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1111 Annie Olah Crescent, South Chesapeake
$767,000
4 Beds ⋅ 3.1 Baths ⋅ 10628755 MLS
Gorgeous home in sought after Olah’s Landing. This spacious property offers 4 bedrooms 3.5 baths, attached 3 car garage. The inviting family room features gas FP & is wired for surround sound, perfect for cozy nights in. FROG & dedicated first floor office provide flexible living & working space. The chef’s kitchen is a standout, complete w/stainless steel appliances, gas range, double ovens that are ideal for cooking & entertaining. An in-law suite w/private en-suite bath adds convenience for guests or multi-generational living. The primary suite includes his-&-hers closets, tray ceiling, dual vanities, & a luxurious tile shower. Two additional BRs share a Jack & Jill bath. Enjoy outdoor living in the fenced backyard that backs to a wooded greenbelt for added privacy. The yard features a covered patio, plus a pergola w/hot tub, creating an exceptional space for relaxation & entertaining. A sprinkler system & well help maintain the lawn with ease. Call today!

1111 Annie Olah Crescent, South Chesapeake

1026 Woodwind Way, South Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10626225 MLS
A great opportunity to call this well priced, well cared for all brick retreat in Kemp Woods your Home! Situated on a sizable cul-de-sac lot, 1026 Woodwind Way provides a great flow with 4 bedrooms, 2.5 baths and double staircases. A bright, welcoming 2-story foyer greets your guests and opens to both an office/music room and the formal dining room. The family room is the true heart and hearth of the home, opening seamlessly to the eat-in kitchen and out to the deck for easy indoor-outdoor living. The spacious kitchen includes stainless steel appliances, center island, custom countertops, backsplash and breakfast nook. The second level includes a primary suite with walk-in closets and a jetted tub, plus 3 additional bedrooms. A renovated hall bathroom, an abundance of storage, permanent attic stairs and a 2-car garage add everyday ease. The large, fenced backyard and storage shed handle the rest. Minutes to I-64, Bypass-168, Greenbrier dining, shopping, ice skating and more.

1026 Woodwind Way, South Chesapeake

417 Granada Drive, South Chesapeake
$527,500
4 Beds ⋅ 2.1 Baths ⋅ 10624615 MLS
Beautiful 4-bedroom, 2.5-bath brick ranch home located in the desirable Las Gaviotas neighborhood. This home features stunning LVP flooring throughout and a spacious primary bedroom with a walk-in closet. Recent updates include a brand-new roof and garage door (2026). Step outside and fall in love with the updated deck, complete with a ceiling fan and lighting under your covered porch, perfect for relaxing or entertaining while overlooking a private, wooded backyard along the Elizabeth River tidal canal. This home offers the perfect combination of comfort, updates, and peaceful outdoor living. NO FLOOD INSURANCE required! Encapsulated crawlspace with dehumidifier. Community amenities feature a pool, clubhouse, and golf course access; membership is required.

417 Granada Drive, South Chesapeake

2100 Saint Brides Road W, South Chesapeake
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 10619785 MLS
If you’ve been waiting for a home that truly stands apart, this is it. Custom built and perfectly positioned on approximately 3.5 private acres, this property offers peaceful country living just minutes from Edinburgh, shopping, dining, and top-rated schools. Enjoy wide-open skies, stunning star-filled nights, and the privacy you’ve been searching for. Inside, the open floor plan is designed for comfortable living and effortless entertaining. The spacious primary suite is a true retreat, while generously sized secondary bedrooms provide room for everyone. A hidden bonus room adds unique character and charm. Step outside to your backyard oasis featuring a heated saltwater pool and screened porch—great for relaxing or hosting. With 3.5 acres, there’s room to add a detached garage, workshop, in-law suite, or even a pickleball court. Priced below two recent appraisals, this is exceptional value in a rare setting. Homes cared for at this level — in this location — rarely become available.

2100 Saint Brides Road W, South Chesapeake

526 San Pedro Drive, South Chesapeake
$599,000
4 Beds ⋅ 2.1 Baths ⋅ 10630387 MLS
Hurry to see this beautiful home located on the golf course in sought after Las Gaviotas. You will love the white updated eat in kitchen with stainless steel appliances, an island, generous cabinets, granite countertops and open to the den. This home has a formal foyer, office, dining room, den with lovely views and wood stove. The room over the garage is very large with high ceilings. 100% of this giant room is usable. Plus there is a spacious primary bedroom with a dream bathroom and large closet with a surpise inside. Enjoy the covered deck with space for your TV, a bump out to grill your dinners and not be under the covered area, the most fabulous tree house for the littles to enjoy. The deck is gated and the back yard fenced. All with shady views of the rolling golf course. Vinyl siding is insulation, Well pulp connected to sprinkler system, large garage that is painted and ready for you, and a real laundry room and not a laundry closet. Come take a look at your next home.

526 San Pedro Drive, South Chesapeake

401 Pelican Circle, South Chesapeake
$610,000
4 Beds ⋅ 2.1 Baths ⋅ 10630242 MLS
This meticulously maintained 4-bedroom, 2.5-bath home offers approximately 2,400 square feet of living space and is truly move-in ready. The open layout features a gorgeous kitchen with granite countertops, a family room with fireplace, formal dining room, and a formal living room. The spacious primary suite includes a beautifully updated bath with dual sinks and a large walk-in closet. Enjoy entertaining in the large backyard with an in-ground saltwater pool, a huge deck, and stunning landscaped grounds. So many upgrades have already been taken care of for the next homeowner, including new flooring (2019), new blinds (2020), and updated door hardware, switches, outlets, and ceiling fans (2021). Other notable updates: roof (2019), zoned HVAC (units replaced in 2015 and 2018 and serviced twice a year), water heater (2019), salt generator (2019), and more. Fantastic location close to shopping, dining, and highways.

401 Pelican Circle, South Chesapeake

1017 Winchester Way, South Chesapeake
$549,900
4 Beds ⋅ 2.1 Baths ⋅ 10629177 MLS
Welcome Home to your new palace in the serene neighborhood of Kemp Woods! This rare opportunity to own a One Owner, meticulously maintained all brick ranch in a highly sought after area of Chesapeake does not come around often. Enter inside to the foyer and great room that lead into a formal dining room on one side and a large living room ahead. The living room is adorned by a large brick gas log fireplace, skylights and cathedral ceilings. The large Kitchen offers stainless steel appliances and a breakfast area. Large Laundry room includes a deep sink and separate half bath. The primary bedroom and Ensuite is located at the back of the home for privacy. Two other spacious bedrooms and full bath complete the layout on the main level. The large fourth bedroom is located above the garage. Outside you will find lush landscaping, a massive backyard and rear wooden deck equipped with seating areas. Centrally located between 168 and Va. Beach makes this neighborhood even more desirable

1017 Winchester Way, South Chesapeake

1449 Scoonie Pointe Drive, South Chesapeake
$475,000
3 Beds ⋅ 2.1 Baths ⋅ 10626787 MLS
Welcome to elegant living in this beautifully maintained 3-bedroom, one owner home offering 2200 sq ft in the highly desirable Eagle Pointe 55+ community. Step inside to find brand new luxury vinyl flooring throughout the main level, complemented by soaring cathedral ceilings that create an open and airy feel. The first-floor primary suite offers comfort and convenience, featuring new carpet and a private ensuite bath. Upstairs, you'll find two additional spacious bedrooms along with a bright and inviting loft, filled with natural light. Major updates include a brand-new energy efficient furnace and AC. Enjoy a true resort style lifestyle with access to The Eagle Pointe Bay Club amenities, including a social room, billiards room, library, catering kitchen, indoor & outdoor pools, a fitness center and a relaxing hot tub. This is low-maintenance living at its finest in a vibrant, amenity rich community. Come see for yourself- You won't want to leave.

1449 Scoonie Pointe Drive, South Chesapeake

1112 Turtle Rock Trce, South Chesapeake
$400,000
3 Beds ⋅ 2.1 Baths ⋅ 10628948 MLS
Corner lot living in the heart of Greenbrier! This 3-bedroom, 2.5-bath home offers a spacious and connected main level with LVP flooring throughout. The circular floor plan links the living room, dining area, kitchen, and den for easy everyday living and entertaining. The living room includes a wood-burning fireplace, while the kitchen features stainless steel appliances, an island with seating, generous counter space, and a dedicated coffee bar and wine rack area. A rear-facing window provides views of the fenced backyard with a paver patio. Upstairs, the primary suite includes an ensuite bath with a jetted tub and ceramic tile walk-in shower. Convenient access to Greenbrier City Park, shopping, dining, and interstates.

1112 Turtle Rock Trce, South Chesapeake

1955 Canning Pl, South Chesapeake
$435,000
3 Beds ⋅ 2.1 Baths ⋅ 10624944 MLS
Stunning, lakefront one owner and barely used luxury townhome in Hickory school district. Incredible community amenities include ponds and trails, an impressive clubhouse nearby with 24 hour gym access, pool, playground, outdoor grill area! You'll love the daily sunsets over the lake from your spacious rear patio. Tall ceilings, lvp flooring in living area that lets the natural light pour in. Gourmet kitchen with quartz tops, full stainless appliance package including gas range, large bar great for entertaining. Owners' suite boasts lake views and walk in closet along with ensuite bath with double vanity and shower with glass enclosure. Close to nature but easy access to shopping and dining at the same time. This is the lifestyle you've been looking for, welcome home!

1955 Canning Pl, South Chesapeake

1312 Bunker Ridge Arch Unit B, South Chesapeake
$315,000
3 Beds ⋅ 2 Baths ⋅ 10624415 MLS
Welcome home to your new condo in Greenbrier! Located just minutes from I-64, this single living level condo boasts 3 bedrooms and 2 full baths, including a primary suite with attached bathroom. You’ll love the cathedral ceilings and open living space that really take advantage of the expansive layout. The kitchen has seen plenty of updgrades including countertops, newer fridge, and high-end dishwasher. Enjoy the convenience of in-condo laundry with a full size washer and dryer hookup tucked just off the kitchen. With newer LVP flooring, a lovely electric fireplace, and tons of natural light from both the windows and skylights you’ll immediately feel the serenity of this end-unit condo. Don’t wait, schedule your private showing today!

1312 Bunker Ridge Arch Unit B, South Chesapeake

1049 Olmstead Street, South Chesapeake
$630,000
4 Beds ⋅ 3 Baths ⋅ 10628943 MLS
Looking for a home that feels brand new and professionally staged? This 2021 Hudson was upgraded with no expense spared, blending modern comforts w/ high-end luxuries. Step into the sun-filled foyer w/ soaring ceilings & to your left behind glass French doors, a magazine-worthy office w/ custom built-ins. Proceed into the vaulted, open-concept living area flowing into the dining area & chef’s kitchen with massive stone island, farmhouse sink, touch faucet, double oven, LG fridge & ample storage. Main-level guest bedroom w/ moody full bath offers convenience. Upstairs has a second large living area, size-able secondary bedrooms, a spa-like primary suite w/ dual showers & 2 custom walk-in closets. Picture coffee on the front porch swing & sunsets over the pond from the screened-in porch. Live the good life on 0.20 acres in Culpepper Landing w/ pool, clubhouse, playgrounds, dog park, year-round events & minutes to shopping, dining, golf, bases, I-64 & zoned for Deep Creek schools.

1049 Olmstead Street, South Chesapeake

1016 Primrose Lane, South Chesapeake
$230,000
2 Beds ⋅ 2.1 Baths ⋅ 10628414 MLS
Located in the Riverwalk section of Chesapeake, this corner unit offers added privacy and a desirable position tucked toward the backside of the building. Enjoy a quieter setting while still being just minutes from major interstates, shopping, dining, and everyday conveniences. The layout includes bathrooms both upstairs and downstairs for added convenience, along with generous closet space and plenty of storage throughout. A private, fully fenced patio provides a great space to relax or unwind. Additional highlights include an HVAC system replacement (2022) and two reserved side-by-side parking spaces right out front, and pool access. Vacant and move-in ready, this is an easy opportunity to settle in quickly. Opportunities like this tend to move quickly, so it’s one worth seeing sooner rather than later.

1016 Primrose Lane, South Chesapeake

1119 Fenton Quay, South Chesapeake
$465,000
4 Beds ⋅ 2.1 Baths ⋅ 10628395 MLS
Welcome to cul-de-sac living in the heart of Greenbrier. This updated 4 bedroom, 2.5 bath home offers the perfect blend of comfort and style with vaulted ceilings, hardwood floors, and a bright kitchen featuring stainless steel appliances that flows into a second living space with a wood burning fireplace. The main level also includes a beautifully updated half bath. Upstairs, LVP flooring leads to a spacious primary suite with a trey ceiling and private deck, plus an en suite with double vanity, jetted tub, separate shower, and walk in closet. Three additional bedrooms share an updated full bath. Enjoy a fenced backyard with a deck and storage shed, all backing by the 15th hole of Greenbrier Country Club. Complete with a 2 car garage, whole house surge protector, and extra storage. Don’t miss this opportunity.

1119 Fenton Quay, South Chesapeake

715 Paula Drive, South Chesapeake
$771,000
6 Beds ⋅ 3 Baths ⋅ 10626877 MLS
Tucked away on over three private acres in the sought-after King James Colony, this stunning Craftsman-style home offers the excellent blend of space, privacy, and charm. With over 3,200 square feet, this home features six spacious bedrooms and a private office just off the primary suite—great for work or relaxation. The updated chef’s kitchen is designed for both everyday living and entertaining, while vaulted ceilings and abundant natural light create a warm, inviting atmosphere throughout. Step outside to your private back deck complete with a built-in hot tub, great for unwinding. An oversized two-car garage and a separate stable with its own workshop add incredible versatility. Endless possibilities await—experience peaceful country living at its finest.

715 Paula Drive, South Chesapeake

304 Spurlane Circle, South Chesapeake
$495,000
4 Beds ⋅ 2.1 Baths ⋅ 10625030 MLS
GREAT BRIDGE UPDATED 4 BEDROOM 2.5 BATH CORNER LOT HOME, OVER 2,100 SQUARE FOOT OF LIVING AREA, FORMAL LIVING AND DINING ROOMS, OPEN EAT-IN KITCHEN, BOX BAY WINDOW, STAINLESS WHIRLPOOL APPLIANCES SIDE BY SIDE REFRIGERATOR / SMOOTH TOP STOVE / BUILT-IN MICROWAVE AND DISHWASHER, GRANITE COUNTER TOPS, BAR AREA, RECESSED LIGHTS, PANTRY. OPEN FAMILY ROOM GAS LOG FIREPLACE, DELUXE PRIMARY SUITE WALK-IN CLOSET AND SECOND CLOSET, PRIMARY BATH TILE FLOOR, OVER SIZED VANITY, LARGE SHOWER TILE SURROUND. ATTACHED GARAGE WITH ELECTRIC DOOR OPENER. UPGRADED BATHS, FLOORS, LIGHT FIXTURES, APPLIANCES, WINDOW BLINDS, CROWN/CHAIR MOLDING, GAS HEAT AND HOT WATER, HVAC SYSTEM REPLACED DECEMBER 2018. LARGE STORAGE SHED AND DECK, PRIVACY FENCED BACKYARD, PREMIUM CULDESAC LOT.

304 Spurlane Circle, South Chesapeake

517 Long Point, South Chesapeake
$332,500
3 Beds ⋅ 2.1 Baths ⋅ 10625801 MLS
Welcome to 517 Long Point in the highly sought-after Cedar Lakes neighborhood of Great Bridge! This well-maintained home blends comfort, style, and thoughtful updates throughout. Enjoy outdoor living with a brand new deck and balcony—perfect for relaxing or entertaining. Major improvements include an HVAC system replaced in 2022 and a new oven in 2023, giving peace of mind to the next owner. Inside, you’ll love the fresh interior paint, updated light fixtures, and wall repairs that create a clean, modern feel. The kitchen features new flooring, while the downstairs has been refreshed with new baseboards for a polished finish. A storm door at the front entry adds both charm and efficiency. Located in a desirable neighborhood close to top-rated schools, shopping, dining, and more—this move-in ready home checks all the boxes!

517 Long Point, South Chesapeake

720 Dickens Place, South Chesapeake
$595,000
5 Beds ⋅ 2.1 Baths ⋅ 10625048 MLS
Welcome to 720 Dickens Place in sought-after Cheshire Forest in the heart of Great Bridge! This beautifully renovated 5-bedroom home offers space, flexibility, and privacy on a large cul-de-sac lot with no neighbors behind you. Renovations completed 2025–2026 include new LVP flooring throughout, complete interior paint, majority of windows replaced, brand-new HVAC system, encapsulated crawlspace with added insulation, new garage door with opener, full termite treatment, and a brand-new refrigerator (never used). The flexible 5th bedroom can serve as an office, playroom, guest suite, craft/sewing room, theater room, or bedroom. Move-in ready with easy access to the interstate, shopping, dining, and top-rated schools—this home truly checks every box.

720 Dickens Place, South Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.

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