed en-suite bathroom. Conveniently located near shopping, dining, and major commuter routes while still enjoying the privacy of a cul-de-sac setting. This home offers interior comfort, plenty of outdoor entertaining space, privacy, modern updates, & community. This is a must see!

402 Undershot Court, South Chesapeake

$449,900
4 Beds 2 Baths 10637343 MLS
Welcome home to this beautifully maintained 4-bedroom property in the heart of Great Bridge! Pride of ownership is evident throughout, with numerous updates and upgrades completed over the years. The spacious primary suite features a private full bath, while the inviting living room offers a cozy fireplace framed by custom built-in cabinets, creating the perfect gathering space. The versatile room over the garage serves as a fourth bedroom, home office, media room, or additional living area to fit your needs. Step outside to a large deck overlooking an expansive .37-acre fenced backyard with privacy fencing—ideal for entertaining, pets, gardening, or relaxing outdoors. Conveniently located in the Hickory School District and near shopping, dining, entertainment, parks, and commuter routes, this move-in-ready Great Bridge home combines comfort, space, and location. Don't miss this exceptional opportunity!

540 Aylesbury Drive, South Chesapeake

$539,900
4 Beds 2.1 Baths 10636555 MLS
Some houses make you feel like a guest. This one makes you never want to leave. Spread across two spacious stories in one of Chesapeake's most sought-after communities, this home was built for people who actually use their space — whether that's splashing in the private pool on a Virginia summer afternoon, hosting a backyard cookout on the deck, or just enjoying the rare luxury of a completely fenced yard where nobody can see in. Inside, the layout flows the way life actually does: room to cook, room to gather, room to disappear into your own corner. Four generous bedrooms upstairs mean everyone has their own space. The half-bath on the main level keeps guests out of your business. And the attached 2-car garage means no fighting for the driveway. This is the kind of house that sells itself — the only question is whether someone else will schedule a tour before you do.

936 Saddleback Trail Road, South Chesapeake

$465,000
4 Beds 2 Baths 10636036 MLS
Nestled in the sought-after Homestead Acres community of Chesapeake, this beautifully maintained brick ranch offers the perfect blend of comfort, charm, and functionality. Enjoy an inviting open floor plan with spacious living areas, an updated kitchen, bright sunroom, and screened-in porch to enjoy year-round. Step outside to a large backyard retreat complete with a built-in firepit, great for relaxing evenings under the stars. Additional features include reverse osmosis system, water softener maintained by Moody’s, and HVAC less than 3 years old with smart system technology. Conveniently located near top-rated schools, shopping, dining, and more. Please ask details from agent on short sale details.

2744 Horseshoe Drive, 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.