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$965,000
6 Beds ⋅ 5.1 Baths ⋅ 10648547 MLS
Welcome to this impressive all-brick home offering over 5,000 sq. ft. of versatile living space and exceptional indoor–outdoor amenities. With 6 bedrooms, 5.5 bathrooms, and an additional first-floor flex room perfect as a 7th bedroom, home office, or formal living area, this home adapts beautifully to your lifestyle. Five of the bedrooms include private bathrooms, giving everyone their own comfortable retreat. A bright, oversized sunroom— but not included in the home’s total square footage. Step outside to your own backyard oasis. Brick pool house with heating/cooling + full bathroom. In-ground saltwater pool with a new liner ( installed 2025). Hot tub for 6. Expansive patio area for entertaining and relaxing. The property also features a three-car garage plus a half-circle driveway providing abundant parking for guests . Freshly painted, new carpets, refinished wood floors. INTERIOR PHOTOS ARE VIRTUALLY STAGED

844 Greenfield Lane, South Chesapeake

$1,199,000
5 Beds ⋅ 3.1 Baths ⋅ 10648292 MLS
Welcome home!! 28.18 private acres, 3,714 sq ft, 5 bedrooms, 3.5 updated baths, TWO primary suites, a detached 4-car garage and 20x30 workshop—all in Chesapeake’s sought-after Hickory area?! Yes! Here at 509 Ballahack Rd. Extensively improved inside and out, this one-of-a-kind property delivers the space, flexibility and freedom of country living with modern comfort. Abundant natural light fills the spacious living areas, while warm finishes and thoughtful updates create an inviting feel throughout. The kitchen is complemented by a butler pantry with granite countertop, cabinetry and additional storage, adding function for everyday living and entertaining. The rare dual-primary layout offers one suite on each level, both with private ensuite baths—ideal for multigenerational living, extended guests or added privacy. The main-level primary has been refreshed with new flooring, paint, lighting and hardware. Upstairs, the second primary features a showstopping spa-inspired ensuite with an oversized wet room, rainfall shower, body jets, two-person soaking tub, porcelain tile and polished marble mosaic. All 3.5 bathrooms have been updated with fresh flooring, lighting, paint, mirrors and hardware. Outside, enjoy a nearly wraparound front porch, expansive 20x40 composite deck, outdoor kitchen setup, custom fire pit, fruit trees, grape vines and 28+ acres to explore. Proven deer and turkey hunting is literally steps from your back door, with private shooting and archery areas already in place. The detached 4-car garage provides exceptional storage, while the 20x30 workshop features concrete flooring, lighting and its own electrical panel. Additional improvements include 33 solar panels (to be paid off with acceptable offer), Level 2 EV charger, major electrical upgrades, crawlspace encapsulation, updated HVAC and a private well with NO monthly water bill. A rare combination of acreage, recreation, extensive improvements and flexible living in Southern Chesapeake. See attached Feature & Upgrade Sheet for even more! Make this an easy day and stop here first!

509 Ballahack Road, South Chesapeake

$935,000
5 Beds ⋅ 3 Baths ⋅ 10648261 MLS
Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, South Chesapeake

$532,500
3 Beds ⋅ 2.1 Baths ⋅ 10647647 MLS
Welcome home to easy, low-maintenance, luxury living in Eagle Pointe, Chesapeake’s premier 55+ community! This move-in-ready Hamilton plan features brand-new flooring, a new water heater, and TWO spacious primary suites - one on each level - perfect for guests or multi-generational living. The eat-in granite kitchen offers an island and stainless steel appliances and opens to a bright, sunny morning room. A formal dining room features a box-bay window and tray ceiling. The 1st-floor primary includes two closets, a ceramic shower, and a double vanity. Enjoy generous finished walk-in storage, too! At the heart of Eagle Pointe is the Bay Club with indoor & outdoor pools, hot tub, fitness center, billiards, library, game rooms, grand celebration room, catering kitchen, and so much more. Come experience the Eagle Pointe lifestyle! Call today to schedule your personal tour. Some pics digitally staged.

420 Dundee Lane, South Chesapeake

$699,900
4 Beds ⋅ 3 Baths ⋅ 10647939 MLS
PRICE IMPROVEMENT! A fantastic opportunity to get more for your money—this spacious home offers nearly 3,000 sq ft on a full acre with beautiful water views! Located in desirable Etheridge Lakes on a large corner lot overlooking the neighborhood pond, the flexible layout includes a first-floor bedroom & full bath—ideal for guests. The kitchen features granite countertops, SS appliances, abundant cabinetry & opens to the living room. A formal dining room is perfect for gatherings, while the separate den-like space offers even more flexibility as a playroom, library, home office or cozy retreat. Upstairs, the spacious primary suite includes a jetted tub, separate shower & massive walk-in closet! Outside, enjoy the composite deck, paver patio, mature trees, & circle firepit overlooking the peaceful pond views. As fall approaches, picture evenings around the firepit roasting marshmallows & making s'mores! With so much space inside and out, this one offers a setting that's hard to find!

1239 Pacels Way, South Chesapeake

$570,000
5 Beds ⋅ 3 Baths ⋅ 10647738 MLS
Welcome to the kind of home that feels good the moment you enter. Set on just over 2 peaceful acres, this 5-bed, 3-bath home offers the perfect blend of space, comfort, and modern style. Sunlight pours through the windows, filling every room with warmth, while the open layout creates an easy flow for everyday living and gathering with the people you love. The home features two spacious primary suites, one located on the first level, both with private baths and large closets, making it ideal for guests, or multigenerational living. You'll also love the luxury vinyl plank flooring, granite countertops, stainless steel appliances, and the beautiful laundry room! The backyard is just as inviting. Whether you're roasting marshmallows around the fire pit, spending summer afternoons in the saltwater pool, or simply enjoying the quiet views with your morning coffee, the backyard feels like your own private escape. Peaceful, welcoming, and full of room to grow!

1108 Shell Road, South Chesapeake

$799,900
5 Beds ⋅ 3 Baths ⋅ 10647712 MLS
New Home by Custom Builder in Martin’s Point (Western Branch) main floor living, 4 or 5 bedroom plan. First floor primary bedroom with luxury bath- zero entry tiled shower & free standing tub, Open floor plan with Huge Gourmet Kitchen w/ Quartz counter tops, 36” gas cooktop with built-in microwave/oven, Cathedral Ceiling Family Room w/ Beamed ceiling, amazing stone fireplace with built-in bookcases, expansive covered porch (29’x10’) overlooks a privately wooded backyard & scenic view .42 acre. 3 Bedrooms & Study with French doors on 1st floor with 2 add'l large rooms on the second floor, 3 baths. Excellent location, easy access to I-664, near schools, shopping, Custom Builder is a member of Southern Living Custom Home Builder Program (since 1993). Superior quality features include Trane HVAC system, tankless hot water heater, custom cabinetry, large utility room/drop zone, Hardie Plank exterior, quality upgrades throughout. Fully sodded and irrigated yard.

3909 Bruce Road, West Chesapeake

$449,900
3 Beds ⋅ 2.1 Baths ⋅ 10647748 MLS
Rain or shine, the screened porch is calling. This move-in ready end-unit Nansemond floorplan in The Retreat at Western Branch offers low-maintenance living with a first-floor primary suite, 2-car garage, open-concept layout, and abundant natural light. The kitchen features bar seating overlooking the living room with a cozy gas fireplace, plus a spacious walk-in pantry to keep everything organized. Your favorite spot just might be the screened, covered rear porch. Upstairs offers two additional bedrooms, a loft, guest bath, and walk-in attic. Resort-style amenities include a clubhouse, pool, outdoor kitchen, fire pit, billiards, fitness center, community garden, dog park, and beautifully landscaped grounds.

4607 Longleaf Place, West Chesapeake

$460,000
4 Beds ⋅ 2.1 Baths ⋅ 10647376 MLS
Welcome home to this spacious property located in a quiet neighborhood with only one entrance, offering a peaceful setting and minimal through traffic. Situated on a large lot, this home features generous living spaces, including a large family room, formal dining room, and a versatile living room that can also serve as a home office. The open kitchen offers a center island, built-in desk, and plenty of workspace, making it suitable for everyday living and entertaining. Upstairs, the oversized primary suite provides a relaxing retreat with a large garden tub, double-sink vanity, and ample space to unwind. Recent updates include newer laminate flooring throughout the first floor, newer carpet upstairs, and an HVAC system and roof that are approximately four years old. Step outside to enjoy the large screened-in porch overlooking the spacious backyard—suitable for relaxing, entertaining, or enjoying the outdoors.

4921 Clifton Street, West Chesapeake

$1,200,000
4 Beds ⋅ 3.1 Baths ⋅ 10647623 MLS
Rare opportunity for true multi-generational living with exceptional flexibility, privacy, and space! This beautifully updated ranch offers one-level living with a finished room over attached 2-car garage, soaring ceilings, formal dining, first-floor laundry, and a luxury granite kitchen featuring KitchenAid appliances, built-in desk and a sun-filled eat-in. Relax year-round in the vaulted sunroom with a wood-burning fireplace or step outside to your private resort with a an inground saltwater pool, luxury landscaping, and expansive patio. The standout feature is the detached 3-car garage with a separate 3-bedroom, 1-bath apartment complete with kitchen, laundry, and private living space. Additional highlights include RV storage/hangar, workshop, Tesla charger, whole-house water filtration and softener, geothermal HVAC, encapsulated crawl space, buried drainage, sprinkler system, high-speed Cox WiFi, oversized walk-in attic, and extensive updates throughout.

1717 Long Ridge Road, South Chesapeake

$599,999
4 Beds ⋅ 3 Baths ⋅ 10647231 MLS
Welcome home to this beautifully updated all-brick detached condo tucked away in a quiet, peaceful community. Enjoy relaxing mornings on the inviting covered front porch with porch swing or covered rear porch and patio overlooking the beautifully maintained yard with extensive irrigation upgrades and lush landscaping throughout. Designed for easy living, this home offers mostly one-level living with a spacious room over the garage featuring its own en-suite bath. The luxurious remodeled kitchen opens seamlessly to the living area and boasts top-of-the-line stainless steel appliances, granite countertops, and a walk-in pantry. Engineered bamboo flooring, fresh paint, updated lighting and ceiling fans, plus a whole-home gas generator add comfort and peace of mind. A massive walk-in attic offers incredible storage or future expansion. HVAC replaced in 2020, and a tankless water heater was installed in 2023.

522 Bells Hollow Court, South Chesapeake

$604,900
3 Beds ⋅ 2.1 Baths ⋅ 10647287 MLS
To Be Built - Financing 5.75 rate, NO PMI! Nestled in Greenbrier, Joseph’s Meadow is the newest community by a renowned local builder. The Primrose Cottage welcomes you with a charming full front porch, soaring two-story family room, and beautiful Mohawk flooring throughout the main living areas. Designed for effortless living and entertaining, the open layout connects the family room, dining area, and HGTV-inspired chef’s kitchen featuring oversized quartz island, custom hood & floating shelves, designer finishes, and mudroom. The first-floor primary suite offers a custom walk-in closet, spa-like bath with quartz dual vanity, tiled shower, and private laundry. Upstairs two spacious bedrooms, tons of storage and large laundry room. (Opt. to add 4th BR or Loft) Professionally managed grounds provide a low-maintenance lifestyle, giving you more time to enjoy the comfort, quality, and craftsmanship of your Primrose haven. To be built to your specs from designer showroom. Intimate neighborhood with limited building opportunities.

MM Primrose A, South Chesapeake

$749,000
5 Beds ⋅ 3 Baths ⋅ 10646970 MLS
Welcome to this beautifully updated 5-bedroom, 3-bath brick ranch tucked away on a quiet cul-de-sac in sought-after Emerald Lakes. Offering approximately 3,200 square feet, this home features a bright open-concept design with soaring cathedral ceilings, Brazilian walnut floors, custom trim, wainscoting, wood ceiling beams, and extensive upgrades throughout. The remodeled kitchen boasts quartz countertops, custom range hood, newer appliances, subway tile backsplash, and overlooks the spacious living area with gas fireplace and striking wood accent wall. The first-floor primary suite offers private patio access, a cedar-lined walk-in closet, jetted tub, separate shower, and dual vanities. The finished FROG with full bath is ideal as a guest suite, media room, or fifth bedroom. Additional highlights include a 3-year-old HVAC, 2018 water heater, rebuilt rear stairs (2026), irrigation system, custom landscaping, in-wall surround sound, oversized driveway, no HOA, and a private fenced backyard.

1204 Lingale Court, South Chesapeake

$599,900
4 Beds ⋅ 2 Baths ⋅ 10646894 MLS
This is the one you’ve been waiting for! Beautifully updated & filled w/ character, this 2,800-square-foot ranch delivers 4 bedrooms, 2 baths and an incredible blend of indoor comfort & outdoor resort-style living. Covered front porch welcomes you to a light-filled interior where floor-to-ceiling windows surround the sunroom, while the family room showcases a fireplace, built-in bookcase & extensive molding. The spacious primary suite offers walk-in closets plus a versatile sitting area perfect for a home office, reading retreat or private escape. Outside, prepare to be wowed! The expansive backyard is your own private oasis with a 26,000-gallon saltwater pool (new pump 2025, salt cell 2026), deck, gazebo, fire pit, hammocks, pool house, sheds, fish pond with fountain, weeping willow, mature Japanese maple, peach tree and lush gardens. Smart-home features and Wi-Fi irrigation add modern ease. Finished room over garage, expansive attic, numerous updates & low traffic dead-end street.

318 Rio Drive, South Chesapeake

$829,900
4 Beds ⋅ 3 Baths ⋅ 10646857 MLS
Stunning all brick home features 4 bedrooms, 3 full bath, spacious 4 season sunroom, in ground pool in sought after Great Bridge School District. Living room/office & dinning room with hardwood floors. The large main living area offers an open floor plan featuring vaulted ceiling, gas fireplace flowing into the kitchen. Updated kitchen showcases SS appliances, New solid surface counters w/single sink & new faucet, two-tone cabinetry, bar for additional seating and flows directly into the dining room and eat-in breakfast for easy meals and entertaining. Large primary bedroom with trey ceiling, walk-in closet, remodeled ensuite bathroom with spa-like features, including a soaking tub, water closet, double vanity and, separate shower & tub. Additional downstairs bedrooms are generously sized, with hard wood floors. Large private 4th bedroom is located upstairs offers a full bath. The laundry room includes cabinetry and shelving for ample storage. Walk-in attic for additional storage. Beautiful landscaped back yard has all the amenities for entertaining show casing vinyl fencing, a solar panel heated in-ground L shape salt water pool with fountain, stone pavers throughout, trek decking and a 4 season sunroom to enjoy the view. New: carpet in family room, mini split in 4 season room, SS gas stove/microwave/refrigerator, coretec flooring in 4th bedroom, fixtures, 2023 pool liner, 2021 tankless water heater, 2015 gas furnace. 2015 Roof replacement, Mr Rogers Windows and Door, gutters with gutter guards, vinyl trim wrapped. Ask agent for a full list of home improvements. THIS IS A MUST SEE!

825 Waterfall Way, South Chesapeake

$665,000
4 Beds ⋅ 3 Baths ⋅ 10646600 MLS
LUXURY COASTAL RESORT STYLE RIVER FRONT COMMUNITY! Welden Field & Rowe Custom Home on a Premium .44-acre lot backs to Nature Preserve. Resort like lifestyle w/ waterfront Gazebo, deep water access, Kayak launch, Clubhouse, Pool, Fitness Room, Green Space, Nature Preserve w/Trails. Welcome to this meticulously maintained Craftsman-style home w/ Southern Living front porch & thoughtfully designed luxurious light-filled floor plan. Chef's kitchen w/ expansive island, bar seating, range, tile back splash tile backsplash & SS appliances. Comfortable open living spaces that flow seamlessly throughout w/fireplace, high ceilings. Spacious downstairs owner's suite w/ Spa concept bathroom, tile floors, glass shower, over-sized Garden tub + custom walk-in closet + FF guest bedroom/Home Office w/ add storage. Outdoor oasis that backs to Nature Preserves w/ spacious covered porch, irrigation system, back up generation & MORE! Easy access to I-64, Edinburgh. WELCOME HOME!

409 Tranquility Trace, South Chesapeake

$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10646630 MLS
Beautiful, brick front, 4 bedroom home in sought after Greenbriar Estates. The newly renovated kitchen boasts SS appliances, new cabinets, Quartz counters with a large island that is open to the family room. Other features include an architectural roof, wood floors, HVAC and wood floors all replaced approximately 5 years ago! The large primary suite features a walk-in closet, dual sinks, a separate soaker tub, a skylight and a custom glass shower door. LOCATION-LOCATION! Less than 30 minutes to Naval Station Norfolk & little creek bases, as well as the Virginia Beach Oceanfront . Chesapeake City Park is at the end of the street, and Greenbriar Mall is just minutes away. Schedule your showing soon, this one won't last!

602 Windward Drive, South Chesapeake

$995,000
6 Beds ⋅ 4 Baths ⋅ 10645935 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$725,000
5 Beds ⋅ 3.1 Baths ⋅ 10646366 MLS
See features sheet & survey attached — you’ll be amazed by this NEW custom home by Overholt Contracting (40+ yrs)! Must see now: modern floorplan with 2 spacious primary suites (or use one as a game room), 4 large bedrooms, first-floor home office, high-end kitchen & baths with quartz, freestanding tub + tiled shower, smart-home Wi-Fi, and full landscaping with sod. Sited on almost 1/2 acre in Hickory (Chesapeake) on city/county septic & water — NO HOA, additional buildings allowed, room for pool, boat or RV. James Hardie siding, carriage garage door with glass, brushed concrete patio. Closing cost assistance available with preferred lender Wes Flowers, Southern Trust. Also see something you would love to have but it’s not here. Contact me and my builder will have his design team work on it. He is easy going and ready to make your new home all about you!!! You wont find another build of this quality at this amazing price.

343 Ewell Lane, South Chesapeake

$649,900
4 Beds ⋅ 3.1 Baths ⋅ 10646358 MLS
LUXURY COASTAL RIVERFRONT LIVING W/ AT IT'S FINEST! Breathtaking sunrises, sunsets & an effortless Coastal Lifestyle on the Elizabeth River. Elegant Craftsman style home w/ First Floor Primary Suite. Luxurious Chefs kitchen, expansive island w/ bar seating, granite counter tops & extended 48' wood cabinets w/ extra storage. Comfortable open living spaces w/fireplace, 8 ft doors, high ceilings & wood floor package. First Floor FLEX SPACE for 5th bedroom/Home Office. Spacious owner's suite w/ Spa Concept bathroom, tile floors, glass shower + custom walk-in closet. ENTERTAINERS DELIGHT! Screened in porch, professionally landscaped yard w/ OLP Lighting Design, fenced in yard + 2 car detached garage. All the BELLS & WHISTLES you can Dream of. Community amenities include waterfront Gazebo w/ access to deep water, Kayak Launch, Clubhouse w/ pool, Fitness Room, Green Spaces & Nature Preserves w/ private trails throughout. TURNKEY & MOVE IN READY. WELCOME HOME!

224 Wildlife Trace, South Chesapeake

$597,740
3 Beds ⋅ 3 Baths ⋅ 10646287 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2205 Edwin Drive, South Chesapeake

$849,900
5 Beds ⋅ 4.1 Baths ⋅ 10646141 MLS
Under Construction – Luxury New Construction with Timeless Coastal Farmhouse Style! This stunning 3-level home blends classic board-and-batten architecture, clean lines, black-framed windows, and thougthful accents to create exceptional appeal. Inside, an open-concept first floor is designed for modern living, featuring a spacious family room, dining area, and a designer kitchen with a large center island, custom cabinetry, and premium finishes. The second level offers four generously sized bedrooms, including an impressive owner's suite with a spa-inspired bath, plus two full bathrooms to comfortably accommodate family and guests. The third floor provides incredible flexibility with a spacious bonus room or fifth bedroom, a full bath, and convenient walk-in attic storage. With 5 bedrooms, 4.5 baths, thoughtful craftsmanship, and stylish finishes throughout, this exceptional new home offers the perfect blend of luxury, comfort, and functionality for today's lifestyle.

1833 Shillelagh 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.