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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

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

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

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

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

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

811 Twin Peak Court Court, South Chesapeake
$600,000
4 Beds ⋅ 3 Baths ⋅ 10660090 MLS
Welcome to this stunning beautiful home nestled on a quiet cul-de-sac! From the moment you enter, you’ll appreciate the grand condition of this home, featuring 4 bedrooms, 3 full bathrooms and thoughtful updates throughout. Gorgeous hardwood floors running through the main living area and in the expansive room over the garage. At the heart of the home is a fully renovated gourmet kitchen featuring sleek white quartz countertops, premium stainless steel appliances, and ample cabinet space—flawless setting for everyday living and entertaining. Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired ensuite bath featuring dual vanities and a custom dual shower. Roof is approx. 7 years old, brand-new replacement windows, dual-zone HVAC system and encapsulated crawl space, for year-round comfort. Step outside to take in serene lake views and enjoy the peaceful backyard setting. Truly turn-key and move-in ready—schedule your tour today!

811 Twin Peak Court Court, 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

1441 Whittamore Road, South Chesapeake
$455,000
5 Beds ⋅ 2 Baths ⋅ 10659859 MLS
Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank, appliances and more. Inside, fresh modern finishes create a bright, move-in-ready home with room for everyone. Outside, the expansive acre lot opens the door to gardens, outdoor entertaining, hobbies, animals or simply having more room to enjoy the outdoors. With golf courses nearby and easy access to everything Chesapeake has to offer, this property delivers a unique blend of space, location and modern living. Nearly everything has been refreshed or replaced- just bring your furniture and start enjoying the Hickory lifestyle!

1441 Whittamore Road, South Chesapeake

1072 Mesa Loop, South Chesapeake
$500,000
4 Beds ⋅ 3.1 Baths ⋅ 10659945 MLS
Ready Now:LuxuryTownhome w/2-car garage, covered entry,fenced front yard w/gate to multi trail,covered entry. 19x12 rear deck,LVP floors select areas.2nd floor:Kitchen center island w/shiplap, GE Cafe Matte Black appliances w/refrigerator,pantry,living area w/linear fireplace w/ shiplap surround w/built ins,dining area access to covered front deck.3rd flr: Primary:tile shower 2-shower heads, dual sinks, 2 closets, 2 bedrooms, full hall bath, linen closet, laundry. 1st floor flex room/bedroom dual entry bath, mudroom. Quartz tops in kitchen and baths-designer mirrors, wood shelving in all closets. Pet Friendly. Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board. 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central location in the Greenbrier area. .

1072 Mesa Loop, South Chesapeake

632 Willow Oak Drive, South Chesapeake
$470,000
4 Beds ⋅ 2 Baths ⋅ 10659611 MLS
Welcome to 632 Willow Oak Drive, where timeless character, inviting spaces, and room to make it your own come together! This charming 4-bedroom, 2-bath brick home offers a versatile layout with two separate living areas, perfect for relaxing, entertaining, or creating spaces that suit your lifestyle. Step inside to discover warm wood accents, beautiful architectural details, and a formal dining room featuring elegant crown molding, chair rail detailing, and a chandelier. The spacious kitchen offers abundant wood cabinetry, stainless steel appliances, generous counter space, and a nearby breakfast area. The second living area is full of character, showcasing exposed wood ceiling beams, rich wood paneling, built-in shelving, and a striking brick wood-burning fireplace, fully functional and ready for cozy evenings. Three main-level bedrooms and a fourth upstairs provide flexibility for guests, hobbies, or a home office. Outside, a covered front porch welcomes you home, while the spacious, fully fenced backyard offers mature shade trees, an outdoor patio, and a storage shed. An attached garage provides additional parking and storage. With its distinctive charm, multiple gathering spaces, and opportunities to add your personal touches, this home offers a wonderful canvas for its next chapter!

632 Willow Oak Drive, South Chesapeake

817 Wickford Drive, South Chesapeake
$260,000
3 Beds ⋅ 2 Baths ⋅ 10658699 MLS
3 BEDROOM 2.0 BATH SINGLE STORY END UNIT TOWNHOME. LIVING ROOM LAMINATE WOOD FLOOR, BOOKSHELVING, LIGHTED CEILING FAN AND BRICK FIREPLACE. OPEN DINING AREA TO THE UPDATED KITCHEN, BREAKFAST BAR AREA, STAINLESS APPLIANCE PACKAGE, REFRIGERATOR, SMOOTH TOP STOVE, BUILT IN MICROWAVE/DISHWASHER, DOUBLE STAINLESS SINK. PRIMARY SUITE LIGHTED CEILING FAN AND WALK-IN CLOSET. PRIMARY BATH RAISED VANITY TUB/SHOWER. LAUNDRY AREA CABINET AND SHELVES. TWO ADDITIONAL BEDROOMS, FULL HALL BATH, TUB/SHOWER, MARBLE TOP VANITY, LVP PLANK FLOOR, MEDICINE CABINET AND OVAL MIRROR. FEATURES: NEW ROOF, NEWER PAINT AND FLOORING, DIGITAL AC THERMOSTAT, UPGRADED BLINDS, CEILING FANS, STORMDOOR, PRIVACY FENCED BACKYARD, PATIO, TREES, STORAGE SHED, SIDE BY SIDE DRIVEWAY PARKING. AVAILABLE FOR QUICK CLOSING.

817 Wickford Drive, South Chesapeake

405 Bridle Court, South Chesapeake
$485,000
4 Beds ⋅ 3 Baths ⋅ 10659847 MLS
Move-in ready and packed with so many thoughtful upgrades and extras that set it apart, this beautifully maintained 4 bed/3 FULL bath brick ranch offers so much more than meets the eye! Tucked away on a quiet cul-de-sac and sitting on a half-acre lot, the home welcomes you with a generous front porch and features a fully fenced backyard offering plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying the privacy and space. The fully renovated kitchen stuns with quartz countertops, KitchenAid professional appliances, tile backsplash, convection gas range, recessed dimmable lighting, soft-close white cabinetry, and a double pantry offering exceptional storage. A comfortable and versatile floor plan features spacious living and dining areas, A cozy den with a wood-burning fireplace provides a welcoming place to gather, while the expansive sunroom with sliding glass doors offers a bright and relaxing retreat overlooking the backyard. The finished room over the garage serves as the fourth bedroom providing flexibility and privacy for guests, a home office, or additional living space. The impressive list of extras continues with a new HVAC system, extra large fire-pit, an oversized garage, a large detached storage shed, large walk-in attic for additional storage and wiring for a backup generator. Don't miss out on your chance for this truly a one-of-kind gem!

405 Bridle Court, 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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