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616 Big Bear Lane, South Chesapeake
$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10661465 MLS
There’s something special about living in Culpepper Landing, where charming streets, welcoming neighbors, and an incredible sense of community make everyday life feel a little different. Welcome to 616 Big Bear Lane! Beyond your front door, discover a neighborhood designed for connection and enjoyment. Spend summer afternoons at the resort-style pool, stay active at the fitness center, enjoy the walking paths, or gather with friends at the clubhouse. From neighborhood celebrations to regular social events, there’s always something bringing this community together. Tree-lined streets, sidewalks, playgrounds, and dog parks add to the appeal, while convenient access to shopping, dining, interstates, and military bases makes daily life easy. With a new elementary school scheduled to open for the 2027–2028 school year, the community continues to grow! Here, you’re not simply buying a home; you’re becoming part of a community you’ll love coming home to.

616 Big Bear Lane, 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

2203 Edwin Drive, South Chesapeake
$563,640
2 Beds ⋅ 3 Baths ⋅ 10656645 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.

2203 Edwin Drive, South Chesapeake

2172 Edwin Drive, South Chesapeake
$563,640
2 Beds ⋅ 3 Baths ⋅ 10654634 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.

2172 Edwin Drive, South Chesapeake

2170 Edwin Drive, South Chesapeake
$563,640
2 Beds ⋅ 3 Baths ⋅ 10654633 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.

2170 Edwin Drive, South Chesapeake

2160 Edwin Drive, South Chesapeake
$563,640
2 Beds ⋅ 3 Baths ⋅ 10654631 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.

2160 Edwin Drive, South Chesapeake

737 Willow Oak Drive, South Chesapeake
$560,000
4 Beds ⋅ 2 Baths ⋅ 10656926 MLS
This one checks ALL the boxes! Immaculate, beautifully updated, and exceptionally well maintained, this 4 bedroom, 2 bath Chesapeake home truly stands out. The remodeled kitchen features stainless steel appliances, a gas range and hood, beautiful countertops and backsplash, abundant cabinetry, eat-in space, and a custom butler’s pantry. Recessed lighting throughout enhances the bright, modern feel, while the inviting living room showcases beautiful hardwood floors, a large cozy fireplace, and abundant natural light. The separate dining room is ideal for everyday meals and entertaining. The primary suite features an impressive custom designed en-suite bathroom with gorgeous custom cabinetry, double vanity, and an oversized walk-in shower. Outside, enjoy a large, beautifully manicured backyard and expansive deck. An attached garage plus an impressive, detached 2 story garage provides exceptional space for vehicles, hobbies, storage, or a workshop. This home truly has it all! Now offering $10k towards closing cost or rate buy down with full price offer.

737 Willow Oak Drive, South Chesapeake

3204 Eight Star Court, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10656875 MLS
Now This Is a Place You Can Call Home! This beautiful 4-bedroom, 2.5 bath home is nestled on a quiet cul de sac, offering space, comfort, and charm. Featuring a grand two-story foyer, hardwood flooring throughout the first floor, formal living and dining rooms, and a spacious gathering room with a cozy gas fireplace. The eat in kitchen boasts 42-inch cabinets, generous counter space, and a custom backsplash. Enjoy the large sunroom with vaulted ceilings, perfect for relaxing or entertaining. The spacious primary suite features a sitting area, walk in closet, double sink vanity, jetted tub, and separate shower. A huge backyard offers plenty of room for outdoor fun and gatherings, plus a storage shed. This home has it all! Schedule your showing today and make it yours!

3204 Eight Star Court, South Chesapeake

1108 Shell Road, South Chesapeake
$558,000
5 Beds ⋅ 3 Baths ⋅ 10658985 MLS
Welcome to the kind of home that feels good the moment you enter. Set on just over 2 peaceful acres, this 5-bed, 3-bath home offers the perfect blend of space, comfort, and modern style. Sunlight pours through the windows, filling every room with warmth, while the open layout creates an easy flow for everyday living and gathering with the people you love. The home features two spacious primary suites, one located on the first level, both with private baths and large closets, making it ideal for guests, or multigenerational living. You'll also love the luxury vinyl plank flooring, granite countertops, stainless steel appliances, and the beautiful laundry room! The backyard is just as inviting. Whether you're roasting marshmallows around the fire pit, spending summer afternoons in the saltwater pool, or simply enjoying the quiet views with your morning coffee, the backyard feels like your own private escape. Peaceful, welcoming, and full of room to grow! *One year Choice home warranty

1108 Shell Road, South Chesapeake

122 Lenas Way, South Chesapeake
$555,900
3 Beds ⋅ 3.1 Baths ⋅ 10658772 MLS
$15,000 for Buyer to use for permanent rate by down, closing cost or options with use of builder trusted lender/attorney! Ready for NEW YEAR! Minutes to Greenbrier - GPS Joseph’s Meadow: 369 Scotland Lane or TOUR model home: 910 Bernard Ln. Award-winning builder - Elegant END Row home with upgraded building package - Airy 10’ ceilings with 9’ lower and upper floors - Oversized windows - Extensive hardwood - First-floor bedroom w/ensuite bath - 10x20 Covered porch and front porch - Chef’s kitchen: 10’ island, quartz counters, Custom hood, GE Cafe appliance package - Luxurious primary retreat w/two custom closets - Spa bath oversized tiled shower, dual heads, large niche and Dual vanities - Large laundry room - Secondary petite suite w/huge closet and ensuite bath - Nat. Gas Tankless water heater - Massive storage in finished insulated 2-car garage - Professional ground maintenance! Easy living!

122 Lenas Way, South Chesapeake

1102 Loxdell Court, South Chesapeake
$555,000
4 Beds ⋅ 2 Baths ⋅ 10660093 MLS
Don't miss this stunning ranch tucked away on a cul-de-sac in one of Chesapeake's most sought-after communities within the Hickory School District. Situated on a quarter-acre lot, this beautifully updated home features an open-concept floor plan, granite countertops, renovated bathrooms, and a spacious finished room over the garage. A hidden bookcase door reveals a unique bonus space perfect for a playroom, home office, guest suite, or media room. Additional highlights include a hypoallergenic HVAC system, encapsulated crawl space, whole-yard irrigation system, and walk-in attic with potential for future expansion. Thoughtfully maintained and filled with upgrades throughout, this home offers the perfect combination of comfort, character, and functionality.

1102 Loxdell Court, South Chesapeake

933 Brenner Road, South Chesapeake
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10661011 MLS
This beauty is PACKED with upgrades and truly feels brand new! Gorgeous hardwood flooring, cased windows, upgraded moldings, and beautiful finishes throughout set this home apart! The stunning kitchen features gas cooking, a large island, soft-close cabinetry, quartz countertops, and stylish backsplash. Upstairs, the spacious primary suite impresses with a tray ceiling, crown molding, separate tub and shower, walk-in closet, plus a second oversized closet! Generously sized secondary bedrooms offer ample storage. Enjoy a 2-car garage with EV 240V outlet, whole-house surge protector, and low-maintenance fenced backyard. Convenient to military bases, shopping, dining, and interstate access. AND THE BONUS, A VA assumable loan at 5.5% interest, subject to servicer approval and buyer qualification! All the upgrades without the new construction wait!

933 Brenner Road, South Chesapeake

1504 Prospect Drive, South Chesapeake
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10657158 MLS
Location, Size and Schools...what more can you ask for! Nestled on a spacious lot in a desirable cul-de-sac setting, this wonderful 4-bedroom, 2.5-bath home offers 2,560 square feet of comfortable living space, well designed for everyday living... indoors and out. Come inside and discover a welcoming floor plan which includes a separate living and dining room, a Large eat-in chef's kitchen that opens seamlessly to the family room, creating the perfect gathering space for everything from casual mornings and memorable celebrations. Did I mention...No HOA...which means no restrictions or extra fees. With its generous living spaces, inviting layout, and exceptional lot, this home offers the lifestyle you've been looking for.

1504 Prospect Drive, South Chesapeake

408 Brandon Way, South Chesapeake
$549,900
5 Beds ⋅ 3 Baths ⋅ 10661712 MLS
Welcome home to this immaculate meticulously maintained original owner home in sought after Clearfield Estates. Numerous improvements gas water tank 10/26, LG Refrigerator 5/26, dishwasher 3/26, windows 12/25, roof 30-year architectural 10/23, AC 2013. Triple French patio door looks out to expansive private .30 acre back yard. First floor guest bedroom with full bath, first floor features Brazilian engineered wood floors, open concept with cozy gas fireplace, 4 additional spacious second floor bedrooms including a massive 14.5 X 28 FROG with walk in attic & built ins great for entertaining! Spacious primary features a cathedral ceiling large walk in closet, duel vanities and jetted tub. Central Greenbrier location with easy commute to multiple bases, VB and Norfolk. Sq ft per tax record

408 Brandon Way, 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

404 Niles Court, South Chesapeake
$549,900
4 Beds ⋅ 2.1 Baths ⋅ 10660000 MLS
Welcome home to this beautiful 4 bedroom, 2.5 bathroom, two story home with an attached 2 car garage! The first floor offers a gorgeous, updated kitchen with a charming breakfast nook overlooking the backyard, along with spacious living and dining areas that are perfect for family dinners and entertaining guests. Upstairs, you'll find four generously sized bedrooms, including a lovely primary suite complete with a large walk in closet and a private, spa inspired bathroom with a double vanity set up. Step outside to enjoy the backyard, featuring a spacious deck and a nicely sized yard with plenty of room for pets, outdoor activities, and gatherings. A storage shed provides additional space for all your outdoor essentials. With its inviting layout, generous living spaces, and wonderful outdoor features, this home is ready to welcome its next owners!

404 Niles Court, South Chesapeake

616 Rutherford Drive, South Chesapeake
$549,900
3 Beds ⋅ 1.1 Baths ⋅ 10657745 MLS
Well-maintained, move-in-ready brick ranch in an established neighborhood with wide sidewalks! Features attractive LVP flooring throughout, three bedrooms, and a primary suite with a walk-in closet. Enjoy the gas log fireplace and additional storage with floored attic space. The converted attached garage is currently equipped as a beauty salon with styling station, shampoo sink, built-in cabinetry, and laundry area. A bright 20' x 20' sunroom with three walls of casement windows overlooks the backyard. Outdoor amenities include a 20' x 20' composite deck, fenced yard, and a 20' x 40' in-ground pool with cover. The detached three-bay garage includes power, workbenches, and pull-down access to a large, floored attic. A rare combination of comfort, functionality, and exceptional indoor and outdoor living space.

616 Rutherford Drive, South Chesapeake

144 Downing Drive, South Chesapeake
$549,900
4 Beds ⋅ 3 Baths ⋅ 10655754 MLS
Welcome to 144 Downing Drive in sought-after Hickory, Chesapeake! This spacious & well-maintained 4-bed, 3 full-bath, brick & vinyl ranch offers plenty of flexible living space on a .27-acre lot. The inviting great room features a vaulted ceiling & fireplace, while the spacious kitchen offers granite countertops, abundant cabinetry, stainless steel appliances, breakfast area, & bright sunroom. The finished room over the garage with a full bath offers excellent flexibility for an in-law suite, guest space, home office, or bonus room. Enjoy a fenced backyard built for entertaining with a deck & above-ground pool. Additional highlights include an attached 2-car garage & generous driveway parking space. Located in the desirable Tunbridge Station community with NO HOA and convenient access to Hickory schools, shopping, entertainment, dining, military bases, & major routes to get around Hampton Roads. Schedule your private showing today!

144 Downing Drive, South Chesapeake

552 Saddlehorn Drive, South Chesapeake
$549,900
3 Beds ⋅ 2 Baths ⋅ 10654878 MLS
Set on approximately 1.5 beautiful acres, this well-maintained brick ranch offers comfortable living with room to enjoy the outdoors, pursue hobbies, and make it your own. Closing cost assistance and/or interest-rate buydown are negotiable with acceptable offer. Inside you’ll find 3 bedrooms and 2 full baths, custom closet systems, a thoughtfully designed kitchen with a large island and abundant cabinet storage, and a newly renovated mudroom/laundry room! A climate-controlled two-story attached 2-car garage/workshop provides space for vehicles, projects, and hobbies, with upstairs flex space for more options. Step outside and the property truly comes to life. Entertain, relax or just enjoy the privacy of your own space on the new deck. A raised bed garden, chicken run, grape arbors, barn, and storage shed add character and functionality. Located in desirable Hickory School District, just 20 minutes from Redmill and Landstown commons!

552 Saddlehorn Drive, South Chesapeake

1916 Orangewood Road, South Chesapeake
$549,900
4 Beds ⋅ 2.1 Baths ⋅ 10649467 MLS
Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or future entertaining. Recent updates provide added value and peace of mind, including a new hot water heater (2026), new air conditioner condenser (2025), new living room carpet (2026), updated downstairs toilet (2026), and new primary bathroom faucets (2026). Outdoor improvements include a back patio (2020), new back porch (2023), and new front porch/deck stairs (2024), creating welcoming spaces to enjoy both the front and backyard.

1916 Orangewood Road, South Chesapeake

907 Jennings Ln, South Chesapeake
$548,900
3 Beds ⋅ 3.1 Baths ⋅ 10661597 MLS
Better than NEW! Built in 2025 by award-winning Stephen Alexander, this beautiful 3BR/3.5BA, 3-story end-unit townhome is filled with thoughtful upgrades and charm! From the moment you enter, the spacious foyer, wide stairway, tall ceilings, and oversized windows create a bright, welcoming feel. The open-concept living area flows into a gorgeous chef's kitchen featuring a large island, beautiful finishes, and a custom-built cabinetry nook that adds both character and function. With a first-floor bedroom and two bedrooms featuring private ensuite baths, the layout offers flexibility and comfort. Storage is no afterthought here, with generously sized closets throughout! Enjoy your morning coffee or unwind after a long day on the screened porch. Plantation shutters and additional attic insulation are just a few of the upgrades already in place. Conveniently located near highways, shopping, dining, breweries, and everyday essentials. Zoned for Great Bridge schools. PLUS, a potential rate buydown incentive is available with a local lender! Welcome HOME!

907 Jennings Ln, South Chesapeake

908 Jennings Ln, South Chesapeake
$545,900
3 Beds ⋅ 3.1 Baths ⋅ 10648688 MLS
NOVEMBER MOVE IN - $12,500 closing costs*, Low Loan Rate, No PMI! End Unit! Modern Design UPGRADES GALORE! Built by award-winning builder. Stunning home with curated features uniquely designed in this home. Extensive Mohawk flooring mid-level with Gourmet Kitchen with Custom hood, 10’ island, Quartz counters, GE Cafe 6 Burner Gas range, GE Cafe Dishwasher, and GE Cafe Microwave Drawer. 10' ceilings main, 9' First & Third Floors, Nat. Gas Tankless water heater, 2-zone HVAC. Primary bedroom with 2 custom closets and Spa ensuite bath. Second Petite Suite with ensuite bath and large walk-in closet. Large laundry room w/linen closet. First floor bedroom with ensuite bath! Extend your living on oversized Screened covered porch with composite decking. 2-car garage! LOW $95 condo fee- Cabana, Fire pits, Bocce ball and Professional landscape and lawn maintenance for easy living! Legacy is waiting for you!

908 Jennings Ln, South Chesapeake

1021 Grantham Lane, South Chesapeake
$545,000
4 Beds ⋅ 2 Baths ⋅ 10656531 MLS
Loved by one owner for years, this meticulously maintained home in sought-after Etheridge Woods is competitively priced with some minor updating in mind — a rare opportunity to make it truly your own! Hardwood floors flow through the living room, dining room, primary bedroom, and family room, while granite counters shine in the kitchen and guest bath. The kitchen's breakfast area overlooks the backyard and opens to a spacious family room with vaulted ceilings and skylights, filling the space with natural light. Just off the family room, the FROG/4th bedroom offers flexible space for guests, a home office, or playroom. Enjoy a screened-in section of the front porch and a deck out back, perfect for entertaining. Zoned for Hickory/Butts Road schools and just minutes from major highways and shopping. Schedule your showing today!

1021 Grantham Lane, South Chesapeake

1044 Olmstead Street, South Chesapeake
$544,900
4 Beds ⋅ 3.1 Baths ⋅ 10648745 MLS
Welcome to 1044 Olmstead St in Chesapeake! This almost new home was built in 2022 & still feels like new! Featuring 4 bedrooms, 3.5 bathrooms spread out over 2337sq ft. Entering into the home from your covered front porch you will be greeted by natural sunlight beaming into the foyer. A home office/flex space is on the left & a half bath & laundry room on the right. Proceeding to the rear of the home you will walk into the open floor plan style kitchen w/a large island w/ seating for 4, stainless appliances & granite tops. With no walls separating the kitchen, living room, & formal dining room spending quality time w/ friends & family is easy in this space. Upstairs you will find all 4 bedrooms to be good sized with the primary bedroom being oversized w/a large walk-in closet, an en-suite bathroom w/ soaking tub, a separate shower area, & double sinks. The room over the garage is the 4th bedroom & has its own separate entrance w/a dedicated full bathroom. Call to schedule your showing!

1044 Olmstead Street, 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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