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$290,000
3 Beds ⋅ 2.1 Baths ⋅ 10653125 MLS
Short sale — offer accepted and currently pending lender approval.

526 Windward Drive Drive, South Chesapeake
$269,900
3 Beds ⋅ 1.1 Baths ⋅ 10653121 MLS
Welcome home to this 3-bedroom, 1.5-bath home featuring a spacious living room with a fireplace, stainless steel appliances, and a kitchen with abundant cabinet storage. Three bedrooms and a full bath are located upstairs, with a convenient half bath on the main level. Enjoy the fully fenced backyard w/ storage, and the added value of a new HVAC system to be installed prior to closing. Conveniently located with easy access to shopping, dining, and everyday amenities.

1007 River Birch Court, South Chesapeake
$629,000
4 Beds ⋅ 3 Baths ⋅ 10652961 MLS
$10K DECORATING ALLOWANC ON FPO. WATERFRONT LIVING IN SOUGHT-AFTER HUNNINGDON LAKES! THIS BEAUTIFULLY MAINTAINED RANCH OFFERS 4 BEDROOMS, 3 FULL BATHS, FORMAL LIVING AND DINING ROOMS, A SPACIOUS FAMILY ROOM, 2 FIREPLACES, CATHEDRAL CEILINGS, AND 3 SKYLIGHTS THAT FILL THE HOME WITH NATURAL LIGHT. THE UPDATED INTERIOR FEATURES NEW FLOORING, REPLACEMENT WINDOWS, CUSTOM MOSAIC-STYLE KITCHEN CABINET DOORS, AND AN ENCAPSULATED CRAWL SPACE. THE FIRST FLOOR PRIMARY SUITE PROVIDE COMFORT AND CONVENIENCE. ENJOY YEAR-ROUND COMFORT, WITH 4 SEPARATE HVAC ZONES. STEP OUTSIDE TO YOUR PRIVATE LAKESIDE RETREAT WITH A LARGE DECK, PATIO, TRANQUIL 2-TIER WATERFALL KOI POND WITH KOI FISH, AND PEACEFUL WATER VIEWS. YOU CAN EVEN FISH FROM YOUR OWN YARD! A BRAND-NEW EMBANKMENT OFFERS LASTING SHORELINE PROTECTION. ADDITIONAL FEATURES INCLUDE 2 STORAGE SHEDS AND A TRANSFERABLE TERMINIX WARRANTY. PERFECT HOME TO LIVE, ENTERTAIN, UNWIND, AND ENJOY THE WATERFRONT LIFESTYLE RIGHT FROM YOUR BACKYARD!

1104 Copper Stone Circle Circle, South Chesapeake
$220,000
2 Beds ⋅ 2 Baths ⋅ 10652873 MLS
This 2-bedroom, 2-bath condominium is located in Chesapeake’s desirable Greenbrier area. The home features new interior paint, new windows, new doors, and new carpet throughout, creating a clean and comfortable setting for everyday living, entertaining, or working from home.Enjoy living near the golf course while remaining close to Greenbrier Mall, Summit Pointe, Chesapeake Regional Medical Center, Norfolk International Airport, and the Port of Virginia terminals. The location also offers convenient access to Norfolk Naval Shipyard, Naval Station Norfolk, Naval Air Station Oceana, Joint Expeditionary Base Little Creek–Fort Story, Naval Support Activity Hampton Roads, U.S. Coast Guard Base Portsmouth, and Naval Medical Center Portsmouth.With shopping, dining, entertainment, and major highways nearby, many of Hampton Roads’ popular destinations are within easy reach. Schedule your showing today!

1013 Saint Andrews Way Unit C, South Chesapeake
$304,000
2 Beds ⋅ 2.1 Baths ⋅ 10652872 MLS
Welcome to this charming 2-bedroom, 2.5-bath condo offering comfortable living with a peaceful pond-front setting! The first-floor primary bedroom features a spacious walk-in closet. Inside, you’ll find updated windows, beautiful Norman plantation shutters throughout, and easy-care LVP and ceramic tile flooring. Step outside and relax by the pond while enjoying views of the fountain and local wildlife. Additional features include two reserved parking spaces conveniently located directly in front of the condo. The roof, water heater, and refrigerator are approximately 5–6 years old. Washer and dryer convey as-is. A wonderful combination of comfort, convenience, and serene waterfront views!

504 Tunnel Ct Court, South Chesapeake
$350,000
3 Beds ⋅ 1.1 Baths ⋅ 10652815 MLS
Bring your vision and make this one yours! Located in Chesapeake’s convenient Greenbrier area, this 3-bedroom, 1.5-bath home offers the perfect blank slate for a first-time buyer, downsizer, or anyone ready to create a space that reflects their own style. With an additional flexible bonus room, 2-car garage, and nearly half-acre lot, there’s plenty of room to personalize and add value along the way. Enjoy the freedom to update at your own pace and turn this home into exactly what you want it to be. Conveniently located near shopping, dining, major interstates, military bases, and everyday essentials. 1020 Vanderploeg Dr. is full of potential and ready for its next chapter! OPEN HOUSE FRI. 5-7pm & Sat. 10am - 12pm.

1020 Vanderploeg Drive, South Chesapeake
$719,810
4 Beds ⋅ 3.1 Baths ⋅ 10652698 MLS
Beautiful lot backing to mature tree line. Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

2052 Charwood Drive, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10652632 MLS
Welcome to 712 Appalachian Court in Centerville Commons! Move right into this detached single-family home featuring a second-floor loft converted into a true, spacious 4th bedroom! Built in 2014, this 2,389 sq ft home perfectly pairs classic charm with an inviting, modern layout optimized for comfortable living and entertaining. Main Level Highlights: Step into a bright, open-concept floor plan with natural light, custom blinds, and wood/laminate flooring. The expansive living room offers a cozy electric fireplace, flowing into an updated kitchen with stainless steel appliances, modern tile backsplash, crisp cabinetry, large pantry, and sunlit breakfast area. Upper Level Retreats: Features 4 bedrooms, highlighted by the newly converted 4th bedroom and a primary suite with an en suite bath and large walk-in closet. Outdoor Living & Efficiency: Relax on the rear deck overlooking a fenced backyard with peaceful local farm views. Large modern playset is negotiable. Capital updates include a 2025 HVAC system, tankless water heater, smart home features, and energy-efficient window tinting. Attached 2-car garage is ideal for parking, storage, or a home gym. Centrally located near bases and interstates. Bonus: Seller's preferred lender is offering closing cost assistance if utilized—ask LA for details!

712 Appalachian Court Court, South Chesapeake
$399,900
3 Beds ⋅ 2.1 Baths ⋅ 10652491 MLS
Welcome home to this beautifully appointed, thoughtfully designed townhome for effortless everyday living. The open floorplan invites connection - for entertaining friends and family or cozy nights in - while the large primary suite offers a retreat complete with a spacious walk-in closet and a luxurious soaking tub to relax and unwind. Say goodbye to weekend chores with low-maintenance living and enjoy the convenience of second-floor laundry right where you need it. A garage with automatic opener plus parking for up to three cars means you'll never circle the block again. Effortless style, smart design, and room to breathe - this townhouse has it all. Schedule your showing today!

1152 Chatham Lane Unit 14, South Chesapeake
$429,900
3 Beds ⋅ 2.1 Baths ⋅ 10652385 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.

661 Allery Road, South Chesapeake
$452,900
4 Beds ⋅ 3.1 Baths ⋅ 10652383 MLS
Now preselling by appointment. This Marlow plan includes our 4th bedroom & full bath on 1st floor already spec'd and included in price. 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.

649 Allery Road, South Chesapeake
$399,999
3 Beds ⋅ 2.1 Baths ⋅ 10652128 MLS
Welcome home! This move-in ready townhome offers low-maintenance living in a convenient Chesapeake location near Greenbrier. Enjoy a fully renovated primary bath, a low-maintenance patio with AstroTurf, and community amenities including a pool and park. Conveniently located near shopping, dining, entertainment, and major roadways, this home offers the perfect blend of comfort, convenience, and easy living. Don't miss the opportunity to make this home your own!

1117 Winsford Lane, South Chesapeake
$703,705
4 Beds ⋅ 3.1 Baths ⋅ 10652119 MLS
Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Estimated March 2027 closing. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

2037 Charwood Drive, South Chesapeake
$310,000
2 Beds ⋅ 2.1 Baths ⋅ 10651432 MLS
Welcome to this fully remodeled 2-bedroom, 2.5-bathroom condo offering approximately 1,256 square feet of living space. Remodeled in 2026, this home offers updated finishes and a refreshed interior. The community features association-maintained trails and a playground, providing convenient access to outdoor amenities. Located near shopping and the local intermediate school, with everyday conveniences just minutes away. Condo association fees are due every six months. An excellent opportunity to own a recently remodeled condo in a convenient location.

1904 Woodgate Arch, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10651374 MLS
Beautiful 3-bedroom, 2.5-bath condo offering 1,870 sq ft of spacious, low-maintenance living! This condo has been UPDATED with new flooring, lighting, and fixtures throughout, along with a newly upgraded kitchen and bathrooms featuring beautiful cherrywood cabinets. The condo also features a pantry, two walk-in closets, a private primary bath, and a convenient half bath on the main level. Washer and dryer included. Enjoy the private patio and community pool. Great location just 5 MINUTES from Greenbrier Mall and next to Greenbrier Golf Course. Move-in ready and waiting for its new owner!

1440 Rollesby Way, South Chesapeake
$534,900
4 Beds ⋅ 2.1 Baths ⋅ 10651368 MLS
This stunning home combines waterfront living, a cul-de-sac location and the convenience of being just minutes from the heart of Greenbrier! Meticulously maintained and extensively refreshed, this 2,400 SF home offers 4 bedrooms, 2.5 baths, a spacious FROG & an expansive backyard overlooking the water. Watch the seasons change from your windows and enjoy the serene setting that water views provide. Major 2025 updates include dual HVAC systems, gas water heater, appliances, engineered hardwood floors, fresh interior paint, blinds, lighting, faucets, switches, receptacles, door hardware & more. The kitchen features new tile, backsplash & lighting, plus a large pantry. Enjoy a primary suite with walk-in closet, spa tub, tiled shower & double vanity. A large deck & pergola overlook the lawn and lake, complemented by mature landscaping, new fencing & a shed. Approx. 5 minutes to Greenbrier shopping, dining & the future Chesapeake Costco!

1629 Waterside Drive, South Chesapeake
$345,000
3 Beds ⋅ 2.1 Baths ⋅ 10651317 MLS
Welcome to 1561 Rollesby Way! This well-appointed 3-bedroom, 2.5-bathroom home offers a spacious and functional layout in the desirable Greenbrier area of Chesapeake. The first-floor primary suite features a large walk-in closet & private bathroom for added convenience. The kitchen offers stainless steel appliances, ample cabinetry, & a convenient bar overlooking the dining area. The living room provides a comfortable gathering space with a sliding glass door leading to the fenced-in backyard & patio, great for relaxing or entertaining. A first-floor half bath is conveniently located for guests. Upstairs, you’ll find two additional bedrooms, both featuring walk-in closets, along with a full bathroom & a versatile bonus room that would make an ideal home office, reading room, or flex space. Condo dues include access to the community pool, ground maintenance, trash pickup, & water service. Conveniently located in Greenbrier with easy access to shopping, dining, & entertainment.

1561 Rollesby Way, South Chesapeake
$309,900
3 Beds ⋅ 2.1 Baths ⋅ 10651219 MLS
Looking for low-maintenance living without giving up space? This 3-bedroom, 2.5-bath condo in the heart of Greenbrier has plenty to offer! The bright living area features great natural light, while the spacious kitchen provides plenty of cabinet and counter space, a walk-in pantry, and an easy flow into the dining area. A first-floor bedroom gives you options for guests, an office, or additional living space. Go outside to your private fenced patio for morning coffee, grilling, or relaxing. Upstairs are two spacious bedrooms, each with a private bath and walk-in closet. The primary bath includes a soaking tub and separate shower. Even laundry gets an upgrade with a second-floor laundry room and utility sink! Community amenities include a pool, yard maintenance, trash pickup, sewer, and water. Within close proximity to Greenbrier shopping, dining, and interstates.

1519 Rollesby Way, South Chesapeake
$289,900
2 Beds ⋅ 2 Baths ⋅ 10651196 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #204, South Chesapeake
$267,500
2 Beds ⋅ 1.1 Baths ⋅ 10650836 MLS
Remodeled townhome around the corner from all your daily necessities including restaurants, shopping, interstate access and parks. New paint, new carpet, new LVP flooring, updated kitchen with new appliances, new light fixtures and hardware throughout, new bathrooms.

1974 Woodgate Arch, South Chesapeake
$633,105
4 Beds ⋅ 2.1 Baths ⋅ 10650669 MLS
Q1 2027 Delivery. Elegant two-story home with approx. 2,652 square feet of meticulously designed living space. The main level boasts an open-concept layout with soaring 9-foot ceilings throughout. The heart of the home is the large kitchen, equipped w/tons of storage & countertops for meal prep & entertaining. A flex space on the first floor provides versatility for a home office, playroom, or den, catering to your household's needs. Upstairs, 4 spacious bedrooms ensure comfort for everyone & the large, upstairs laundry room simplifies household chores. Fenced back yard with large patio, backing mature tree line. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before 1st visit or 1st communication with listing agent & Agent must accompany Buyer on 1st visit, see agent for details. Photos & video are of other Everett's completed, not actual home, finishes vary.

2048 Charwood Drive, South Chesapeake
$275,000
3 Beds ⋅ 2 Baths ⋅ 10650616 MLS
Welcome home to this beautifully updated 3-bedroom, 2-bath home, completely renovated in 2022! Thoughtfully refreshed from top to bottom, this move-in-ready gem offers a stylish, modern feel with updates designed for comfortable everyday living. The beautifully updated kitchen features crisp cabinetry, sleek countertops, stainless steel appliances, and plenty of space for cooking and gathering. All three bedrooms are bright and inviting, while both updated bathrooms offer fresh, modern finishes. With the major renovations already completed, you can simply move in and enjoy! Conveniently located near shopping, dining, schools, and major interstates, this home offers the perfect combination of comfort, style, and convenience. Whether you're entertaining, relaxing, or making new memories, this one is ready to welcome you home.

1940 Woodgate Arch Unit A, South Chesapeake
$294,900
2 Beds ⋅ 2 Baths ⋅ 10650606 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #303, South Chesapeake
$324,900
2 Beds ⋅ 2 Baths ⋅ 10650599 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #103, South Chesapeake
$309,900
2 Beds ⋅ 2 Baths ⋅ 10650593 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #201, South Chesapeake
$344,900
2 Beds ⋅ 2 Baths ⋅ 10650588 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a 1st floor corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #101, South Chesapeake
$319,900
2 Beds ⋅ 2 Baths ⋅ 10650581 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #302, South Chesapeake
$688,900
5 Beds ⋅ 3 Baths ⋅ 10650242 MLS
Proudly offered by its original owner, this beautifully maintained 5-bedroom, 3 bathroom home is a rare opportunity in one of the area's most desired neighborhoods. The thoughtfully designed floor plan features a spacious downstairs bedroom and full bath, ideal for guest or multi-generational living along with a Great room, well-appointed kitchen, dining room, and flex room. Upstairs you will find 4 additional generous sized bedrooms, including the primary suite with a beautifully updated bathroom and large closet. Enjoy gathering with family and friends in the inviting family room complete with a built-in bar. Start your mornings on the welcoming front porch and unwind in the evenings on the spacious back patio, perfect for outdoor dining, entertaining, or simply relaxing. Find out why Warrington Hall is one of the most desired communities with all of its amenities including: pool, playgrounds, ball fields, and tennis courts.

816 Poquoson Crossing, South Chesapeake
$280,000
3 Beds ⋅ 1.1 Baths ⋅ 10650367 MLS
Well maintained townhouse in Chesapeake's Woodgate Commons community. 3-bedroom, 1.5 baths townhouse with extra natural light that only an end unit can provide! Large primary bedroom with walk-in closet. Freshly painted throughout. Fenced backyard with new deck 2026. Large storage shed with electric and playhouse to convey. Ideally located near restaurants, shopping, interstate access, military bases, and a nearby golf course, this home offers both convenience and value.

1920 Devonwood Common, South Chesapeake
$282,500
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

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.