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1108 Cumberland Court, South Chesapeake
$600,000
4 Beds ⋅ 3 Baths ⋅ 10657974 MLS
Welcome to 1108 Cumberland Ct, a beautifully staged Chesapeake home with a pool and a fenced backyard made for entertaining. Inside, enjoy bamboo flooring and premium crown molding throughout the main level. The kitchen features granite counters, tiled backsplash, a pocket door, a gas range (2022), a 2024 dishwasher, and whole-house plus reverse-osmosis water filtration. A full downstairs bath with a walk-in shower adds convenience, and the wood-burning fireplace is perfect for cool evenings. Major updates include roof and skylights (2015), gas furnace and A/C (2017), front windows (2020), and an encapsulated crawl space with new vapor barrier (2022). Walk-in attic, garage shelving, and comfort-height toilets. Open house Saturday, 10/17. Schedule your showing today!

1108 Cumberland Court, South Chesapeake

2112 Willow Point Arch, South Chesapeake
$240,000
2 Beds ⋅ 2 Baths ⋅ 10657769 MLS
Move-in ready 2-bedroom, 2-bath condo with spacious loft in the sought-after Riverwalk community! Freshly painted throughout with a new water heater and HVAC replaced in 2018. Bright, open floor plan features a kitchen overlooking the dining and living areas, creating a comfortable space for everyday living and entertaining. Generous first-floor bedroom offers a walk-in closet and direct access to a full bathroom. Upstairs features a versatile loft with built-ins and a spacious primary suite with ample closet space and private bath. Enjoy your own fenced front patio and additional storage shed. Conveniently located near shopping, restaurants, major highways, and military installations throughout Hampton Roads. Low-maintenance living, thoughtful updates, and an excellent location make this condo a fantastic opportunity. Schedule your showing now.

2112 Willow Point Arch, South Chesapeake

530 San Pedro Drive, South Chesapeake
$670,000
4 Beds ⋅ 3 Baths ⋅ 10657170 MLS
Welcome to Las Gaviotas, where golf course living meets your own backyard oasis! This sprawling 4-bedroom brick ranch offers beautiful golf course and water views, impressive vaulted ceilings, exposed beams, and a stunning two sided fireplace connecting the great room and sunroom. The beautifully renovated kitchen features a large center island and gas cooktop, while the spacious primary suite offers peaceful views and a luxurious bath. Step outside to your private retreat featuring an inground pool with updated liner, hot tub, gorgeous new paver patio, and outdoor gas kitchen for entertaining! Additional highlights include updated bathrooms, kitchen, expansive laundry room, new fixtures, Updated Flooring and Paint, HVAC (2024), roof (2019), and new water heater. Seller to provide a clear termite and moisture letter. A rare opportunity to enjoy single level living, incredible outdoor entertaining, and scenic surroundings!

530 San Pedro Drive, South Chesapeake

737 Willow Oak Drive, South Chesapeake
$560,000
4 Beds ⋅ 2 Baths ⋅ 10656926 MLS
This one checks ALL the boxes! Immaculate, beautifully updated, and exceptionally well maintained, this 4 bedroom, 2 bath Chesapeake home truly stands out. The remodeled kitchen features stainless steel appliances, a gas range and hood, beautiful countertops and backsplash, abundant cabinetry, eat-in space, and a custom butler’s pantry. Recessed lighting throughout enhances the bright, modern feel, while the inviting living room showcases beautiful hardwood floors, a large cozy fireplace, and abundant natural light. The separate dining room is ideal for everyday meals and entertaining. The primary suite features an impressive custom designed en-suite bathroom with gorgeous custom cabinetry, double vanity, and an oversized walk-in shower. Outside, enjoy a large, beautifully manicured backyard and expansive deck. An attached garage plus an impressive, detached 2 story garage provides exceptional space for vehicles, hobbies, storage, or a workshop. This home truly has it all!

737 Willow Oak Drive, South Chesapeake

1021 Grantham Lane, South Chesapeake
$559,900
4 Beds ⋅ 2 Baths ⋅ 10656531 MLS
Loved by one owner for years, this meticulously maintained home in sought-after Etheridge Woods is competitively priced with some minor updating in mind — a rare opportunity to make it truly your own! Hardwood floors flow through the living room, dining room, primary bedroom, and family room, while granite counters shine in the kitchen and guest bath. The kitchen's breakfast area overlooks the backyard and opens to a spacious family room with vaulted ceilings and skylights, filling the space with natural light. Just off the family room, the FROG/4th bedroom offers flexible space for guests, a home office, or playroom. Enjoy a screened-in section of the front porch and a deck out back, perfect for entertaining. Zoned for Hickory/Butts Road schools and just minutes from major highways and shopping. Schedule your showing today!

1021 Grantham Lane, South Chesapeake

3342 Martin Johnson Road, South Chesapeake
$1,650,000
5 Beds ⋅ 3.2 Baths ⋅ 10656180 MLS
Quiet Luxury. Architectural Artistry. This Custom Built Estate was designed not simply to be lived in, but to be experienced on 4 acres, 5,900 sqft (plus add'l 980 ROG). The dramatic, soaring ceilings & windows throughout a 2-story family rm w/stone fireplace, along w/every custom architectural detail make a statement of true Luxury. From the picturesque curb appeal to first floor Primary Suite & your own private spa, a cedar-lined wellness retreat w/hot tub. The expansive fl plan provides flexibility for formal gathering & relaxed everyday living. This home was thoughtfully designed, w/ 4 add'l spacious bedrms, generous living & entertainment areas, abundant nat'l light & craftsmanship throughout. New 6 burner-gas Wolf range in large kitchen, Trex board decking outside, endless possibilities to entertain & peace/privacy. An inground pool, pool house, pergola & plenty of open space. Large ROG is ready for you to make it your own movie/game room! Ask your agent for feature sheet!

3342 Martin Johnson Road, South Chesapeake

1407 Hawick Terrace, South Chesapeake
$499,999
3 Beds ⋅ 3 Baths ⋅ 10656063 MLS
Welcome home to Chesapeake’s premier 55+ community! This move-in-ready home offers a fantastic and flexible floor plan featuring TWO spacious primary suites—one on each level—providing plenty of room for guests. The beautiful family room features soaring vaulted ceilings, luxury vinyl plank flooring, and a cozy gas fireplace. Just off the main living area is an additional first-floor flex space, perfect for a home office, reading room, or a relaxing spot to enjoy your morning coffee. The spacious eat-in kitchen features new stainless steel appliances and recessed lighting, while the formal dining room provides the perfect space for entertaining. The large first-floor primary suite offers a private bath with double vanity, separate shower, and oversized jetted tub. At the heart of the community is the Bay Club, featuring indoor and outdoor pools, hot tub, fitness center, billiards, library, game rooms, and so much more. Come experience resort-style living at Eagle Pointe!

1407 Hawick Terrace, South Chesapeake

241 Sign Pine Road, South Chesapeake
$950,000
4 Beds ⋅ 3.1 Baths ⋅ 10655919 MLS
Your dream home awaits!! Craftsman bones, a custom remodel, and a horse barn out back: acreage living with refined character. Every inch of this home was designed by the sellers who were contractors with love over the years. Inside, coffered ceilings meet warm cedar and wood-plank ceilings, giving every room a crafted, finished feel, and Brazilian cherry hardwoods run underfoot toward a stone gas-log fireplace that anchors the living space. Floor-to-ceiling windows and skylights flood the home with light, while custom barn doors and Restoration Hardware fixtures make even the transitions between rooms feel intentional. The kitchen is built to gather around. An oversized honed granite island with a built-in microwave takes center stage, backed by custom cabinetry, an etched tile backsplash, a built-in pantry, newer appliances, and purified water at the sink. Next door, color-changing upper lighting lets the dining room shift from weeknight dinner to late-night celebration at the flip of a switch. The first-floor and second story primary suite comes with its own bath, the bathrooms have been updated throughout, and a sun room, bar and mudroom with drop zone give the layout room to breathe. Then step outside, where the property really shows off. A 40,000-gallon saltwater pool, 8 feet deep with a diving board and fountain, sits beside a koi pond and gazebo linked by brick walkways. Made for a party or a wedding. Beyond it, a fenced acre of pasture leads to a barn with two stalls, a wash stall, a brick-paved breezeway, tack room, and horses are allowed. Wrapped in Hardie plank and stone, heated and cooled by geothermal, and tucked into a wooded setting of nearly five acres neighboring Greenbrier Farms in the Hickory school zone. Morning coffee in the sun room, afternoons at the barn, evenings by the pool: this home makes every part of the day worth staying for. And let's talk privacy.

241 Sign Pine Road, South Chesapeake

1345 Oak Ridge Drive, South Chesapeake
$629,900
4 Beds ⋅ 2 Baths ⋅ 10655393 MLS
Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home!

1345 Oak Ridge Drive, South Chesapeake

1414 Loose Strife Place, South Chesapeake
$268,000
3 Beds ⋅ 2 Baths ⋅ 10654280 MLS
Experience airy, sun-drenched living in this beautifully updated two-story home. Enjoy an open living and dining space elevated by soaring ceilings, architectural skylights, and expansive windows that maximize natural light. Refreshed in 2026, the interior showcases brand-new flooring across both levelsfresh paint, and a new water heater. The fully serviced HVAC ensures year-round comfort. The sleek kitchen features premium granite countertops, stainless steel appliances, and a breakfast bar. A rare main-level bedroom and full bath offer ultimate flexibility. Upstairs, the primary retreat boasts vaulted ceilings, a walk-in closet, and an upgraded bath. Complete with clever storage and 2 assigned spaces, this home sits in a vibrant neighborhood featuring scenic ponds, green spaces, a pool, and a playground.

1414 Loose Strife Place, South Chesapeake

1547 Orchard Grove Drive, South Chesapeake
$289,000
2 Beds ⋅ 2 Baths ⋅ 10654011 MLS
**SELLER OFFERING A 1-YEAR INTEREST RATE BUYDOWN!** Tucked away on a quiet street in Orchard Grove, this spacious 2-bedroom, 2-bath condo has more to offer than meets the eye! Soaring ceilings, skylights, and a gas fireplace make the living room feel bright, open, and inviting. The updated kitchen features new cabinets, quartz countertops, stainless steel appliances, and a dedicated coffee bar to start your mornings right! Need extra space? The upstairs loft offers endless possibilities for a home office, workout area, hobby room, or additional flex space. Enjoy the convenience of condo living with shopping, dining, military installations, and interstate access just minutes away. **Updated kitchen, flexible living space, and a seller-paid interest rate buydown. What's not to love? Schedule your showing today!**

1547 Orchard Grove Drive, South Chesapeake

302 Honey Locust Way, South Chesapeake
$635,000
4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS
Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way, South Chesapeake

808 Bay Laurel Court, South Chesapeake
$634,000
4 Beds ⋅ 3.1 Baths ⋅ 10653860 MLS
Welcome home to this beautiful brick home, ideally situated on a large corner lot in a cul-de-sac in Chesapeake’s desirable Cedarwood community. Offering more than 3,000 square feet, this move-in-ready home features an open, light-filled floor plan with tall ceilings and gorgeous wood flooring. The spacious kitchen flows seamlessly into the living area, creating the perfect setting for entertaining. Relax beside the wood-burning fireplace surrounded by charming built-in shelving, or enjoy the backyard with its generous deck, gazebo and delightful garden house. Two primary bedrooms with private full baths provide wonderful flexibility for guests or multigenerational living. Other highlights include updated bathrooms, upgraded windows and architectural shingles. New refrigerator installed in 2026. All appliances convey. A two-car attached garage and additional street parking, conveniently located near shopping, dining and sought-after Chesapeake schools. Schedule your private tour today!

808 Bay Laurel Court, South Chesapeake

1910 Hallmark Way, South Chesapeake
$998,895
5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS
Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem. **Bookshelves do not Convey**

1910 Hallmark Way, South Chesapeake

1052 Stockleybridge Drive, South Chesapeake
$725,000
5 Beds ⋅ 3 Baths ⋅ 10651967 MLS
Gorgeous 2 story Home situated on a private and lushly landscaped lot in the Etheridge Lakes neighborhood in Southern Chesapeake. Step into the elegant 2 story foyer and be amazed by the beautiful details throughout this spacious home that has been well maintained and lovingly cared for by the original owners. The vaulted Family Room opens to the large and updated Eat in Kitchen and both offer perfect views of the privacy fenced backyard oasis boasting a stunning and resort style saltwater pool with waterfall and stamped concrete surround, deck, storage shed, and outdoor shower. Additional Details: 1st floor Bedroom and full bath, Primary Suite with walk in closet and updated full bath, Formal Dining Room, new LVP flooring on 1st floor, nice sized bedrooms with ceiling fans, dual staircases, FROG is 5th bedroom, 2nd floor Laundry Room, freshly painted interior, newer carpeting, zoned HVAC, well/sprinkler system, 2 car sideload garage, gutter system, and more! Attends Hickory schools.

1052 Stockleybridge Drive, South Chesapeake

1104 Copper Stone Circle Circle, South Chesapeake
$599,000
4 Beds ⋅ 3 Baths ⋅ 10652961 MLS
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

1213 Killington Square, South Chesapeake
$319,000
2 Beds ⋅ 2.1 Baths ⋅ 10650185 MLS
MOVE-IN READY end-unit townhome in highly desirable Greenbrier! Fresh paint and brand-new carpet throughout give this home a clean, modern feel. The bright eat-in kitchen features stainless steel appliances and granite countertops, perfect for everyday living and entertaining. The spacious great room includes a dining area, cozy fireplace, and direct access to a large fenced backyard with storage shed and utility room (shed conveys As-Is). A convenient half bath and laundry complete the first floor.Upstairs offers two spacious en-suite bedrooms filled with natural light. The third-floor loft provides flexible space ideal for a home office, media room, playroom, or guest suite.Enjoy low-maintenance living in a prime location close to shopping, dining, parks, and major highways making commuting a breeze. Don’t miss this stylish, move-in ready home!

1213 Killington Square, South Chesapeake

2213 Wildwood Road, South Chesapeake
$429,900
4 Beds ⋅ 2 Baths ⋅ 10649889 MLS
Welcome home to this classic 4 bedroom, 2 bath brick home offering timeless character and plenty of space to enjoy inside and out. A charming side porch adds to the home’s inviting appeal, while the spacious backyard is made for warm-weather living with a large in-ground pool and plenty of room to relax or entertain. An additional detached brick building, formerly used as a garage, offers flexible bonus space and includes a full bathroom and kitchenette. Use it as a workshop, home office, pool house, hobby space, or additional storage. The possibilities are yours. With its classic brick exterior, great outdoor spaces, and versatile detached building, this property offers a combination of character, function, and potential.

2213 Wildwood Road, South Chesapeake

816 Forest Lakes Circle, South Chesapeake
$685,000
4 Beds ⋅ 3 Baths ⋅ 10649561 MLS
Highly Sought after neighborhood in highly rated Grassfield High School (9/10), Great Bridge Middle School (9/10), and Cedar Road Elementary School (8/10) districts. Appraisal and Home Inspection fees paid if using Preferred Lender. Welcome home to this lovely Larry Hill built Brick Colonial home in Forest Lakes. The home has an Architectural roof installed 2013. It sits on a beautifully landscaped yard to include a double gated fenced-in back yard w/ irrigation system. Go up the back steps to a 12x34 deck built in 2019 to enjoy grilling on those wonderful summer evenings and into the sunroom that is great for entertaining. Adjourn into the cozy den with a natural gas fireplace, move into the home office with attached French doors and dining room both with white oak wood floors. The kitchen is well laid out with Skylights, stainless steel Bosch appliances, double oven, surface range, Granite counter tops and Oak cabinets. The Primary Bath is something to see with its marble walk-in shower, new soaking tub, Italian tile floors, walk-in closet and tray ceiling. Newer Skylights and vaulted ceilings make the home light and airy. Storage thru out, also in the attic. Termite Bond provided. If buyer uses preferred mortgage broker, lender will pay for Home Inspection and Appraisal.

816 Forest Lakes Circle, South Chesapeake

2808 Willows Arch, South Chesapeake
$469,900
4 Beds ⋅ 2.1 Baths ⋅ 10648837 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home on a desirable corner lot in a sought-after, sold-out Chesapeake neighborhood. Tucked away on a quiet cul-de-sac, this home offers a spacious contemporary floor plan perfect for everyday living & entertaining. The main level features a formal living room, dining room, den, & open kitchen with stainless steel appliances and a bright sunroom. The spacious primary suite offers beautiful skylights, abundant natural light, & a private en-suite bath with a relaxing soaking tub. Enjoy outdoor living on the large deck overlooking the expansive backyard, perfect for gatherings, grilling, or relaxing. With generous living spaces, a functional layout, & a prime location, this home is a wonderful opportunity to own in an established neighborhood with No POA & minutes from everything!

2808 Willows Arch, South Chesapeake

609 Edgewood Arch, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10646683 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

2505 Sylvia Court, South Chesapeake
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 10642797 MLS
Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great room with a see-through gas fireplace. The island kitchen features granite, stainless, and a wet bar. The primary suite is a private retreat with a tray ceiling and a spa bath with a soaking tub. A temperature-controlled pool room, a rarity in Hunters Ridge, holds a heated pool beneath vaulted, skylit ceilings for year-round swimming and entertaining. A detached guest suite of about 715 finished square feet adds a kitchenette and full bath, ideal for extended family or long-term guests. A three-car garage, brick-pillar drive, pergola with hot tub, and patios complete the grounds.

2505 Sylvia Court, 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.