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$540,000
4 Beds 2.1 Baths 10646908 MLS
Beautifully updated 2-story traditional home tucked away on a quiet cul-de-sac in Chesapeake's desirable Greenbrier area! This move-in-ready home offers 4 bedrooms, 2.5 bathrooms, and an attached 2-car garage. The main level features formal living and dining rooms, a spacious family room, half bath, utility/laundry room, and an inviting kitchen with a Butler's pantry. Laminate flooring flows through the living, dining, and family rooms, while new tile flooring enhances the kitchen, bathrooms, and laundry room. Fresh interior paint throughout and brand-new carpeting upstairs provide a modern, refreshed feel. The spacious primary suite includes a walk-in closet and private ensuite bath. Conveniently located just minutes from Greenbrier Mall, shopping, dining, Chesapeake City Park, the Chesapeake Arboretum, and major commuter routes including I-64, I-464, and Route 168. Don't miss this exceptional opportunity!

800 Crescent Trace, South Chesapeake

$675,000
5 Beds 3 Baths 10646827 MLS
Welcome to Viridian Reserve at Hickory, where comfort, space, and peaceful wooded views come together in one exceptional South Chesapeake home. From the moment you step inside, you'll be greeted by soaring cathedral ceilings, an inviting multi-landing staircase, and a warm, open layout designed for everyday living and entertaining. The spacious family room features a cozy gas fireplace, while the incredible kitchen is truly the heart of the home, offering beautiful wood cabinetry, abundant cabinet space, updated appliances, and a convenient wine/beverage refrigerator. The formal dining area provides plenty of room for gatherings, and the first floor also includes a private office, bedroom, and full bathroom—great for guests, multigenerational living, or working from home. Upstairs, the oversized primary suite is a true retreat with room for a sitting area, three closets, and a luxurious ensuite bath featuring granite countertops, dual vanities, a walk-in shower, private water closet, and an additional spacious walk-in closet. Outside, relax on the charming covered porch overlooking the large backyard and peaceful wooded views, with the option to easily screen it in for year-round enjoyment. Enjoy extremely low electricity costs with a fully paid-off solar system. The oversized two-car garage offers exceptional storage, a built-in workbench, and plenty of room for hobbies, while the extended driveway provides additional parking. Located in the highly desirable Hickory area, this home offers the perfect combination of space, functionality, privacy, and energy efficiency.

308 Wisdom Path, South Chesapeake

$650,000
5 Beds 3 Baths 10646878 MLS
Welcome home to this spacious 5-bed, 3-bath home offering 3,842 sq ft of beautifully designed living space on a generous .84-acre lot. With multiple living areas, a HUGE bonus room over the garage, plus a formal living room, dining room, family room, and bright sunroom, there's plenty of space to spread out. The open kitchen flows seamlessly into the family room and sunroom. Upstairs, the spacious primary suite boasts a spa-like bath with a jetted tub, separate shower, and dual vanities. Brand-new carpet was installed upstairs. Step outside to your private backyard retreat featuring a Trex deck, outdoor kitchen, stamped concrete patio, and an expansive fenced yard with a newer vinyl privacy fence with four gates. A storage shed with power provides plenty of extra storage. Additional highlights include stunning curb appeal, a stamped concrete driveway, epoxy-coated garage floor, EV charger, and easy access to military bases, major highways, shopping, dining, and entertainment.

3204 Hearring Way, South Chesapeake

$674,900
5 Beds 3.1 Baths 10646835 MLS
If you've been searching for a spacious, move-in-ready home with a private in-law suite on a large lot in the heart of Chesapeake, your search is over! This one-of-a-kind property offers the blend of comfort, flexibility, and space. The traditional in-law suite features its own multiple entrances, full kitchen, living room with a cozy gas fireplace, recently remodeled bathroom, bedroom, and dedicated laundry area—use for multi-generational living or extended guests. Step outside to a large backyard for relaxing or entertaining, complete with a recently built gazebo with electricity and a storage shed for all your gardening and outdoor needs. Located in a neighborhood with sought-after schools, you'll enjoy convenient access to shopping, dining, parks, and more. Don't miss this rare opportunity to make this exceptional Chesapeake home yours!

1307 Channing Way, South Chesapeake

$499,900
4 Beds 2.1 Baths 10646861 MLS
This beautifully maintained home that offers the look and feel of new construction. . . without the wait! Thoughtfully upgraded with custom finishes throughout, this home perfectly blends modern style with everyday comfort. Step inside to discover an open, light-filled floor plan featuring a stunning custom accent wall that adds warmth and character to the main living space. The spacious kitchen flows seamlessly into the dining and living areas for entertaining or spending time with family. Retreat to the generously sized bedrooms, each offering plenty of space for relaxation, a home office, or growing families. The primary suite provides a peaceful escape with exceptional closet space and a well-appointed ensuite bath. Conveniently located near shopping, dining, schools, and major highways. Schedule your private showing today!

539 Schaefer Avenue, West Chesapeake

$574,900
4 Beds 2.1 Baths 10646764 MLS
Meticulously maintained by its original owner, this 4-bedroom home offers a spacious, thoughtfully designed layout with an extended living room, formal dining room, and a versatile bonus area that can serve as a home office, playroom, gym, or flex space. The kitchen features newer appliances, while additional updates include a tankless water heater, updated HVAC system, and recently painted exterior. The garage has been upgraded with durable speckled flooring and built-in storage for added organization. Step outside to enjoy the in-ground pool, installed three years ago, a storage shed, and a backyard that backs to a wooded area, providing a natural backdrop and added privacy. Tucked away in the Western Branch area, the neighborhood offers connections to adjacent communities with opportunities for walking, running, biking, and golf cart access. Conveniently located near shopping, dining, major highways, military installations and hospitals.

4721 Lake Shore Drive, West Chesapeake

$825,000
5 Beds 2.1 Baths 10646792 MLS
Space to gather, land to enjoy, and a separate apartment for the people who matter most. Nearly 3,900 square feet in the main home, 3 private acres, a detached three-car garage, and an approximately 1,000-square-foot apartment above it. This sprawling ranch offers four first-floor bedrooms, including the spacious primary suite with dual closets, beautifully refinished hardwoods, fresh paint, updated lighting, newer roof, new carpet and an expansive kitchen with gas cooking and newer appliances. A finished bonus room upstairs serves as the fifth bedroom or flexible space for guests, hobbies, or a quiet retreat. An enormous walk-in attic provides rare expansion potential, with room to add finished living space for an even more complete upstairs retreat. Enjoy the new Trex deck and peaceful backyard with room to entertain, garden, play, and bring your horses-picture them grazing outside your kitchen window while your coffee brews. Dreaming of an inground pool and backyard oasis? There is room for that too. Need space for your in-laws? Above the detached garage, the separately metered apartment includes its own bedroom, full bath, kitchen, living area, and laundry, creating true independent space for extended family, guests, a studio, or private home office. The apartment is not counted in sq ft/bedroom/bath count in this listing. Well and septic mean no monthly city water or sewer bill. Located in Riverwood, a quiet acreage community known for spacious homesites, mature trees, room for horses, and a neighborhood boat launch for enjoying nearby waterways. Enjoy the space and privacy of South Chesapeake in the Grassfield school district. Come see the lifestyle you have been searching for.

3700 Riverwood Crescent, 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, Dual-Fuel Range, tile back splash tile backsplash & Cafe SS appliances. Comfortable open living spaces that flow seamlessly throughout w/fireplace, 8 ft doors, 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

$720,000
5 Beds 3 Baths 10646838 MLS
Model Home to Be Built - James II Model at Riverview Landing by Wetherington Homes. This thoughtfully designed floor plan offers an Owner's Suite, two additional bedrooms, and a utility room conveniently located on the first floor. Buyers may select their lot and personalize available design options. The home includes a variety of well-appointed features designed to support modern living. The community offers eight floor plan options along with multiple exterior elevations that highlight architectural detail and curb appeal. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this thriving new community in Chesapeake!

MM James 2, South Chesapeake

$520,000
4 Beds 2 Baths 10646823 MLS
Welcome to your oasis in Great Bridge, a beautifully maintained home tucked away on a quiet cul-de-sac in one of Chesapeake?s most desirable communities. This spacious property offers comfortable living with bright, inviting interiors, a functional floor plan, and generous living spaces perfect for everyday life and entertaining. Step outside to your private backyard oasis featuring an in-ground pool, ideal for relaxing or hosting family and friends. In addition to the attached garage, a second detached garage provides exceptional space for vehicles, a workshop, hobbies, or extra storage. Situated on a cul-de-sac and conveniently located near top-rated schools, shopping, dining, parks, and major commuter routes, this home offers the perfect combination of privacy, functionality, and convenience.

813 Woodrow Court, South Chesapeake

$489,900
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

$658,900
3 Beds 3.1 Baths 10646723 MLS
QUICK CLOSE! Financing 5.75 rate, NO PMI! Less than year old and exceptional value with over $100,000 in upgrades. Professionally designed decorated showcase home by an award-winning builder blends elegance with modern comfort. Exceptional details include custom lighting throughout, designer wallpaper, culinary bars, white oak beams/shelves, and full Matte White GE Cafe appliance package w/Brushed Brass accents. French doors open to custom 12x30 paver and turf courtyard w/black fencing and landscaping. HW first floor, to include first floor BR with ensuite tiled shower, first-floor laundry for convenient one-level living (and full laundry up). Upstairs hardwood flooring Primary BR, hall and loft. Loft with custom bar for relaxing evenings. Stunning primary BR with 10'x13' custom walk-in closet and TWO 5' x '10' finished storage closets. Spa-inspired bath with 9' vanity, WOW shower, free-standing tub, all champagne ready. Professionally managed community. *Special loan programs.

200 Traditions Way, South Chesapeake

$589,000
4 Beds 2.1 Baths 10646724 MLS
Welcome to this beautiful move in ready Stephen Alexander home, nestled on a cul-de-sac lot in the highly sought-after Grassfield School District in Great Bridge. Enjoy relaxing on the charming front porch or entertaining on the spacious new deck. Inside, you'll find an open floor plan with hardwood floors, a family room with a gas fireplace, a spacious kitchen with a center island, a formal dining room, and a versatile bonus room perfect for a home office, playroom, or flex space. The oversized primary suite offers a private retreat with an en-suite bath, while the additional bedrooms provide plenty of room for family or guests. Updates include: Roof (2022), Windows (2019), Water Heater (2020), HVAC serviced (2026), gas fireplace serviced and kitchen appliances (2022). Conveniently located near shopping, dining, and interstates, this home offers the perfect blend of comfort, style, and location. Schedule your private tour today! Seller is offering 1 year home warranty. Assumable loan at 2.5% for qualified buyers, subject to lender approval.

1102 Watsons Glen Court, South Chesapeake

$345,900
3 Beds 2.1 Baths 10646754 MLS
Beautifully updated detached end-unit condo in the desirable River Breeze community! Enjoy the privacy and feel of a single-family home with the convenience of low-maintenance condo living. This move-in-ready home features a new roof (2026), luxury vinyl plank flooring (2026), fresh interior paint, and a new privacy fence. The open, bright interior offers a welcoming atmosphere with modern updates throughout, for everyday living and entertaining. The condo association covers ground maintenance, water, sewer, and trash service, providing exceptional value and convenience. Conveniently located near shopping, dining, schools, military bases, and major highways. Whether you’re a first-time buyer, downsizing, or looking for a low-maintenance lifestyle, this well-maintained home is ready for its next owner. Schedule your private showing today!

4107 River Breeze Circle, West Chesapeake

$540,000
4 Beds 2.1 Baths 10646728 MLS
Beautifully updated and move-in ready, this home offers the perfect blend of comfort, style, and community. Recent improvements include luxury vinyl plank flooring throughout, a beautifully renovated primary bath with a spacious walk-in shower, and the addition of a fourth bedroom for added flexibility. Outside, the large backyard is framed by mature weeping willow trees, creating a peaceful retreat on a quiet side street. Beyond your front door, enjoy a lifestyle that’s hard to find—golf cart rides to the clubhouse, afternoons at the resort-style pool, workouts in the fitness center, visits to the dog parks and playgrounds, and a calendar full of neighborhood events including community picnics, book club, cigar & bourbon nights, festive holiday celebrations, and the beloved Christmas golf cart parade. Experience everything this vibrant, close-knit community has to offer in sought-after Culpepper Landing.

3145 Codorus Street, South Chesapeake

$769,740
5 Beds 4 Baths 10646721 MLS
Welcome to The Summit at Riverview Landing, where you’ll discover thoughtfully designed living space across 2 luxurious floors-perfect for families of every size. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the gourmet kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. Enjoy a vibrant, amenity-rich community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches and mountains-your ideal lifestyle begins here. Photos and renderings are from builder's library, actual finishes and features may vary.

321 Riverview Road, South Chesapeake

$799,990
5 Beds 3.1 Baths 10646719 MLS
Introducing the Tillman, a spacious home that offers both comfort and style. With 5 bedrooms, 3,5 bathrooms, and a 2-car garage. Upon entering the Tillman, you'll be greeted by a large, welcoming dining room that seamlessly flows into the expansive kitchen. The kitchen features a generous center island, ideal for meal prep or casual dining, and opens to a spacious family room, creating the perfect space for entertaining. A conveniently located powder room is just off the main hallway, adding to the home's functionality. The first floor also boasts a luxurious primary suite, providing a private retreat with a massive walk-in closet, a large double vanity, and a private water closet for ultimate convenience and privacy. Upstairs, you'll find four additional bedrooms. The second floor also features two bathrooms and a large loft area that could serve as a separate lounge, playroom, or additional living space. Photos and renderings are from builder's library, actual finishes and features may vary.

109 Lilypad Court, South Chesapeake

$430,000
3 Beds 2.1 Baths 10646317 MLS
Welcome home to this beautifully updated traditional home in the desirable Logans Mill community of Chesapeake! Offering 3 bedrooms, 2.5 bathrooms, and approximately 1,750 square feet, this move-in ready home features bamboo, ceramic, carpet, and LVP flooring, an inviting living space with a fireplace, and a spacious kitchen with Energy Star stainless steel appliances. Upstairs, the generous primary suite includes a walk-in closet and private ensuite bath, while two additional bedrooms provide plenty of space for family, guests, or a home office. Step outside to enjoy the fully fenced backyard with a deck, storage shed, and wooded backdrop for added privacy. Conveniently located near Greenbrier shopping, dining, parks, military bases, and major commuter routes, this home offers the perfect blend of comfort and convenience.

1913 Shepherds Gate, South Chesapeake

$620,000
4 Beds 2.1 Baths 10646683 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

$512,000
4 Beds 2.1 Baths 10646160 MLS
This charming brick colonial home is on a corner lot of a cul-de-sac in the desirable Silverwood development. The spacious 20x40 ft. pool boasts of a new liner in 2024, complemented by a brand-new back porch added three years ago and a freshly renovated front porch completed this summer. Inside, the updated kitchen shines with granite countertops, freshly painted cabinets (including upper cabinets repainted this summer), a new sink, and modern cabinet pulls. Beautiful hardwood floors grace the front half of the downstairs (recently refinished) and all of the upstairs, creating a warm and inviting atmosphere. Western Branch High School, middle school, and elementary school all located within the development, along with festive community events like the annual Holiday parade with firetruck and spring egg hunt. Restaurants, shopping all nearby and just a quick trip to downtown Norfolk, this home offers the ideal blend of comfort, updates, and community charm.

3316 Kindlewood Crescent, West Chesapeake

$699,900
5 Beds 3 Baths 10646613 MLS
Beautiful 5-bedroom, 3-bath home tucked away on a quiet cul-de-sac in the desirable Great Bridge area of Chesapeake. Built in 2018, this move-in ready home features an open-concept floor plan filled with natural light, a spacious living area, and a well-appointed kitchen that's perfect for entertaining. A first-floor bedroom and full bath offer flexibility for guests or a home office. Upstairs, the spacious primary suite provides a private retreat, along with generously sized secondary bedrooms. Situated on nearly half an acre, the backyard offers plenty of room to relax, play, or entertain. Conveniently located near shopping, dining, parks, and major commuter routes. Don't miss this exceptional opportunity—schedule your private tour today!

1021 Mimi Court, South Chesapeake

$734,900
5 Beds 3 Baths 10646525 MLS
There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first floor, PLUS an office/flex room AND loft-style second living area. Crown molding, hardwood stairs, custom window treatments, a gas fireplace, quartz countertops, stainless appliances, gas cooking, under-cabinet lighting, upstairs laundry, walk-in attic, tankless water heater, smart garage opener, security system, and a custom 36-foot patio add comfort and refinement. Trusted lender Steve Hawley, NMLS #1813927, with Southern Trust Mortgage, NMLS #2921, will provide a 1% lender-paid buydown on this listing. Ask the listing agent for details. Subject to borrower qualification and lender approval.

1741 Watershed Court, 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

$425,000
3 Beds 2.1 Baths 10646473 MLS
Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, 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.