Chesapeake VA Real Estate | Chesapeake VA Homes with a Pool for Sale

Welcome to the kind of home that feels good the moment you enter. Set on just over 2 peaceful acres, this 5-bed, 3-bath home offers the perfect blend of space, comfort, and modern style. Sunlight pours through the windows, filling every room with warmth, while the open layout creates an easy flow for everyday living and gathering with the people you love. The home features two spacious primary suites, one located on the first level, both with private baths and large closets, making it ideal for guests, or multigenerational living. You'll also love the luxury vinyl plank flooring, granite countertops, stainless steel appliances, and the beautiful laundry room! The backyard is just as inviting. Whether you're roasting marshmallows around the fire pit, spending summer afternoons in the saltwater pool, or simply enjoying the quiet views with your morning coffee, the backyard feels like your own private escape. Peaceful, welcoming, and full of room to grow! *One year Choice home warranty

1108 Shell Road, South Chesapeake

$525,000

5 Beds ⋅ 3 Baths ⋅ 10658716 MLS

Spacious brick rancher offering 5 bedrooms and 3 full baths with an abundance of living space and approximately $250,000 in improvements over the past 13 years! The home features a living room, formal dining room, and inviting family room with fireplace. The kitchen offers granite countertops and plenty of cabinet space. The primary suite includes a private bath and walk-in closet, while the finished room over the garage provides additional flexibility for a home office, recreation room, or guest space. Enjoy outdoor living on the large covered deck overlooking the above-ground saltwater pool and fenced backyard. Additional highlights include an oversized attached 1-car garage and an oversized detached 2-car garage with workshop, valued at approximately $60,000. With generous space, extensive improvements, and exceptional garage and workshop space, this property offers plenty to appreciate!

461 Gloria Drive, South Chesapeake

$345,000

5 Beds ⋅ 2 Baths ⋅ 10658681 MLS

Discover the potential in this 5-bedroom, 2- bathroom ranch nested on New Mill Creek. This home features tons of updates throughout, providing a great head start while leaving room for your personal cosmetic touches. Head outback to the large lot, where natural scenery creates a peaceful backdrop for everyday living. Flood insurance is required.

1753 Burson Drive, South Chesapeake

$418,899

4 Beds ⋅ 2 Baths ⋅ 10658565 MLS

Charming brick home with plenty of character, versatile living spaces, and a backyard made for entertaining! Offering 4 bedrooms and 2 full baths, this home features hardwood floors, a cozy gas fireplace, and a first-floor bedroom for added flexibility. The upper level provides additional bedrooms with their own unique character. Enjoy outdoor living on the screened porch or deck overlooking the fenced backyard and in-ground swimming pool. A detached brick building with its own kitchenette and full bathroom offers additional possibilities for a hobby space, workshop, or poolside entertaining. Situated on approximately a quarter-acre lot with no HOA, this property offers a wonderful combination of indoor and outdoor space, distinctive features, and the opportunity to make it your own! Opportunity for up to $3500 lender credit with use of preferred lender.

2213 Wildwood Road, South Chesapeake

$419,900

4 Beds ⋅ 2 Baths ⋅ 10658446 MLS

Welcome to 2716 Lake Ridge Ct, a 4-bedroom, 2-bath home on a quiet cul-de-sac in Woodlake Forest with a private backyard retreat. The updated kitchen has stainless appliances, a farmhouse sink, two-tone cabinetry and a center island, and it opens to the living room with a fireplace. Both baths have been updated, and the primary bedroom has its own private bath. There are three bedrooms on the main level plus a spacious 4th bedroom/bonus room over the garage. Out back you’ll find a covered porch, composite deck and in-ground pool, all behind a privacy fence and ready for next summer. You won't find an HOA for this neighborhood and there is an attached 1 car garage. It’s minutes to I-64, Route 17, shopping and dining. Schedule your showing today!

2716 Lake Ridge Court, South Chesapeake

1266 Auburn Hill Drive, South Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10657857 MLS

Experience refined comfort in sought-after Albemarle River! Tucked away on a beautiful corner lot yet near I-64, shopping, dining, & all Greenbrier has to offer, this exceptional one-owner Craftsman home has been meticulously maintained. Beautiful Craftsman trim, columns on front porch, hardwood floors, & an inviting open floor plan create a warm, elegant feel. The kitchen features Cortez countertops and stainless-steel appliances. The expanded primary suite offers a custom dream closet & spa-inspired bath with dual vanities, walk-in shower, & oversized soaking tub. The FROG offers flexible space for a 4th bedroom, office, or media room. Step outside to your private backyard oasis with a sparkling heated saltwater in-ground pool, & plenty of room to entertain. Beautifully cared for and move-in ready, this is the one you've been waiting for!

1266 Auburn Hill Drive, South Chesapeake

$950,000

6 Beds ⋅ 5.1 Baths ⋅ 10658157 MLS

All-brick home offering over 5,000 sq. ft. of versatile living space and exceptional indoor–outdoor amenities. With 6 bedrooms, 5.5 bathrooms, and an additional first-floor flex room perfect as a 7th bedroom, home office, or formal living area, this home adapts beautifully to your lifestyle. Five of the bedrooms include private en-suite bathrooms, giving everyone their own comfortable retreat. A bright, oversized sunroom—equipped with heating and cooling but not included in the home’s total square footage—adds even more year-round living space. Step outside to your own backyard oasis. Brick pool house with heating/cooling + full bathroom. In-ground saltwater pool with a new liner ( installed 2025). Hot tub for 6. Expansive patio area for entertaining and relaxing. The property also features a three-car garage plus a half-circle driveway providing abundant parking for guests. freshly painted, new carpets, refinished wood floors. Interior pics virtually staged.

844 Greenfield Lane, South Chesapeake

$639,900

4 Beds ⋅ 2.1 Baths ⋅ 10658002 MLS

Welcome to 660 Middleton Way! This well-maintained 4-bedroom, 2.5-bath home features a stunning backyard oasis with a private swim spa, covered patio, and extended concrete slab, great for relaxing and entertainment. Inside, enjoy a primary suite with an ensuite bathroom featuring double sinks, plus convenient upstairs laundry. A storage shed provides extra space for outdoor equipment. Community amenities include a clubhouse, grounds maintenance, pool, gym, and trash pickup. Conveniently located near shopping, dining, and major interstate access. Schedule your showing today!

660 Middleton Way, 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

$850,000

5 Beds ⋅ 3 Baths ⋅ 10657808 MLS

This is the kind of Chesapeake home that feels substantial the second you walk in. Restored inside and out, it carries the scale and character of an established traditional home, with beautiful arched doorways, refinished hardwoods, fresh paint, new carpet, and thoughtful updates that make the entire house feel fresh again. The main level is generous without feeling disconnected. The kitchen sits between the formal dining room, the vast open living space, and the screened porch, making it the natural link between everyday living and entertaining. Ample white cabinetry wraps the room, while an oversized island, thick warm granite countertops, a ceramic Kohler sink, and new appliances give it both presence and function. From there, the screened porch opens to the rear deck and draws you straight out toward the pool. That backyard deserves its own moment. The in-ground pool sits within a wide paver surround and includes a diving board and built-in sitting ledge, all framed by decorative iron fencing. But the fence is not the end of the yard. The property continues beyond it with additional lawn space and an in-ground fire pit, giving the outdoor space far more depth than the pool area first reveals. Inside, nearly every turn brings another room with a purpose. A dedicated library adds character to the main level, while the separate billiard room creates another substantial place to gather. A first-floor bedroom sits near a modern updated full bath, and upstairs, a finished attic adds even more usable space with room for movies, games, hobbies, or whatever comes next. Then there is the primary suite, and it is genuinely oversized. Beyond the sleeping area is a separate sitting room, an enormous walk-in closet, and an ensuite with a jetted soaking tub and separate stand-up shower. Set in Carriage House Estates in Chesapeake’s 23322 with Hickory schools and a central location, this is a home where the size, flow, and character show up in all the right places—inside, outside, and in the spaces you do not expect until you are standing in them.

603 Oxbow Court, South Chesapeake

$980,000

6 Beds ⋅ 4 Baths ⋅ 10657839 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

$379,900

4 Beds ⋅ 3.1 Baths ⋅ 10657809 MLS

Situated in Chesapeake's Norfolk Highlands neighborhood, this 4-bedroom, 3.5-bath home offers approximately 2,000 square feet with a flexible floor plan and plenty of indoor and outdoor space to enjoy! Inside, find inviting living and dining areas that flow into an updated kitchen featuring granite countertops, shaker-style cabinetry, stainless steel appliances, and a center island with additional seating. The flexible floor plan features two bedrooms on the first floor, including one with a private ensuite bathroom, and two additional bedrooms upstairs, one also featuring its own ensuite bathroom. This layout offers great options for guests, home offices, or multigenerational living. Recent improvements include updated bathrooms (2024), plumbing (2021), and fresh interior paint. An encapsulated, unfinished basement offers additional storage or workspace. Out back, the fully fenced yard is ready for entertaining with an above-ground pool, multiple decks, and a separate man shed with power, a bar, and a window unit. Additional highlights include dual driveways, an electric vehicle charging station, and a roof replaced in 2020. 3.5 PERC ASSUMABLE VA LOAN!! Incentives may be available through preferred partners. Contact the listing agent for details and eligibility.

1129 Hazel Avenue, Central Chesapeake

$549,900

3 Beds ⋅ 1.1 Baths ⋅ 10657745 MLS

Well-maintained, move-in-ready brick ranch in an established neighborhood with wide sidewalks! Features attractive LVP flooring throughout, three bedrooms, and a primary suite with a walk-in closet. Enjoy the gas log fireplace and additional storage with floored attic space. The converted attached garage is currently equipped as a beauty salon with styling station, shampoo sink, built-in cabinetry, and laundry area. A bright 20' x 20' sunroom with three walls of casement windows overlooks the backyard. Outdoor amenities include a 20' x 20' composite deck, fenced yard, and a 20' x 40' in-ground pool with cover. The detached three-bay garage includes power, workbenches, and pull-down access to a large, floored attic. A rare combination of comfort, functionality, and exceptional indoor and outdoor living space.

616 Rutherford Drive, South Chesapeake

3616 Riverwood Crescent, South Chesapeake

$749,000

4 Beds ⋅ 3 Baths ⋅ 10657714 MLS

COUNTRY LIVING AT ITS BEST!Imagine sipping your morning coffee while deer graze in your backyard! This incredible 3-acre property in desirable Hickory/Grassfield offers privacy, space, and endless possibilities!2,200 sq ft home with 4 bedrooms and 3 fully renovated bathrooms, a cozy wood-burning fireplace, new waterproof laminate flooring throughout, and a 2-car attached garage.The 1,500 sq ft heated workshop features a vehicle lift, compressor — perfect for car enthusiasts, hobbies, or business needs! Enjoy one of the largest above-ground pools available, extensive decking, and a recently repaired and painted shed. Additional features include newer HVAC and appliances, an ivwr thw top water softener, and a sealed crawlspace with dehumidifier and warranty. Not in a designated flood zone! Three acres, a spacious heated workshop, and your own private backyard oasis in the sought-after Hickory/Grassfield school district!Country charm, modern comforts, and room to live your way!

3616 Riverwood Crescent, 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

4748 Barn Swallow Drive, West Chesapeake

$570,000

4 Beds ⋅ 3 Baths ⋅ 10656599 MLS

Welcome home to this beautifully updated property located in the Jolliff Woods neighborhood in Western Branch! Featuring a fully remodeled kitchen and 3 full baths (2020), this home offers the perfect blend of comfort, style, and functionality. Step outside to your own backyard retreat, complete with a sparkling saltwater pool featuring a new liner and newer pump, a spacious deck great for entertaining, and a screened porch great for relaxing evenings. The primary bedroom features 2 walk-in closets and a soaking tub with a large, oversized shower. Additional highlights include dual-zone HVAC systems and a one-year-old storage shed. Anderson windows installed in 2006. Whether you're hosting summer gatherings or enjoying a quiet evening at home, this property offers wonderful indoor and outdoor living spaces. Move right in and start enjoying all this home has to offer! Amazing tucked-away .38 acre corner lot and just minutes to the interstate, with quick access to the Peninsula and the rest of Hampton Roads

4748 Barn Swallow Drive, West Chesapeake

$674,900

4 Beds ⋅ 2.1 Baths ⋅ 10657194 MLS

Beautifully maintained home in highly sought-after Dominion Meadows in Grassfield. Spacious floor plan with abundant kitchen storage, counter space and oversized granite island. Gleaming hardwood floors and ceramic tile. Enjoy the 16' x 36' Grecian-style inground pool with automated system. Expanded patio and pool deck create an ideal entertaining space. Private fenced yard with automated well irrigation and matching 8' x 14' shed. Home theater with five in-ceiling speakers and built-in cabinet. Home features include Nest thermostats, cameras and garage automation. Convenient to shopping and interstate access. Desirable Grassfield High School district. Call today !

605 Wood Nymph Lane, South Chesapeake

$390,000

4 Beds ⋅ 3 Baths ⋅ 10656783 MLS

Dazzling one story home Nestled in the back of the neighborhood on a no outlet road with exquisite updates throughout. New Flooring (all Ceramic and LVP), Paint, Lighting, and Roof. Luxurious primary bedroom with ensuite featuring double vanity Sinks, walk in Shower with a Rain Shower Head, and Walk-in Closet. Lots of Storage throughout the home. Serene Fenced Backyard Patio for relaxing, grilling, outdoor entertaining with a Gazebo ready for your patio furniture. The Inground salt water Pool is calling you to Relax. Minutes to Indian River Park South Side & Indian River trail. Schedule a tour today of the captivating home.

2121 Speedy Avenue, Central Chesapeake

$599,900

4 Beds ⋅ 3 Baths ⋅ 10656993 MLS

Stunning 4-bedroom home in the highly coveted Las Gaviotas community, overlooking the golf course. The spacious interior offers a comfortable blend of living and entertaining spaces, including a generous living room, dining room, and family room with a fireplace. At the heart of the home, the kitchen features ample cabinet and counter space, stainless steel appliances, and a breakfast area. Four spacious bedrooms and three full bathrooms include a primary suite with a walk-in closet and ensuite bath. Enjoy additional living and entertaining space in the sunroom or screened-in porch (added 2021) with views of the 40ft heated fiberglass in-ground pool ( added 2021). Other updates include: water heater (2022), HVAC upstairs zoned inside and out (2026), new carpet and mini split for FROG (2023), Bathrooms downstairs converted (2023).

709 Aguila Drive, South Chesapeake

3316 Kindlewood Crescent, West Chesapeake

$498,250

4 Beds ⋅ 2.1 Baths ⋅ 10657022 MLS

This charming brick colonial home is on a corner lot of a cul-de-sac in the desirable Silverwood development. The spacious 20x40 ft. pool boasts of a new liner in 2024, complemented by a brand-new back porch added three years ago and a freshly renovated front porch completed this summer. Inside, the updated kitchen shines with granite countertops, freshly painted cabinets (including upper cabinets repainted this summer), a new sink, and modern cabinet pulls. Beautiful hardwood floors grace the front half of the downstairs (recently refinished) and all of the upstairs, creating a warm and inviting atmosphere. Western Branch High School, middle school, and elementary school all located within the development, along with festive community events like the annual Holiday parade with firetruck and spring egg hunt. Restaurants, shopping all nearby and just a quick trip to downtown Norfolk, this home offers the ideal blend of comfort, updates, and community charm. Seller has recent clear Termite and Moisture reports.

3316 Kindlewood Crescent, West Chesapeake

$525,000

4 Beds ⋅ 2.1 Baths ⋅ 10656722 MLS

This 4-bedroom, 2.5-bath home offers 2,326 sq ft on a 0.29-acre corner lot at the end of a cul-de-sac. The fully fenced backyard features an in-ground saltwater pool with a diving board, with a pool pump approximately 3 years old. Inside, enjoy brand-new carpet throughout, remodeled bathrooms, and new ceiling fans. A two-car garage plus a driveway with parking for four vehicles provides plenty of room for cars and guests. The roof is approximately 12 years old, and the HVAC and water heater are approximately 8 years old. Built in 2000. Schools: Cedar Road Elementary, Hugo A. Owens Middle, and Grassfield High. Don't forget to check out the virtual tour!

116 Ash Hill Landing, South Chesapeake

$434,000

5 Beds ⋅ 3.1 Baths ⋅ 10656972 MLS

Welcome to this spacious 5-bedroom, 3.5-bath home offering the size, features, and flexibility today’s buyers are looking for. With major items already in place, this property gives buyers the opportunity to add their own finishing touches while enjoying strong long-term value. The functional layout includes two ensuite bedrooms with private full bathrooms, two HVAC units for separate area comfort, a dedicated laundry room, and plenty of room for everyday living or entertaining. Outside, enjoy your own private pool, detached garage, and outdoor space made for relaxing or gathering. Conveniently located with easy access to major routes, shopping, dining, and local amenities, this home offers a rare combination of space, features, and opportunity.

316 Tudor Place, Central Chesapeake

$750,000

4 Beds ⋅ 2.2 Baths ⋅ 10656562 MLS

Welcome to the ultimate Entertainer’s Dream - the Hangout House everyone will want to call home! Centrally located in the sought-after Hickory school district, this beautifully updated 4-bedroom, 2-story home literally has it all. Inside, enjoy a custom bar, remodeled kitchen with under cabinet lighting, custom cabinetry, granite countertops, 6 burner gas stove, large pantry with barn door, updated baths, Closet Maid designed closet, climate-controlled sunroom, full home Sonos surround sound system, plantation blinds, hardwood floors, central vacuum, tankless water heater, and an incredible theater room with all equipment conveying. Step outside to your own private resort featuring an inground pool, professional-grade artificial turf 2-hole putting green, covered outdoor bar with storage and half bath, covered deck, tree house, irrigation system, and powered storage shed with lights and thermostatic fan. Professionally landscaped and designed for unforgettable gatherings, movie nights, pool days and endless fun—this is the Dream Home you never have to leave! No HOA, Numerous Items to Convey including 10 professionally mounted TVs- Ask Your Agent for the Feature List and Come LOVE where You Live in Hickory!

809 Leleon Court, South Chesapeake

$669,000

5 Beds ⋅ 3 Baths ⋅ 10656320 MLS

Beautifully cared for and truly move in ready, this nearly 3,000 sf home sits at the end of a quiet cul de sac with exceptional outdoor living space. Built in 2017 and lovingly maintained, it offers 5 bedrooms, 3 full baths and plenty of space for everyone. The open living room, kitchen with gas range and eat in area flow effortlessly into a beautiful formal dining room and a flex bonus space perfect for an office, den or playroom. A first floor bedroom with full bath is perfect for hosting guests or multigenerational living. Upstairs, find a spacious primary suite, 3 additional bedrooms, full bath and laundry. A benched drop zone sits off the side load garage with extended concrete. Outside find a standout backyard – fenced in, mature landscaping, covered patio, custom stamped concrete areas, above ground pool with deck, playset and trampoline – ideal for relaxing, entertaining and making memories. Immaculate and in sought-after school district. The school bus stop is conveniently located in the cul de sac for this home. Seller is willing to remove trampoline and closet built-ins in bedroom at buyer's request. Seller will provide 1 year home warranty with Choice in the amount of $660.00. This home is a must see!

920 Covenant Way, 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

$695,000

4 Beds ⋅ 3.1 Baths ⋅ 10656163 MLS

Your own private retreat in the heart of Cheshire Forest! This beautifully maintained 4 bedroom, 3.5 bath home offers over 3,100 sq ft with a floor plan made for everyday living and entertaining. Inside, enjoy gorgeous oak floors, an updated open concept kitchen, formal living and dining rooms, a sun-filled family room with fireplace, and a spacious primary suite with its own fireplace. Outside is where this home truly shines; take a dip in the heated in-ground pool, relax on the deck, or unwind in your private, fully fenced backyard. An impressive list of improvements includes a new pool liner (2025), upstairs A/C (2024), refinished hardwood floors, updated roof, gutters, garage door, HVAC, water heater and more. Two-car garage plus Cheshire Forest amenities including a clubhouse, community pool, playground and tennis courts. A rare combination of space, updates and resort-style living in Great Bridge!

801 Keeling Drive, 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

111 Goldcrest Drive Drive, Central Chesapeake

$465,000

3 Beds ⋅ 2 Baths ⋅ 10655863 MLS

Nestled off two quiet cul-de-sacs, this beautiful riverside ranch is the ultimate canvas for your custom dream home. Boasting exceptional bones and incredible profit potential, the spacious interior features original hardwood floors waiting to be restored. The layout offers a large front den centered around a classic wood-burning fireplace, three sizable bedrooms with generous closets, a formal dining area, and a secondary rear den that opens to a large, screened-in porch. Off the kitchen, a sun-flooded breezeway provides ideal flexible square footage for a home office or gym.The true highlight is the outdoor oasis. Framed by palm trees, the backyard features an in-ground pool with a diving board, fully fenced on the sides for privacy while leaving the rear wide open to serene water views. The waterfront infrastructure is already complete, including a concrete seawall and an existing dock. Schedule your showing today to unlock this property's full potential!

111 Goldcrest Drive Drive, Central Chesapeake

$569,900

4 Beds ⋅ 3 Baths ⋅ 10655754 MLS

Going live on 10/8. Welcome to 144 Downing Drive in sought-after Hickory, Chesapeake! This spacious & well-maintained 4-bed, 3 full-bath, brick & vinyl ranch offers plenty of flexible living space on a .27-acre lot. The inviting great room features a vaulted ceiling & fireplace, while the spacious kitchen offers granite countertops, abundant cabinetry, stainless steel appliances, breakfast area, & bright sunroom. The finished room over the garage with a full bath offers excellent flexibility for an in-law suite, guest space, home office, or bonus room. Enjoy a fenced backyard built for entertaining with a deck & above-ground pool. Additional highlights include an attached 2-car garage & generous driveway parking space. Located in the desirable Tunbridge Station community with NO HOA and convenient access to Hickory schools, shopping, entertainment, dining, military bases, & major routes to get around Hampton Roads. Schedule your private showing today!

144 Downing Drive, South Chesapeake

2410 Centerville Turnpike, South Chesapeake

$879,000

3 Beds ⋅ 2 Baths ⋅ 10655763 MLS

If these walls could talk, they would tell you 176 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake

2536 Seven Eleven Road, South Chesapeake

$975,000

6 Beds ⋅ 3.1 Baths ⋅ 10655175 MLS

Room to spread out, space for horses, and a country setting without giving up Chesapeake conveniences. Set on approx. 5 treelined acres in Grassfield, this all brick estate offers 2 primary suites w/ one on first floor providing flexibility for guests. Watch wildlife from your back deck, cool off in the pool, & unwind in the hot tub! Two horse barns, lamb barn, feeding shelter and add. storage support equestrian interests. No HOA. Roof & windows replaced 2017. Upstairs HVAC 2024. Shopping/dining Grassfield Pkwy/Cedar Rd. Grassfield Highschool. Bring your vision & make it yours!!

2536 Seven Eleven Road, South Chesapeake

$475,000

3 Beds ⋅ 2.1 Baths ⋅ 10654644 MLS

This Great Bridge home simply makes everyday life more enjoyable. Imagine summer days spent by the in-ground pool, entertaining with friends and family, or hanging out in the detached garage with its wood stove, working on projects in a workshop that gives you room to spread out. This 3-bedroom home offers formal living room, dining room, family room and a primary bedroom with an updated ensuite. The updated kitchen and bathrooms are complimented by hardwood floors and fresh paint. Recent improvements including the roof, heat pump, pool liner and garage door all make this home ready for its next chapter. Come see why the pool, garage and location make this one worth stopping for.

349 Bartell Drive, South Chesapeake

1824 Lancing Crest Lane, South Chesapeake

$1,100,000

5 Beds ⋅ 4.1 Baths ⋅ 10654932 MLS

Welcome to an exceptional 4,800 sq. ft. all-brick home in Chesapeake's sought-after Grassfield area! Offering 5 bedrooms and 4.5 baths, this spacious home features a private primary wing designed as its own retreat, complete with an incredible oversized walk-in shower that truly has to be seen. Each additional bedroom is a suite with access to its own bath, providing privacy and comfort for family and guests. Enjoy outdoor living on the screened porch overlooking the inground pool with a fountain perfect for relaxing or entertaining. The community offers its own boat ramp and marina area with water access to the Elizabeth River. Conveniently located near shopping, dining, and interstate access, this home combines space, privacy, recreation, and an outstanding Chesapeake location.

1824 Lancing Crest Lane, South Chesapeake

$749,818

4 Beds ⋅ 3.1 Baths ⋅ 10654534 MLS

Welcome to 4413 Liam Close in Miars Plantation, Chesapeake! This impeccably maintained four-bedroom, three-and-a-half-bath home offers 3,653 square feet, an open floor plan, formal dining room, updated kitchen, spacious bedrooms, and ample storage. The oversized primary suite features an adjoining bath with a walk-in shower. Updates include a new roof, new carpet, and a completely renovated swimming pool. Enjoy the gorgeous outdoor setting with a large backyard, storage shed, and plenty of room to entertain. A deluxe two-car garage completes this beautiful home. Please provide 24-hour notice for showings.

4413 Liam Close Drive, West Chesapeake

$615,000

5 Beds ⋅ 3.1 Baths ⋅ 10654210 MLS

Space, space and more space! With over 3,600 square feet, this HOME gives you room to spread out, work, gather and entertain. Hardwood floors flow throughout the majority of the home, while the spacious kitchen features granite countertops and stainless steel appliances. Do you work remotely? There’s a private first-floor office, too. Outside, enjoy an in-ground saltwater pool, Trex deck and gazebo for pool days, cookouts and relaxing at home. And there’s more—the detached garage is ideal for a workshop, hobby space, teen retreat or extra storage. Pool, detached garage, first-floor office, cul-de-sac and no HOA—all wrapped into one very spacious home. If space and flexibility are at the top of your list, this one deserves a look!

803 Gresham Way, South Chesapeake

$849,900

4 Beds ⋅ 2.1 Baths ⋅ 10654253 MLS

The perfect farmhouse that’s a mix of privacy and closeness to local amenities. Sitting on approx 3 acres in Albemarle Farms, this home offers the updates you've been looking for. Step inside to a bright, welcoming interior with engineered hardwood floors, fresh paint throughout, new trim, and a beautifully updated kitchen. Completed in 2025, the kitchen features all-new cabinetry, quartz countertops, a large island, white stone backsplash, new appliances, and a new sink and faucet. Just beyond, the great room is centered around a new stone fireplace and mantle, while the 4-season room offers a flexible space to relax, work, or enjoy views of the property. Upstairs, the primary suite features a soaking tub and walk-in shower, with two additional bedrooms and bonus space offering plenty of flexibility. Major improvements include new heating and cooling units, new ductwork upstairs and downstairs, a new tankless water heater, and new downstairs subfloor. Outside is where this property really shines, with a saltwater in-ground pool, expansive deck, covered rear porch, circular driveway, and plenty of room to enjoy the wooded setting. An oversized garage with a finished room above adds even more usable space. Located in the Hickory school district with no HOA, this is a home with room to settle in, spread out, and enjoy both indoors and out. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

609 Fairfield Drive, South Chesapeake

1733 Head Of River Road, South Chesapeake

$839,900

4 Beds ⋅ 3 Baths ⋅ 10654135 MLS

Interior pics coming!! Welcome to the Hickory lifestyle, where space, privacy, & possibilities come together on 3 acres! This 4-bedroom, 3-bath home offers 2,912 square feet of comfortable living space & plenty of room to enjoy the outdoors. The kitchen features granite countertops & opens to the family room, creating an easy gathering space for everyday life. A formal living room & additional space provide room for an office, playroom, library, or whatever fits your needs. Upstairs, all four bedrooms are generously sized, including a spacious primary suite with a large bathroom featuring a separate walk-in shower & soaking tub & 2 walk-in closets! Outside, the in-ground pool sets the stage for relaxing afternoons at home. And with 3 acres to call your own, there’s room to dream—whether that means a vegetable garden, chickens, outdoor hobbies, or simply enjoying the extra elbow room that makes Hickory living so desirable. Come see all this home & its expansive setting has to offer!

1733 Head Of River Road, South Chesapeake

$335,000

3 Beds ⋅ 1.1 Baths ⋅ 10654025 MLS

Make this your first stop! This beautifully maintained brick ranch in Western Branch offers the perfect combination of comfort, functionality, and outdoor living. Featuring 3 bedrooms, 1.5 bathrooms, spacious living areas, and a well-appointed kitchen, this home is move-in ready and has been exceptionally cared for by its owners. The open layout creates a great flow for everyday living and entertaining, while the large family room provides plenty of space to gather with family and friends. Major improvements include an encapsulated crawl space, whole-house generator system, and a backyard oasis complete with an above-ground pool. The oversized backyard offers plenty of room to relax, entertain, or enjoy outdoor activities. With pride of ownership evident throughout and desirable features that are hard to find, this is a home you'll want to see in person!

4504 Greendell Road, West 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

$547,150

4 Beds ⋅ 3.1 Baths ⋅ 10653856 MLS

Timeless qualities with some modern flare in this Solid Custom Built home by CHARLES D JOHNSON. This home offers Just over 2500 sq ft. with the perfect layout, 4 bedrooms, 3.5 baths on a .25 acre lot in the quiet, sought-after Miars Farm neighborhood. Huge, open & bright kitchen with granite countertops, built in storage bench along bay window. Island with Bar. Separate pantry. Separate formal dining room and Great room with beautiful wood floors. Laundry room on 1st level & a 2nd. Access to 2nd floor Finished Room over Garage with full bath from kitchen. Primary bedroom & bath, walk in closets with built ins. 2 additional bedrooms & another full bath offers plenty of living space options. Peaceful enjoyment on the deck with pool. Cute Shed and fully fenced back yard. 2 car garage with plenty of driveway space. No HOA.

3421 Anita Circle, West Chesapeake

$999,999

4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS

Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake

1128 Sir Galahad Drive, South Chesapeake

$357,000

3 Beds ⋅ 2.1 Baths ⋅ 10653187 MLS

PCS timing just right! Welcome to 1128 Sir Galahad Dr, an updated 3-bedroom, 3-bath Chesapeake home offering the flexibility, location, and lifestyle so many Hampton Roads buyers are looking for. Conveniently positioned near major commuter routes with easy access to Norfolk, Portsmouth, Virginia Beach, shopping, dining, and multiple military installations, this home makes getting around the region easy. Planning a PCS but not arriving until later this fall? This property offers a unique head start. Previously operated as a short-term rental and currently occupied by a long-term tenant through the end of November, the existing tenancy provides income in place during the transition and may help offset ownership costs before you’re ready to move in. It can also be a great fit for buyers looking for an approximately 60-day closing timeline. Inside, you’ll find an updated, move-in-ready interior with modern flooring, a refreshed kitchen featuring stainless steel appliances, generous cabinet and counter space, a fireplace, and comfortable living and dining areas. Large glass doors bring in natural light and lead directly to the backyard, creating an easy flow for everyday living and entertaining. The standout feature is your own in-ground pool! Whether you’re hosting friends, relaxing after work, or enjoying warm Hampton Roads days at home, the backyard adds a lifestyle feature that’s hard to beat. Whether you’re relocating to the area, planning ahead for your next move, or looking for a property with rental history and future flexibility, 1128 Sir Galahad Dr offers an uncommon combination of convenience, updates, rental potential, and a private pool. Secure your Chesapeake home now and make your move when the timing is right!

1128 Sir Galahad Drive, South Chesapeake

$539,900

4 Beds ⋅ 2.1 Baths ⋅ 10653218 MLS

Welcome to this spacious, thoughtfully designed home offering generous living areas and a floor plan that blends comfort with functionality. Several updates have already been completed, to include: HVAC, roof, house trim, soffit, & gutter system, electric stove, carpet/LVT flooring, some interior paint, new pool salt system & Dolphin pool vacuum. The expansive backyard is a true retreat, featuring beautiful mature trees, a sparkling in-ground saltwater pool, and a spacious deck perfect for entertaining or unwinding. Situated on a large lot with a two-car garage, this property offers the ideal combination of space, privacy, and potential. Conveniently located in the sought after Hickory school district and near shopping, dining, and major commuter routes, this is a home you'll want to experience in person.

1505 Hilltop Drive, South Chesapeake

3708 Riverwood Crescent, South Chesapeake

$750,000

5 Beds ⋅ 2.1 Baths ⋅ 10653033 MLS

Welcome to 3708 Riverwood Crescent! Situated on approx. 3 acres in sought after Chesapeake 23322, this nearly 3,000 sq. ft. home offers space, privacy & extensive updates! Enjoy a private backyard retreat with pool, screened porch & updated deck. Inside features a remodeled kitchen with quartz countertops, mostly stainless steel appliances, soft-close cabinetry, recessed lighting, hardwood & luxury vinyl plank flooring, plus new carpet upstairs, and solar hallway lighting. Updated baths include new countertops, toilets, fixtures, ceramic tile, tub/shower & an enlarged porcelain-tiled primary shower. Major improvements include dual-zone HVAC (2019/2021), 2024 water heater, water softener, encapsulated crawl space with pump & dehumidifier, replaced exterior/garage doors, vinyl windows & 2011 roof with 50-yr warranty. Shed and lawn tractor conveys! A rare combination of acreage, updates, pool & location; come see it!

3708 Riverwood Crescent, South Chesapeake

$619,000

4 Beds ⋅ 2.1 Baths ⋅ 10652797 MLS

Welcome to 311 Lancing Way! This beautiful 4-bedroom, 2.5 bath home in Chesapeake's desirable Grassfield area features a backyard oasis with a large, 33,000-gallon lagoon-style saltwater pool, 8-ft deep end, variable-speed pump, water feature, plumbing for a future waterslide/waterfall, and a buried pool drain line with pump-controlled discharge to the street. The pool is surrounded by a beautiful stamped concrete, complemented by a spacious screened porch with dual variable-speed fans, a poolside bar shed, and a garden shed with front and rear access. Inside, enjoy programmable dual-zone A/C with independently controlled thermostats and an automatic generator transfer switch. Parking for 4 cars, including an oversized 2-car garage, PLUS additional concrete parking for a boat or 2 more vehicles! No HOA fees! Conveniently located near Grassfield schools, shopping, dining, parks, major interstates, and military installations throughout Hampton Roads. Schedule your private showing today!

311 Lancing Way, South Chesapeake

$725,000

5 Beds ⋅ 2.1 Baths ⋅ 10652400 MLS

Welcome to this spacious 5-bedroom home set on nearly half an acre in the Grassfield school district! Designed for comfortable everyday living and effortless entertaining, the light-filled layout features soaring ceilings and generous living spaces. Kitchen showcases granite countertops, abundant cabinetry, and stainless steel appliances, opening naturally to the main living areas. A first-floor bedroom offers flexibility for guests, a home office, or playroom. Upstairs, the expansive primary suite features a sitting area with fireplace, oversized walk-in closet, dual vanities, soaking tub, and tiled walk-in shower. Outside, enjoy a large deck, hot tub, and fully fenced backyard with plenty of room to gather, play, and unwind. An above-ground pool is currently in place for buyers who would like it, with removal also an option. Oversized two-car garage, ample driveway parking, and convenient access to shopping, dining, and major roadways complete this exceptional Chesapeake home.

905 Washington Drive, South Chesapeake

228 Country Club Boulevard, South Chesapeake

$619,000

4 Beds ⋅ 2.1 Baths ⋅ 10652285 MLS

Fantastic location close to shopping, major hwys primary and secondary schools and so much more! The already large/oversized primary suite has a large additional private flex room for office or nursery, workout room or whatever your heart desires. Complete with private bath and large walk in closet. For additional privacy the ancillary bedrooms are on the opposite side of the home. This home is a one owner former model home. New carpet just for you! The neighborhood is low turnover, well established and quiet. Beautiful foyer and open hall say "elegance" while having "cozy home" feel. 2 large sheds so you can park both cars in the garage. Smartly laid out with oversized rooms thru out. Separate zone HVAC for large sunroom with tile flooring. updated kitchen with abundant cabinets!

228 Country Club Boulevard, South Chesapeake

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10652101 MLS

Perfectly situated in the heart of Great Bridge, this spacious 4-bedroom, 2.5-bath home offers nearly 2500 square feet in the established Sandy Hill neighborhood with no HOA. Enjoy the convenience of being just minutes from shopping, dining, parks, and everyday essentials while benefiting from sought-after Great Bridge schools. Inside, you'll find generous living spaces, brand-new carpet, and a room over the garage that can be a bedroom or a hang out space. Outside, the fully fenced backyard is ready for entertaining with an in-ground pool featuring a brand-new liner, an expansive paver patio, outdoor bar area, and storage shed. Offering space, flexibility, and recent updates in one of Great Bridge's most desirable neighborhoods, this home is ready for its next owners.

505 Sandy Hill Way, South Chesapeake

$860,000

4 Beds ⋅ 3.1 Baths ⋅ 10651664 MLS

Quick close! No HOA. Solar panels are paid off and average electric bill is around $20 a month. Enjoy peaceful country living on 3 beautiful acres, just 5 miles from all your city favorites. This immaculate light-filled 4-bedroom, 3.5-bath home offers 9ft ceilings, detailed crown molding, custom built-ins, a main-level primary suite with a full bath, plus a convenient first-floor laundry room and mudroom. The chef's kitchen features leathered granite countertops, custom tile backsplash, SS appliances, and a center island. Upstairs offers 3 additional bedrooms, a large loft, and a second primary suite with a full bath, standalone tub, dual vanity, and 2 large walk-in closets. Outdoors, enjoy a resort-style backyard with a fenced inground saltwater pool surrounded by stamped concrete and a gazebo. The property also features solar panels, 2 barns, raised garden beds, a playset, a fire pit, and an extended driveway with ample space for an RV or boat. A rare blend of privacy, upgrades, and convenience!

2517 Number Ten Lane, South Chesapeake

$1,519,000

5 Beds ⋅ 4.1 Baths ⋅ 10651679 MLS

Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath, new paint and new flooring! HUGE primary suite complete with fireplace, fantastic walk-in closet and beautiful new bath. The detached 3.5 car garage includes a garage apartment with kitchenette and full bath. New windows, roof, gutters, soffits and pool liner. Absolutely amazing opportunity to secure this gorgeous, move-in ready property. Awesome enclosed patio with hot tub as well as an outdoor kitchen/bar area. This is an entertainer's dream! See it today before it is SOLD!

641 Ravenwoods Drive, South Chesapeake

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