Refine Search
Sort by
301 Sikeston Lane, South Chesapeake
$449,000
4 Beds ⋅ 3 Baths ⋅ 10660542 MLS
Welcome home to this luxurious 4-bed, 3 full bath home located in the highly sought-after Great Bridge school district. The open floorplan is enhanced by 9-foot ceilings on both levels, recessed lighting, and plenty of natural light. The kitchen serves as the heart of the home, offering a large island, quartz countertops, and stainless-steel appliances— for both entertaining and everyday living. Upstairs, enjoy freshly installed carpet throughout, convenient upstairs laundry room, and a spacious primary suite that features both a generous walk-in closet and spa-like bathroom complete with a soaking tub, oversized shower, and double vanity. Additional highlights include a covered porch, relaxing back patio, and attached garage with extra driveway parking. Conveniently situated near interstates, shopping, schools, and military bases, this home combines modern style with low-maintenance living—an ideal opportunity to own in one of Chesapeake’s most desirable communities!

301 Sikeston Lane, South Chesapeake

1336 Hillside Avenue, South Chesapeake
$508,500
4 Beds ⋅ 2 Baths ⋅ 10660500 MLS
Welcome to this beautifully maintained Stonegate home featuring 4 bedrooms, 2 full baths and 1,811 sq. ft. of inviting living space! A special highlight is the additional 260 sq. ft. glass-enclosed sunroom filled with natural light, complete with its own Trane mini-split heating and cooling system and access from both the living room and primary bedroom. Inside, vaulted ceilings, fresh paint, rich wood-tone flooring in the living room, dining area and hallway, and updated kitchen/bathroom lighting create a warm feel. The kitchen features granite countertops and new stainless steel appliances. Enjoy the backyard with an inground saltwater pool, privacy fence and spacious deck for relaxing or entertaining. Fresh carpet on the stairs and finished room over the garage. Additional features include a whole-house Generac generator, well with inground sprinkler system and 2-car garage. So much to enjoy both inside and out. Come see for yourself what makes this Stonegate home amazing!

1336 Hillside Avenue, South Chesapeake

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

2101 English Avenue, Central Chesapeake
$429,900
4 Beds ⋅ 2.1 Baths ⋅ 10660643 MLS
Like new spacious 4-bedroom, 2.5-bath Chesapeake home located on a corner lot offers nearly 2,000 square feet of comfortable living space with a modern, open floor plan designed for everyday living and entertaining. Enjoy generous living areas, a welcoming kitchen with new refrigerator, stove and microwave offering peace of mind and plenty of room to gather. The upstairs boasts four bedrooms offering flexibility for guests, a home office, or whatever fits your lifestyle. The attached garage provides convenient parking and additional storage, while the private backyard offers outdoor space for entertaining and relaxing. Conveniently located near shopping, restaurants, entertainment, and military bases, this home combines space, comfort, and accessibility in a great Chesapeake location. Don't miss your opportunity to make it yours!

2101 English Avenue, Central 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

2012 Lockard Avenue, Central Chesapeake
$265,000
3 Beds ⋅ 1.1 Baths ⋅ 10660506 MLS
Opportunity awaits in this spacious 3-bedroom, 1.5-bath brick ranch! Offering a functional layout with plenty of room to spread out, this home features a welcoming living room, eat-in kitchen, separate den for additional living space, and a dedicated utility/laundry room. Outside, you’ll find a backyard with a storage shed for added convenience. With solid bones, a great floor plan, and plenty of potential, this home is an excellent opportunity for someone looking to add their personal touch. While some cosmetic updates could make this home truly shine, it is priced accordingly, offering a fantastic chance to build equity and make it your own. Don’t miss the opportunity to see the possibilities this home has to offer!

2012 Lockard Avenue, Central 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

1931 Martin Avenue Unit Ave, Central Chesapeake
$295,000
3 Beds ⋅ 2 Baths ⋅ 10660535 MLS
Welcome to 1931 Martin Avenue! This refreshed 3 bedroom, 2 bathroom ranch offers nearly 1,200 square feet of comfortable, single-level living in Chesapeake. Featuring a brand new roof, new flooring, and fresh paint throughout, this home has been updated with some of the big-ticket improvements already taken care of! The functional floor plan offers a comfortable living area, spacious bedrooms, and a primary suite with its own private bathroom. Outside, enjoy a fenced backyard with room to relax, entertain, or make it your own. Conveniently located near shopping, dining, major highways, and everyday amenities, this home offers a great combination of updates, convenience, and affordability. Schedule your private showing today!

1931 Martin Avenue Unit Ave, Central 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

909 Railroad Avenue, Central Chesapeake
$399,000
3 Beds ⋅ 2.1 Baths ⋅ 10660618 MLS
The Crossing @ Wilmund Place-A welcoming Neighborhood of 19 new homes, thoughtfully designed to create a place to call home. AND Seller will pay up to $12,000 in CC with preferred lender and attorney. This beautiful 3-bedroom, 2.5-bath home offers 1,654 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday living. Inside, the kitchen shines with soft-close cabinets and granite countertops. Bathrooms are appointed with granite countertops and soft-close cabinetry for a cohesive, upscale look. Throughout the home you'll find a blend of durable LVP flooring and plush carpet. Tray ceiling in the primary bedroom with walk-in closet. Also features a 1-car garage, porch and patio. Perfect blend of comfort, style, and convenience. Don't miss your chance to own in the heart of Chesapeake!

909 Railroad Avenue, Central 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

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.

Copyright 2026 NCRMLS. All rights reserved. North Carolina Regional Multiple Listing Service, (NCRMLS), provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. NCRMLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of NCRMLS.

How much is your home worth?

Get instant property value now!