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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 cabanas. 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, and a rear-loading two-car garage. Step inside to a welcoming foyer with wood flooring, 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. 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 a jetted tub, separate 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. Step outside to the rear patio, accessible from the breakfast area, offering space for outdoor dining and relaxation. Enjoy Warrington Hall's community amenities, including a swimming pool, tennis courts, playgrounds, walking 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

409 Cairns Road, South Chesapeake
$729,900
4 Beds ⋅ 2.1 Baths ⋅ 10660244 MLS
Make this your first stop! Pride of ownership shines throughout this immaculate Hickory Landing home that has been exceptionally cared for by the seller. The open floor plan offers a great flow between the living spaces, with updated flooring and fresh paint throughout giving the home a clean, move-in-ready feel. The spacious kitchen features granite countertops, a large island, gas range, butler's pantry, and plenty of cabinet space. The primary suite offers generous closet space and a beautifully tiled ensuite bath, while the additional bedrooms provide plenty of room for family or guests. Step outside to your own backyard oasis featuring an in-ground pool, putting green, quality storage shed, and plenty of space to entertain. Located in the highly sought-after Hickory School District, this home offers the space, condition, and location you've been looking for!

409 Cairns Road, South Chesapeake

891 Bells Mill Road, South Chesapeake
$525,000
4 Beds ⋅ 3.1 Baths ⋅ 10660202 MLS
Welcome Home! Privacy, functionality, and convenience come together in this exceptional Grassfield property! Set back from the street along a private driveway, this nearly one-acre property is surrounded by mature woods and lush greenery. Inside, fresh paint and a flexible floor plan offer something for everyone. A rare find, the home features two distinct main-level suites, including an in-law suite with its own living room, great for multi-generational living, extended guests, a fifth bedroom, or home office. The primary bathroom features live-edge wood countertops, dual showerheads, and a custom walk-in closet system. Outside, enjoy a storage shed, chicken coop, separate hookups for a future pool and hot tub, and a massive detached two-car workshop/garage with carport and RV hookup. Over $17,000 in crawlspace work has been completed, and a survey is available in the listing documents. A truly unique Grassfield property offering flexibility and room to make it your own!

891 Bells Mill Road, South Chesapeake

1451 Rollesby Way, South Chesapeake
$330,000
2 Beds ⋅ 2.1 Baths ⋅ 10660184 MLS
Lovely 2 primary bedroom condo with an extra room on the 1st floor in the lovely Greenbrier area. Lot's of upgrades throughout and very well cared for. A better deal than todays new construction! Newer LVP flooring on the 1st floor and newer plush carpet on the 2nd floor. Lovely kitchen with stainless appliances and solid surface countertops. Newer updated paint throughout. Priced to sell quickly! Condo fee of $387 covers water, sewer, trash pick up, landscaping, access to the neighborhood pool, and even the roof maintenance. This area is super convenient to the mall, golf course, bases, shopping, schools, churches and just a short way to the interstate. An awesome place to call home! Beautiful easy care living. Don't miss this beauty!!!

1451 Rollesby Way, South Chesapeake

1605 Mary Lou Lane, South Chesapeake
$475,000
3 Beds ⋅ 2.1 Baths ⋅ 10659685 MLS
Welcome to 1605 Mary Lou Lane in Cardinal Meadows! Built in 2022, this beautifully maintained condo feels brand new, with new carpet throughout and nearly 2,300 sq. ft. of stylish, low-maintenance living. The bright, open main level features high ceilings and a gorgeous kitchen with upgraded cabinetry and quartz countertops. A builder upgrade provides a larger first-floor primary suite and upstairs bedrooms than most homes in the community! The primary suite features a dual-vanity bath and walk-in closet. Upstairs offers a versatile loft, two bedrooms with walk-in closets, a full bath, and walk-in storage with potential for future finished space. Enjoy your private oasis with a newly fenced backyard backing to peaceful woods. Community amenities include a pavilion with grill, splash pad, playground, dog park, and walking trails. Conveniently located near Grassfield schools, shopping, and major interstates. Move-in ready!

1605 Mary Lou Lane, South Chesapeake

609 Edgewood Arch, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10660136 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

1128 Plantation Lakes Circle, South Chesapeake
$635,000
5 Beds ⋅ 3 Baths ⋅ 10658679 MLS
Spacious 5-bedroom, 3-full-bath home offering approximately 2,800 square feet in Chesapeake's desirable Plantation Lakes neighborhood! Featuring a generous floor plan with formal living and dining rooms, a large family room with custom built-ins, and an inviting kitchen with granite center island, breakfast bar, and plenty of room to gather. The primary suite offers a jetted tub and separate shower, while the finished room over the garage provides additional flexible living space. Step outside and enjoy your own backyard retreat featuring an above ground swimming pool, deck, and privacy-fenced yard. Additional highlights include a welcoming front porch, attached 2-car garage, and solar panels for potential energy savings. Conveniently located in the Greenbrier area near shopping, dining, and major commuter routes. Home, swimming pool, and all appliances convey AS IS. Solar panels will be paid off at closing.

1128 Plantation Lakes Circle, 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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