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744 Helmsdale Way, 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, Chesapeake

717 Treetop Lane, 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, Chesapeake

2359 Old Greenbrier Road, 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, Chesapeake

515 Sweet Leaf Place, 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, Chesapeake

601 Lord Byron Court, 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, Chesapeake

1513 Wingfield Avenue, 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, Chesapeake

2924 Taylor Road, 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, Chesapeake

900 Golden Cypress Court, 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, Chesapeake

415 Prince Phillip Court, 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, Chesapeake

4504 Greendell Road, Chesapeake
$335,000
3 Beds ⋅ 1.1 Baths ⋅ 10654025 MLS
Make this your first stop! This beautifully maintained brick ranch in Western Branch offers the perfect combination of comfort, functionality, and outdoor living. Featuring 3 bedrooms, 1.5 bathrooms, spacious living areas, and a well-appointed kitchen, this home is move-in ready and has been exceptionally cared for by its owners. The open layout creates a great flow for everyday living and entertaining, while the large family room provides plenty of space to gather with family and friends. Major improvements include an encapsulated crawl space, whole-house generator system, and a backyard oasis complete with an above-ground pool. The oversized backyard offers plenty of room to relax, entertain, or enjoy outdoor activities. With pride of ownership evident throughout and desirable features that are hard to find, this is a home you'll want to see in person!

4504 Greendell Road, Chesapeake

1547 Orchard Grove Drive, Chesapeake
$290,000
2 Beds ⋅ 2 Baths ⋅ 10654011 MLS
Welcome home to easy living in Orchard Grove! This spacious 2-bedroom, 2-bath condo offers a flexible layout designed for both everyday comfort and entertaining. Start your morning at the dedicated coffee bar before settling into the light-filled living room, where soaring ceilings and skylights create an open, airy feel. When the weather cools down, the gas fireplace makes the perfect spot to unwind. The updated kitchen features new cabinets, quartz countertops, stainless steel appliances, and plenty of space for preparing meals and gathering. Upstairs, the loft adds even more flexibility—create a home office, workout space, reading nook, hobby room, or explore modifications for an additional sleeping area. With two bedrooms and two full baths, there’s room to spread out while still enjoying the convenience of condo living. Orchard Grove puts shopping, dining, interstate access, military installations, and everyday conveniences nearby, making it easy to spend less time getting where you need to go and more time enjoying home.

1547 Orchard Grove Drive, Chesapeake

1118 Commerce Avenue, Chesapeake
$389,900
4 Beds ⋅ 3 Baths ⋅ 10653792 MLS
Located in the heart of Chesapeake’s South Norfolk community, this well-maintained residence offers 4 bedrooms and 3 full bathrooms, giving you plenty of space whether you need room for guests, hobbies, or simply a place to hide from laundry you meant to fold. The home features a spacious layout with thoughtfully designed rooms throughout. The downstairs bedroom includes newly installed LVP flooring (2026) and a walk-in closet — storage, organization, or pretending you’re in a dramatic movie scene while picking out an outfit. Upstairs, you’ll find carpeted bedrooms, including a primary suite with its own walk-in closet (because one walk-in is never enough). Enjoy easy access to downtown Norfolk, major shipyards, and nearby interstates, making commutes simple and efficient. This inviting property is ready to welcome its next owner.Come see this gem and explore all it has to offer ---your future self might thank you for it!

1118 Commerce Avenue, Chesapeake

100 Alice Street, Chesapeake
$369,000
4 Beds ⋅ 2.1 Baths ⋅ 10653943 MLS
Welcome Home to Deep Creek! This beautifully renovated brick ranch offers 4 bedrooms, 2.5 baths, and an impressive list of brand-new updates. Step inside to discover brand-new gray carpet and luxury vinyl flooring throughout, complemented by fresh finishes that give the home a clean, modern feel. The updated kitchen features brand-new white cabinetry, a center island, granite countertops, and stainless steel appliances, creating a functional space for everyday living and entertaining. Both full bathrooms have been refreshed with brand-new ceramic marble tile in the showers for a polished, spa-inspired touch. And the updates continue beyond the interior! This home features a brand-new roof, HVAC system, and water heater, offering peace of mind for years to come. With two front and two back entry points, the layout also provides added flexibility for how you enter and use the home. Located in the desirable Deep Creek subdivision and just moments from the Gilmerton Bridge, this home offers convenient access to surrounding areas while providing the space and comfort of a brick ranch-style home. Four bedrooms. Two and a half baths. Brand-new major systems and finishes. Move-in ready. Come see all this home has to offer!

100 Alice Street, Chesapeake

4327 Taylor Road, Chesapeake
$479,900
4 Beds ⋅ 2.1 Baths ⋅ 10653864 MLS
This stunning new EDC home offers 4 spacious bedrooms, 2.5 baths, a formal dining room, living and family rooms, and a 2-car garage. The open floor plan features 9-ft ceilings, luxury vinyl plank flooring, and a gourmet kitchen with granite countertops, stainless steel appliances, peninsula island, and custom soft-close cabinetry. The primary suite includes a vaulted ceiling, walk-in closet, and en suite bath with picture window, tub, and stand-up shower. Enjoy upgraded carpet in bedrooms, brushed-nickel fixtures, crown molding, craftsman-style doors, and a wide front porch great for relaxing. Built with quality craftsmanship and attention to detail, every EDC home is loaded with upscale finishes and thoughtful design throughout. Ask about how we can assist with your closing costs! Seller offering up to 2% from builder and 1% from lender in concessions with acceptable offer when using builder’s preferred lender and title company

4327 Taylor Road, Chesapeake

3527 Radford Circle, Chesapeake
$230,000
2 Beds ⋅ 1.1 Baths ⋅ 10653212 MLS
Welcome to this spacious 2-bedroom townhome in sought-after Western Branch with no HOA! The main level features a comfortable living area with a wood-burning fireplace, convenient half bath, and sliding glass doors leading to the back deck. The kitchen offers an eat-in dining area and includes a stainless steel appliances, disposal, and dishwasher. The washer and dryer are conveniently located on the main floor in the utility closet. Upstairs, the primary bedroom features a dual-entry ensuite bathroom with a large vanity and water closet with shower. Enjoy one of the largest fenced backyards in the neighborhood, with plenty of space for outdoor activities and entertaining. Great location with easy access to shopping, dining, major roads, and highly sought-after Western Branch schools.

3527 Radford Circle, 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.