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$569,900
4 Beds 2.1 Baths 10645253 MLS
Move in ready and less than 5 years old with impressive builder upgrades. The gourmet kitchen boasts of high-end appliances including induction stovetop, wine fridge and huge walk-in pantry. This kitchen features elegant quartz countertops, artistic backsplash with large bar area completely open to living area with fireplace. A luxurious primary suite with spa inspired bath features huge shower and quartz vanity. A tasteful neutral palate with wide planked flooring and tons of natural light throughout the home. Enjoy almost half acre fenced in backyard wired for 50 amps and home is plumbed for gas. Conveniently located near dining, shopping , military bases and interstates. Schedule your showing today to make this wonderful house YOUR HOME! Seller will consider closing cost assistance with full price offer.

240 Hurdle Drive, South Chesapeake

$629,000
6 Beds 3 Baths 10645483 MLS
Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, 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

$551,900
4 Beds 2 Baths 10645495 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch-style living with 4 bedrooms, including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering 3% CCA (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2207 Hampton Roads Parkway, West Chesapeake

$578,645
4 Beds 2.1 Baths 10645480 MLS
Home is 100% complete. 30 Day close is available. This traditional floor plan that offers 4 Bedrooms, 2.5 Baths, and 2400+ sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & a utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and tree-lined sidewalks. The builder is offering 4% CCA (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

5112 Annapolis Drive, West Chesapeake

$599,900
4 Beds 2.1 Baths 10645491 MLS
Upon a quiet drive, beneath the sweeping arms of ancient trees, there stands a home of uncommon grace, a residence renewed, refined, and prepared to captivate all who cross its threshold. Golden light spills through the windows, illuminating rooms shaped by thoughtful improvements and timeless comfort. At the heart of the home awaits a magnificent kitchen, adorned with stone countertops, newer cabinetry, gleaming stainless steel appliances, and resilient LVT flooring. It is a setting worthy of grand feasts, intimate gatherings, and countless evenings shared among family and friends. Above the garage rises a vast and versatile chamber—the fourth bedroom. Offering endless possibility as a distinguished home office, private gym, spirited playroom, guest retreat, or sanctuary of quiet thought. Beyond the walls, an expansive backyard unfolds beneath the open sky, inviting celebrations, laughter, peaceful mornings, and memories yet to be written. The home itself has been transformed from within and without, with polybutylene plumbing replaced by PEX, an upgraded electrical panel, most windows replaced, updated lighting and flooring, select exterior doors, siding, trim, and a private well connected to the irrigation system. The roof was replaced in 2014. Set within the highly regarded Hickory school district, this remarkable property is less than one mile from the interstate and only moments from the shopping, dining, and conveniences of Edinburgh. The tree-lined streets and welcoming neighborhood lend the setting an air of distinction rarely found.

712 Woodcott Drive, South Chesapeake

$609,000
4 Beds 2.1 Baths 10645393 MLS
Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready

1416 Pine Grove Lane, West 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

$584,900
5 Beds 2.1 Baths 10645337 MLS
A versatile floor plan with ample space for entertaining! Tha Palm offers 5 Bedrooms , 2.5 Baths, a large Family room, open to the kitchen, all BR's on 2nd floor, large patio space for outdoor living. A desirable Primary Suite bath & walk-in closet.The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2202 Wilmington Avenue, West Chesapeake

$315,000
3 Beds 1 Baths 10645059 MLS
This lovely 3 bedroom/1 bath abode is fresh, charming and a perfect fit for the whole family! Enjoy the benefits of solar panels that keep energy costs low. The spacious backyard is ideal for curious kids to explore, energetic pups to play fetch or a small-scale gardener’s dreams to come true. Gorgeous warm wooden cabinets , coffee bar, custom island , pantry and gas stove create a luxurious feel in this gourmet kitchen. Enjoy time in the open family room complete with striking wood flooring, a cozy and comfortable space for family movie nights and memory making, find a bonus room that offers endless possibilities creates a cozy playroom, a productive home office or transform it into an extra bedroom. Take comfort in the attractive brick exterior of the home as it’s sure to stay tidy and effortless to maintain for years to come. Check out this wonderful opportunity to live the good life in Chesapeake!

3944 Port Road Road, Central Chesapeake

$319,900
3 Beds 1.1 Baths 10645365 MLS
Welcome home to this well-maintained 3-bedroom, 1.5-bath brick ranch nestled on a quiet cul-de-sac in the desirable Deep Creek area of Chesapeake. This charming home offers 1,392 square feet of comfortable living space, including a spacious den/family room perfect for entertaining, relaxing, or creating the ideal flex space. Major updates completed approximately 7 years ago include the roof, HVAC, windows, water heater, and encapsulated crawlspace, providing added peace of mind. The attached garage offers additional storage and convenience, while the washer and dryer convey with the home. Being sold As-Is, with the seller willing to consider reasonable buyer concessions with an acceptable offer. Don't miss this wonderful opportunity to make this home your own!

1213 Lakeview Court, South Chesapeake

$295,000
2 Beds 2 Baths 10645362 MLS
Welcome HOME to this gorgeously remodeled, from top to bottom 2BR/2BA one-story ranch house. It has EVERYTHING you've been searching for: open concept layout, large updated windows, new luxury LVP flooring throughout, modern light fixtures, custom tile work, freshly painted, you name it! Completely NEW spacious chef’s kitchen shines with expensive QUARTZ countertops, large island with built-in cabinetry, soft-close white cabinets extending up to the ceiling with LED lighting, and NEW stainless steel appliances. Spacious Primary suite with 2 closets, and a beautifully remodeled bath with a new vanity, tiled floor, new tub, floor-to-ceiling designer tile surround, separate toilet area, and deep linen closet. Second Bedroom with big closet. Contemporary remodeled Hall Bathroom with contemporary floating vanity, new toilet, and tiled shower with designer accents. Spacious laundry room, instant hot water heater, long driveway for multi-car parking or RV parking, and fenced backyard complete the package! NO HOA fees, and no flood insurance required. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1002 Mayfield Avenue, Central Chesapeake

$299,900
4 Beds 2.1 Baths 10645218 MLS
Welcome to 1243 Damyien Arch, a beautiful townhome in the heart of Chesapeake's Greenbrier area! This spacious 3 possible 4-bedroom, 2.5-bath home offers an open and inviting floor plan designed for comfortable everyday living and effortless entertaining. The bright living area flows seamlessly into the dining space and kitchen, while the generous primary suite provides a private retreat with ample closet space and an en-suite bath. Enjoy low-maintenance living with a private patio, attached garage, and convenient access to shopping, dining, parks, major interstates, military bases, and Chesapeake Regional Medical Center. Located in an established neighborhood, this home is an excellent opportunity for anyone seeking a centrally located home with easy access to everything Hampton Roads has to offer. Schedule your private showing today and make this Chesapeake gem your new home!

1243 Damyien Arch, South Chesapeake

$645,000
4 Beds 2.1 Baths 10645288 MLS
First Time Buyer 5.5 rate, low down, NO PMI! Joseph’s Meadow MODEL GPS 369 Scotland Ln. Chesapeake. Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage welcomes you w/ a full front porch, soaring 10-foot ceilings, & beautiful hardwood floors throughout the first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, & stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, & oversized walk-in pantry. Mudroom & powder room are conveniently tucked away by 2-car garage. Upstairs, a sun-filled loft, two spacious bedrooms, loft (opt 4th), & a large laundry room provide exceptional functionality. The private primary suite offers a custom walk-in closet & spa-inspired bath w/ quartz countertops, dual vanities, freestanding tub, tiled shower, & private water closet. Easy living with professionally managed grounds ensures low-maintenance living, making your dream truly a peaceful haven.

365 Scotland Lane, South Chesapeake

$674,000
5 Beds 2.1 Baths 10645285 MLS
Welcome home to a beautiful one owner home in the highly sought after neighborhood of Dominion Meadows, and Grassfield High School District. Built in 2020, this home offers a bright open-concept design, with 5 spacious bedrooms, and 2.5 baths. Versatile living room or home office, formal dining room, gourmet kitchen with large island, custom cabinetry, granite countertops, stainless appliances, and pantry flows into the spacious family room. Upstairs you will find a laundry room, and generously sized bedrooms. Luxurious primary suite with tray ceiling, spa bath, oversized custom closet. Outside unwind in the screen porch, or the large patio enjoying privacy in the fenced backyard while spending time with family or entertaining with friends. Easy commute to all military bases, and a few minutes away from shopping, restaurants, and entertainment.

815 Angel Wing Drive, South Chesapeake

$285,000
2 Beds 2.1 Baths 10645264 MLS
This beautifully updated 2 bedroom, 2.5 baths, 2 story condo features 2 full primary ensuite bedrooms w/updated bathrooms including new sinks, counter, vanities, lighting, & toilets. In addition, brank new LPV flooring, new upgraded carpet 2nd floor, fresh paint throughout, new kitchen cabinets, new granite counters and new stainless-steel appliances create a clean and modern feel. There is a reserved parking spot plus plenty of visitor parking. Enjoy maintenance free living with condo fees, that include access to clubhouse, community pool maintenance & trash pickup. Convenient Greenbrier location near shopping, dining, easy I-64 access. This move-in ready home offers comfort and convenience and makes this home a must see!

2351 Old Greenbrier Road, Central Chesapeake

$9,900
10645258 MLS
Lot 100 Farmington Acres, approximately 0.36ac. Lot is located at 3509 Sigmon Dr. which is a paper street. 150' in from where Newport Dr. currently stops then turn right onto Sigmon Dr. heading back North approximately 300'. A gorgeous lot, will require improvements including but not limited to: wetlands delineation, and improvement of Newport Dr. and Sigmon Dr. to city standards before construction, lot is priced accordingly.Fantastic opportunity for sweat equity, or buy and hold as part of diversifying your investments or long term retirement. The property is minutes away from the booming North Suffolk area. Neighborhood also borders the north side of the gorgeous Retreat at Western Branch Subdivision as well as the Dunedin neighborhood.Don't miss the chance to scoop up your piece of Western Branch now at a discount!Please be mindful of neighbors when parking on Newport Dr. to view. Call listing agent with any questions!

3509 Sigmon Drive, West Chesapeake

$275,000
3 Beds 2 Baths 10645162 MLS
Beautifully renovated 3-bedroom, 2-bath home in the historic South Norfolk neighborhood! Blending classic character with fresh, modern updates throughout, we start just past the brick porch and swing with a 2-story foyer. Just off the stairs, the first of three bedrooms has fresh paint, carpet, and 6-inch baseboards. Through the living room, the home boasts an expansive eat-in kitchen with new stainless-steel appliances. Off the kitchen, the first of the home's 2 bathrooms and a sunroom complete the first floor. Upstairs, the second bathroom and two large bedrooms at each end of the hall provide maximum privacy and a small office. Outside, enjoy a spacious yard enclosed by a brand-new fence being installed. New HVAC being installed. Conveniently located near shopping, dining, interstates, and all that Chesapeake and nearby Norfolk have to offer.

1312 Hull Street, Central Chesapeake

$577,740
3 Beds 3 Baths 10645211 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.

2166 Edwin Drive, South Chesapeake

$585,000
4 Beds 2.1 Baths 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, 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.