Chesapeake, VA Real Estate | Chesapeake, VA Homes with a 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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10640809 MLS

Welcome home! Come view this beautiful 4-bedroom, 2.5-bath brick home is nestled in a highly attractive neighborhood. Priced to make it your own!! Inside, you’ll find a spacious family room with a cozy gas fireplace, a large primary bedroom with ensuite, featuring tiled shower. Plantation shutters throughout. The large kitchen offers an island and plenty of storage and room for cooking & entertaining. A versatile room over the garage, provides the flexibility you need for a home office, playroom, or guest space. Step outside to enjoy your private backyard oasis, complete with a full privacy fence, a saltwater pool, and low-maintenance Trex decking—great for gatherings or quiet afternoons at home. A detached garage with electricity adds convenience and additional storage. This home truly has it all—space, comfort, and great outdoor living in a fantastic location! No HOA!

4105 Margaret Ann Court, West Chesapeake

$475,000

3 Beds ⋅ 2 Baths ⋅ 10640771 MLS

Nestled off two quiet cul-de-sacs, this beautiful riverside ranch is the perfect candidate for a custom dream home transformation. Inside, the spacious layout kicks off with a large den centered around a classic wood-burning fireplace, showcasing original hardwood floors ready to be restored. The plan offers three sizeable bedrooms with large 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 excellent flexible square footage, great for a home gym or office. The real profit potential lies in the outdoor oasis. The backyard features an in-ground pool with a diving board, framed by palm trees. Fully fenced for privacy on the sides, the rear remains open to water views. Valuable waterfront infrastructure is already in place, including a concrete seawall and existing dock. Schedule your showing today! Some photos enhanced with AI to show maximum potential.

111 Goldcrest Drive, Central Chesapeake

$700,000

4 Beds ⋅ 2.1 Baths ⋅ 10640623 MLS

Welcome to 609 Shasta Drive! A thoughtfully designed property in the peaceful Flagstone Quay community. Inside, the open-concept layout features a spacious living room with an electric fireplace flowing into the dining area and gorgeous kitchen with marble countertops, tile backsplash, stainless steel appliances, gas range, large island, chef's sink, and walk-in pantry. Additionally you will find a private study, mudroom with built-ins, 9' ceilings on both levels, and first-floor LVP flooring. Upstairs features a versatile loft, laundry room, and generously sized bedrooms, each with a walk-in closet, including a beautiful primary suite with a custom closet and tiled shower. Home has been wired for whole home Ethernet. Outside, enjoy the wrap-around front porch, a fully fenced backyard with brand new in-ground pool, covered rear patio, and Tuff Shed for added storage. Pool is equipped with a premium Dryden Aqua® Activated Filter Media filtration system imported from Europe. Tour today!

609 Shasta Drive, South Chesapeake

$719,000

5 Beds ⋅ 3.1 Baths ⋅ 10640430 MLS

Beautiful home in Hickory school district nestled on a spacious cul-de-sac lot. This home boasts a formal LR w/FP, DR, huge Fam Rm, spacious gourmet Kit w/stainless steel appliances. There's two primary suites, two closets in each located on opposite sides the of home. Updates include new LVP on the 1st floor and new carpet on the 2nd, new roof, new storage shed , new interior and exterior paint, replacement windows and kitchen granite counters and tile backsplash (2025), also a few new ceiling fans and fixtures. Enjoy the outdoor space on the custom paved patio w/ built in firepit & inground pool. Great yard for entertaining. Move in ready as this home offers comfort, space and great location!

1225 Woodstream Court, South Chesapeake

$669,000

5 Beds ⋅ 3.1 Baths ⋅ 10639977 MLS

Beautifully appointed transitional style home offers the perfect balance of comfort, style & privacy. Nestled in cul-de-sac w/ no HOA, the home welcomes you w/ elegant natural stone accents that frame the covered front porch and enhance its timeless curb appeal. Inside, hardwood floors & ceramic tile complement a bright, thoughtfully designed layout. A versatile first-floor room provides an ideal space for a private office, guest suite, or flex room. The open-concept great room flows seamlessly into a well-equipped kitchen featuring granite countertops, stainless steel appliances, and generous workspace. Formal living and dining rooms offer inviting spaces for entertaining or everyday gatherings. Go outside to enjoy a private backyard retreat complete w/ an elevated Trex deck, saltwater pool, hot tub, gazebo & det. garage—creating an ideal setting for relaxing, entertaining & making the most of life at home. VA assumable loan.

803 Gresham Way, South Chesapeake

$435,000

5 Beds ⋅ 3.1 Baths ⋅ 10639654 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

$675,000

4 Beds ⋅ 3.1 Baths ⋅ 10639506 MLS

Rare opportunity to restore a true waterfront gem in Chesapeake's sought-after Western Branch area. Nestled on more than 1.5 private acres at the end of a secluded cul-de-sac, this 3,679-square-foot estate is a diamond in the rough awaiting its return to better-than-ever glory. Enjoy the ease of one-level living with breathtaking deep-water views stretching across the river from the rear of the home. Mature trees create a peaceful, park-like setting, offering unmatched privacy and natural beauty. Outdoor amenities include a pool, private pier, and riparian rights, providing endless opportunities for boating, fishing, and waterfront recreation. A detached three-car garage is connected to the home by a breezeway and features a spacious office suite above, ideal for a home business, studio, or guest retreat. Set well back from the road, this hidden paradise offers the perfect combination of seclusion, expansive water frontage, and incredible potential. Bring your vision and transform this exceptional property into a stunning waterfront showcase. Some photos are virtually staged.

3000 Voyager Court, West Chesapeake

$599,500

5 Beds ⋅ 2.1 Baths ⋅ 10639614 MLS

Welcome to your new home! Tucked away on a quiet, private cul-de-sac in the highly desirable Miller's Run neighborhood, this beautiful property is completely move-in ready and waiting for its next chapter. Whether you love to entertain or simply want a private everyday retreat, this house delivers. The spacious backyard is a true summer paradise, featuring a gorgeous in-ground saltwater pool absolutely perfect for cooling off, relaxing, and making memories on hot days. Fresh & Modern Upgrades: Step inside to find brand new flooring throughout, giving the home a clean, updated feel from the moment you walk through the door. Outdoor Living Spaces: Enjoy your morning coffee on the brand new front porch and host weekend BBQs on the spacious, brand new backyard deck. Flexible Layout: With 5 total bedrooms, you have all the space you need. The convenient first-floor bedroom is easily adaptable and makes an ideal quiet home office or guest room. Schedule your private tour today!

3404 Louise James Court, South Chesapeake

$535,000

4 Beds ⋅ 2 Baths ⋅ 10638636 MLS

Check out this cream puff! Beautifully maintained and thoughtfully updated, this standout home in sought-after Pines of Warrick is ready to impress. Situated on an oversized lot, the backyard is an entertainer's dream with a sparkling in-ground pool and plenty of space to relax and unwind. Gorgeous hardwood floors flow throughout the first floor. The expanded primary suite features two closets and a beautifully updated bath with dual vanities, a walk-in shower, and oversized soaking tub. Updated kitchen and baths offer timeless appeal. The FROG provides a flexible fourth bedroom, office, or media room, while abundant storage includes a floored attic. Meticulously maintained and move-in ready, this is the one you've been waiting for in Great Bridge!

504 Bonsack Court, South Chesapeake

$1,190,000

6 Beds ⋅ 4.1 Baths ⋅ 10639205 MLS

Welcome to a lifestyle few will ever experience. Tucked away on 1.18 private waterfront acres at the end of a quiet cul-de-sac,this extraordinary custom-built Elizabeth River estate offers over 6,900 square feet of luxury living with direct access to the Intracoastal Waterway. This is more than a home—it is a private waterfront retreat where luxury,tranquility & unforgettable entertaining come together. Imagine mornings with coffee overlooking the water as boats drift by,afternoons cruising from your private dock & 15,000-pound boat lift,& evenings enjoying breathtaking sunsets from your balcony or around the custom firepit with family & friends under the stars. Designed to impress yet comfortable for everyday living,the light-filled open floor plan showcases soaring ceilings,walls of windows,& breathtaking water views creating a seamless connection between indoor & outdoor living. Every space was designed to make everyday living extraordinary. At the heart of the home,the chef’s kitchen opens to multiple gathering spaces,creating the perfect setting for holiday celebrations,elegant dinner parties,& relaxed weekends at home. With 3 private ensuites,including a first-floor guest suite,this layout offers rare flexibility for multigenerational living,extended guests,or those who value privacy & comfort. Over $260,000 in recent improvements reflect pride of ownership,including extensive landscaping,custom firepit,underground drainage & pump system,updated flooring,renovated baths,updated kitchen,finished third floor (+600 SF),new upstairs HVAC,new water heaters,& generator connection. Dock approx. 4 years old. Water depth approx. 10' at high tide & 2–3' at low tide. Add'l features incl a 100-year roof,lifetime fence warranty,oversized 3-car garage,& dedicated storage room. Homes of this caliber rarely become available. Offering privacy,prestige,deep-water access,& resort-style waterfront living in a prime location,this exceptional estate delivers the coastal luxury lifestyle most only dream about. This is Elizabeth River living at its finest.

4200 Quailshire Court, West Chesapeake

$439,900

4 Beds ⋅ 2 Baths ⋅ 10639152 MLS

Welcome Home to this charming Ranch in the Western Branch section of Chesapeake! Newly poured concrete to create oversized driveway offer utmost convenience. Ideally situated at the entrance to Point Elizabeth and the Chesapeake public walking trail, this location is sure to impress! Enter into your inviting foyer which leads to your open concept living, dining, den and kitchen area. Newer LVP floors flow throughout and lead to your newly renovated kitchen with wood cabinets, quartz tops, and newer stainless appliances. Gas stove for the chef in the family! Other gas features include new tankless water heater, & heat. Kitchen leads to FROG serving as 4th bedroom, laundry, & garage. Opposite direction off foyer is large primary bedroom with large closet and ensuite bath. Two secondary bedrooms and hall bath complete this lovely layout. Backyard features in-ground pool, newer liner, and plenty of patio space and green space for entertaining needs. Newer windows, paid off solar offering bundles of savings, and newer mechanical components make this a slam dunk. Call this beauty Home Today!

3004 Tyre Neck Road, West Chesapeake

$449,000

4 Beds ⋅ 2 Baths ⋅ 10639147 MLS

Welcome Home to this charming and up to date ranch in the desirable Point Elizabeth section of Chesapeake's Western Branch. Upon arrival you are greeted with the Home's stately & classic curb appeal. Enter onto front porch awaiting the soon to be added white PVC railings and into the foyer. Den is large, light, and bright! Room is big enough to serve dual purposes like dining space/flex space & great room or as one massive great room. Kitchen feat. open concept dining, freshly painted wood cabinets, ceramic tile backsplash, quartz counters, and newer stainless appliances. Floors are newly installed adding peace of mind with new subfloor as well. Off kitchen is access to laundry room, garage, and finished room over garage serving as fourth bedroom. Down hall is multiple storage closets, full and updated luxurious hall bath w/ ceramic tile surround, ceramic tile floors, new vanity, lighting, and more! Primary bedroom features oversized closet with storage racks, ensuite bath with tile shower, fresh paint, finishes, & vanity. Two secondary bedrooms on hall are spacious and well laid out. Yard is tranquil with well maintained above ground pool and large swim deck. Deck is freshly painted and offers a plethora of entertaining space. Room to spare in backyard with lush landscape makes this a Home-run. Well & pump make pool care a breeze. Call this Home Today!

3727 Hardwick Terrace, West Chesapeake

$599,900

4 Beds ⋅ 3 Baths ⋅ 10638728 MLS

Come see this solid, all brick 2 story home sitting on a quiet cul-de-sac lot with almost half an acre. This well maintained home offers 3,444 sq. feet with 4 bedrooms and 3 full baths. On the first floor you will find a desirable, massive primary bedroom and second bedroom with hallway full bath. The first level also features a large foyer, dining room, family room and gorgeous living room with built in bookshelves, pocket doors, fireplace & cathedral ceilings looking into an upstairs loft area. Walk into a large kitchen with breakfast area that leads to a 4 seasons sunroom overlooking a newer fully fenced backyard with newer above ground salt water pool. Windows galore with tons of natural light throughout the home. Downstairs laundry room completes the first floor. Upstairs, a spacious 3rd bedroom with full bath and walk-in closet. You will find the 4th oversized bedroom over the garage that feels a separate area. Spacious 2 car garage. This home has a whole house backup generator, tankless water heater, storage shed and well irrigation system. Fresh paint within the last few years. Minutes from all Western Branch Schools, baseball field, interstate and military bases.

3120 Deans Court, West Chesapeake

$710,000

5 Beds ⋅ 2.1 Baths ⋅ 10638474 MLS

Welcome home to 2209 Beeblossom Lane located in the sought-after Grassfield High School well-known for its STEM Academy! Built in 2016, this move-in ready 5-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and energy efficiency. Inside, you’ll find wood flooring, a kitchen with sunny eat in nook open to a den w/ cozy gas fireplace ready for the Fall& Winter holidays. Enjoy living , dining & extra office flex space room , ideal for entertaining or everyday living. The expansive primary suite is a true retreat, featuring a dual-entry oversized walk-in closet and a private en suite bath complete with a soaking tub and separate shower. Upstairs, the dedicated theater room with a big-screen setup is ready for unforgettable movie nights, game days, or family gatherings. Step outside to your own backyard oasis! Relax or entertain around the inground saltwater pool, all within a fully fenced backyard designed for privacy and fun. Additional highlights include a Rinnai tankless water heater and paid-off solar panels, providing energy savings and peace of mind. Dominion Meadows offers planned community events throughout the year, scenic sidewalks, & beautiful fountains that make every stroll through the neighborhood enjoyable. Convenient to interstates to bases, shopping , dining & more. Schedule a showing today & start making new memories in your new home!

2209 Beeblossom Lane, South Chesapeake

Chesapeake, VA Homes with a Pool for Sale

Newest Chesapeake, VA Homes with a Pool for Sale