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313 Gale Avenue, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10654338 MLS
Welcome home to this charming 3-bedroom, 2.5-bath, two-story home in Chesapeake! Fresh paint throughout and new carpet upstairs give the home a clean, refreshed feel, while brand-new appliances make the kitchen move-in ready. The spacious, open floor plan, two-story layout offers comfortable living with plenty of room to spread out. Come see all that 313 Gale Ave has to offer and make it your new home!

313 Gale Avenue, South Chesapeake
1703 Cheslie Arch, South Chesapeake
$629,000
4 Beds ⋅ 2.1 Baths ⋅ 10654343 MLS
Welcome to 1703 Chelsie Arch! This spacious 4-bedroom, 2.5-bath ranch offers approximately 2,500 sq ft in a beautiful Chesapeake neighborhood zoned for highly sought-after Grassfield High School. Freshly painted throughout, including all walls and trim, this home is move-in ready! The ranch floor plan offers convenient one-level living, with three bedrooms on the main level and a spacious FROG serving as the 4th bedroom—great for guests, a home office, or additional living space. Enjoy your own backyard oasis with a large inground pool, great for summer fun and entertaining. An oversized 2-car garage provides plenty of storage, while a ramp and lift offer convenient exterior access. Easy access to major interstates makes commuting throughout Hampton Roads convenient, with multiple military installations, shopping, dining, parks and everyday amenities nearby. Fresh paint, a private pool and Grassfield schools make this home a must-see!

1703 Cheslie Arch, South Chesapeake
744 Helmsdale Way, South Chesapeake
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake
717 Treetop Lane, South Chesapeake
$480,000
4 Beds ⋅ 2.1 Baths ⋅ 10654173 MLS
Welcome to this beautiful one-owner ranch-style home featuring FIVE bedrooms, 2 1/2 baths and a 2-car garage. Situated on a cul de sac and in a neighborhood where homes rarely come on the market, this home is a real find! Enter via the spacious foyer, flanked by formal living and dining rooms, each boasting tray ceilings. Continue in and cozy up by a centrally-featured fireplace in the huge, open family rm, w/ full view of kitchen & large breakfast area. Brand new stainless steel appliances & new flooring are highlights of the kitchen, and brand new carpet runs through the entire downstairs. The en-suite primary lies on one side of the home with three bedrooms and full bath located on the other side. The room over the garage serves as the 5th bedroom. Entire home has been professionally painted & cleaned. Notes: new roof in 2020, extra replacement windows in storage, tons of garage cabinets, shed. Washer, dryer, well/pump work but convey AS IS. Location is so convenient to everything!

717 Treetop Lane, South Chesapeake
1608 Jackson Avenue, Central Chesapeake
$315,000
3 Beds ⋅ 2 Baths ⋅ 10654311 MLS
Come see this 3 Bed, 2 Bath home located in Chesapeake. Recent improvements include fresh paint throughout, new LVP flooring, and new carpet. The property also features a detached 2-car garage offering additional parking and storage space. Some photos have been AI generated to help show case the homes true potential.

1608 Jackson Avenue, Central Chesapeake
1209 Sir Galahad Drive, South Chesapeake
$359,000
3 Beds ⋅ 2 Baths ⋅ 10654313 MLS
Welcome to 1209 Sir Galahad! This beautifully updated one-owner home offers a comfortable, inviting flow with plenty of natural light throughout. Recent improvements include new LVP flooring, fresh paint, updated light fixtures, and a completely renovated primary bathroom. The kitchen features all-new GE appliances, quartz countertops, and new soft-close cabinetry. Tucked away on a quiet street in a mature, established neighborhood with convenient access to the interstate, this home offers the perfect combination of thoughtful updates, comfort, and accessibility.

1209 Sir Galahad Drive, South Chesapeake
2359 Old Greenbrier Road, Central Chesapeake
$219,900
2 Beds ⋅ 2.1 Baths ⋅ 10654277 MLS
PRICE DROP!! Generous Sellers reducing price by $5,000!! Take advantage of this SWEET DEAL!! Sizable, Double-Primary-Bedroom Condo, each with their own En-suite! Brand new hot water heater and garbage disposal. Association is repairing gutters. Owner receives one reserved parking space, and there is an ABUNDANCE of visitor parking available. Amenities include Pool, Clubhouse, Grounds Maintenance and Trash Collection. 2 Pets under 30 lbs. each allowed! *All loan types may be approved! Agent has details!* Kind sellers are providing 1-year Home Owners warranty! Centrally located in Greenbrier area with easy access to Highway, Dining, Shopping, Hospital, Chesapeake City Park and MORE! HURRY! Don’t miss out on this remarkable opportunity. This will be going, Going, GONE in One Hot Minute! Call TODAY for a private tour!

2359 Old Greenbrier Road, Central Chesapeake
515 Sweet Leaf Place, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10654218 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
803 Gresham Way, South Chesapeake
$615,000
5 Beds ⋅ 3.1 Baths ⋅ 10654210 MLS
Space, space and more space! With over 3,600 square feet, this HOME gives you room to spread out, work, gather and entertain. Hardwood floors flow throughout the majority of the home, while the spacious kitchen features granite countertops and stainless steel appliances. Do you work remotely? There’s a private first-floor office, too. Outside, enjoy an in-ground saltwater pool, Trex deck and gazebo for pool days, cookouts and relaxing at home. And there’s more—the detached garage is ideal for a workshop, hobby space, teen retreat or extra storage. Pool, detached garage, first-floor office, cul-de-sac and no HOA—all wrapped into one very spacious home. If space and flexibility are at the top of your list, this one deserves a look!

803 Gresham Way, South Chesapeake
5144 Ballahack Road, South Chesapeake
$415,000
4 Beds ⋅ 2 Baths ⋅ 10654279 MLS
Welcome home to peaceful country living on approximately 0.71 acres! This inviting ranch-style home offers 4 bedrooms and 2 full bathrooms, with fresh paint throughout, new LVP flooring, and new carpet making it move-in ready. The spacious living room features vaulted ceilings, while the kitchen opens to a cozy breakfast nook perfect for morning coffee or casual meals. Out back, enjoy a private yard surrounded by wooded views, an ideal setting for relaxing, entertaining, or simply enjoying a little extra peace and quiet. Tucked away in a country setting yet conveniently located just off Highway 17, this home gives you the best of both worlds: room to breathe with easy access to everything you need.

5144 Ballahack Road, South Chesapeake
1012 Willow Green Court, South Chesapeake
$207,000
2 Beds ⋅ 2 Baths ⋅ 10654027 MLS
Move-in ready and meticulously maintained is this first-level 2BR/2BA condo in Chesapeake's sought-after Riverwalk. Greenbrier area. It is the perfect blend of comfort and convenience. Step inside to beautiful LVP flooring and newer paint in the living and dining areas, plus freshly cleaned carpet in both the bedrooms. Generous sized Primary Ensuite. Your private fenced patio with storage shed is ready for morning coffee or weekend grilling. Two assigned parking spaces right at your front door. Willow Point Association maintains it's well appointed landscaped, pool, and trash pickup. Come home and just relax. Close to schools, hospital, restaurants, shopping and interstates. Great location.

1012 Willow Green Court, South Chesapeake
402 Undershot Court, South Chesapeake
$565,000
5 Beds ⋅ 2.1 Baths ⋅ 10654262 MLS
Charming, Spacious and Functional Living throughout this ultimate retreat in the heart of Grassfield! Nestled in a quiet cul-de-sac in the highly sought-after Sawyers Mill community, this expansive 5-bedroom, 2.5-bath home features vaulted ceilings with a bright open floor plan. New light fixtures, New Ceiling Fans, New Vanity, New Flooring & Carpet, Fresh Paint. The Wide open kitchen is equipped w/ granite countertops, SS appliances, kitchen island and new tile backsplash. Step through the relaxing sunroom onto a sprawling backyard deck serving as an outdoor oasis designed for grand-scale entertaining. First Floor Bedroom or Office with Primary bedroom featuring tray ceilings, big walk-in closet, a large & elegantly designed en-suite bathroom. Located near shopping, dining, and major commuter routes. This home offers interior comfort, plenty of outdoor entertaining space, privacy, modern updates, & community. Large Open Floor Plan and Completely Move-In Ready...This is a must see!

402 Undershot Court, South Chesapeake
1085 Bells Mill Road, South Chesapeake
$420,000
4 Beds ⋅ 2 Baths ⋅ 10653838 MLS
Welcome home to 1085 Bell Mill Rd.! This beautifully refreshed 4-bedroom, 2-bath Chesapeake home is move-in ready and filled with features you'll love. Fresh paint throughout creates a bright, inviting feel, while the updated kitchen and bathrooms add a modern touch. The cozy gas fireplace creates the perfect gathering spot in the living area. Step outside to enjoy the backyard, complete with established blueberry bushes and apple trees - a wonderful bonus for enjoying fresh fruit right at home. With comfortable living spaces, thoughtful updates, and a convenient Chesapeake location, this home offers the perfect blend of charm, functionality, and everyday living. Come see all this home has to offer!

1085 Bells Mill Road, South Chesapeake
1816 Sunsprite Loop, South Chesapeake
$599,900
6 Beds ⋅ 3 Baths ⋅ 10654192 MLS
DON'T NEED 6 BEDROOMS? Think flexibility! NOW $599,000! Use all 6 bedrooms or create the office, guest room, fitness space or playroom you've been looking for. The first floor offers a bedroom, adjacent flex room and modified curb less shower—great for guests or anyone who prefers fewer stairs. Neutral décor, 9' ceilings, hardwood floors, crown molding and a huge FROG. Spacious primary suite with hardwood floors and two walk-in closets, plus second-floor laundry. Outside, enjoy a large fenced backyard with room for a pool, detached shed, private well for lawn irrigation and attached 2-car garage. Meticulously maintained with annual HVAC, tankless water heater and crawl-space service contracts. Seller to provide termite/moisture letter. Convenient to Millville Rd. and Veterans Bridge

1816 Sunsprite Loop, South Chesapeake
1205 Aaron Court, South Chesapeake
$348,900
4 Beds ⋅ 2 Baths ⋅ 10653794 MLS
This renovated ranch is nestled in the neighborhood and boasts new paint and LVP and lighting throughout. Brand new kitchen (with new SS appliances) with eye-catching quartz countertops, overlooks the dining room . Updated bathrooms with new ceramic tile and vanities. All this plus a new roof! Walk in and enjoy the open floor plan of your new home! Both sheds sold "as is".

1205 Aaron Court, South Chesapeake
604 Colonel Byrd Street, South Chesapeake
$540,000
4 Beds ⋅ 3.1 Baths ⋅ 10653623 MLS
Gorgeous planned community with neighborhood clubhouse, swimming pool, fitness center and recreation spaces. At the center of the home, the chef-inspired kitchen features an oversized prep island, stone countertops, stainless steel appliances, premium soft-close cabinetry, and a walk-in pantry. The primary suite is conveniently situated on the main level, complete with a generous walk-in closet and en-suite bath. Upstairs, you will find two sizable secondary bedrooms, a full bath, and an open loft enhanced with custom built-ins. A private fourth bedroom or versatile bonus suite sits above the garage, featuring its own dedicated full bath and integrated shelving—ideal for guests, a home office, or a media room. Outdoor living is a standout feature, highlighted by a screened porch, an open patio, and a wood-burning firepit overlooking peaceful water views within a fully fenced backyard.

604 Colonel Byrd Street, South Chesapeake
102 Diamond Avenue Unit D, South Chesapeake
$246,500
2 Beds ⋅ 1.1 Baths ⋅ 10654041 MLS
A Diamond Condo with NO FEES! Located in the highly sought-after Grassfield school district, this condo has had a complete transformation. Walk into a beautiful cathedral ceiling and unique reading nook under the stairs. New SS Appliances in the kitchen, new luxury vinyl floors, bedroom/office downstairs with laundry,Beautifully renovated full bathroom. Private upstairs bedroom with half bath spacious closet space and attic storage access. Partially fenced backyard. This is in a quiet neighborhood conveniently located near interstates and shopping. Hurry, before this one is gone!

102 Diamond Avenue Unit D, South Chesapeake
601 Lord Byron Court, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10653788 MLS
Welcome home to this stunning 3-bedroom, 2.5-bathroom gem nestled in one of Chesapeake's most serene and desirable neighborhoods. The main level boasts a bright and cozy living room that flows seamlessly into a stylish kitchen, making everyday living and entertaining a breeze. Upstairs, you will find spacious, private bedrooms and well-appointed bathrooms. Outside is a generous backyard that serves as your own private oasis, perfect for hosting weekend gatherings, gardening, or relaxing in the sun. Situated in a peaceful community just minutes from local shopping, dining, schools, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this house your home sweet home! Schedule your private tour today! Listing photos contain virtually staged media.

601 Lord Byron Court, South Chesapeake
622 Ambrose Street, South Chesapeake
$625,000
5 Beds ⋅ 3 Baths ⋅ 10654148 MLS
Proposed new construction by an award-winning builder featured in past Homearama! Custom open design with a desirable 1st-floor bedroom, spacious living areas and upgraded features included. Enjoy a great yard with room to spread out and the feel of country living while still convenient to major shopping, dining, schools and everyday amenities. NO HOA fees! Anticipated delivery late 2026/early 2027. Get involved early for the opportunity to make certain selections, subject to builder schedule and allowances. One inventory home is currently available for more immediate delivery, and smaller plans may also be available. Great opportunity and value for new construction! Room to install a pool. Call listing agent for plans, pricing, specifications, allowances, construction status and available options.

622 Ambrose Street, South Chesapeake
1513 Wingfield Avenue, Central Chesapeake
$324,900
3 Beds ⋅ 2 Baths ⋅ 10653971 MLS
Welcome to 1513 Wingfield Avenue! This spacious ranch-style home in Indian River offers three bedrooms, two full bathrooms, and an additional room off the primary bedroom—great for a home office, sitting room, dressing room, or private retreat. Laminate floors flow throughout the home, while the updated kitchen provides a fresh and inviting space for everyday living. Outside, enjoy a large fenced-in yard with a storage shed, an oversized driveway, and a full garage offering plenty of parking and storage. Conveniently located near the interstate, shopping, dining, and schools, this home brings together space, flexibility, and a convenient location. Schedule your showing today! Avg electric bill for the past 6 months - $9.33 p/mo!

1513 Wingfield Avenue, Central Chesapeake
1453 Whittamore Road, South Chesapeake
$699,900
5 Beds ⋅ 3 Baths ⋅ 10653763 MLS

1453 Whittamore Road, South Chesapeake
704 Woodcott Drive, South Chesapeake
$565,000
3 Beds ⋅ 2.1 Baths ⋅ 10654136 MLS
Welcome home to 704 Woodcott Drive. This beautifully refreshed 4 bedroom 2 1/2 bath home is full natural light and lovingly updates. The bright, inviting interior features new LVP flooring, new carpet, and fresh paint throughout, giving the home a beautiful, fresh feel. The updated kitchen is great for gatherings, with quartz countertops, stainless steel appliances, and a gorgeous double sided fireplace shared with the living room. The loft can be used as a flex room, office or media room. Enjoy the barbecues on the back deck overlooking the huge backyard. Make this the perfect spot to enjoy cozy evenings or entertaining family and friends. Seller to offer buyer 2/1 rate buy down as well as a new driveway with full price offer.

704 Woodcott Drive, South Chesapeake
2426 Livesay Road, South Chesapeake
$290,000
4 Beds ⋅ 2 Baths ⋅ 10654129 MLS
Come see this updated 4 Bed, 2 Bath home in Chesapeake! Recent improvements include fresh paint throughout, new carpet, new LVP flooring, and a refreshed kitchen featuring new cabinets and appliances. Additional updates include a new HVAC system and new ductwork. Outside, enjoy a fully fenced backyard offering plenty of space for outdoor activities and entertaining. Some photos have been AI Generated to help show case the homes true potential.

2426 Livesay Road, South Chesapeake
2309 Tapscott Avenue, Central Chesapeake
$345,000
3 Beds ⋅ 2 Baths ⋅ 10654010 MLS
Completely updated throughout and move-in ready! Features include a gorgeous kitchen with stainless steel appliances & a pantry. Updated bathrooms with granite vanity tops and tiled showers. Plus a newer roof and water heater! The attached garage includes a laundry/mudroom area. Outside, enjoy a beautifully maintained lawn, huge fully fenced backyard with double and single gate access, and a large detached shed for extra storage.

2309 Tapscott Avenue, Central Chesapeake
2924 Taylor Road, West Chesapeake
$384,000
3 Beds ⋅ 2 Baths ⋅ 10654099 MLS
Rare GEM in the Western Branch school district! This meticulously maintained brick ranch was renovated in 2021 and offers 3 bedrooms, 2 baths, and a functional floor plan with spacious living and dining rooms, a sunken family room, good-sized bedrooms, and a primary bedroom with a private bath. Features include newer LVP flooring, modern updated bathrooms, and a stylish kitchen with granite countertops, stainless steel appliances, and newer cabinets. Two wood-burning fireplaces have been maintained and used during winter. Enjoy the screened-in back porch, large backyard, and wooded views. Major improvements include a new roof ('21), new hot-water heater tank and gutters ('26). Two parcels total approximately 0.78 acre: a 0.45-acre homesite and a rear parcel of approximately 0.33 acre. Attached 1-car garage with ample room to expand parking. NO HOA! Move-in ready and close to bases, interstates, shopping, and restaurants. Schedule your showing today!

2924 Taylor Road, West Chesapeake
28 Hinton Avenue, South Chesapeake
$345,900
4 Beds ⋅ 2 Baths ⋅ 10654130 MLS
Experience total move-in readiness in this beautifully updated Chesapeake home! Featuring fresh paint and new flooring throughout, the bright interior flows into a modern kitchen equipped with shaker cabinets and stainless steel appliances. Bathrooms boast stylish tile updates, while peace of mind comes standard with a new roof, HVAC, some new windows and new water heater. There is also a bonus florida room and lovely front porch. Perfectly blending comfort and modern upgrades, this property is an absolute must-see today!

28 Hinton Avenue, South Chesapeake
2409 Leytonstone Drive, West Chesapeake
$310,500
3 Beds ⋅ 2.1 Baths ⋅ 10654118 MLS
Welcome home to this beautifully maintained 3-bedroom condo featuring an open and functional floor plan. The spacious primary suite offers a private sitting area and an ensuite bath with a separate soaking tub and shower. A versatile first-floor media room or office provides the perfect space for working from home, entertaining, or relaxing. The gourmet kitchen boasts ample cabinetry, generous counter space, and a walk-in pantry. Enjoy low-maintenance living with HOA amenities that include a clubhouse, pool, water, and grounds maintenance. Schedule your private showing today!

2409 Leytonstone Drive, West Chesapeake
900 Golden Cypress Court, South Chesapeake
$425,000
5 Beds ⋅ 2 Baths ⋅ 10653879 MLS
Tucked at the end of a quiet cul-de-sac in the heart of Greenbrier, one of Chesapeake’s most desirable areas, with easy interstate access to everything! Situated on a large 11,327 sq ft lot, this home features a fenced backyard, large shed, firepit, front & rear decks, mature cypress tree & Japanese maple. Inside offers an open-concept layout, luxury vinyl tile, built-in entertainment cabinet & spacious primary bedroom (15’3”x19’) with large walk-in closet. Kitchen features double oven, new 36” SS gas cooktop, glass electric cooktop, new SS refrigerator & dishwasher. Updates include new roof, siding, carpet, blinds & 3/4-glass front door. Additional features include 2 hotel-style shower valves, 2 commercial thermostats, hot water recirculating pump & laundry room with deep sink. Heated & cooled 2-car garage includes workbench & extensive cabinetry, plus 4 off-street parking spaces and a beautifully landscaped yard.

900 Golden Cypress Court, South Chesapeake
2904 Scotia Drive, Central Chesapeake
$259,900
3 Beds ⋅ 1 Baths ⋅ 10653987 MLS
Charming freshly appointed home. Newer carpet, new paint, new flooring in kitchen and bath, new light fixtures and ceiling fans. Great attached garage with access through additional living space. Breakfast area in kitchen, vaulted ceiling add to this easy living home. Laundry closet with stackable washer/dryer convey! Bedrooms are spacious with all new closet doors. Large parking pad for additional off street parking. This home is move in ready and waiting for you!

2904 Scotia Drive, Central Chesapeake
415 Prince Phillip Court, South Chesapeake
$409,000
3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS
Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, 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.