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$609,900
4 Beds 3.1 Baths 10644569 MLS
100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, South Chesapeake

$379,900
3 Beds 2.1 Baths 10644759 MLS
Welcome home to this beautifully maintained townhome in the highly desirable Great Bridge area of Chesapeake! This spacious 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is filled with natural light and features gleaming wood floors, granite countertops, stainless steel appliances, and crisp white cabinetry. The primary suite boasts a granite vanity and dual shower heads for a spa-like retreat. Pride of ownership shines throughout with a fresh interior paint refresh and a newly installed backyard gravel area, creating a low-maintenance outdoor space perfect for relaxing or entertaining. Complete with an attached garage and driveway parking, this move-in ready home is ideally located just minutes from shopping, dining, top-rated schools, parks, military bases, hospitals, and the area’s beautiful beaches. Don’t miss the opportunity to own this well-cared-for home in one of Chesapeake’s most sought-after communities!

432 Charleston Street, South Chesapeake

$699,900
5 Beds 3.1 Baths 10644549 MLS
Welcome to this beautifully upgraded Ashburne floorplan, where comfort, style, and thoughtful design come together. With over $90,000 in custom upgrades, this exceptional home sits on a large lot with peaceful pond views and a spacious covered patio perfect for relaxing or entertaining. Inside, 9' ceilings, wide-plank oak flooring, thoughtful lighting, and custom white cordless blinds create a bright, inviting feel. The designer kitchen features white shaker cabinetry with custom pull-outs, a striking blue island, quartz countertops, and an upgraded appliance package. Two primary suites—one on each level—plus three additional bedrooms offer incredible flexibility. Highlights include a custom-tiled, frameless-glass shower, crown moulding, wood-shelved walk-in closets, and a 2-car garage with epoxy flooring and 220V/50A EV outlet. Enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic lakes.

410 Middleton Way, South Chesapeake

$499,900
4 Beds 2.1 Baths 10644597 MLS
Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car garage nestled in the heart of Chesapeake. This meticulously crafted residence offers a perfect blend of modern convenience & classic charm promising a lifestyle of comfort & sophistication. The heart of the home lies in the gourmet kitchen adorned w/luxurious granite countertops & equipped with stainless steel appliances. Whether you're whipping up a culinary masterpiece or enjoying a casual meal at the breakfast bar, this culinary haven is sure to inspire your inner chef. As you venture outdoors, discover & enjoy your own oasis in the backyard waiting for your personal touch. With its prime location in Chesapeake, you'll enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach. Projected completion is mid August 2026. The lot is almost 9400 sq ft. LVP flooring will be installed throughout the 1st floor. Photos from previous build. Make your appt today. Backyard fence being installed soon.

120 Taxus Street, South Chesapeake

$315,000
4 Beds 2 Baths 10644591 MLS
Charming one-level brick ranch offering 4 bedrooms plus a versatile bonus 5th bedroom attached to primary suite, perfect for a nursery, home office, sitting room, or flex space. Two updated full bathrooms. Equipped with two central air systems to serve addition to property, both less than 6 years old. Newer kitchen with granite countertops, new dishwasher and newer big size washer and dryer. The spacious primary suite includes two oversized closets with built-in shelving and drawers, providing exceptional storage and organization. Step outside to a large private backyard with a wood privacy fence- ideal for entertaining, cookouts, or relaxing outdoors. Conveniently located near shopping, dining, and with easy access to major interstates.

2641 Gilmerton Road, South Chesapeake

$315,000
3 Beds 2.1 Baths 10644227 MLS
Beautifully maintained townhouse in sought-after Cedar Lakes community with 3 bedrooms and 2 1/2 baths. The kitchen shines with brand-new stainless-steel appliances, including a gas range, microwave, French door refrigerator, and dishwasher, along with a new disposal and faucet. The entire home has been professionally painted, offering a fresh, move-in ready feel. Major systems are updated with a roof approximately 10 years old, HVAC replaced in 2020, and a brand-new hot water heater with an Apollo system providing supplemental heat, and windows replaced about 6 years ago. All toilets are new. Enjoy relaxing in the screened-in porch. Washer/Dryer and Gas Fireplace convey as-is. Great Bridge school district and just minutes from shopping, dining, parks, City Hall and easy access throughout Hampton Roads. Homeowner's Association includes a pool and clubhouse.

626 South Lake Circle, South Chesapeake

$420,000
3 Beds 2 Baths 10644472 MLS
Experience the charm of country living without sacrificing convenience! Nestled in Chesapeake's highly desirable Grassfield area, this property offers the perfect blend of privacy, open space, and everyday comfort. Enjoy peaceful surroundings with room to relax, entertain, garden, or simply take in the natural beauty. The thoughtfully designed home features inviting living spaces filled with natural light and a layout that's great for both everyday living and special gatherings. Located just minutes from shopping, dining, schools, and major commuter routes, you'll loving having the best of both worlds-quiet rural living with city conveniences nearby. Whether you're looking for your forever home or your own private retreat, this is a rare opportunity you won't want to miss. Schedule your private tour today!

4321 Ballahack Road, South Chesapeake

$639,900
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

$500,000
4 Beds 2.1 Baths 10643980 MLS
Welcome to this beautiful 4-bedroom, 2.5-bath home tucked away at the end of a quiet cul-de-sac in the highly sought-after Hickory School District. With a spacious, family-friendly layout. The open-concept kitchen features custom cream-colored KraftMaid cabinetry, stainless appliances, a breakfast bar, and a pantry, making it optional for both everyday living and entertaining. The kitchen flows seamlessly into the inviting family room, complete with a cozy gas fireplace. Durable laminate flooring extends throughout the entire first floor, adding warmth and style. Step outside to enjoy the large backyard, offering plenty of space for children, pets, gardening, or entertaining. A storage shed provides additional space for lawn equipment, tools, or outdoor gear. This home offers the perfect combination of comfort, functionality, and location.

901 Lela Lane, South Chesapeake

$360,000
2 Beds 1 Baths 10644104 MLS
Opportunity awaits in desirable Deep Creek! Charming one-level home AND 1,440 sq ft detached garage. Located on over 1.3 acres, this charming bungalow is ready for you to call it home. Charming original wood flooring throughout the spacious living area. Eat-in kitchen with solid wood cabinetry, offering plenty of storage space. Granite counters & stone backsplash. The two bedrooms offer solid hardwood flooring and ample closet space. Conveniently located shared hall bath. Bonus space off the kitchen would be great for a home office. Bright sunroom allows an abundance of natural light and offers a great space for a third bedroom. Detached garage of your dreams offers plenty of opportunity for car enthusiasts, entrepreneurs, rental income, and much more. With over 500ft of road frontage. Call today to seize the opportunity!

3124 Old Mill Road, South Chesapeake

$350,000
3 Beds 3 Baths 10643626 MLS
Experience waterfront living at its finest in this well maintained and beautifully updated condo on the Elizabeth River. Featuring LVP flooring throughout, this residence offers a seamless blend of style and durability. The updated kitchen shines with quartz countertops and stainless steel appliances, flowing effortlessly into the living space anchored by a cozy gas fireplace. The oversized primary suite is a true retreat, complete with a stunning en-suite bath showcasing floor-to-ceiling tile, dual sinks, and a new vanity with updated countertops. Two additional baths have been fully renovated with modern finishes. Go outside to your covered rear deck and take in serene water views, perfect for relaxing or entertaining. Community amenities include a pool, boat slip access, clubhouse, and more, offering a lifestyle of comfort and convenience.

143 Harbor Watch Drive, South Chesapeake

$444,000
3 Beds 2.1 Baths 10643564 MLS
Welcome to your golfer’s paradise on the 14th hole of Greenbrier Country Club! Meticulously updated, this stunning home blends modern elegance with everyday comfort. Come into a breathtaking living area showcasing soaring cathedral ceilings, high-end LVP flooring, and massive, picturesque windows that bathe the space in natural light while framing panoramic fairway views. Retreat to the first-floor primary suite—a true sanctuary beautifully reimagined with contemporary, spa-like finishes. Enjoy the lifestyle in the heart of Chesapeake, conveniently located just minutes from premier dining and shopping. Don't miss this rare opportunity to live on the green! Seller offering a $2,500 appliance credit.

927 Thatcher Way, South Chesapeake

$599,999
3 Beds 2.1 Baths 10643390 MLS
Move right into this beautifully upgraded, detached single-family home that perfectly pairs charm with an inviting, modern design. Built in 2014, this roughly 2,389 sq ft masterpiece is fully optimized for comfortable daily living and effortless entertaining. Main Level Highlights: Step through the welcoming entry foyer into a bright, open-concept floor plan radiating with natural light, custom blinds, and beautiful wood and laminate flooring. The expansive living space features a cozy electric fireplace. The updated kitchen boasts stainless steel appliances, a modern tile backsplash, crisp cabinetry, a large pantry, and a sunlit breakfast and dining area. Upper Level Retreats: Find ultimate comfort upstairs with a versatile second-floor loft that could be a home office, play area or convert into 4th Bedroom. The spacious primary bedroom suite serves as your personal oasis, offering a private retreat complete with an en suite bath and a large walk-in closet. Outdoor Living & Efficiency: Relax on the rear deck overlooking a sprawling, fully fenced backyard that directly overlooks a peaceful local farm. Large Modern Play-set conveying to buyer is negotiable. High-value capital updates include a new HVAC system in 2025, a tankless water heater, smart house features, and energy-efficient window tinting. Features an attached 2-car garage used for parking, storage, or a home gym. Centrally located near shopping, interstates, and area military bases. Bonus: Seller's preferred lender is offering closing cost assistance if utilized by buyer ask LA for more information!

712 Appalachian Court, South Chesapeake

$295,000
2 Beds 1.1 Baths 10642955 MLS
Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in desirable Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace, fresh finishes, and an inviting layout perfect for everyday living or entertaining. Recent improvements include fresh paint, new flooring, new carpet, an updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry bath, and a large hall closet for extra storage. Enjoy a private fenced backyard with a new deck, ideal for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major interstates, Chesapeake City Hall, and award-winning Grassfield schools, this move-in ready home is ready for its new owner.

300 San Roman Drive, South Chesapeake

$684,900
5 Beds 2.1 Baths 10642890 MLS
This property is a gardener's dream. It has a variety of flowering plants that provide blossoms throughout the growing season. Blooms are sequenced for near year round color. There are 10 field-stone edged garden beds add stunning features to the landscape. One garden bed in the back has a goldfish pond. One in the front features an unique natural stone bench. Back yard includes vegetable garden plot that faces the sun for garden fresh produce. Back yard oasis includes a hot tub and six foot privacy fence. Two patios are connected by a master-crafted pave walk-way. Oversized garden shed helps keep garage clutter free. Two lockable gates one on each side of the property. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well and two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized primary bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk in closet is medium sized with plenty of storage space. Washer and dryer are on the second floor for convenience to bedrooms.

707 River Gate Court, South Chesapeake

$490,000
4 Beds 2.1 Baths 10642834 MLS
This home is a Wellspring gem with valuable upgrades. The front lawn and spacious 2 car garage create a warm and inviting first impression. Inside, the thoughtfully designed first floor offers multiple living spaces including a formal living room, dining room, eat in kitchen and cozy den featuring a gas fireplace. A convenient half bath makes everyday living and entertaining a breeze. Upstairs has four generously sized bedrooms including a primary suite with vaulted ceilings. Throughout the home, you'll appreciate having no carpet and LVP in every bedroom. The deck right outside the patio door is superb for hosting, overlooking an expansive newly fenced backyard with endless possibilities for play, gardening, pets or outdoor gatherings. A storage shed provides additional space for tools and equipment. TESLA EV charger conveys. Loan is assumable.

405 S Monterey Drive, South Chesapeake

$879,000
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

$524,900
3 Beds 2 Baths 10642197 MLS
Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, South Chesapeake

$440,000
4 Beds 2.1 Baths 10641959 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake

$349,900
4 Beds 2.1 Baths 10641818 MLS
Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car garage. Situated in a prime location just minutes from shopping, local dining, entertainment, major interstates, and area bases. This property is a wonderful opportunity to bring a little elbow grease, add your personal touches, and truly make it your own. Call today to schedule your private showing! Some virtual staging utilized in pictures.

844 Parapet Road, South Chesapeake

$850,000
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

$385,000
3 Beds 2.1 Baths 10641471 MLS
Welcome home to this beautiful detached condo featuring an open and inviting floor plan designed for comfortable living and entertaining. The two-story living room fills the home with natural light and creates a spacious airy feel. The first-floor primary suite offers convenience and privacy complete with dual walk-in closets and an en-suite bath featuring dual vanity sinks. The kitchen boasts granite countertops, stainless steel appliances and a breakfast bar with counter seating, perfect for dining and gathering with guests. Upstairs you will find 2 additional bedrooms, a full bath and a loft overlooking the living room. This move-in ready home combines style, functionality and low maintenance living in the Greenbrier area. Don't miss this exceptional opportunity!

1519 Tallwood Circle, South Chesapeake

$419,900
3 Beds 2.1 Baths 10641328 MLS
This end unit townhome has been meticulously cared for by the original owners since purchasing it new in 2023. From the welcoming foyer, LVP flooring throughout the 1st floor leads to a stunning great room, which flows nicely into the dinette and gourmet kitchen that provides abundant counter space for all your kitchen storage needs. Upstairs, 3 spacious bedrooms and 2 full bathrooms provide privacy and comfort. Your luxurious owner’s suite includes tray ceilings, a generous sized walk-in closet, a double vanity sink and large stand up shower. When you live in Cardinal Meadows, you’ll love the easy access to Route 17, Cedar Road, I-64 and I-464, not to mention being located right off Cahoon Parkway puts you just minutes away from all your shopping needs at Cahoon Commons.

1607 Songbird Lane, South Chesapeake

$553,900
3 Beds 3 Baths 10641052 MLS
Enjoy peaceful country living on 1.77 acres in the highly sought-after Hickory School District! This charming 3-bedroom, 3-full-bath home offers plenty of space both inside and out, making it perfect for those seeking privacy, comfort, and room to roam.Step inside and discover a welcoming open layout designed for everyday living and entertaining. The spacious heated sunroom deck provides the perfect spot to relax year-round. Huge pantry storage room off kitchen to keep those grocerie store runs to a minimum. The expansive 1.77-acre lot includes a chicken coop, large detach garage, fenced area, carport, and open fields making this property ideal for hobby farmers, homesteaders, or anyone looking to embrace a more self-sufficient lifestyle. With plenty of room for gardening, recreation, and outdoor activities, the possibilities are endless. The back half of detached garage needs work, but has lots of potential for a nice workshop, game room, mancave, apartment, etc.

2420 Mount Pleasant Road, South Chesapeake

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