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$399,900
4 Beds ⋅ 2.1 Baths ⋅ 10652642 MLS
Opportunity knocks in Chesapeake! This property offers a chance to create something truly special in a desirable location. Bring your vision and your renovation plans to unlock the full potential of this home. The expansive lot is a standout feature, providing an abundance of space and endless possibilities for outdoor living, entertaining, gardening, recreation, or future improvements. Whether you're an investor searching for your next project or a buyer looking to build equity and make a home your own, this property is ready for its next chapter. Conveniently located near shopping, dining, schools, parks, major roadways, and everything Chesapeake has to offer. Properties with this much potential and land don't come around every day. Come see the possibilities for yourself! Schedule your showing today!

2609 Mossgate Court, Chesapeake

$1,100,000
5 Beds ⋅ 4.1 Baths ⋅ 10654932 MLS
Welcome to an exceptional 4,800 sq. ft. all-brick home in Chesapeake's sought-after Grassfield area! Offering 5 bedrooms and 4.5 baths, this spacious home features a private primary wing designed as its own retreat, complete with an incredible oversized walk-in shower that truly has to be seen. Each additional bedroom is a suite with access to its own bath, providing privacy and comfort for family and guests. Enjoy outdoor living on the screened porch overlooking the inground pool with a fountain perfect for relaxing or entertaining. The community offers its own boat ramp and marina area with water access to the Elizabeth River. Conveniently located near shopping, dining, and interstate access, this home combines space, privacy, recreation, and an outstanding Chesapeake location.

1824 Lancing Crest Lane, Chesapeake

$715,000
6 Beds ⋅ 3 Baths ⋅ 10654725 MLS
Your weekends just got an upgrade at 728 Angel Wing Drive! Located in the sought-after Grassfield school district, this meticulously maintained home offers 5 bedrooms, 3 full baths, and a media room that could serve as a 6th bedroom. A first-floor bedroom and full bath are ideal for multigenerational living or guests, while a space for a home office and formal dining room add flexibility. Your private backyard oasis features a heated saltwater pool, spacious patio, and pergola overlooking peaceful woods with no rear neighbors. Perfect for poolside afternoons and football Sundays! The oversized garage includes shelving and a dedicated workspace. Freshly painted inside and out within the past 3 years and cared for by just two owners, this home also features a whole-house water softener, separate drinking water system, and 32 fully paid-off solar panels for potential monthly energy savings. Thoughtful upgrades, exceptional outdoor living, and room for everyone. Your next chapter starts here!

728 Angel Wing Drive, 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, 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, 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, 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, Chesapeake

$675,000
10653549 MLS
Great and rare opportunity in the southern countryside of Chesapeake. 42.4 acres with about 28 acres cleared and ready for your custom home in a quiet country atmosphere. This property is great for that custom home you have been waiting to build. It would also make a nice horse farm or the family compound you have been dreaming of. To the rear is 14 acres of tall timber and borders 1,000 acres of the Nature Conservancy. Cornland Park, a municipal property, is the neighbor to the west with beautiful tall timber also. Sit on your back porch and watch the wildlife. Road front of this property is zoned R-15s which may present opportunity for an additional building lot and also the possibility for "cluster" development as well. 339 feet of total road frontage. Grassfield and Owens school districts. Only minutes from schools, shopping, restaurants, banks, and a Hospital. Convenient to all of Hampton Roads.

42.4 Acres Benefit Road, Chesapeake

$635,000
4 Beds ⋅ 3.1 Baths ⋅ 10653324 MLS
Located in the highly coveted Grassfield High School District, this beautifully maintained 2021-built home offers modern style, thoughtful design, and plenty of natural light. The bright, open floor plan features hardwood floors throughout the entire first floor and a desirable downstairs in-law suite and finished back room. The chef’s kitchen is the heart of the home, showcasing quartz countertops, a gas range, and a deep island providing generous seating and additional prep space. The primary bath continues the elevated finishes with quartz countertops, dual shower heads, and beautiful upgraded tile. A first-floor laundry room adds everyday convenience, while the spacious all-seasons screened-in porch creates the space to relax or entertain year-round. With its inviting layout, quality finishes, and abundance of natural light, this home offers the perfect blend of comfort and style. HUGE Inlaw suite as well for people looking.

2065 Shipyard Road, Chesapeake

$685,000
5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS
Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, Chesapeake

$408,000
4 Beds ⋅ 2 Baths ⋅ 10653157 MLS
Renovated over the past few years, this beautifully kept brick ranch home is ready to welcome its next owners! Inside, the kitchen offers a fresh, modern feel with crisp white shaker cabinets, gleaming granite countertops, and newer stainless-steel appliances that make every day cooking a pleasure. Enjoy the charm of the hardwood floors, and other cozy features throughout this home as you add your own touch of decor! Before entering your backyard, enter into your fully screened and covered sunroom from your back door, enjoying the sounds and peace of your backyard. The adjoining fully enclosed sunroom provides a bright, inviting space for relaxing or entertaining, while the large backyard offers plenty of room for gatherings, play, or quiet evenings outdoors. Recent updates - including a newer installed roof and windows (2022), new front fencing (2025) newly remodeled bathroom showers (2024), and newly encapsulated crawl space by JES (2025), and for added peace of mind and long-term value with transferrable warranties! This charming home is truly move-in ready. Schedule your showing today!

2615 Cedar Road, Chesapeake

$998,895
5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS
Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem. **Bookshelves do not Convey**

1910 Hallmark Way, Chesapeake

$650,000
5 Beds ⋅ 2.1 Baths ⋅ 10652716 MLS
Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, Chesapeake

$619,000
4 Beds ⋅ 2.1 Baths ⋅ 10652797 MLS
Welcome to 311 Lancing Way! This beautiful 4-bedroom, 2.5 bath home in Chesapeake's desirable Grassfield area features a backyard oasis with a large, 33,000-gallon lagoon-style saltwater pool, 8-ft deep end, variable-speed pump, water feature, plumbing for a future waterslide/waterfall, and a buried pool drain line with pump-controlled discharge to the street. The pool is surrounded by a beautiful stamped concrete, complemented by a spacious screened porch with dual variable-speed fans, a poolside bar shed, and a garden shed with front and rear access. Inside, enjoy programmable dual-zone A/C with independently controlled thermostats and an automatic generator transfer switch. Parking for 4 cars, including an oversized 2-car garage, PLUS additional concrete parking for a boat or 2 more vehicles! No HOA fees! Conveniently located near Grassfield schools, shopping, dining, parks, major interstates, and military installations throughout Hampton Roads. Schedule your private showing today!

311 Lancing Way, Chesapeake

$989,900
4 Beds ⋅ 3.1 Baths ⋅ 10652733 MLS
Grace, Beauty, Functionality, Beautiful private location (acreage on a cul de sac) , only 10 lots on clear land bordered by mature trees as a backdrop. The primary opulent primary bath including an extra large closet and another large en suite are on the first floor along with a flex room. Our newest option is a "butlers kitchen" complete with full sink tucked just behind the well equipped main kitchen. Two additional large bedrooms upstairs. Covered rear porch with an amazing view! You couldn't ask for more. This semicustom building package is hard to beat! We have additional lots and plans available. This will be the last acreage neighborhood to be approved within the city. No main road lots here! If you are looking for new construction it a definite 'MUST SEE"! Ponds, wildflower field, private walking trail and more add up to an exceptional "positive vibe" . No upgrades needed, come see! Preferred lender incentives be sure to ask for details. We have 1 acre 3 acre and a 20 acre lot

4020 Tucker Lane, Chesapeake

$1,000,000
6 Beds ⋅ 3 Baths ⋅ 10652479 MLS
Open House 9/26 & 9/27 1-3pm Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on serene acreage with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, Chesapeake

$539,900
4 Beds ⋅ 2.1 Baths ⋅ 10651217 MLS
Welcome to 2809 Cistern Circle! This beautifully maintained home offers spacious living areas, abundant natural light, and a flexible floor plan with space for a home office or study. Smart Home Ready with Samsung SmartThings potential and compatible lighting, locks, cameras, thermostats, sensors, and more. The living room features built-in surround sound, and the garage offers two additional 240V outlets. Enjoy a large fenced backyard, deck, patio, and fire pit area. Community amenities include a pool, clubhouse, playground, picnic areas, and green space. A VA loan at a 3% interest rate may be assumable by a qualified buyer, subject to loan servicer approval and applicable terms. Ask for details about this potential financing opportunity!

2809 Cistern Circle, Chesapeake

$430,000
3 Beds ⋅ 2.1 Baths ⋅ 10652100 MLS
Built in 2022, this beautiful townhome in Bryan’s Cove is truly move-in ready and offers a wonderful combination of space, comfort, and convenience. With three levels of living space, there’s plenty of room for everyone. The first floor includes a flexible bonus room that would make a great home office, workout room, playroom, or guest space, along with an attached two-car garage. The main level features an open floor plan with lots of natural light. The kitchen has granite countertops, stainless steel appliances, a large island, and plenty of space for cooking and gathering. The dining area opens to a private back porch, where you can sit and relax while enjoying the view of one of the community playgrounds directly behind the home. It’s especially nice to be able to keep an eye on the kids while they play. Upstairs, the spacious primary bedroom offers a tray ceiling, walk-in closet, and a double vanity in the primary bath. The additional bedrooms provide plenty of space for family, guests, or whatever fits your needs. Bryan’s Cove has so much to offer, with a clubhouse, fitness center, swimming pool, dog parks, playgrounds, pier, and docks. The location is also incredibly convenient to shopping, restaurants, military bases, and major interstates. If you’re looking for a newer, low-maintenance home with plenty of space, great amenities, and a backyard view that’s hard to beat, this is definitely worth seeing!

961 Gabion Way, Chesapeake

$869,000
4 Beds ⋅ 3.1 Baths ⋅ 10651664 MLS
Enjoy peaceful country living on 3 beautiful acres, just 5 miles from all your city favorites. This immaculate light-filled 4-bedroom, 3.5-bath home offers 9ft ceilings, detailed crown molding, custom built-ins, a main-level primary suite with a full bath, plus a convenient first-floor laundry room and mudroom. The chef's kitchen features leathered granite countertops, custom tile backsplash, SS appliances, and a center island. Upstairs offers 3 additional bedrooms, a large loft, and a second primary suite with a full bath, standalone tub, dual vanity, and 2 large walk-in closets. Outdoors, enjoy a resort-style backyard with a fenced inground saltwater pool surrounded by stamped concrete and a gazebo. The property also features solar panels, 2 barns, raised garden beds, a playset, a fire pit, and an extended driveway with ample space for an RV or boat. A rare blend of privacy, upgrades, and convenience!

2517 Number Ten Lane, Chesapeake

$610,000
4 Beds ⋅ 2.1 Baths ⋅ 10651226 MLS
This well-maintained home features hardwood floors throughout the main living areas. The kitchen includes stainless steel appliances, 42-inch cabinets, quartz countertops, a large deep sink, two pantries, and a spacious island with bar seating. The family-room offers a fireplace, and the dining room features French doors. Upstairs, the primary suite includes a vaulted ceiling and private bath with dual sinks, a custom tiled shower, and a jetted tub. Three additional bedrooms, a full bath with dual vanities, and a laundry room complete the second floor. The sunroom overlooks the fenced backyard and extended patio, providing additional space for outdoor living and entertaining. Exterior recently repainted. Located in the Grassfield school district with convenient access to the expressway, shopping, and dining.

1853 Rockwood Drive, Chesapeake

$695,000
5 Beds ⋅ 2.1 Baths ⋅ 10651057 MLS
Don't miss this Beautiful & Spacious 5 bedroom 2.5 bath home in the Grassfield High Zone! Outside,Your private backyard oasis awaits you w/ Saltwater pool, patio,& 2 pergolas w/tables perfect for entertaining & making memories! Inside,the Foyer leads to living & dining room areas & a convenient 1/2 bath. Open Sunny kitchen w/ granite counters, a center island, pantry & eat-in nook flows to family room w/gas Fireplace. First-floor flex room off kitchen is ideal for office,gym, playroom or whatever your needs may be! Upstairs offers an expansive primary suite w/ dual-entry walk-in closet & spa-like bath,tiled shower & double vanity.You will also find add’l bedrooms,hall bath, Laundry Room & a Theater room ready for Movie nights that can be 5th bedroom. Paid-off solar panels, dual-zone HVAC, tankless water heater & 2-car garage. Dominion Meadows has 5 parks, 2 lakes w/ fountains & community events. Close to interstates, bases, Dining,Shopping& more!—Come see & make this Home Yours!

2209 Beeblossom Lane, Chesapeake

$820,000
6 Beds ⋅ 4 Baths ⋅ 10650808 MLS
Welcome to this fully renovated 6-bedroom, 4-bathroom home in the highly sought-after Grassfield community of Chesapeake. Completely rehabbed from top to bottom, the home features new appliances, modern fixtures, new flooring, fresh paint, and beautifully updated finishes throughout. Situated on an impressive 1.5-acre corner lot, this property offers one of the largest lots in the neighborhood with plenty of space for outdoor living, entertaining, and future possibilities. The spacious layout provides plenty of room for a large family, guests, or multi-generational living. With its extensive renovation, oversized lot, and desirable Grassfield location, this is a rare opportunity to own a move-in-ready home with space and style to match.

2602 Cecilia Terrace, Chesapeake

$595,000
5 Beds ⋅ 4 Baths ⋅ 10650611 MLS
This meticulously maintained home in the sought-after Grassfield area of Chesapeake is waiting for you! Featuring 5 bedrooms and 4 full bathrooms, this spacious home offers plenty of room for everyday living and entertaining. The upstairs primary suite provides a relaxing retreat with two closets, a double vanity, stand-up shower, and garden tub. Three additional bedrooms and two full bathrooms complete the upstairs living space. The downstairs bedroom with an en-suite bathroom offers flexibility for guests, an in-law suite, or home office. The well-appointed kitchen features granite countertops, a breakfast bar, and updated appliances. The spacious living room is warmed by a gas fireplace, creating a cozy gathering space. A bright sunroom offers peaceful views of the wooded backyard, where mature trees create a private and tranquil setting. Don't miss the opportunity to make this home in the desirable Grassfield area your next home! Come see today!

705 Creekwood Drive, Chesapeake

$799,900
4 Beds ⋅ 2.1 Baths ⋅ 10650499 MLS
The Aspen Barndominium! Customize this 4b/ 2.5b barndo with your style, colors and finishes with the builder. Stunning Covered Front Porch leads to the Open Great Room designed with 18ft vaulted ceiling for the perfect open Living, Dining and Kitchen space. Kitchen with Stainless Steel Appliances, granite counters, tile backsplash, and walk-in pantry. Large Primary with huge walk-in closet and Spa-like Bathroom. Large laundry room, mudroom with lots of storage space and wash area. Bedrooms 2, 3, 4 share a bathroom with rec/bonus space. Best spot may just be the huge covered back porch with lovely nature views and access from the kitchen great room. Pics of previously built Aspen and may show upgrades. Listing price includes Turn-Key Cost to build with a Construction Loan including cost of Land, Well, Septic, and Land Development.

2907 Seven Eleven Road, Chesapeake

$726,960
4 Beds ⋅ 4 Baths ⋅ 10649866 MLS
Under Construction Feb 2027 Delivery - 4 BR each with generous ensuite. Honoring the natural setting with waterfront living surrounded by egrets, wildlife and protected land. The oversized windows will immerse you in light at every turn. Open and Elegant modern home. Entertainers' kitchen - Quartz counters, custom backsplash, Matte-finish GE Cafe appliance package, and custom range hood. Extensive upgraded HW flooring & 10' ceilings midlevel, HUGE 2nd floor Screened Porch with composite decking overlooks estuary rear yard. True entertainers' home! Stunning primary bedroom with gorgeous views, egrets, and serene trees swaying in the breeze. The spa-like primary suite boasts a freestanding tub, zero-entry tiled shower, and 12' Quartz vanity. Exterior black windows and black gutters. Custom Paver driveway and extensive landscaping. Breathe in the fresh air and NO HOA!

1906 Mccoy Rd, Chesapeake

$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10649467 MLS
Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or future entertaining. Recent updates provide added value and peace of mind, including a new hot water heater (2026), new air conditioner condenser (2025), new living room carpet (2026), updated downstairs toilet (2026), and new primary bathroom faucets (2026). Outdoor improvements include a back patio (2020), new back porch (2023), and new front porch/deck stairs (2024), creating welcoming spaces to enjoy both the front and backyard.

1916 Orangewood Road, 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.