Chesapeake VA VA Real Estate, Homes with Pool for Sale

Welcome to this inviting 4-bedroom ranch in the sought after Mill Creek neighborhood. Freshly painted throughout with brand new carpet and a new roof, this home is truly move-in ready. Enter into a bright living room featuring vaulted ceilings and a cozy wood-burning fireplace, seamlessly opening to the fully remodeled kitchen. The kitchen shines with white shaker soft-close cabinets, quartz countertops, and stainless steel appliances. Two bedrooms sit just off the living room, accompanied by a beautifully updated hall bathroom and laundry room. The spacious primary bedroom offers a remodeled en-suite bathroom and a generous walk-in closet. The FROG provides flexibility as a 4th bedroom, guest space, or bonus room. Out back, enjoy a wood deck overlooking an above-ground pool and a peaceful backyard with views of the wooded area maintained by the Army Corps of Engineers along the Dismal Swamp Canal. The property extends about 10 ft beyond the back fence line. Don't miss this one.

500 Willow Bend Drive, South Chesapeake

$225,000

2 Beds ⋅ 2 Baths ⋅ 10645008 MLS

Tranquil and serene condo living, welcome to this desirably located greenbriar community just a short walk to local dinning and shopping. This property also offers quick access to major interstate Hwy and just a few blocks over from Chesapeake General Hospital,

401 Bracknell Arch. Arch Unit F, South Chesapeake

$420,000

4 Beds ⋅ 3 Baths ⋅ 10645787 MLS

Welcome to 601 Hopewell Drive, a spacious 4-bedroom, 3-full-bath home situated on a desirable corner lot in deep creak area of Chesapeake. Fresh paint throughout creates a bright, refreshed interior that is ready for its next owner. The flexible floor plan offers plenty of room for everyday living, entertaining, a home office, or guest accommodations. Accessibility features throughout the property provide added convenience and functionality for a variety of needs. Outside, the corner lot offers generous yard space, while the above-ground pool with attached deck right off the back of the house creates the perfect setting for relaxing, entertaining, and enjoying warm summer days. With three full bathrooms, multiple living possibilities, and thoughtful accessibility options, this home offers comfort and versatility inside and out.

601 Hopewell Drive, South Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10645753 MLS

This meticulously cared for home has an open floor plan! Bedroom and full bath downstairs to use for guests or office! Living room is large with gas fireplace and has surround sound. Granite countertops and breakfast bar in the kitchen with a stainless appliance package, custom built ins and large pantry plus a breakfast area. Huge Primary suite has custom closet factory walk in closet. Large bedrooms. Screened in porch overlooks saltwater in ground pool. Sprinkler system, and beautiful views of the water. Amenities in this neighborhood include lakes with fountains, a park, natural landscaping and trails.

136 Bella Drive, South Chesapeake

$699,900

4 Beds ⋅ 4 Baths ⋅ 10645397 MLS

Welcome home to Rollingwood Estates in the highly sought after Great Bridge school district. This one owner brick transitional home offers 4 bedrooms and 4 full baths with an open, bright floor plan designed for comfortable living and effortless entertaining. The spacious FROG serves as the fourth bedroom and features its own private full bath, making it ideal for guests or multigenerational living. The kitchen offers Corian countertops, generous workspace and opens to the main living areas. Step outside to your own backyard retreat with a sparkling inground pool, dedicated pool bath, stamped concrete patio, outdoor bar/kitchen area, screened porch, and professionally landscaped yard. A two car attached garage, irrigation well, and thoughtful layout add to the appeal. Offering exceptional value in an established neighborhood, this home is priced to sell and ready for its next owner to make it their own.

837 Greenfield Lane, South Chesapeake

$430,000

4 Beds ⋅ 2 Baths ⋅ 10645625 MLS

Make this your first stop! This well-maintained split-level home in Strawberry Acres offers the perfect blend of space, functionality, and outdoor living—and best of all, NO HOA! Fresh paint throughout and a beautifully updated kitchen featuring all-new cabinets and countertops make this home feel bright and inviting from the moment you walk in. The flexible floor plan includes a versatile front room that can serve as a home office, playroom, guest space, or additional living area. Outside, you'll find an above-ground pool, a large storage shed with electricity, and an oversized fully insulated detached garage that's perfect for a workshop, hobbies, storage, or parking. Situated on a spacious lot in a quiet neighborhood, this home offers plenty of room to relax, entertain, and make it your own. Conveniently located near schools, shopping, dining, and major commuter routes, you'll love the combination of space, updates, and freedom that this property provides!

3217 Pryor Court, South Chesapeake

$625,000

4 Beds ⋅ 2.1 Baths ⋅ 10645501 MLS

Built in 2020, this gorgeous 4-bedroom, 2.5-bath home offers the quality and peace of mind of newer construction—without the wait! Step outside to your own private backyard oasis featuring an in-ground pool on a pie-shaped lot. While the property is approximately 1/4 acre, the unique shape creates an expansive backyard that feels much larger, giving you plenty of room to entertain, relax, and enjoy the outdoors. The spacious sunroom (not included in the home's square footage) adds an incredible amount of usable living space and is the perfect place to enjoy your morning coffee while overlooking the pool or keep an eye on all the backyard fun. The partially completed pool house is already plumbed for an outdoor shower, making it easy for guests to rinse off after a swim and providing an excellent opportunity for the next owner to finish the space to fit their lifestyle. Ideally located in the desirable Kempsville corridor, you'll enjoy convenient access to shopping, a wide variety of restaurants, local breweries, coffee shops, parks, and everyday conveniences, all while being tucked away in a beautiful neighborhood. Why wait months for new construction when you can move into a beautifully maintained, nearly new home today? Skip the crowded community pool and enjoy your own private backyard retreat all season long.

201 Ians Way, South Chesapeake

$529,900

4 Beds ⋅ 2.1 Baths ⋅ 10645403 MLS

You have seen the pictures and now I am sure you are curious about everything this house has to offer. Well, it is absolutely 100% turn-key, move-in ready with all of the bells and whistles. The home feels so good and invites tons of natural light. The kitchen has been thoughtfully remodeled adding tons of cabinet space, a center island, a pot filler and more functional layout. The cabinets, flooring (hand scraped bamboo), counters and appliances have all been recently upgraded as well. The bathrooms have all been remodeled and the primary bath is a small piece of heaven. Separate sinks, dual shower heads in the tile/glass shower and a separate soaking tub. Go outside and you might not go back in for quite a while. A covered porch and expansive deck greet you with the hot tub around the corner. Drop down to the 28,000 gallon in-ground pool complete with a built-in endless pool for serious swimmers. Backing up to the woods, this private, backyard paradise awaits you!

2107 Sunset Maple Lane, South Chesapeake

$335,000

4 Beds ⋅ 1 Baths ⋅ 10645441 MLS

This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, new flooring throughout, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily serve as a 4th bedroom, home office, playroom, or home workout space to fit your lifestyle. Step outside to your fully fenced backyard retreat, designed for both relaxation and entertaining. Enjoy summer days in the above-ground pool and unwind or host gatherings under the pergola on the patio while appreciating the privacy this backyard provides. Conveniently located near shopping, dining, schools, and major interstates, this move-in-ready home combines thoughtful updates, flexible living space, and exceptional outdoor setting you won't want to miss.

2801 Southport Ave., Central Chesapeake

$1,195,000

4 Beds ⋅ 4.1 Baths ⋅ 10644941 MLS

Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

377 Homestead Road, West Chesapeake

$825,000

5 Beds ⋅ 3 Baths ⋅ 10644737 MLS

Beautiful 5 Bedroom Brick Home featuring a spacious open floor plan perfect for everyday living and entertaining. The large kitchen offers stainless steel appliances, abundant cabinetry, and ample prep space. A standout feature of the home is the custom library, complete with French doors, built-in shelving, and a rolling ladder, creating an elegant and inviting space for work, reading, or relaxation. The main level includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a luxurious bathroom featuring a jetted tub, separate shower, a double vanity and private toilet room. Be sure to notice the built-in light-up stairs going up to the second floor! Enjoy your own private backyard oasis with mature landscaping, an in-ground saltwater pool, hot tub, and an expansive custom paver patio, ideal for relaxing or entertaining. Extended driveway with Boat/RV pad. Located in the sought after Great Bridge school district and community, local shops and restaurants, and close to the interstate for a quick trip to OBX!

208 Leicester Court, South Chesapeake

$415,000

3 Beds ⋅ 1.1 Baths ⋅ 10644736 MLS

Beautifully updated, this spacious home features an open-concept floor plan ideal for everyday living and entertaining. The remodeled kitchen offers quartz countertops, custom soft-close cabinetry, an 8-foot island, pantry, and matching Frigidaire Professional appliances. Recessed lighting flows throughout the kitchen, dining room, and living room with a wood-burning fireplace. Additional features include large bedrooms, updated bathrooms, a dedicated office, and a heated and cooled laundry/flex space plus an additional breezeway. Major updates include new siding in 2026, HVAC and ductwork in 2025, garage doors and openers in 2025, updated electrical and plumbing, refinished hardwood and LVP flooring, and most replacement windows. Situated on approximately .75 acre with two driveways, a front porch, fenced backyard, large deck, and in-ground pool with a 2022 liner. The roof roughly 10 years young.

2829 Forehand Drive, South Chesapeake

$650,000

6 Beds ⋅ 3 Baths ⋅ 10644555 MLS

Only 4 yrs young, this thoughtfully designed home offers exceptional space, flexibility, and stylish finishes throughout. The versatile first-floor room with access to a full hall bath is ideal for a guest room, office, or playroom. The open-concept kitchen is beautifully appointed with quartz countertops, s/s appliances, a large island and generous prep space, flowing seamlessly into the main living areas. Upstairs, the spacious primary suite is a true retreat featuring a spa-inspired bath w/an oversized shower & two showerheads & a large walk-in closet. Total of 6 bedrooms provide endless possibilities for today's lifestyle & multi-generational living. Step outside to your private backyard oasis complete with an in-ground swimming pool, built-in hot tub, and plenty of room for relaxing or entertaining. Other highlights include an EV charger and modern construction, offering the peace of mind that comes with a newer home.

4026 Scotfield Drive, West Chesapeake

$499,900

4 Beds ⋅ 2 Baths ⋅ 10644453 MLS

Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, South Chesapeake

$820,000

5 Beds ⋅ 3 Baths ⋅ 10643909 MLS

Spacious 5 Bedroom, 3 Bath home on a beautiful 3-acre lot in the Grassfield High School district! On the main level you'll find LVP flooring, elevated lighting, updated Eat-in Kitchen w/huge island, stainless steel appliances including a Viking gas range, pantry and reverse osmosis drinking water, Family room with gas fireplace, Living and Dining Rooms and full bath. Primary Bedroom with walk-in closet and luxury ensuite bath, 4 secondary bedrooms, laundry (combo W/D unit) and full hall bath complete the 2nd floor. 2-car garage and abundant storage. Outside is made for fun and entertaining with an in-ground pool, stamped concrete patio, and an outdoor kitchen with grill, smoker, and pizza oven. A wonderful space to make memories with family and friends! Major updates include a brand-new dual-zone HVAC (2026), water heater (2025), water softener, garage doors and openers, repaved driveway, new soffits, fascia, gutters, window wrap, and front railing. No HOA! Enjoy the best of both worlds with a peaceful private setting while just minutes from shopping, restaurants, highways and everyday conveniences. Move-in ready!

1932 Foxwood Drive, South Chesapeake

$645,000

4 Beds ⋅ 2.1 Baths ⋅ 10644442 MLS

Experience the lifestyle you've been searching for in one of Chesapeake's most desirable communities, just minutes from top-rated Grassfield High School. This beautifully maintained home welcomes you with a charming front porch and gleaming hardwood floors throughout the main level. A versatile flex room that can be used for a home office, playroom, or sitting area, while the formal dining room flows into the updated chef's kitchen featuring granite countertops, refreshed cabinetry, and new stainless steel appliances. The kitchen opens to a spacious family room centered around a cozy fireplace and an inviting sunroom filled with natural light. Upstairs, the expansive primary suite offers a spa-inspired bath with dual vanities, a jetted tub, and a glass-enclosed shower, along with three additional bedrooms, a full bath, and a convenient second-floor laundry room. Step outside to your own private backyard retreat complete with a stamped concrete patio, sparkling in-ground pool, and fully fenced yard—ready for relaxing or entertaining all summer long. Additional upgrades include a tankless water heater, solar panels that significantly reduce electric costs, updated main-level lighting, and a VA assumable loan with an incredible 3% interest rate for qualified buyers. Tesla EV charger.

2101 Beeblossom Lane, South Chesapeake

$1,299,997

4 Beds ⋅ 2.1 Baths ⋅ 10644328 MLS

Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, South Chesapeake

$439,900

4 Beds ⋅ 2 Baths ⋅ 10644168 MLS

Do not look any further, this wonderful brick ranch is just waiting for you! Make this your home with 4 spacious bedrooms, 2 full baths, large living room with electric F/P and HW floors, dining room for all your family meals, family room with electric F/P. The kitchen has breakfast bar and all appliances convey, Large 2 car garage. You will be delighted with the backyard deck or enjoy the 4 seasons sunporch (approx 185 sq ft) to relax in after swimming in your luxurious 20x40 salt water pool. Backyard shed for pool toys and lawn equipment. Plenty of storage in the partially floored attic with walk up stairs.Home freshly painted, roof replaced 2020, pool liner 2021, pool pump 2025, Hot water heater 2023, Dishwasher 2026. Close to schools, shopping and interstate. This home is just waiting for you to move on in. Call for your appointment today before its gone!!

4117 Hawksley Drive, West Chesapeake

$335,000

4 Beds ⋅ 2 Baths ⋅ 10644133 MLS

Welcome home to this beautifully renovated property, perfectly situated on a spacious 0.38-acre cul-de-sac lot! Enjoy the privacy and space this lot provides, plus backyard access convenient for parking a boat or RV. Inside, you'll find a stunning kitchen featuring soft-close cabinetry, granite countertops, a stylish backsplash, and all-new appliances — a true chef's dream. The home was completely renovated in 2017, including a new roof, windows, and hot water heater, giving you peace of mind for years to come. Additional highlights include an expansive laundry room with ample storage, new LVP flooring throughout (2024), a sparkling above-ground pool (2024), and a brand-new backyard patio (2025) — great for entertaining. The versatile back shed, complete with a window AC unit, offers the perfect workshop, hobby space, or "man cave/she-shed" retreat. Don't miss your chance to own this move-in-ready gem — schedule your showing today!

4321 Fontana Court, Central Chesapeake

$699,900

5 Beds ⋅ 2.1 Baths ⋅ 10644122 MLS

Welcome to this beautifully updated 5-bedroom, 2.5-bath home in the highly sought-after Hickory school district! Major improvements have already been completed, including a new roof, both HVAC systems, windows, soffit and fascia, water heater, and deck—giving buyers added peace of mind. Inside, you'll find two tastefully updated bathrooms, spacious living areas, and a functional floor plan with room for everyone. Step outside to enjoy the fully fenced backyard featuring an above-ground pool, great for relaxing or entertaining all summer long. Conveniently located near shopping, dining, military bases, and major interstates. The sellers are relocating out of state and are looking for a quick closing. Don't miss your chance to make this move-in-ready home yours! **Updates** 2021 - upstairs air ducts, 1st HVAC, oven, dishwasher. 2022 - roof, 2nd HVAC, hot water heater, pool 2023 - windows, front door, toilets 2024 - two bathroom remodels, soffit and fascia 2025 - backyard deck

908 Bahama Way, South Chesapeake

$645,000

4 Beds ⋅ 2.1 Baths ⋅ 10644240 MLS

Vacation at home! Beautifully updated 4-bedroom, 2.5-bath home in sought-after Cheshire Forest and the desirable Great Bridge school district. The backyard is the star, transformed in 2024 with a saltwater in-ground pool with built-in hot tub, expansive patio, refreshed deck, fire pit, and hardtop gazebo with Blackstone grill, Traeger smoker, and two mini refrigerators. Fully fenced yard backs to the neighborhood lake with access for fishing or a lakeside stroll. Powered shed with well, plus deck furniture and pool accessories convey. Inside offers LVP flooring throughout, a spacious great room with gas fireplace, formal dining room with pocket doors, and a sunroom with mini-split (2024). Recent updates include HVAC (2025), water heater (2026), electrical panel (2024), windows (approx. 2021), new gutters, bath tile, plantation shutters, shiplap, roof (2014) and more. 2-car garage. Community amenities complete the package!

656 Parker Road, South Chesapeake

$420,000

4 Beds ⋅ 2.1 Baths ⋅ 10643689 MLS

Ranch in the heart of Great Bridge. Great floor plan with large great room and high ceilings. Fireplace has been converted to natural gas. Brand new LVP in all the common areas. New paint and carpet. Updated primary bathroom. Newer fridge and dishwasher. New roof in 2016-2017. This home DOES have a garage, but not a traditional garage door. Seller to provide clear termite and moisture letter.

560 Denver Avenue, South Chesapeake

$559,900

4 Beds ⋅ 2.1 Baths ⋅ 10643811 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, while some needed cosmetic enhancements, provide an excellent opportunity to add your own style and value. Priced to reflect these improvements, this home is an exceptional opportunity. 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. Brand new HVAC; ROOF, trim, soffit and gutters less than 2 years old.

1505 Hilltop Drive, South Chesapeake

$700,000

4 Beds ⋅ 3.1 Baths ⋅ 10643713 MLS

Welcome home to this classic brick home tucked in a cul-de-sac, with comfortable living spaces, thoughtful updates, and a backyard made for enjoying Virginia summers. The main level offers inviting living and dining areas, a large bright kitchen with island seating, and an easy flow into the vaulted family room with skylights, a brick fireplace, and access to the deck and pool area. Upstairs, the spacious bedrooms offer flexibility for guests, hobbies, work, or everyday living. The primary suite features vaulted ceilings, generous closet space, and a large bath with a soaking tub set beneath a window-filled nook. Outside, enjoy an in-ground pool, deck space for relaxing or entertaining, mature landscaping, and a peaceful setting. Recent updates include new flooring, upstairs, HVAC, a new pool liner, an updated front door, refreshed lighting and fixtures, and new fencing. Come see all this home has to offer!

701 Aspen Forest Court, South Chesapeake

$756,000

6 Beds ⋅ 3 Baths ⋅ 10643666 MLS

Welcome to this beautiful brick home in the heart of Great Bridge! Situated on a quiet cul-de-sac, this home has it all! The foyer and entrance way are stunning and extend two stories and include a beautiful stair case. A gorgeous new primary shower, trayed primary bedroom ceiling, hardwood flooring and a private deck that offers a peaceful, wooded view. The first floor bedroom/office has direct access to a full bathroom with newer vanity and is just right for multi-generational living. Both HVAC systems are two years young. The heavying lifting has been done here, this one won't last long! See it today before it is SOLD!!!

909 Brice Court, South Chesapeake

$609,900

4 Beds ⋅ 2.1 Baths ⋅ 10643428 MLS

Welcome home to this beautifully updated 4-bedroom, 2.5-bath ranch in the desirable Ethridge Woods neighborhood! This move-in-ready home features newly installed hardwood flooring & a brand-new roof (2025/2026)! Open concept living & kitchen area that is great for entertaining. Cozy breakfast nook, wood burning fireplace in the living room, soaring cathedral ceilings in the sunroom/ office area & a huge walk in closet in the primary bedroom. So many great features throughout! Step outside to your own private backyard retreat complete with a large inground pool (liner 2018) & an expansive deck. Additional highlights include an energy-efficient geothermal heating and cooling system (2018). With its recent upgrades, exceptional outdoor living, and sought-after location, this home is ready for its next owners to move in and enjoy! (Some photos were photoshopped, but they keep their core details)

829 Donnington Drive, South Chesapeake

$429,900

4 Beds ⋅ 2 Baths ⋅ 10643538 MLS

Welcome home to this charming brick ranch near Summit Pointe in Chesapeake, Virginia.Brick ranch near Summit Pointe! The heart of the home is the inviting country kitchen, equipped with stainless steel appliances and plenty of space for gathering with family and friends. The standout feature is the oversized primary suite, providing a private retreat with room for a sitting area, home office, or workout space! The huge backyard features a 2-year-old above-ground saltwater pool surrounded by a wraparound deck with recess lighting, creating the ideal setting for cookouts, entertaining, and relaxing weekends at home. Spacious floor plan featuring a welcoming living room and cozy den, both complete with fireplaces, perfect for relaxing on cool winter evenings. Upgrades for peace of mind include newer paint, newer windows, newer stainless steel appliances, newer vapor barrier, newer drain line, newer roof, newer ceiling fans and 200 amp electric panel. Call today to view!

224 Essex Drive, South Chesapeake

$700,000

4 Beds ⋅ 3 Baths ⋅ 10643450 MLS

Welcome to this beautiful 4-bedroom, 3-bath home nestled on just over 3 acres in the highly sought-after Grassfield area of Chesapeake. Tucked away in a community with no HOA, this property offers the perfect blend of privacy and convenience. Relax on the spacious front porch. Inside, find soaring ceilings that create an open, airy feel in the living room. The home features a water filtration system, a beautifully renovated primary bath, and a huge flex room over the garage ideal for a media room, home office, gym, or guest space. Out back, enjoy your own private retreat with a patio and swimming pool, perfect for entertaining or unwinding after a long day. With generous indoor and outdoor living spaces, this property offers the lifestyle you've been looking for in one of Chesapeake's most desirable locations.

1116 Tundrah Court, South Chesapeake

$585,000

4 Beds ⋅ 2.1 Baths ⋅ 10643196 MLS

Welcome to this one of a kind custom all brick home designed for buyers who appreciate true craftmanship, architectural character, and timeless traditional design. Offering nearly 3000 sqft, 4 bedrooms and 2.5 baths, this home showcases features rarely found in newer construction, including a stunning wood spiral staircase, custom millwork, rich hardwood flooring, and 3 fireplaces that bring warmth and character throughout. This is not a builder grade flip or cookie cutter renovation, but a home built with quality, detail, and lasting charm. Outside, enjoy a private backyard retreat with a saltwater inground pool. Ideally located near local bases, shopping, dining, and major interstates, this is a rare opportunity to own a home with true character and lasting value.

913 Montebello Circle, South Chesapeake

$775,000

4 Beds ⋅ 3 Baths ⋅ 10643343 MLS

Live the fresh life! Rarely does something this special come to market. Come see one of Western Branch's loveliest riverfront properties in an established neighborhood with no HOA. Designed for a lifetime of family fun and multigenerational living, this beautifully crafted 2-story on the Elizabeth River combines timeless elegance with all modern comforts. Through the soaring two-story foyer, you'll discover thoughtful details around every corner...signature hardwood floors, spa-like bathrooms, custom kitchen cabinetry, and more. A luxurious primary suite awaits you upstairs with its own balcony overlooking the pool. This lot has deep water access with beautiful views of the water. Relax in the saltwater pool during the hot summer days or relax in the hot tub for those cooler winter evenings. New roof (2025), water heater (2022), pool pump (2024), and salt cell (2026). A truly rare waterfront retreat.

3808 Stonebridge Landing, West Chesapeake

$540,000

4 Beds ⋅ 2 Baths ⋅ 10642998 MLS

Welcome to 233 Downing Drive, where everyday living feels easy, comfortable, and connected. Set in Chesapeake’s Tunbridge Station, this 4-bedroom, 2-bath home offers approximately 2,046 square feet with an open floor plan designed for gathering, relaxing, and enjoying time at home. Start your mornings in the bright all-season room, host dinner with room to spread out, then step outside to your own backyard retreat. The above-ground pool is surrounded by Trex decking, creating the perfect setting for summer afternoons, weekend cookouts, and unwinding with friends. When the day slows down, the hot tub conveys and is ready for quiet evenings under the stars. The detached workshop with power gives you space for projects, storage, hobbies, or tools. Inside, enjoy a first-floor bedroom and full bath, updated kitchen, refreshed baths, walk-in attic, pantry, and flexible spaces. With a fenced backyard, attached 2-car garage, and thoughtful updates, this home is ready for its next chapter.

233 Downing Drive, South Chesapeake

$755,000

5 Beds ⋅ 3.2 Baths ⋅ 10642808 MLS

A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Motivated sellers! Renovated 5-bedroom home on a full acre in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today.

1833 Benefit Road, South Chesapeake

$550,000

4 Beds ⋅ 2 Baths ⋅ 10642398 MLS

Welcome to 529 Royal Grant Drive in the desirable Cheshire Meadows area of Chesapeake. This well-maintained 4-bedroom, 2-bath ranch offers approximately 2,064 square feet of living space with a comfortable layout, office/study, finished room over the garage, and attached 2-car garage. The updated kitchen features granite countertops and stainless appliances, along with cathedral ceilings, skylights, a wood-burning fireplace, updated bath tile and fixtures, new interior paint, updated exterior vinyl trim, new exterior doors, and a new garage door and opener. The backyard is perfect for relaxing or entertaining with a deck, patio, privacy fence, storage shed, and salt system in-ground pool with new liner. Conveniently located near Great Bridge schools, shopping, restaurants, and commuter routes. A wonderful opportunity in a sought-after Chesapeake location. Listed at $550,000.

529 Royal Grant Drive, 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

$950,000

5 Beds ⋅ 4 Baths ⋅ 10642562 MLS

Welcome to your own private backyard retreat! This beautifully updated home offers the perfect blend of stylish interior living and incredible outdoor entertaining. Step outside to a true backyard oasis featuring a stunning 6-foot in-ground pool with a new liner and pump, a covered lounge area, outdoor fire pit, built-in bar, outdoor kitchen with grill, and plenty of space to host family and friends all season long. A screened porch conveniently connects the outdoor living space to the home, creating seamless indoor-outdoor living. Inside, the nearly renovated kitchen is the heart of the home, showcasing gorgeous marble countertops, a spacious center island, all LG appliances, bar-height seating, and a built-in desk area great for working from home or everyday organization. The open-concept design flows effortlessly into the inviting living room, making entertaining easy. Upstairs, you'll find generously sized bedrooms with abundant closet space, including a spacious room over the garage that offers endless possibilities for a media room, playroom, guest suite, or home office. The luxurious primary suite is a true retreat, featuring a cozy sitting area with its own fireplace, an oversized walk-in closet, and a beautifully appointed en-suite bath complete with dual-height vanities, a private water closet, soaking tub, and separate walk-in shower. Light wood-look luxury vinyl plank flooring adds warmth and elegance throughout the main living areas, while plush carpeting creates comfort upstairs. Thoughtfully updated and impeccably maintained, this home offers the perfect combination of comfort, style, and resort-style outdoor living. Don't miss the opportunity to make this exceptional property your next home!

129 Greengable Way, South Chesapeake

$545,000

4 Beds ⋅ 2.1 Baths ⋅ 10642683 MLS

WELCOME HOME! Check out this beautifully updated 4 bed, 2.5 bath home in the highly desirable Stonegate neighborhood and Great Bridge School District! This home features a cook's dream kitchen w/ tons of cabinets, granite counters, new LVP downstairs and updated bathrooms. Outside enjoy an above ground pool with a deck, spacious patio fire pit and pergola. Seller is offering 2.375% VA assumption to VA buyers with substitution of eligibility. No HOA/POA or flood insurance. There is a voluntary Civic League in this community. Call now for your private tour!

909 Cantor Street, South Chesapeake

$889,000

3 Beds ⋅ 2 Baths ⋅ 10642255 MLS

If these walls could talk, they would tell you 175 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

$554,500

4 Beds ⋅ 3.1 Baths ⋅ 10642380 MLS

Welcome to Miars Farm in sought-after Western Branch! This beautifully maintained 4BR, 3.5BA home offers ~2,500 sq ft of inviting living space on a .25-acre lot with timeless curb appeal and modern farmhouse touches. Enjoy a classic front porch, spacious driveway, and attached garage. Inside, the open layout features a stunning eat-in kitchen with granite countertops, stainless steel appliances, gas cooking, an island seating area, and a sunny breakfast area overlooking the backyard. The family room shines with exposed beams and a cozy fireplace. The vaulted primary suite features a spa-like bath with a soaking tub and a tiled shower. A large FROG/bonus room with a full bath adds flexibility. Step outside to your private fenced yard with a deck, above-ground pool, and storage/workshop shed with electricity. Convenient to schools, shopping, and commuting—this home truly has it all!

3421 Anita Circle, West Chesapeake

$624,900

6 Beds ⋅ 4.1 Baths ⋅ 10642445 MLS

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

501 Thornloe Ln Lane, South Chesapeake

$650,000

4 Beds ⋅ 3 Baths ⋅ 10642285 MLS

Welcome to luxury living in this stunning all-brick home with an incredible backyard sanctuary retreat and sought after schools. From the moment you arrive you notice natural light fills spacious living areas, and the layout is ideal for both everyday living and entertaining, with generous gathering areas and well-sized bedrooms. This impressive 4-bedroom pristine home also has a versatile flex room ideal as a 5th bedroom, office, media room, or playroom adapting to your lifestyle. The open-concept design showcases an amazing chef's kitchen centered around a breathtaking 10-foot imported quartz island, custom cabinetry with custom pull out drawers, bespoke refrigerator, high-end appliances and premium finishes throughout. Enjoy 3 beautifully renovated full baths to easily accommodate everyone. A walk-up attic provides exceptional storage, and an encapsulated crawlspace with dehumidifier for added peace of mind. Oversized, extended driveway can be used for extra vehicles, a boat or RV, as there's No Hoa! Step outside to your private backyard oasis featuring a sparkling inground pool and expansive entertaining space with a newly added deck, creating the perfect setting for unforgettable gatherings with friends and family or simply relaxing making every day feel like a getaway. Even comes with a dedicated fenced dog run and huge new shed for extra storage. Water views from some areas of the home. Ideally located near beaches, military bases, shopping, dining, and entertainment, this exceptional home offers the perfect blend of luxury, convenience, and resort-style living. Rarely does a home of this caliber become available, offering timeless appeal, exceptional craftsmanship, and the lifestyle buyers dream of.

3618 Point Elizabeth Drive, West Chesapeake

$619,900

4 Beds ⋅ 2.1 Baths ⋅ 10642204 MLS

Built in 2018 and showing like new, this stunning 4-bedroom home is a must-see! Situated on a beautiful lot backing to a wooded area, the backyard is an entertainer’s dream, featuring a paver patio and an in-ground salt water pool for relaxing or hosting family and friends.The chef’s kitchen opens seamlessly to the spacious family room, creating an ideal layout for everyday living and entertaining. Custom built-ins add both style and functionality, while the mudroom/drop zone provides convenient organization.Upstairs, the versatile loft offers endless possibilities as a sitting area, playroom, home office, or media space. Generously sized bedrooms provide comfort for everyone, and additional features include a whole-house backup generator and a 3-car garage.Meticulously maintained and reflecting true pride of ownership, this exceptional home is ready for its next owners to enjoy.

3637 Kathys Way, South Chesapeake

$935,000

6 Beds ⋅ 3.1 Baths ⋅ 10642291 MLS

Welcome to luxury living in Chesapeake's coveted Cahoon Plantation community! This custom brick home was built in 2012. The stunning 6-bedroom home showcases a spacious open-concept design that works for both everyday living & entertaining. The beautifully appointed kitchen flows seamlessly into the main living and dining areas, creating a bright, inviting space filled with natural light & modern elegance. The kitchen offers maple cabinets, range hood, backsplash granite countertops & brand-new matte black Kitchen Aid appliances. The first-floor primary bedroom has an ensuite bathroom w/ shower, soaking tub, dual vanities and large walk-in closet. Upstairs the generously sized bedrooms provide flexibility for family, guests, or a home office. Step outside to your backyard retreat featuring a large, heated saltwater in-ground pool, play area, gas fire pit all while overlooking the woods. This home has been meticulously maintained and is ready for its new owners. Just minutes from interstates, restaurants & shopping.

409 Torre Pine Court, South Chesapeake

$649,900

3 Beds ⋅ 3 Baths ⋅ 10641913 MLS

Discover exceptional single-level living in this stunning Homearama ranch, offering over 3,000 square feet of thoughtfully designed space and high-end craftsmanship. This impressive home blends luxury, comfort, and entertainment-ready amenities in one seamless layout. Go outside to your private backyard oasis featuring a beautiful in-ground pool, perfect for summer relaxation and hosting guests. The outdoor experience continues with a fully equipped outdoor kitchen—ideal for grilling and dining al fresco—as well as a convenient outdoor bathroom, adding both style and functionality to your entertaining space.

4500 Mcrae Close, West Chesapeake

$750,000

4 Beds ⋅ 3 Baths ⋅ 10641597 MLS

Welcome to 1028 Pleasant Ridge Drive, where space, privacy, and comfort come together on a beautifully wooded three-acre homesite. From the moment you arrive, the setting is peaceful and private with natural light filling spacious living areas. The layout is ideal for both everyday living and entertaining, with generous gathering areas and well-sized bedrooms. This custom ranch-style residence offers approximately 3,700 square feet of thoughtfully designed living space, featuring four bedrooms, three full baths, and flexible areas suited for a growing family and today’s lifestyle. The first-floor primary suite provides a relaxing escape with a large walk-in closet and an ensuite bath featuring a beautiful tiled shower, separate tub and large vanity. This home opens to serene outdoor views of your private backyard retreat, complete with an in-ground saltwater pool, mature trees, and room to enjoy the peaceful setting that makes this one of Chesapeake’s most sought-after addresses. Whether you’re looking for space for family, hobbies, recreational vehicles, or simply a quieter way of life, this property delivers the rare combination of acreage, convenience, and versatility. Located within the highly regarded Hickory area, residents enjoy a rural atmosphere while remaining minutes to shopping and major highways. Also conveniently located to beaches, amazing restaurants and military bases with No HOA making this property truly the perfect blend of tranquility and accessibility.

1028 Pleasant Ridge Drive, South Chesapeake

$899,999

6 Beds ⋅ 3.1 Baths ⋅ 10641499 MLS

Welcome to your own private retreat in the heart of Grassfield! Nestled on approximately 5 acres, this beautifully maintained 6-bedroom, 3.5-bath home offers more than 4,200 square feet of space designed for both everyday living and unforgettable entertaining. Inside, you'll find generous living areas with room for everyone—whether you're hosting holiday gatherings, working from home, or simply enjoying quiet evenings with family. Go outside to enjoy the peaceful surroundings, then unwind in the hot tub, which conveys with the home, making it easy to relax under the stars after a long day. Now offered at an improved price, this exceptional property also includes a seller-paid carpet allowance with an acceptable offer, giving you the opportunity to add your own personal style before moving in. If you've been dreaming of acreage, privacy, and a home that offers the perfect blend of comfort, flexibility, and room to grow, this Grassfield gem is ready to welcome you home. Schedule your private tour today and experience everything this incredible property has to offer.

2536 Seven Eleven Road, South Chesapeake

$1,175,000

5 Beds ⋅ 4 Baths ⋅ 10641376 MLS

Welcome to this exceptional 5-bedroom, 4-bath custom home in the sought-after Hickory Station community in the sought-after Hickory School District! Situated on over 3 acres with beautiful wooded views, this stunning property offers the perfect blend of luxury, space, and modern updates. Boasting more than 4,200 square feet of living space, this home features a beautifully renovated kitchen, a spacious primary suite with a newly renovated bath, and an updated guest bathroom. Fresh paint throughout, new LED lighting, refinished hardwood floors, new windows, and new garage doors add style and efficiency throughout the home. Designed for both everyday living and entertaining, you'll love the expansive media room, generous living spaces, and seamless indoor outdoor flow. Step outside to your private backyard retreat featuring a beautiful 20' x 40' inground pool. A detached two-car garage provides additional storage and flexibility. Other recent improvements include a new roof, new second-floor HVAC system, Kinetico water treatment system for added peace of mind. This rare Hickory Station gem offers privacy, acreage, exceptional updates, and access to one of Chesapeake's most desired school districts. Don't miss the opportunity to make this remarkable property your next home.

2104 Hickory Forest Dr, South Chesapeake

$1,229,000

5 Beds ⋅ 4 Baths ⋅ 10641173 MLS

A beautiful brick waterfront home located in Mariners Pointe! This 4 bedroom plus flex home has been completely upgraded. Some of the highlights include -a complete kitchen renovation including new cabinets, quartz countertops, GE Cafe stainless steel appliances and a full downstairs bathroom renovation. Other upgrades include a new roof ('25), windows ('23), water heater ('24), a dock upgrade ('24), 1st floor HVAC ('24), 2nd Fl. HVAC ('25), Gutters and French drains ('25). This home is made for outdoor entertaining -featuring a screened-in porch with outdoor heaters, in-ground pool -pump and filter('22), pool liner ('25), large backyard, children's playset, and dock. Solar panels ('24) ($40,000. -power averages $9/mo). This house has it all! Please call for a tour!

1905 Lancing Crest Lane, South Chesapeake

$882,000

4 Beds ⋅ 2.1 Baths ⋅ 10641127 MLS

Some homes offer a backyard. This one offers a lifestyle. This exceptional property showcases a resort-inspired outdoor retreat featuring a saltwater pool, Trex decking, multiple gathering spaces, a waterfront firepit, & breathtaking views that set the stage for unforgettable entertaining. From quiet mornings overlooking the water to evenings spent poolside with family & friends, every detail was designed to be enjoyed. Inside is every bit as stunning; a grand foyer welcomes you inside, where soaring ceilings, beautiful hardwood floors & stunning lake views create an unforgettable first impression. The spacious kitchen features brand-new quartz countertops, SS appliances, & overlooks the heart of the home. The luxurious primary suite offers a spa-like bath & an incredible custom closet. The 4th bedroom upstairs? The choice is yours: gym/movie room or extra guest room…and don’t miss the additional attic storage! This one-of-a-kind home won’t last, schedule your showing today!

1307 Old Coach Road, South Chesapeake

$575,000

4 Beds ⋅ 3 Baths ⋅ 10640968 MLS

This spacious 4 bedroom home offers the perfect blend of indoor comfort and outdoor enjoyment. Overlooking a peaceful creek, the backyard is designed for entertaining and relaxation and features an in-ground swimming pool, expansive outdoor living space, and tranquil views. Enjoy your morning coffee from the private balcony off the primary suite, unwind in the sunroom overlooking the backyard, or host gatherings around the pool all summer long. Inside, you'll find over 3,000 square feet of living space, including a large updated kitchen with center island, abundant cabinetry, stainless appliances, high-end granite and plenty of room for meal prep and entertaining. The great room features a brick fireplace and built-ins, while the finished walk-out basement provides flexible space for a media room, game room or home gym. The primary suite includes an updated bath and walk-in closet. New windows and new carpet. 2 zone HVAC, water heater replaced in 2025. Must see!

4 Sol Thorpe Lane, Central Chesapeake

$1,150,000

5 Beds ⋅ 4 Baths ⋅ 10640805 MLS

Nestled on 3 acres in the Hickory area of Chesapeake, this impressive brick estate offers almost 4,000 sq. ft. with 5 bedrooms & 4 full bathrooms. The open design is enhanced by travertine tile, tray ceilings, updated lighting, & a spacious living area anchored by a cozy fireplace. The revamped kitchen features new countertops, sinks, fixtures, & appliances- including dual dishwashers & stoves (gas & induction), all centered around a large island & breakfast area. The first-floor primary suite offers tray ceilings & a beautifully updated bath with dual sinks, soaking tub, & custom tiled shower with built-in speaker. You'll also find 4 additional bedrooms- each with their own spacious custom closet systems, 3 more fully renovated bathrooms and multiple flex spaces in the home. Outside is just as impressive with a spacious deck overlooking the inground pool & a detached garage with carport featuring a renovated upper-level studio complete with 2 offices, hardwood floors, and fresh paint.

1452 Taft Road, South Chesapeake

Browse All Chesapeake VA VA Properties with Pool for Sale

Chesapeake VA Homes with Pool