Refine Search
Sort by
$284,900
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

$290,000
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

$579,000
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

$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 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

$765,000
5 Beds 2.1 Baths 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake

$16,500
10645088 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 9 Tuck Street, South Chesapeake

$16,500
10645087 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 8 Tuck Street, South Chesapeake

$16,500
10645086 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 7 Tuck Street, South Chesapeake

$16,500
10645083 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 6 Tuck Street, South Chesapeake

$16,500
10645082 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 5 Tuck Street, South Chesapeake

$16,500
10645001 MLS
Six lots to be purchased together totaling 1.5ac +/-. Lot closest to Caddie street falls within city standards for not requiring builder to improve the ROW, meaning there is potential for one home site here without any paving, ditching, or other ROW improvements, gravel drive currently in place. Construction will be subject to a wetlands delineation. Most sites in this neighborhood are on "engineered" septic systems. There is currently no well or septic in place. Listing agent can provide info on estimated costs for septic and well installation as well as give referrals to local professionals. Dominion power is less than 150' away. Bring your environmental consultant and capitalize on this hidden gem Chesapeake has to offer! 10 minutes to Edinburgh, 7 minutes to the heart of Great Bridge, one hour to OBX, 38 minutes to VB oceanfront, 34 minutes to NOB, and 23 minutes to downtown Norfolk. Coveted Hickory schools for elementary and middle. Come take a look today!!

Lot 4 Tuck Street, South Chesapeake

$325,000
3 Beds 2 Baths 10644838 MLS
Discover single-level living at its finest in this charming Chesapeake ranch! Perfectly positioned on a generous corner lot, this 3-bedroom, 2-bath home boasts a bright and open atmosphere. The spacious living area flows seamlessly into a fully updated kitchen featuring modern appliances, a moveable island, and a cheerful breakfast nook. Down the hall, the primary suite offers a peaceful everyday escape, highlighting a beautifully updated closet and an inviting en-suite bathroom. The two additional bedrooms provide endless flexibility to suit your lifestyle. The outdoor space is a true highlight, featuring a brand-new deck that overlooks a spacious yard with endless possibilities for gardening or relaxing. With a new water heater already installed and a prime location near local parks, top-rated schools, and vibrant shopping, this home is completely turnkey!

1553 Forest Cove Drive, South Chesapeake

$599,999
4 Beds 2 Baths 10644979 MLS
Welcome to this beautifully remodeled all-brick ranch tucked into the peaceful Hickory area of Chesapeake, where country charm meets modern comfort on approximately 3 sprawling acres. This 4-bedroom, 2-bath gem has been thoughtfully updated from top to bottom, featuring luxury vinyl plank flooring, tiled showers, granite countertops, and stainless steel appliances throughout a bright, open layout made for both everyday living and easy entertaining. Step outside and fall in love with the lifestyle this property offers: relax on the covered front porch, host gatherings on the expansive rear deck, or unwind on your own private deck just off the primary suite. Dreaming of homegrown eggs? The property includes chicken coops, ready for you to raise your own flock and enjoy farm-fresh living right in your backyard. A newly poured driveway and a 50-AMP power pole with RV hookup round out the practical upgrades, making this move-in-ready retreat as functional as it is charming. With updated finishes, room to roam, and space to grow your own little homestead, this Chesapeake beauty is ready to welcome you home.

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

$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

$325,000
3 Beds 1.1 Baths 10644798 MLS
Own A Piece Of "Country Living" In "The City!" Original Farmhouse Type Home Situated On Approx. 2 Acres - Very Unusual Lot! Really Private Setting! Home Needs Renovating...Has Lots Of Potential! Located Off Shell Rd. (Firman St) With Flag Driveway To Back Of Properties. HVAC System 2 Years Old, Roof Approx 16 Years Old, 3 Bedrooms, 1 Bathroom Upstairs, Half Bath Downstairs. Good Sized Kitchen With Real Knotty Pine Cedar Cabinets! Laundry Room Off Kitchen. French Doors Into Living Room And Columns Into Dining Room. Original Hardwood Floors Downstairs. Just A Charming House...Needs Renovation! Huge "Pie Shape" Additional Lot...All On One Deed. Interested In Building Another Dwelling? Look Up The New Senate Bill 531 Which Requires All Localities To Allow Assessory Dwelling Units (ADVs) "By Right" In Single Family Residential Zones...It Might Apply! Buyer Would Do Their Own Due Diligence On This Property.

772 Shell Road, South Chesapeake

$226,900
2 Beds 2 Baths 10644713 MLS
Welcome home to this beautifully maintained condo offering the perfect blend of comfort, style, and low-maintenance living. The spacious first floor features LVP flooring throughout and a well-appointed kitchen with granite countertops, providing both beauty and functionality. Step outside to your private patio—ideal for morning coffee, outdoor dining, or entertaining—with the added convenience of a storage shed. Upstairs, you'll find two generously sized bedrooms and beautifully updated bathrooms featuring elegant quartz and marble countertops. The spacious primary suite offers a large closet and a beautifully renovated bath with walk-in shower, creating a peaceful retreat at the end of the day. Enjoy resort-style amenities, including a community pool and scenic pond, while the condo assoc takes care of water, sewer, and grounds maintenance for truly carefree living. Conveniently located near shopping, dining, military bases, and major interstates. Schedule your private showing today!

400 Bracknell Arch Unit A, South Chesapeake

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

1933 Reefwood Road, South Chesapeake

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

432 Charleston Street, South Chesapeake

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.