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$800,000
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
$729,900
4 Beds ⋅ 3.1 Baths ⋅ 10648559 MLS
Prepare to fall in love with this stunning ranch home! Nice touches throughout! Lovely kitchen with upgraded cabinets, countertops, appliances, breakfast bar, and backsplash. Open formal dining room and family room. Cozy study/den with built-in bookshelves and a second fireplace. Generously sized bedrooms. Lots of wonderful closet space. Primary includes dual sinks, a jetted tub, and a separate shower. Huge bedroom and closet upstairs with a full bath. Perfect for mother-in-law suite. Plenty of attic space with easy access. Fenced-in backyard includes a screened-in porch and a large storage shed with two separate sides. Muilty car driveway and so much more! Convenient location!

1328 Waycroft Reach, South Chesapeake
$269,500
2 Beds ⋅ 1.1 Baths ⋅ 10648888 MLS
LOVELY TOWNHOUSE FRESHLY PAINTED. FEATURES 2 LARGE BEDROOMS. KITCHEN UPDATED, NEW STOVE, NEW HOOD, NEW DISHWASHER, NEW FANCY SINK WITH FAUCET AND EXTRAS. ELECTRIC HEAT PUMP -2023, NEW WATER HEATER. LAUNDDRY ON 2ND FLR. FENCED REAR YARD. CONVENIENT TO SHOPPING, DINING AND SCHOOLS, GREENBRIER MALL, UNIVERSITIES AND I64. MINUTES TO MILITARY BASES. LOW HOA FEES, NO CONDO FEES.

1063 Still Harbor Circle, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10648263 MLS
Stunning waterfront views! Spacious Brick front ranch with a new kitchen, quartz countertops, new stainless appliances, slow close cabinets, large island and 42" upper cabinets. Eat in kitchen with bay windows overlooking the lake! Large family room, LVP flooring, separate laundry room and an oversized deck with an awning. Sits on over 1/4-acre with a 2-car garage, an entire house generator and a recent solar panel installation. There is structural termite and moisture damage in the crawl space and the home. Only CASH offers will be considered. Buyer must assume the solar panel lease @$145.00 a month, electric bills as low as $10.00 a month.

1121 Copper Stone Circle, South Chesapeake
$625,000
4 Beds ⋅ 3 Baths ⋅ 10648242 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 Ct Court, South Chesapeake
$215,000
10648163 MLS
Outstanding 1.75-acre building lot in Chesapeake! This beautiful homesite offers approximately 134 feet of road frontage, a peaceful setting, and plenty of room to create the home you've always envisioned. Zoned R-15S, with city water available, this property combines the charm of country living with the convenience of nearby shopping, restaurants, and major highways. Enjoy the space and privacy that only a 1.75 acre homesite can provide while remaining close to everything Chesapeake has to offer. Don't miss this exceptional opportunity to own one of the area's most desirable building sites. Private septic system will be required. Buyer is responsible for conducting all due diligence regarding soil evaluation, septic permitting, and installation requirements.

260 Centerville Turnpike N, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10648047 MLS
One owner condo - shows like a model - professionally decorated - updates include flooring - kitchen - baths - systems - so well cared for - maintained - Cul-de-sac that borders the golf course - no thru traffic - duplex style condo with a garage and driveway parking - In the heart of Greenbrier on the 11th green of the Greenbrier Golf Course - wooded view out the back of the fenced in yard.

1016 Winged Foot Court Unit B, South Chesapeake
$469,900
4 Beds ⋅ 3.1 Baths ⋅ 10647812 MLS
Beautiful like-new townhome with a two-car garage! This three-level condo features a gourmet kitchen with center island, quartz countertops, stainless steel appliances, and an open-concept living area with a linear fireplace and LVP flooring. The first-floor flex room with a full bath is great for guests or an in-law suite. Upstairs offers a spacious primary suite with dual walk-in closets and a ceramic tile shower, plus two additional bedrooms, a full bath, and laundry. All appliances convey. Conveniently located near shopping, dining, and interstate access. Some photos have been edited using AI.

1055 Butte Lane, South Chesapeake
$333,000
3 Beds ⋅ 2.1 Baths ⋅ 10647568 MLS
Approved for VA, FHA, and conventional loan. Welcome home to this beautifully maintained 3-bedroom, 2.5-bath condo in the highly desirable Greenbrier area of Chesapeake. This well designed home features two primary suites, each with a private bath, offering exceptional flexibility for guests, roommates, or multigenerational living. The bright open floor plan provides comfortable living and entertaining space, while the 1st floor bedroom can be used as a home office or guest room. Conveniently located near shopping, dining, parks, and major interstates, this low-maintenance home combines comfort, convenience, and an unbeatable location.

1439 Rollesby Way, South Chesapeake
$330,000
3 Beds ⋅ 2.1 Baths ⋅ 10647646 MLS
WELCOME HOME TO EASY, LOW MAINTENANCE LIVING. MOVE RIGHT INTO THIS WELL MAINTAINED 3 BEDROOM, 2 1/2 BATH CONDO THAT OFFERS A SPACIOUS LAYOUT THAT IS PERFECT FOR EVERYDAY LIVING AND ENTERTAINING. CONDO ASSOCIATION AMENITIES INCLUDE GROUNDS MAINTENANCE, MASTER INSURANCE POLICY, POOL AND CLUBHOUSE. ROOF IS SCHEDULE TO BE INSTALLED THIS YEAR. $100 SPECIAL ASSESSMENT PER MONTH THROUGH 2027 FOR NEW ROOF. VACANT AND EASY TO SEE!

1470 Otterbourne Circle, South Chesapeake
$514,000
4 Beds ⋅ 2.1 Baths ⋅ 10646662 MLS
Beautifully maintained 4BR, 2.5BA home with a versatile floor plan, multiple living spaces & oversized finished room over the garage (FROG), ideal as a 4th bedroom or bonus space. Main level features a welcoming foyer, formal living & dining rooms, spacious family room with gas fireplace & bright breakfast area adjoining the kitchen. Upstairs are 3 additional bedrooms, FROG/4th bedroom & laundry room. Enjoy the covered rear deck overlooking a fully fenced backyard with mature landscaping, irrigation, storage shed & charming fish pond surrounded by brickwork on the patio. Recent improvements include brand-new HVAC plus substantial replacement of the rear deck. Additional updates include replacement windows, encapsulated crawl space with dehumidifier & sump pump, water heater, dishwasher & updated gutters. No HOA. Convenient to shopping, restaurants, schools, military bases & major highways.

420 Brandon Way, South Chesapeake
$995,000
6 Beds ⋅ 4 Baths ⋅ 10645935 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10646316 MLS
Just six years young, this beautifully maintained home offers thoughtful upgrades and an open layout perfect for everyday living and entertaining. The welcoming entryway features custom shiplap accents, leading into a spacious main living area filled with natural flow. The kitchen stands out with abundant cabinetry, subway tile backsplash with black accents, upgraded light fixtures, gas stove, pantry, and views overlooking the living room with cozy gas fireplace. One of the sellers? favorite features is the backyard, offering privacy with peaceful pond views and open fields beyond. Upstairs, every bedroom is generously sized, while the oversized primary suite includes two walk-in closets and a large walk-in shower. Convenient second-floor laundry and carefully selected colors throughout make this home move-in ready. If you love open-concept living and private backyard views, this home is a must-see!

1668 Teton Court, South Chesapeake
$725,000
6 Beds ⋅ 3.1 Baths ⋅ 10646118 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.

1548 Waterside Drive N, South Chesapeake
$598,900
4 Beds ⋅ 2.1 Baths ⋅ 10646261 MLS
Step into this beautifully renovated home featuring all-new flooring, fresh paint, and a completely new open-concept kitchen perfect for entertaining. With 2.5 fully renovated bathrooms and a new deck, this home combines modern elegance with functional living. Every detail has been upgraded to offer comfort and style, making it move-in ready. Don’t miss your chance to own this turnkey gem in a desirable neighborhood! The large backyard is great for outdoor entertaining, pets, or simply relaxing in your private oasis. Located in an established neighborhood with mature trees, you're minutes from Greenbrier business center, parks, shopping, and dining.

1032 Copper Stone Cir Circle, South Chesapeake
$325,000
2 Beds ⋅ 2.1 Baths ⋅ 10645916 MLS
Enjoy low-maintenance living in this move-in ready townhome-style condo in the desirable Warrington Hall community! Conveniently located just minutes from shopping, restaurants, parks, and major interstates, you'll have easy access to everything Chesapeake and Hampton Roads have to offer. Community amenities include a clubhouse, pool, tennis courts, and ground maintenance for a carefree lifestyle. Inside, the spacious layout features a kitchen with abundant cabinetry, all appliances, pantry, and a breakfast bar which opens up to the dining room. The inviting family room provides lots of natural lighting, and there is a convenient powder room for guests. Upstairs, both spacious bedrooms offer walk-in closets and private ensuite bathrooms. The primary suite features a dual vanity and tub/shower combination. Step outside to enjoy your own private patio, perfect for morning coffee or relaxing at the end of the day. Just move in and start enjoying all this community has to offer!

1115 Warrington Boulevard, South Chesapeake
$450,000
3 Beds ⋅ 2.1 Baths ⋅ 10645658 MLS
Nestled among mature trees in a sought-after, amenity-rich community, this charming brick end-unit blends warmth with everyday functionality. Step inside to freshly finished hardwood floors on the main level and an abundance of natural light that fills the home with a bright, welcoming feel. This home is like brand new. New paint throughout and every item on the home inspection has already been done. The kitchen offers generous counter space and flows seamlessly into the living and dining areas, great for everyday living or entertaining. Upstairs, you'll find brand-new carpet, generously sized bedrooms, a cozy reading nook, and a spacious primary suite featuring a soaking tub, step-in shower, and private water closet. Enjoy a peaceful, tucked-away setting just minutes from shopping, dining, and all the conveniences of this thriving area. The community itself is packed with perks: The HOA cover the exterior to include the roof, yard and exterior pressure wash, a large pool, basketball court, tennis/pickleball courts, soccer and volleyball fields, a dog park, scenic trails, and abundant green space. With charm, location, and lifestyle all in one, this home checks every box—schedule your private tour today!

816 Great Marsh Avenue, South Chesapeake
$269,900
2 Beds ⋅ 2 Baths ⋅ 10645506 MLS
This fantastic move-in-ready condo has undergone numerous recent upgrades (too many to list).LVP flooring and carpet, fresh paint throughout. 1st floor features include a BR with an attached bath and soaring vaulted ceilings. Tucked away in a private area, this property backs up to a private grassy area. Community amenities include a pool.

1641 Orchard Grove Drive, South Chesapeake
$619,000
4 Beds ⋅ 2.1 Baths ⋅ 10645551 MLS
Welcome to Warrington Hall in Greenbrier, Chesapeake. This well-maintained brick home offers spacious living with four bedrooms, two and a half baths, and hardwood floors throughout the first floor. Home Features * Bright, airy layout * Well-equipped kitchen * Spacious four-bedroom with 2.5 baths *Community Amenities Enjoy access to a clubhouse, tennis courts, a pool, and playgrounds. Schedule your showing today before this home is gone.

948 Stanhope Gardens, South Chesapeake
$294,900
2 Beds ⋅ 2.1 Baths ⋅ 10644570 MLS
Price Improvement! Take advantage of this exceptional value and add your personal touch with a few cosmetic updates. Private end-unit in desirable Greenbrier Fairways with a first-floor primary suite and spacious second bedroom. Versatile loft with closet overlooks the great room, great for an office, flex space, or potential third bedroom. Kitchen features ample cabinetry, pantry, and breakfast bar. Enjoy a backyard patio and attached storage shed. HVAC & roof (2019), flooring (2017), paint (2023). FHA/VA approved, pet-friendly (up to 35 lbs), and low condo fees. Move-in ready and well maintained! Perfect location to many corporate businesses including Dollar General corporate office, Chesapeake Regional Hospital. Great condo for traveling nurses, relocation for temps, investor for rental opportunity or for Buyer looking to pay less than rent!

1313 Quail Creek Hollow Unit C, South Chesapeake
$524,900
3 Beds ⋅ 2.1 Baths ⋅ 10643243 MLS
Beautifully maintained 55+ condominium in the desirable Greenbrier area. Built by Stephen Alexander Homes, this elegant residence blends historically inspired architecture with timeless craftsmanship, featuring 10-foot ceilings, transom windows, custom crown moulding and trim work, and hardwood floors. Offering 3 bedrooms plus a spacious room over the garage, this home provides exceptional flexibility for guests, hobbies, or a home office. The gourmet kitchen with double ovens is designed for everyday living and entertaining. An interior private elevator provides effortless access to both levels. Additional features include an attached two car garage with overhead storage and utility sink, brand-new dual-zone HVAC, a Rinnai tankless water heater, and a freshly painted exterior. Relax on the spacious front porch or entertain on the private tiled patio with a SunSetter retractable awning. Whole-house audio and family room surround sound add comfort and ambiance throughout. Move in ready!

1016 Briars Landing, South Chesapeake
$599,000
6 Beds ⋅ 4.1 Baths ⋅ 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake
$404,900
3 Beds ⋅ 3.1 Baths ⋅ 10641733 MLS
Now preselling by appointment. Estimated early 2027delivery. The Caldwell plan offers a first-floor bedroom suite with flex space and one-car garage. 2 spacious owner suites are on the 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

657 Allery Road, South Chesapeake
$399,900
2 Beds ⋅ 2.1 Baths ⋅ 10641732 MLS
Now preselling by appointment. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

670 Allery Road, South Chesapeake
$394,900
2 Beds ⋅ 2.1 Baths ⋅ 10641729 MLS
Now preselling by appointment. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

674 Allery Road, South Chesapeake
$498,000
4 Beds ⋅ 2.1 Baths ⋅ 10641660 MLS
Come check out this amazing well kept two story home in the heart of Greenbrier. Conveniently located to shopping, restaurants, parks, military bases and major interstates. Roof was replaced in 2015, HVAC in 016, gutter and vinyl wrap in 2017, master shower replaced in 2022. Home features a huge master bedroom sitting area as a bonus complete with an additional fireplace! Outside folks will love the proximity to the Chesapeake City Park!Romantic gas fireplace in primary suite and more!

527 Windward Drive, South Chesapeake
$674,900
4 Beds ⋅ 2.1 Baths ⋅ 10640623 MLS
Welcome to 609 Shasta Drive! A thoughtfully designed property in the peaceful Flagstone Quay community. Inside, the open-concept layout features a spacious living room with an electric fireplace flowing into the dining area and gorgeous kitchen with marble countertops, tile backsplash, stainless steel appliances, gas range, large island, chef's sink, and walk-in pantry. Additionally you will find a private study, mudroom with built-ins, 9' ceilings on both levels, and first-floor LVP flooring. Upstairs features a versatile loft, laundry room, and generously sized bedrooms, each with a walk-in closet, including a beautiful primary suite with a custom closet and tiled shower. Home has been wired for whole home Ethernet. Outside, enjoy the wrap-around front porch, a fully fenced backyard with brand new in-ground pool, covered rear patio, and Tuff Shed for added storage. Pool is equipped with a premium Dryden Aqua® Activated Filter Media filtration system imported from Europe. Tour today!

609 Shasta Drive, South Chesapeake
$434,900
3 Beds ⋅ 2.1 Baths ⋅ 10638670 MLS
Now preselling by appointment. The Marlow plan offers three 3rd floor bedrooms with the option to add an additional 4th bedroom & full bath on 1st floor. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $8,000 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $15,000 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

668 Allery Road, South Chesapeake
$682,000
5 Beds ⋅ 3.1 Baths ⋅ 10635971 MLS
This home has it all! Perfect for multi-generational living. Open Concept! 3 beds, 2 1/2 baths down (with Jack & Jill bath between 2 bedrooms), 2 VERY large rooms and a full bath upstairs. Closet space is in abundance! Laundry on first level. Two dinging areas plus the kitchen island. Plantation shutters in main living areas, blinds on most windows. Tankless Gas Water Heater. NO CARPET IN THIS HOME. Fenced back yard, 2 car garage. Primary has stand up shower and soaker tub, dual vanities, water closet, and walk in closet. Screened porch. Gutters drain to dry well. Low HOA's. All appliances convey.

1352 Auburn Hill Drive, South Chesapeake
$479,972
3 Beds ⋅ 2.1 Baths ⋅ 10630789 MLS
Move right in to this beautifully maintained home, built in 2016 and perfectly situated on over 3/4 of an acre at the end of a quiet cul-de-sac. Designed with both comfort and entertaining in mind, this home features 9-foot ceilings, an open-concept floor plan, quartz countertops, and stainless steel appliances.Upstairs, you’ll find a convenient laundry room with washer and dryer that convey. The expansive backyard offers endless possibilities, with plenty of room to add a pool, garden, or outdoor living space—all enhanced by attractive fencing.Enjoy a tucked-away, private setting while still being just minutes from shopping, interstates, and military bases. This home truly offers the best of space, style, and location. NEW PAINT and CARPET, Seller to Provide 5 K CLOSING COST ASSISTANCE on a full price offer when using the Seller's Attorney for closing. VERY FAVORABLE RATES AND LOAN PROGRAMS USING THE SELLER'S LENDER. BE SURE TO INQUIRE ABOUT THIS!!!!

1121 Kinderly Lane, 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.