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1555 Rollesby Way Unit 5, South Chesapeake
$315,000
3 Beds ⋅ 2.1 Baths ⋅ 10647123 MLS
Welcome home to this charming 3 bedroom, 2.5 bath condo in the heart of Greenbrier, offering the perfect blend of comfort, convenience, and low maintenance living. The thoughtfully designed floor plan features a first floor bedroom and half bath, potentially for guests, a home office, or flexible living. The spacious kitchen is equipped with granite countertops, rich cherry wood cabinetry, abundant counter space, and a breakfast bar that's for everyday living or entertaining. Upstairs, both bedrooms offer private en suites and walk in closets. The primary suite features a relaxing Jacuzzi style soaking tub, a separate shower, and plenty of space to unwind. An upstairs laundry room, complete with the washer and dryer, adds everyday convenience. Step outside to your private patio with an attached storage unit, providing additional space for your outdoor essentials. The condo association covers water, trash, landscaping, access to the community pool, and individual roof maintenance, making homeownership even easier. Conveniently located just minutes from Greenbrier Mall, golf courses, shopping, dining, schools, and major interstates, this move in ready home offers the ideal combination of location, comfort, and carefree living. Schedule your private tour today!

1555 Rollesby Way Unit 5, South Chesapeake

1933 Reefwood Road, South Chesapeake
$610,000
4 Beds ⋅ 3.1 Baths ⋅ 10644569 MLS
100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, South Chesapeake

143 Harbor Watch Drive, South Chesapeake
$350,000
3 Beds ⋅ 3 Baths ⋅ 10643626 MLS
Experience waterfront living at its finest in this well maintained and beautifully updated condo on the Elizabeth River. Featuring LVP flooring throughout, this residence offers a seamless blend of style and durability. The updated kitchen shines with quartz countertops and stainless steel appliances, flowing effortlessly into the living space anchored by a cozy gas fireplace. The oversized primary suite is a true retreat, complete with a stunning en-suite bath showcasing floor-to-ceiling tile, dual sinks, and a new vanity with updated countertops. Two additional baths have been fully renovated with modern finishes. Go outside to your covered rear deck and take in serene water views, perfect for relaxing or entertaining. Community amenities include a pool, boat slip access, clubhouse, and more, offering a lifestyle of comfort and convenience.

143 Harbor Watch Drive, South Chesapeake

1301 Simon Drive, South Chesapeake
$1,000,000
6 Beds ⋅ 4.1 Baths ⋅ 10632029 MLS
Luxury Redefined at 1301 Simon Drive Experience the pinnacle of Chesapeake living in this custom 4,767 sq. ft. brick estate. Nestled on a spacious corner lot in Greenbrier, this 6-bed, 4.5-bath masterpiece blends timeless elegance with modern high-tech luxury. The Interior Experience: Chef’s Dream: Gourmet kitchen with high-end appliances and a sleek wet bar. Grand Design: Cathedral ceilings and a dramatic winding staircase. Your Private Oasis: Step outside to a brand-new, gorgeous pool oasis. Whether you're hosting a summer gala or a quiet evening by the water, this backyard is designed for pure relaxation. The Bells & Whistles: Oversized 3-car garage. Lavish primary suite with a champagne bubble spa-tub. Premium finishes throughout. 1301 Simon Drive | Luxury is in the details.

1301 Simon Drive, South Chesapeake

716 Crestfield Drive, South Chesapeake
$799,350
4 Beds ⋅ 3.1 Baths ⋅ 10614522 MLS
Somerset Ranch with 4th bedroom/FROG for that extra media room or guest suite. Experience the perfect blend of modern design & customizable luxury. The Owner’s Retreat is a sanctuary at the rear of the home featuring a massive walk-in closet & a spa-inspired bath with a soaking tub & separate shower. The heart of the home boasts a chef-inspired kitchen with a generous island, flowing seamlessly into the main living areas. A front-of-house flex room serves as a formal dining room or a quiet home office. Enhance your hosting with the optional butler’s pantry! Fenced backyard includes large patio for outdoor entertaining. Seller will pay up to $10,000 in closing costs with preferred lender—ask agent for details. Buyer must register agent on or before 1st visit or 1st substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & video are of a completed home, finishes, elevation & upgrades may vary.

716 Crestfield Drive, South Chesapeake

940 Sydenham Boulevard, South Chesapeake
$730,000
5 Beds ⋅ 3 Baths ⋅ 10651092 MLS
Welcome to this exceptional five bedroom residence in the desirable Etheridge Lakes community, where spacious interiors, abundant natural light, and serene lake views create an inviting retreat. Designed with both everyday living and entertaining in mind, the home features vaulted ceilings and a thoughtfully appointed layout with multiple spaces to gather and unwind. The home offers a dining room, sitting room, and comfortable living room anchored by a cozy fireplace and built in shelving. At the heart of the home, the spacious kitchen provides generous cabinetry and counter space, stainless steel appliances, and convenient counter seating. Five spacious bedrooms provide generous closet space, complemented by three full bathrooms. The screened porch, sunroom, patio, and expansive backyard overlook the lake, creating a beautiful backdrop for relaxing, gathering, and enjoying the home’s natural surroundings. Thoughtfully designed for both comfort and connection, this home offers a wonderful blend of beautiful views, and inviting spaces to enjoy throughout the seasons.

940 Sydenham Boulevard, South Chesapeake

917 Redleafe Circle, South Chesapeake
$788,000
5 Beds ⋅ 3 Baths ⋅ 10648827 MLS
Beautiful brick home in the desirable Greystone Community! This spacious home features a formal living room, dining room, two-story great room with a double-sided fireplace shared with the sunroom, and a main-level primary suite with a large ensuite bath and walk-in closet. An additional first-floor bedroom is currently used as an office, with three more bedrooms upstairs. The kitchen offers an island gas cooktop, double ovens, a microwave, and pantry. Enjoy the fenced backyard with an updated deck overlooking protected, unbuildable woodlands for added privacy. Recent updates: HVAC and furnace (2021), whole-house generator (2021), windows replaced (2022), exterior trim painted (2025), new gas cooktop to be installed and new roof to be replaced Sept 21st.(2026)

917 Redleafe Circle, South Chesapeake

514 Waters Road, South Chesapeake
$539,000
5 Beds ⋅ 3.1 Baths ⋅ 10647572 MLS
Welcome home to this beautifully updated 5-bedroom home, where thoughtful upgrades and spacious living come together perfectly. The heart of the home is the stunning kitchen featuring quartzite countertops, a Sub-Zero refrigerator, butler's pantry, and an open layout overlooking the dining area and expansive family room—great for entertaining and everyday living. A first-floor bedroom with its own private en-suite bath offers the perfect space for guests or multi-generational living. Upstairs, retreat to the impressive primary suite with vaulted ceilings, a generous sitting area, and a walk-in closet. Convenient second-floor laundry includes a granite folding counter for added functionality. Enjoy abundant parking with a half-moon driveway plus additional gravel parking. Generator conveys as-is; sellers have never used it. 1.5% closing cost assistance with a full priced offer!

514 Waters Road, South Chesapeake

1220 Kidbrooke Street, South Chesapeake
$863,589
6 Beds ⋅ 4.1 Baths ⋅ 10632716 MLS
Welcome to the Tillman at Riverview Landing! This property is great for multigenerational families! The spacious home includes 6 bedrooms, 4.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy for guests, teens, or extended family. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. This house is complete with a basement. Photos are from the builder's library, actual finishes and features may vary.

1220 Kidbrooke Street, South Chesapeake

910 Jennings Ln, South Chesapeake
$550,950
4 Beds ⋅ 3.1 Baths ⋅ 10617027 MLS
Fall delivery! CHOOSE your MOOD to style your home with UPGRADES GALORE! Built by award-winning builder. Stunning home with curated features uniquely designed. 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!

910 Jennings Ln, South Chesapeake

3117 Kenelm Drive, South Chesapeake
$329,000
3 Beds ⋅ 2 Baths ⋅ 10652903 MLS
Welcome Home to Deep Creek! Don’t miss this charming and well-maintained 3-bedroom, 2-bath ranch-style home nestled in an established neighborhood. Offering approximately 1,388 square feet of comfortable living space, this home has plenty of room to live, work, and entertain. The home features a spacious living room and a versatile flex room that can easily be used as a home office, playroom, second living area, hobby space, or whatever best fits your lifestyle. The spacious bedrooms offer plenty of room for comfort, while the kitchen includes a convenient eat-in area perfect for everyday meals. Step outside to the huge, fully fenced backyard, offering plenty of space for entertaining, outdoor gatherings, pets, gardening (check out the fruit trees), or simply relaxing and enjoying the outdoors. With its flexible floor plan, spacious backyard, and convenient Deep Creek location, this home is ready for its next owner. Schedule your private showing today!

3117 Kenelm Drive, South Chesapeake

3405 Parr Lane, South Chesapeake
$450,000
4 Beds ⋅ 2 Baths ⋅ 10650919 MLS
Looking for a lovingly maintained brick ranch where care is evident inside & out? This pristine 4-bedroom, 2-bath ranch blends timeless character with thoughtful updates & an open, functional layout. Feel the difference of real hardwood floors underfoot as you explore room to room. Recessed lighting, granite counters, a gas fireplace & new dishwasher add style & comfort. Storage? An expansive walk-in attic runs the full length of the house. Outside, professional landscaping & meticulous grounds reflect true pride of ownership. Improvements are too numerous to list, but highlights include replacement windows & siding, extensive vinyl & aluminum exterior wrapping, and seamless gutters with guards. And under the house? A new dehumidifier helps keep the crawl space crisp, clean & dry, with an annual termite contract in place. With Deep Creek continuing to grow & evolve, this is your chance to own an exceptional value, something long-lasting, well cared for & truly special!

3405 Parr Lane, South Chesapeake

3410 Marla Court, South Chesapeake
$590,000
5 Beds ⋅ 2.1 Baths ⋅ 10648409 MLS
Welcome to 3410 Marla Court, tucked away on a quiet cul-de-sac in the sought-after Millers Run community of Chesapeake. Built in 2004, this beautifully maintained 5-bedroom, 2.5-bath home offers over 3,156 square feet of thoughtfully designed living space, combining generous room sizes with modern updates and a fantastic private setting. Brand new roof being installed 2026. Fresh paint with newer luxury vinyl plank flooring, the home features an inviting open floor plan that's for both everyday living and entertaining. The spacious family room flows seamlessly into the updated eat-in kitchen, offering abundant cabinetry, ample counter space, high-end stainless-steel appliances and plenty of room for family gatherings. A first-floor bedroom provides excellent flexibility as a guest room, home office, or playroom. Upstairs, the spacious primary suite features a walk-in closet and a private ensuite bath with dual vanities, while the updated hall bathroom has a new walk-in shower which adds a stylish touch for family and guests alike. A two-zone HVAC system helps keep the home comfortable year-round. Step outside to enjoy the screened-in porch overlooking a huge, fully fenced backyard that backs to peaceful woods, creating a private retreat for relaxing, entertaining, or letting children and pets play. Offering space, privacy, modern updates, and a desirable cul-de-sac location, this exceptional Millers Run home is ready to welcome its next owners.

3410 Marla Court, South Chesapeake

2410 Payne Road, South Chesapeake
$292,500
2 Beds ⋅ 2 Baths ⋅ 10648488 MLS
Welcome to this charming, centrally located home where modern updates meet comfortable living! Step inside to discover a beautifully updated kitchen featuring elegant quartz countertops, soft-close cabinetry, and brand-new stainless-steel appliances. Gorgeous LVP flooring, recessed lighting, and fresh new paint throughout create a bright, modern, and inviting atmosphere. Nice-sized backyard is perfect for gardening, entertaining, family gatherings and weekend cookouts. Whether you're a first-time homebuyer, looking to downsize, or ready to stop renting and start building equity, this home is a wonderful opportunity to make homeownership a reality. Come and see this lovely home and make it yours today!

2410 Payne Road, South Chesapeake

1118 Fairway Drive, South Chesapeake
$657,000
5 Beds ⋅ 2.1 Baths ⋅ 10644518 MLS
Beautifully maintained 5-bedroom, 3,383-square-foot home offering peaceful golf course views in sought-after Wedgewood Estates. The thoughtfully designed floor plan features spacious living areas, an updated kitchen with a large center island, abundant cabinetry, and an open flow into the family room, creating a welcoming space for everyday living and entertaining. Large rear windows fill the home with natural light while overlooking the golf course and a beautiful wooded backdrop. Step outside to enjoy the screened porch and expansive patio, creating a private outdoor retreat. Thoughtfully maintained and exceptionally cared for, this home combines timeless character, quality updates, and outstanding curb appeal. Conveniently located in the heart of Greenbrier, just minutes from shopping, dining, parks, major highways, military installations, and healthcare, while offering the privacy and charm of one of Chesapeake's most desirable established neighborhoods.

1118 Fairway Drive, South Chesapeake

1535 Hambledon Loop, South Chesapeake
$286,000
2 Beds ⋅ 2.1 Baths ⋅ 10649710 MLS
Well maintained townhouse-style condo in the highly sought-after Brighton Park at Greenbrier community! Bright and open two-story home features an open-concept layout, fresh paint and all appliances convey to include washer and dryer. Kitchen features a brand new microwave and the home is freshly painted and cleaned. New roof installed in this year. Two primary suites each offer a private en-suite bath and large walk-in closets. Fully fenced private patio, and storage shed. Amenities include a community pool, water, sewer, trash, exterior & ground maintenance, siding, roof coverage for easy, low-maintenance. So just relax and enjoy your new home. Conveniently located near shopping, dining, and interstate access. Schedule your showing today.

1535 Hambledon Loop, South Chesapeake

640 Appalachian Court, South Chesapeake
$640,000
4 Beds ⋅ 2.1 Baths ⋅ 10645606 MLS
Ask Agent about a potential VA assumable loan opportunity! Better Than New and Built in 2023, this beautifully and thoughtfully upgraded home offers the benefits of newer construction without the wait. Move-in ready with quick closing available. Bright, open-concept floor plan with abundant natural light. Gourmet kitchen features quartz countertops, oversized island, premium gas range, stainless steel appliances, walk-in pantry, and custom cabinetry. Spacious primary suite includes tray ceiling, dual walk-in closets, soaking tub, tiled shower, and dual vanities. Enjoy covered front and rear porches, extended patio, fully fenced backyard with wooded views, irrigation system, storage shed, custom window treatments, and exceptional attic storage. Convenient to military bases, shopping, dining, and major commuter routes. Trusted lender Steve Hawley (NMLS #1813927) from Southern Trust Mortgage (NMLS #2921) will provide a 1% lender-paid buydown on this listing. Ask Listing Agent for details.

640 Appalachian Court, South Chesapeake

410 Middleton Way, South Chesapeake
$699,900
5 Beds ⋅ 3.1 Baths ⋅ 10644549 MLS
Welcome to this beautifully upgraded Ashburne floorplan, where comfort, style, and thoughtful design come together. With over $90,000 in custom upgrades, this exceptional home sits on a large lot with peaceful pond views and a spacious covered patio perfect for relaxing or entertaining. Inside, 9' ceilings, wide-plank oak flooring, thoughtful lighting, and custom white cordless blinds create a bright, inviting feel. The designer kitchen features white shaker cabinetry with custom pull-outs, a striking blue island, quartz countertops, and an upgraded appliance package. Two primary suites—one on each level—plus three additional bedrooms offer incredible flexibility. Highlights include a custom-tiled, frameless-glass shower, crown moulding, wood-shelved walk-in closets, and a 2-car garage with epoxy flooring and 220V/50A EV outlet. Enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic lakes.

410 Middleton Way, South Chesapeake

3204 Hearring Way, South Chesapeake
$640,000
5 Beds ⋅ 3 Baths ⋅ 10646878 MLS
Welcome home to this spacious 5-bed, 3-bath home offering 3,842 sq ft of beautifully designed living space on a generous .84-acre lot. With multiple living areas, a HUGE bonus room over the garage, plus a formal living room, dining room, family room, and bright sunroom, there's plenty of space to spread out. The open kitchen flows seamlessly into the family room and sunroom. Upstairs, the spacious primary suite boasts a spa-like bath with a jetted tub, separate shower, and dual vanities. Brand-new carpet was installed upstairs. Step outside to your private backyard retreat featuring a Trex deck, outdoor kitchen, stamped concrete patio, and an expansive fenced yard with a newer vinyl privacy fence with four gates. A storage shed with power provides plenty of extra storage. Additional highlights include stunning curb appeal, a stamped concrete driveway, epoxy-coated garage floor, EV charger, and easy access to military bases, major highways, shopping, dining, and entertainment.

3204 Hearring Way, South Chesapeake

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