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$579,000
4 Beds 2.1 Baths 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, South Chesapeake

$629,900
4 Beds 2.1 Baths 10645157 MLS
BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, South Chesapeake

$568,000
4 Beds 2.1 Baths 10645016 MLS
*Seller to contribute an amount of $7K toward the Buyer's allowable closing costs and prepaid expenses subject to lender guidelines with an acceptable offer.* Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$750,000
5 Beds 2.1 Baths 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake

$599,999
4 Beds 2 Baths 10644979 MLS
Welcome to this beautifully remodeled all-brick ranch tucked into the peaceful Hickory area of Chesapeake, where country charm meets modern comfort on approximately 3 sprawling acres. This 4-bedroom, 2-bath gem has been thoughtfully updated from top to bottom, featuring luxury vinyl plank flooring, tiled showers, granite countertops, and stainless steel appliances throughout a bright, open layout made for both everyday living and easy entertaining. Step outside and fall in love with the lifestyle this property offers: relax on the covered front porch, host gatherings on the expansive rear deck, or unwind on your own private deck just off the primary suite. Dreaming of homegrown eggs? The property includes chicken coops, ready for you to raise your own flock and enjoy farm-fresh living right in your backyard. A newly poured driveway and a 50-AMP power pole with RV hookup round out the practical upgrades, making this move-in-ready retreat as functional as it is charming. With updated finishes, room to roam, and space to grow your own little homestead, this Chesapeake beauty is ready to welcome you home.

913 Long Ridge Road, South Chesapeake

$550,000
4 Beds 3 Baths 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, South Chesapeake

$524,900
4 Beds 2.1 Baths 10644845 MLS
*PRICE DROP!! $524,900!* PLUS, Home Improvement/Decorators' Allowance INCREASE to $10,000 so YOU can "Make it Your Own!" Sellers are Generous and MOTIVATED!! AAAND, Sellers will paint the Blue and Pink Bedrooms as part of an offer negotiation! (Some digitally altered/virtually staged photos included for Your Creative Mind to Imagine Your Future!!) This Home Sweet Home is located in the Hickory School District in Beautiful Chapel Hill Estates. Don't miss the opportunity to live in this Amazing Community at a "below market" Price... Four Bedrooms, 2 1/2 Baths exist in over 2,000 square feet of a Contemporary, Open Concept floor plan with 2-car garage and a HUMONGOUS BACK YARD... Perfect for Outdoor Entertaining and Recreation. Your NEW LIFE CHAPTER begins HERE! ACT NOW! School starts soon! Call for a Private Showing Appointment TODAY!

1221 Rosebud Lane, South Chesapeake

$609,900
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

$379,900
3 Beds 2.1 Baths 10644759 MLS
Welcome home to this beautifully maintained townhome in the highly desirable Great Bridge area of Chesapeake! This spacious 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is filled with natural light and features gleaming wood floors, granite countertops, stainless steel appliances, and crisp white cabinetry. The primary suite boasts a granite vanity and dual shower heads for a spa-like retreat. Pride of ownership shines throughout with a fresh interior paint refresh and a newly installed backyard gravel area, creating a low-maintenance outdoor space perfect for relaxing or entertaining. Complete with an attached garage and driveway parking, this move-in ready home is ideally located just minutes from shopping, dining, top-rated schools, parks, military bases, hospitals, and the area’s beautiful beaches. Don’t miss the opportunity to own this well-cared-for home in one of Chesapeake’s most sought-after communities!

432 Charleston Street, South Chesapeake

$795,000
5 Beds 3 Baths 10644737 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, abundant cabinetry, and ample prep space. 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 main level includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a luxurious 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

$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

$329,500
3 Beds 3 Baths 10644249 MLS
Be the first to see this stunning 3 bedroom, 3 full bath condo in sought after Riverwalk on the Elizabeth River. Offering 1,776 square feet of living space, this home features soaring cathedral ceilings, skylights, a dramatic two story great room with gas fireplace, and a spacious loft with potential for a fourth bedroom conversion. Recent updates include new carpet, luxury vinyl plank flooring, and stainless steel appliances. Enjoy a private balcony great for relaxing outdoors. Riverwalk residents enjoy an exceptional array of amenities including a clubhouse, pool, tennis courts, pickleball, dock access, playgrounds, weekly food trucks, swim team, garden club, and a community atmosphere. Conveniently located near shopping, dining, and major interstates, this is low maintenance living at its best.

605 Sail Fish Quay, South Chesapeake

$499,900
4 Beds 2.1 Baths 10644597 MLS
Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car garage nestled in the heart of 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. With its prime location in Chesapeake, you'll enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach. Projected completion is mid August 2026. The lot is almost 9400 sq ft. LVP flooring will be installed throughout the 1st floor. Photos from previous build. Make your appt today. Backyard fence being installed soon.

120 Taxus Street, South Chesapeake

$449,500
3 Beds 3.1 Baths 10644557 MLS
Welcome to this stunning, like-new home in the highly sought-after Grassfield area of Chesapeake! Built in 2021, this beautifully maintained 3-bedroom, 3.5-bath home offers 2,140 sqft of thoughtfully designed living space filled with natural light. Step inside to charming hall tree built-ins, soaring cathedral ceilings, and an open-concept layout perfect for everyday living and entertaining. The spacious living room with a cozy fireplace flows into the modern kitchen featuring granite countertops, stainless steel appliances, gas cooking, a large island, and adjoining dining area. The primary suite offers two walk-in closets and a private bath with dual vanities. The third-floor bonus suite includes a bedroom, full bath, walk-in closet, and endless flexibility for guests, a home office, or media room. Complete with a charming white picket fence and located near shopping, dining, interstates, and top-rated Grassfield High School, this move-in-ready home is one you won't want to miss!

433 Asuza Street, South Chesapeake

$793,267
5 Beds 3 Baths 10644581 MLS
The Bellhaven at Riverview Landing by Wetherington Homes. Estimated September 2026 delivery. Flexible 4-5 bedroom floor plan with an open-concept layout. Chef’s kitchen connects to the dining area through a butler’s pantry and features dual ovens, gas range, hood, and large island overlooking the covered rear porch. Upstairs loft and main-level full bath add functional living space. Includes a curated list of standard features, with time to personalize select options. Cul-de-sac lot in an active community with walking trails, fire pit, and convenient access to schools, beaches, parks, restaurants, and more! Contact the sales counselor to schedule an appointment and learn about current incentives.

212 Kwanzan Court, South Chesapeake

$689,000
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

$599,000
5 Beds 3 Baths 10644309 MLS
Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

785 Caddie Street, South Chesapeake

$795,000
6 Beds 3.1 Baths 10643149 MLS
Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler station off the dining room. and exceptional flow throughout. The spacious eat-in kitchen and bar-top seating area open to the inviting family room with a cozy fireplace. Three additional bedrooms are located on the second level, including a versatile FROG that can serve as the 6th bedroom, home office, or recreation room. Current cooktop and built-in microwave to be replaced; buyer can choose. Large back deck with gas hookup. Residents of Riverwalk enjoy exceptional neighborhood amenities, including walking trails, a community pool, boat ramp and dock, playground, and a popular summer swim team. This is a wonderful opportunity to own a meticulously cared-for home in one of Chesapeake’s most desirable communities.

804 River Strand, South Chesapeake

$639,900
4 Beds 2.1 Baths 10644442 MLS
Experience the lifestyle you've been searching for in one of Chesapeake's most desirable communities, just minutes from top-rated Grassfield High School. This beautifully maintained home welcomes you with a charming front porch and gleaming hardwood floors throughout the main level. A versatile flex room that can be used for a home office, playroom, or sitting area, while the formal dining room flows into the updated chef's kitchen featuring granite countertops, refreshed cabinetry, and new stainless steel appliances. The kitchen opens to a spacious family room centered around a cozy fireplace and an inviting sunroom filled with natural light. Upstairs, the expansive primary suite offers a spa-inspired bath with dual vanities, a jetted tub, and a glass-enclosed shower, along with three additional bedrooms, a full bath, and a convenient second-floor laundry room. Step outside to your own private backyard retreat complete with a stamped concrete patio, sparkling in-ground pool, and fully fenced yard—ready for relaxing or entertaining all summer long. Additional upgrades include a tankless water heater, solar panels that significantly reduce electric costs, updated main-level lighting, and a VA assumable loan with an incredible 3% interest rate for qualified buyers. Tesla EV charger.

2101 Beeblossom Lane, South Chesapeake

$1,259,997
4 Beds 2.1 Baths 10644328 MLS
Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, South Chesapeake

$577,740
3 Beds 3 Baths 10644251 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

$506,990
2 Beds 2 Baths 10644247 MLS
The Asheville, one of our quad-style homes, features two bedrooms and two 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. $10,000 closing cost incentive with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary.

2150 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.