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$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

$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

$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

$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

$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

$300,000
3 Beds 1.1 Baths 10645067 MLS
This property is a diamond just waiting to be found. With a little less than 3/4 of an acre, this home offers the country feeling right outside your back door, surrounded by corn fields and plenty of land to spread out on. Plenty of off-street parking, and 1 car attached garage space. Inside, you will find 3 rooms at 1 end of the home, with 1.5 baths spread across a 1,254 sq. ft. home. A fireplace built with craftsmanship and surely a conversation piece. This home is just looking for a little tlc to get it back to prime condition. The dining room is big enough to hold a large table, with an additional space to hold a small table in the kitchen. The garage has an enclosed additional room built to be a workshop with a door and potential for storage as well. Newer septic and newer roof. Sellers are listing well under market value to offset any and all repairs needed. All appliances are as-is, where is.

2423 Herring Ditch Road, South Chesapeake

$629,900
4 Beds 2.1 Baths 10645157 MLS
BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities are just steps away, while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, South Chesapeake

$575,000
4 Beds 2.1 Baths 10645016 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$452,000
4 Beds 3 Baths 10645004 MLS
Welcome home to this beautiful property ideally situated on corner lot. 4 spacious bdrms with one downstairs bedroom w/ large walk-in closet and full bath access perfect for in-law or guest suite. Primary suite offers walk-in closet, jetted tub and double vanity. Upstairs laundry with cabinetry and laundry workspace. Kitchen with breakfast bar, pantry, double oven, and newer refrigerator, microwave and dishwasher. Go outside onto the lanai w/ceiling and beautiful maturing landscaping. Low maintenance exterior with all wrapped exterior and gutter guards. The standout feature is the detached garage w/ recently installed attached 16x20 carport and expanded driveway-A true hobbyist or RV owners dream. Garage is wired with its own 100amp panel accommodating both 30 and 50 amp connections. Garage is heated and cooled by an installed window unit and pull down access to extra attic storage. A true must see.

1332 Hazel Avenue, Central Chesapeake

$1,195,000
4 Beds 4.1 Baths 10644941 MLS
Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

377 Homestead Road, West Chesapeake

$400,000
4 Beds 2.1 Baths 10644987 MLS
Welcome home to 4320 Schooner Trail! This beautifully maintained 4 -bedroom, 2.5 bathroom home in the sought- after Western Branch area of Chesapeake. This home offers an ideal blend of space, comfort, tons of storage and modern convenience. The downstairs features an open- concept floor plan seamlessly connecting the living room, dining area and kitchen area that has stainless steel appliances and a private office with French doors. Upstairs features a huge master bedroom with walk in closets and a massive attached bathroom. Enjoy the private, fully fenced in backyard that is perfect for relaxing and entertaining guests. The HVAC system was replaced in 2024 and the fireplace has never been used by the owner. The fireplace sold as-is. Call today for your private showing of your new home!

4320 Schooner Trail, West Chesapeake

$599,999
4 Beds 2 Baths 10644979 MLS
Welcome to this fully remodeled all-brick ranch located in the Hickory area of Chesapeake. Offering 4 bedrooms, 2 updated bathrooms, and situated on approximately 3 acres, this property provides generous indoor and outdoor living space. Interior updates include luxury vinyl plank flooring, tiled showers, granite countertops, stainless steel appliances, and an open, light-filled layout designed for everyday living and entertaining. Outdoor features include a covered front porch, an expansive rear deck, and a private deck accessible from the primary suite. Additional improvements include a newly poured driveway and a 50-AMP power pole ready for RV hookup. This move-in-ready home combines updated finishes with functional living space in a convenient Chesapeake location.

913 Long Ridge Road, South Chesapeake

$305,000
2 Beds 1 Baths 10644942 MLS
Welcome home to this charming all brick ranch nestled in Brentwood Estates neighborhood. This well-maintained home offers the perfect combination of classic charm and thoughtful updates making it truly move-in ready. Inside you will find a beautifully updated bathroom. The kitchen provides abundant cabinetry, and the dining room has been enhanced with new windows, elegant chandelier creating a nice setting for family dinners. All appliances convey. Enjoy peace of mind with updated roof, windows (2017), along with a brand-new sidewalk, garage floor and driveway offering exceptional curb appeal. Step outside to a large, fully fenced backyard complete with a covered deck, an ideal space for relaxing, grilling and entertaining family & friends.

2209 Wildwood Road, South Chesapeake

$355,000
3 Beds 1 Baths 10644878 MLS
.25 acre Corner Lot 3-4 bedroom home featuring a convenient horseshoe driveway plus a paved driveway leading to the detached garage. Flexible bonus room works perfectly as an office, playroom, or guest space. Recent improvements include newer windows, **2025 roof**, **2024 flooring**, & **2025 HVAC service & cleaning**. The open floor plan connects the kitchen, dining area, and living room, with a dedicated large laundry room just off the kitchen. Enjoy outdoor living on both the welcoming front porch and the private back patio. The oversized **696 sq. ft. detached garage** provides exceptional parking, workshop space, and storage. Move-in ready — schedule your showing today. (Some photos virtually staged.)

1505 Sparrow Road, Central Chesapeake

$360,000
3 Beds 2 Baths 10644772 MLS
Well-maintained ranch in the established Strawberry Acres neighborhood featuring a bright, open floor plan with wood laminate flooring throughout the main living areas. The updated kitchen offers ample cabinetry, granite countertops, stainless steel appliances and ceramic tile flooring. The primary suite includes an updated en-suite bath, while two additional bedrooms share a renovated full hall bath. The rear portion of the garage has been thoughtfully converted into a dedicated laundry room, adding convenience and functionality. Situated on a spacious 0.27-acre lot, the fully fenced backyard features a paver patio with plenty of room for relaxing, gardening, play and entertaining. Conveniently located just minutes from shopping, dining, schools and interstate access. Hot Water Heater - 2021, Roof - 2016, HVAC - 2016.

3204 Hancock Drive, South Chesapeake

$550,000
4 Beds 3 Baths 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, 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.