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1505 Head Of River Road, South Chesapeake
$1,150,000
4 Beds ⋅ 3.1 Baths ⋅ 10660150 MLS
OVER 4 ACRES IN HICKORY, A CUSTOM BRICK ESTATE, DETACHED 3-CAR GARAGE WITH PRIVATE IN-LAW SUITE, AND A VERSATILE ENTERTAINMENT BARN! Discover an extraordinary combination of space, privacy, and possibilities at 1505 Head of River Road in Chesapeake! This meticulously maintained custom brick residence offers approximately 3,538 square feet with four bedrooms, three featuring their own attached full bathrooms, plus a versatile fifth room ideal for a home office or flex space. The spacious kitchen opens to an expansive living area, while the first-floor primary suite adds everyday convenience. Beyond the main residence, a detached three-car garage features an upper-level in-law suite with a full bathroom, mini kitchen and dedicated HVAC system, along with workshop space and RV-accessible garage entry. A versatile entertainment barn with its own HVAC system and full bathroom creates an impressive setting for gatherings, recreation, or hobbies. Thoughtfully cared for over the years, this exceptional property boasts extensive improvements, updated systems throughout, and a remarkable level of attention to maintenance. Set on approximately four acres in Chesapeake's desirable Hickory area, this unique estate offers incredible versatility and features that truly set it apart. The list of upgrades and improvements is extensive, ask for the complete property feature sheet to discover everything this remarkable property has to offer! PLUS, buyers may receive a lender credit of up to 1.25% of the loan amount toward eligible closing costs when using the preferred lender.

1505 Head Of River Road, South Chesapeake

1228 Destiny Way, South Chesapeake
$469,900
3 Beds ⋅ 2.1 Baths ⋅ 10660882 MLS
Welcome to this spacious 3-bedroom, 2.5-bath home offering a versatile floor plan designed for both functionality and entertaining! The main level features 9-foot ceilings, two generous living areas, a dedicated dining space, and a cozy natural gas fireplace. The kitchen offers luxurious granite countertops and stainless steel appliances. Upstairs, the primary suite offers a spacious walk-in closet, dual-sink vanity, and relaxing jetted tub. To top it off, the laundry is located on the second-floor! Attached two-car garage, with lots of space for storage. Go outside to a fully fenced backyard featuring a composite deck overlooking a peaceful wooded setting, great for relaxing. Whether you're enjoying your morning coffee on the covered front porch or hosting friends out back, this home has plenty to offer! Conveniently located near shopping, dining, and major interstates. Schedule your private showing today!

1228 Destiny Way, South Chesapeake

1103 Madison Lynn Way, South Chesapeake
$640,000
5 Beds ⋅ 2.1 Baths ⋅ 10660705 MLS
GREAT BRIDGE SCHOOLS, NO HOA, OVER 2,500 SQUARE FEET, AND AN OPPORTUNITY TO SAVE ON CLOSING COSTS! Located in Chesapeake's established Hanbury Manor neighborhood, 1103 Madison Lynn Way offers the space, flexibility, and features you've been searching for! This spacious home features four upstairs bedrooms plus a versatile first-floor bonus room ideal for a home office, guest room, or additional living space. The open main level showcases generous living and dining areas, LVP flooring, and an updated kitchen featuring quartz countertops, stainless steel appliances, and abundant cabinetry. Upstairs, the primary suite offers cathedral ceilings, a walk-in closet, soaking tub, and separate shower, while a dedicated laundry room with utility sink adds everyday convenience. A fully fenced backyard with patio and storage shed provides space to enjoy the outdoors, complemented by an attached two-car garage. Conveniently situated near shopping, dining, major interstates, and military installations, this property combines a desirable Great Bridge location with approximately 2,557 square feet of possibilities. PLUS, buyers may receive a lender credit of up to 1.25% of the loan amount toward eligible closing costs when using the preferred lender.

1103 Madison Lynn Way, South Chesapeake

1420 Orchard Grove Drive, South Chesapeake
$275,000
2 Beds ⋅ 2 Baths ⋅ 10660766 MLS
Fresh, move-in ready, and near everything! This two-story Orchard Grove condo offers 2 bedrooms, 2 full baths, and a versatile loft, with new carpet, fresh paint throughout, new lighting, and new faucet. The main living area is warmed by a cozy fireplace, and sliding glass doors bring in natural light. A first-floor bedroom and full bath add everyday convenience, while the upstairs loft is ready to become your home office, media room, or creative space. Step outside to relax on the porch or patio, then cool off at the community pool. Grounds maintenance and trash pickup are included in the condo amenities, so your weekends are available for the things you enjoy. Living here puts Greenbrier’s shopping, dining, and entertainment just minutes away, with quick access to I-64 for an easy commute across Hampton Roads. Low-maintenance living in a location that keeps everything within reach. Schedule your showing today!

1420 Orchard Grove Drive, South Chesapeake

1412 Sherbrooke Road, South Chesapeake
$499,900
4 Beds ⋅ 2.1 Baths ⋅ 10660105 MLS
Projected completion is December 2026! Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car side loading garage nestled in Chesapeake. This meticulously crafted residence offers a perfect blend of modern convenience & classic charm promising a lifestyle of comfort & sophistication. The heart of the home lies in the gourmet kitchen adorned w/luxurious granite countertops & equipped with stainless steel appliances. Whether you're whipping up a culinary masterpiece or enjoying a casual meal at the breakfast bar, this culinary haven is sure to inspire your inner chef. As you venture outdoors, discover & enjoy your own oasis in the backyard waiting for your personal touch. You will enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach. LVP flooring will be installed throughout the 1st floor. Photos from previous build. Make your appt today to see a previously built home.

1412 Sherbrooke Road, South Chesapeake

152 Tranquility Trace, South Chesapeake
$549,900
4 Beds ⋅ 3 Baths ⋅ 10660755 MLS
Beautiful craftsman style townhouse meticulously maintained and tastefully decorated. Open and bright with detailed moldings and wainscotting. Large Dining area opens to kitchen with granite counter tops and stainless steel appliances, oversized pantry with grand center island great for entertaining. Dining area and kitchen open to great room with cozy gas fireplace and built in bookshelves, engineered wood floors. First floor primary bedroom with newer flooring has en suite with newer shower and garden tub, dual sinks and large walk-in closet. First level also has an additional office with full bathroom that could be used as a 4th bedroom. Second level has bonus area great for TV/theatre room. Two additional bedrooms with access to a full bathroom. Relax in your screened in porch.

152 Tranquility Trace, South Chesapeake

609 Howelsen Court, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10660728 MLS
Tucked away on a cul-de-sac in desirable Elbow Estates, this beautifully maintained home offers the perfect combination of modern style, exceptional space and a floor plan made for everyday living and entertaining. Built in 2017, the home features a bright, open-concept main living area with fresh neutral paint, sleek contemporary fixtures and an effortless flow between the kitchen, dining and living spaces. Upstairs, generously sized bedrooms offer plenty of room, but the true showstopper is the oversized primary suite. A striking tray ceiling adds architectural interest, while two closets provide exceptional storage. The expansive primary bath feels like a private retreat with a large tiled jetted tub and separate tiled shower. Outside, the spacious backyard offers plenty of room for entertaining, play or relaxing, all surrounded by a high-quality vinyl privacy fence added in 2022. A two-car garage provides additional parking and storage. With modern finishes, oversized rooms and a f

609 Howelsen Court, South Chesapeake

528 Royal Grant Drive, South Chesapeake
$539,900
4 Beds ⋅ 2.1 Baths ⋅ 10660562 MLS
A backyard oasis highlights this 4-bedroom Chesapeake home, featuring an in-ground pool and an expansive deck with extensive built-in seating, a hot tub beneath a pergola, and a tiki hut with a built-in bar and swing seating. A paver patio, palm accents, mature trees, and a fenced yard complete the outdoor space. Inside, approximately 2,118 square feet includes a spacious living room with a brick fireplace and crown molding. The eat-in kitchen features a center island, generous counter space, and a bright dining nook. Upstairs, the primary suite offers a walk-in closet and private bath with abundant cabinet storage, an extended vanity, and a seated vanity area. Additional bedrooms complete the upstairs. Flooring includes hardwood and luxury vinyl plank downstairs, with carpet upstairs. Situated on approximately 0.28 acres.

528 Royal Grant Drive, South Chesapeake

102 Harbor Watch Drive, South Chesapeake
$305,000
3 Beds ⋅ 2.1 Baths ⋅ 10660515 MLS
Tired of yard work? Here’s your chance! Carefree living in a waterfront community with easy, fast access to several restaurants, neighborhood bar and grill, bagel shop, breakfast shop and much more! Picnic by the water on cool fall afternoons and watch the boats go by on the intercoastal. Lovely condo in Harbor Watch (Great Bridge) is move in ready with new kitchen countertops and ceramic subway tile backsplash. This awesome floor plan; The Thomas Point, boasts approximately 2,100 square feet of living space with 3 spacious bedrooms with ensuite bathrooms and a half bath for guests. Upstairs primary is HUGE with room for a sitting area, full bath with garden tub, separate shower and huge walk-in closet! Tons of storage space! Balcony overlooks the pool and pergolas. Spacious clubhouse for private parties or neighborhood gatherings. 2 assigned parking spots right out front of your condo; guest parking nearby. Grab your bags, move in soon, decorate and be ready for Christmas.

102 Harbor Watch Drive, South Chesapeake

908 Porte Crayon Street, South Chesapeake
$659,900
5 Beds ⋅ 3.1 Baths ⋅ 10660510 MLS
Your next chapter comes with a lifestyle to love in Culpepper Landing! Imagine walks along tree-lined streets, afternoons by the resort-style pool, and evenings catching up with neighbors on a golf cart ride. With a clubhouse, fitness room, dog parks, playgrounds, and wide sidewalks, this Chesapeake community makes it easy to enjoy more of every day. A lively neighborhood calendar brings people together for book club, bunco, seasonal celebrations, bourbon nights & more. Whether you prefer a quiet stroll or a weekend filled with community events, there is something here to make your routine feel more special. Enjoy the charm of an established neighborhood with gathering spaces that invite connection and amenities that bring recreation closer to your doorstep. Come discover why Culpepper Landing is more than an address; it is a place to settle in, get connected, and feel at home. New stamped concrete patio to make yard maintenance a breeze! Make this your new home and your invitation to experience it all!

908 Porte Crayon Street, South Chesapeake

1548 Waterside Drive N, South Chesapeake
$689,000
6 Beds ⋅ 3.1 Baths ⋅ 10660651 MLS
Spacious 4,899 sf lakefront home offering 6 bedrooms and 3.5 baths with an exceptional floor plan designed for comfortable living and entertaining. The expansive 1st floor primary suite provides a private retreat, while a 2nd floor ensuite is great for guests or multigenerational living. A massive great room with stunning lake views serves as the heart of the home, flowing seamlessly to a large composite deck great for outdoor gatherings. The oversized 840 sf attached garage offers ample space for vehicles, storage and hobbies. A walk-up attic provides abundant storage or future expansion potential. With generous living spaces, beautiful water views and a great price, this home is ready to accommodate every lifestyle. Photos virtually staged

1548 Waterside Drive N, South Chesapeake

1112 Walnut Neck Avenue, South Chesapeake
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10660307 MLS
Welcome to 1112 Walnut Neck Avenue in Chesapeake's established Warrington Hall community! This spacious two-story brick home offers 4 bedrooms, 2.5 bathrooms, approximately 2,596 square feet of living space, rear-loading two-car garage and a brand new roof! Step inside to a welcoming foyer leading to formal living and dining rooms that provide additional space for entertaining and everyday gatherings. The family room features a gas fireplace and opens to the kitchen and breakfast area, creating a comfortable and connected living space. Interior and exterior have updated paint (October 2026). The kitchen offers abundant cabinetry, generous counter space, and a breakfast bar overlooking the family room. The first-floor primary suite features a spacious bathroom with walk-in shower, and large walk-in closet. A convenient half bath and dedicated laundry room complete the main level. Upstairs, you'll find three additional bedrooms, a full bathroom, and a versatile loft area with options for a home office, recreation space, or additional sitting area. Accessible from the breakfast area, the back patio offers space for outdoor dining and relaxation. Enjoy Warrington Hall's community amenities, including a swimming pool, tennis courts, playgrounds, trails, and green spaces. Convenient access to Greenbrier shopping, restaurants, entertainment, and major commuting routes adds to the property's appeal. Discover the space, functionality, and community amenities available at 1112 Walnut Neck Avenue!

1112 Walnut Neck Avenue, South Chesapeake

544 Wickwood Drive, South Chesapeake
$574,900
4 Beds ⋅ 2.1 Baths ⋅ 10660561 MLS
Welcome home to comfort, connection, and room to make lasting memories! Nestled in the desirable Briarwood neighborhood, this inviting home offers the perfect blend of everyday comfort and spaces designed for gathering with family and friends. Fresh paint downstairs and in the FROG adds a fresh touch, while the lovely kitchen features solid-surface countertops and a cozy breakfast area, perfect for morning coffee, family meals, and everyday moments. Step outside and discover your own backyard retreat! The oversized composite deck and inground pool with a new pool cover create the perfect setting for summer fun, weekend gatherings, or simply relaxing and enjoying the sunshine. Inside, you'll find a spacious primary suite featuring a second fireplace, an impressive walk-in closet, and generously sized guest bedrooms that offer plenty of room for family, visitors, or a home office. A convenient walk-in attic provides additional storage to help keep everything organized. You'll also appreciate the added peace of mind that comes with recent updates including a new water heater in 2025 and one HVAC unit replaced in 2026.

544 Wickwood Drive, South Chesapeake

2205 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10660573 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2205 Edwin Drive, South Chesapeake

720 Paula Drive, South Chesapeake
$670,000
5 Beds ⋅ 3.1 Baths ⋅ 10659692 MLS
Endless possibilities on over 3 acres! Bring your vision and transform this spacious 5-bedroom, 3.5-bath home your own! Offering both upstairs and downstairs primary suites and approximately 3,900 square feet of living space, this property is bursting with potential and features multiple living and entertaining areas, providing plenty of room to spread out and create your dream home. Situated on over 3 acres of beautiful wooded land, the possibilities are endless! The expansive property features the footprint of a former swimming pool, along with an existing brick pool equipment building, offering potential for a future backyard oasis. A separate 320-square-foot workshop with electricity provides excellent space for hobbies, projects, or additional storage. Whether you envision a private wooded retreat, space for gardening, agricultural pursuits, potential livestock use, or simply room to roam and explore, this unique property offers an incredible opportunity to bring your ideas to life. With abundant space both inside and out, this is your chance to create something truly special!

720 Paula Drive, South Chesapeake

2517 Number Ten Lane, South Chesapeake
$859,900
4 Beds ⋅ 3.1 Baths ⋅ 10660465 MLS
Solar panels paid off. Sellers offering a 2-1 rate buy down with full price offer. Enjoy peaceful country living on 3 beautiful acres, just 5 miles from all your city favorites. This immaculate light-filled 4-bedroom, 3.5-bath home offers 9ft ceilings, detailed crown molding, custom built-ins, a main-level primary suite with a full bath, plus a convenient first-floor laundry room and mudroom. The chef's kitchen features leathered granite countertops, custom tile backsplash, SS appliances, and a center island. Upstairs offers 2 additional bedrooms, a large loft, and a second primary suite with a full bath, dual vanity and walk in closet. Outdoors, enjoy a resort-style backyard with a fenced inground saltwater pool surrounded by stamped concrete and a gazebo. The property also features solar panels, 2 barns, raised garden beds, a playset, a fire pit, and an extended driveway with ample space for an RV or boat. A rare blend of privacy, upgrades, and convenience!

2517 Number Ten Lane, South Chesapeake

2166 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10660457 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2166 Edwin Drive, South Chesapeake

2164 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10660454 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more- all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections.

2164 Edwin Drive, South Chesapeake

2162 Edwin Drive, South Chesapeake
$563,740
2 Beds ⋅ 3 Baths ⋅ 10660451 MLS
The Asheville, one of our quad-style homes, features two bedrooms, a large bonus room and 3 full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. Incentives with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary. Photos and renderings are from builder's library, actual finishes and features may vary.

2162 Edwin Drive, South Chesapeake

303 Diamond Avenue, South Chesapeake
$325,000
3 Beds ⋅ 2 Baths ⋅ 10660367 MLS
Welcome to your new home!Offering peace of mind and modern comfort, this home features a brand-new roof, siding, HVAC system, water heater, and windows—giving you the major updates you want without the worry of costly replacements.Inside, you’ll find a comfortable and inviting layout with plenty of natural light and space for everyday living and entertaining. The spacious bedrooms and two full bathrooms provide flexibility. Situated in a desirable Chesapeake location near shopping, dining, schools, parks, and major roadways, this move-in-ready home is an excellent opportunity for buyers looking for convenience, updates, and value. Don’t miss your chance to make this beautifully refreshed home yours!

303 Diamond Avenue, South Chesapeake

543 Bright Red Run, South Chesapeake
$399,900
3 Beds ⋅ 2.1 Baths ⋅ 10660236 MLS
Immaculately maintained & better than new, this 2022 Craftsman-style end-unit townhome is in the sought-after Grassfield School District. The open-concept layout features a light-filled Great Room & gourmet kitchen with Quartz countertops, white shaker cabinetry, stainless steel appliances, gas range, oversized breakfast bar, & pantry. LVP flooring spans the first floor. Upstairs, the spacious primary suite boasts a double tray ceiling, walk-in closet, & en-suite bath with dual vanity & oversized tiled shower with built-in bench. Two additional bedrooms, 2.5 baths, laundry room, tankless water heater, and all appliances convey. Enjoy outdoor living on the patio, just a short distance from community amenities including walking trails, playground, dog park, splash pad, & covered pavilion. Ground maintenance included. Convenient to shopping, dining, military installations, & major interstates. Assumable VA loan at an attractive 3.5% interest rate; Loan can only be assumed by a VA eligible buyer! Call for details.

543 Bright Red Run, South Chesapeake

208 Leicester Court, South Chesapeake
$760,000
5 Beds ⋅ 3 Baths ⋅ 10660322 MLS
Beautiful 5 Bedroom Brick Home featuring a spacious open floor plan perfect for everyday living and entertaining. The large kitchen offers stainless steel appliances, lots of counter space and cabinets. A standout feature of the home is the custom library, complete with French doors, built-in shelving, and a rolling ladder, creating an elegant and inviting space for work, reading, or relaxation. The first floor includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a large beautiful bathroom featuring a jetted tub, separate shower, a double vanity and private toilet room. Be sure to notice the built-in light-up stairs going up to the second floor! Enjoy your own private backyard oasis with mature landscaping, an in-ground saltwater pool, hot tub, and an expansive custom paver patio, ideal for relaxing or entertaining. Extended driveway with Boat/RV pad. Located in the sought after Great Bridge school district and community, local shops and restaurants, and close to the interstate for a quick trip to OBX!

208 Leicester Court, South Chesapeake

1400 Dons Way, South Chesapeake
$529,900
4 Beds ⋅ 3.1 Baths ⋅ 10660222 MLS
Immaculately maintained & better than new, this stunning end-unit townhome in Greenbrier is move-in ready! The entry level offers a 1-car garage, bedroom, full bath, flex room, mudroom with built-ins, & access to the fenced patio. The main level features an open-concept design with a sun-filled Great Room, electric fireplace, dining area, & gourmet kitchen boasting Quartz countertops, white shaker cabinetry with under-cabinet lighting, stainless steel appliances, oversized breakfast bar, & large pantry. Durable LVP flooring spans the first and second levels. The third-floor Primary Suite includes a spacious walk-in closet & private bath with dual vanities, Quartz counters, & a tiled shower. Two additional bedrooms, a full bath, & laundry complete the upper level. All appliances convey. Conveniently located near Greenbrier Mall, dining, medical facilities, military installations, interstates, and tunnels. *Assumable 5.75% VA loan available; Loan can only be assumed by a VA eligible buyer. Call for details.

1400 Dons Way, 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.

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