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1808 Aft Way, South Chesapeake
$400,000
4 Beds ⋅ 2.1 Baths ⋅ 10635872 MLS
This beautiful tri-level 2-car garage condo in the sought-after Grassfield district offers luxurious and maintenance-free living! The first floor features a huge flex room that leads out to the backyard with a wooded view- great for a 4th bedroom, in-law suite, den, or office. The second floor features an open floor plan with a spacious living room, dining area, and the kitchen with an island, granite countertops, pantry, half bath/powder room, and access to an 8'x18' composite deck overlooking the private, tree-lined side of the community. The third floor features 3 bedrooms, 2 full bathrooms, and a convenient laundry room. The primary bedroom has tray ceilings, a walk-in closet, and its own bathroom with an oversized shower and double sinks. This community offers resort-style amenities such as a large pool, clubhouse, fitness center, dog park & huge dock. Welcome home!

1808 Aft Way, South Chesapeake

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake
$112,500
10617958 MLS
Seller would prefer to sell adjacent lot- (In MLS) together. Great opportunity to build 2 homes one on each lot. Very Private but easily accessible, as property is surrounded by protected land and unbuildable for long term security. Property is adjacent to the biking path on The Great Dismal Swamp. Great Hunting and outdoors enthusiast dream in your backyard, property backs to Dismal Swamp Tract of Cavalier Wildlife Management Area. Each lot is ~2.5 acres. Drive by to view. Wetlands study and Topo Survey in Docs. City confirmed both lots buildable and legally accessible. Also, good opportunity for tree farm lease and harvesting, never logged before. Utilities are starting to go in on new road in front of property. These properties do not come up for sale often. Call for more information and a private showing! Take George Washington HWY to Cornland Rd, Cornland dead ends to Dismal Swamp Trail, turn right and lots are on the right hand side.

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake
$112,500
10617956 MLS
Seller would prefer to sell adjacent lot- (In MLS) together. Great opportunity to build 2 homes one on each lot.Very Private but easily accessible, as property is surrounded by protected land and unbuildable for long term security. Property is adjacent to the biking path on The Great Dismal Swamp. Great Hunting and outdoors enthusiast dream in your backyard, property backs to Dismal Swamp Tract of Cavalier Wildlife Management Area. Each lot is ~2.5 acres. Drive by to view. Wetlands study and Topo Survey in Docs. City confirmed both lots buildable and legally accessible. Also, good opportunity for tree farm lease and harvesting, never logged before. Utilities are starting to go in on new road in front of property. These properties do not come up for sale often. Call for more information and a private showing! Take George Washington HWY to Cornland Rd, Cornland dead ends to Dismal Swamp Trail, turn right and lots are on the right hand side.

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake

905 Shillelagh Road, South Chesapeake
$375,000
4 Beds ⋅ 2 Baths ⋅ 10643554 MLS
Welcome home to this charming four-bedroom ranch featuring a spacious, open floor plan designed for comfortable living. The inviting living room is anchored by a classic brick fireplace and flows seamlessly into the dining area and kitchen, complete with a cozy breakfast nook. An oversized utility room provides additional storage and everyday convenience. The home offers four generously sized bedrooms, including a primary suite with a private ensuite bathroom. Outside, enjoy the deck and patio overlooking the large backyard. The detached garage is accompanied by a substantial bonus room, creating endless possibilities for a workshop, hobby space, home gym, recreation room, studio, or additional storage. With its functional layout and versatile spaces, this home offers wonderful opportunities both inside and out

905 Shillelagh Road, South Chesapeake

2428 Annie Circle, South Chesapeake
$551,000
5 Beds ⋅ 2.1 Baths ⋅ 10642746 MLS
Welcome home to lakefront living in sought-after Bryant Farms! From cozy nights by the custom gas fireplace to lazy mornings soaking in peaceful water views. The open-concept family room and kitchen create the perfect heart-of-the-home feel, while formal living and dining rooms offer beautiful hardwood and tile floors for those special gatherings. Chefs will love the eat-in kitchen, featuring a center island, granite countertops, a full pantry, and stainless steel appliances including a Frigidaire Gallery gas range and fridge. Step outside to the screened porch — your new favorite spot for morning coffee or unwinding after a long day. Upstairs, retreat to a spacious primary suite with a walk-in closet, double vanity, soaking tub, and separate shower. Three additional bedrooms, including a generous FROG, offer flexible space for family, guests, or a home office, and full guest bath.

2428 Annie Circle, South Chesapeake

2053 Burson Drive, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10638071 MLS
Located in the sought-after Grassfield School District, this 2021-built home offers 3 bedrooms and 2.5 baths with a bright, open-concept floor plan filled with natural light from numerous windows throughout. The kitchen features granite countertops, a large center island with sink, and ample space for cooking, gathering, and entertaining. The large first-floor primary suite includes a tiled shower and dual-sink vanity, providing convenience and privacy. Upstairs, you'll find two generously sized bedrooms and a full bath, offering flexibility for family, guests, or a home office. Enjoy the inviting front porch, spacious backyard, and convenient access to shopping, dining, medical facilities, entertainment, and major interstates. Modern construction, abundant natural light, and a functional layout make this home a must-see.

2053 Burson Drive, South Chesapeake

959 Gabion Way, South Chesapeake
$440,500
3 Beds ⋅ 2.1 Baths ⋅ 10632508 MLS
This one truly stands apart! Beautiful end-unit opportunity in Bryan’s Cove—. Built in 2022 and nearly backed to the woods, this home offers privacy, natural light, and a prime location within the community. This home shines with abundant light, new window treatments, gorgeous waterproof, scratch-resistant LVP (installed 9 months ago). The primary suite boasts a custom closet system and a beautifully updated bath with new flooring, double vanity, lighting, and fixtures. All baths include linen closets. Additional highlights, tankless water heater (recently serviced), 2-car garage, private balcony, ample storage in attic and garage closet, and LG washer/dryer (less than 1 year old) to convey. Fully vinyl fenced yard. Extra guest parking just steps away. Enjoy resort-style amenities to include a pool, clubhouse, fitness center, parks, dog park, private beach, pier, and boat dock. Grassfield schools and so much more. 2% CCA assistance available on an acceptable offer.

959 Gabion Way, South Chesapeake

1116 Tundrah Court, South Chesapeake
$750,000
4 Beds ⋅ 3 Baths ⋅ 10643450 MLS
Welcome to this beautiful 4-bedroom, 3-bath home nestled on just over 3 acres in the highly sought-after Grassfield area of Chesapeake. Tucked away in a community with no HOA, this property offers the perfect blend of privacy and convenience. Relax on the spacious front porch. Inside, find soaring ceilings that create an open, airy feel in the living room. The home features a water filtration system, a beautifully renovated primary bath, and a huge flex room over the garage ideal for a media room, home office, gym, or guest space. Out back, enjoy your own private retreat with a patio and swimming pool, perfect for entertaining or unwinding after a long day. With generous indoor and outdoor living spaces, this property offers the lifestyle you've been looking for in one of Chesapeake's most desirable locations.

1116 Tundrah Court, South Chesapeake

500 Landmark Court, South Chesapeake
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10642136 MLS
Nestled on a spacious, landscaped corner lot in sought-after Cedar Crossing, this updated detached condo blends comfort, style, and convenience. Offering approx 2,100 sq ft, this 4-bedroom, 2.5-bath home features a spacious, light-filled floor plan w/ vaulted ceilings, crown molding, a cozy wood-burning fireplace, granite countertops, stainless steel appliances, and abundant natural light. Recent updates include luxury vinyl plank flooring throughout the living room, den, & dining room, fresh interior paint, new carpet, updated bathrooms, new wood blinds, & a new refrigerator. Garage improvements include overhead storage racks & a new garage door motor. Head outside to a private backyard, great for relaxing or entertaining. Enjoy low-maintenance living w/ exceptional community amenities, including a pool, tennis courts, & playgrounds. Conveniently located near shopping, dining, interstates, & military bases, this move-in ready home is one you won't want to miss!

500 Landmark Court, South Chesapeake

910 Adventure Way, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10633355 MLS
Welcome to 910 Adventure Way, nestled in the Bryan’s Cove Community and perched alongside Deep Creek and the Elizabeth River. This inviting home offers the perfect blend of comfort, style, & functionality within a friendly community atmosphere. Fresh interior finishes, & spacious living areas create a warm & welcoming atmosphere throughout. The main level features formal living & dining rooms, plus a stunning kitchen with granite countertops, Gas Range and stainless-steel GE appliances. Enjoy relaxing on the screened-in porch overlooking an outdoor living area for gathering and entertaining. Downstairs also features the spacious Primary Suite flowing into the stylish Ensuite with double sinks and generous walk-in closet. Upstairs boasts two bedrooms with a spacious Finished Room over the Garage with walk-in closet. Solar Panels to be paid off at closing, new paint throughout living area and New Carpet installed June 2026 Reach out to the Listing Agent for a Private Showing.

910 Adventure Way, South Chesapeake

1704 Lancing Crest Circle, South Chesapeake
$595,000
5 Beds ⋅ 2.1 Baths ⋅ 10627977 MLS
Welcome home! Experience comfortable living in this beautiful 5 bedroom, 2.5 bathroom home, located in the highly sought- after Grassfield school district. The home's open floor plan and modern kitchen with stainless steel appliances, island and new flooring create a welcoming atmosphere perfect for entertaining. This property boasts energy-efficient solar panels installed in 2021, greatly reducing your energy costs and carbon footprint. The primary ensuite features 2 separate sinks, soaking tub, shower, private toilet and huge walk-in closet. Enjoy the large fenced in backyard ideal for outdoor activities and relaxation. Situated on a cul-de-sac in a family- friendly neighborhood a short distance from schools, shopping, dining and highways, this home offers the perfect balance of community and convenience.

1704 Lancing Crest Circle, South Chesapeake

1719 Ark Royal Rd, South Chesapeake
$434,900
4 Beds ⋅ 3.1 Baths ⋅ 10636081 MLS
Welcome to this beautifully maintained 4BR/3.5BA townhome in the sought-after Grassfield area of Chesapeake. Thoughtfully designed with space and flexibility in mind, this home offers an open-concept layout filled with natural light and stylish finishes throughout. The spacious kitchen features ample cabinetry, generous counter space, and a large island overlooking the main living area, creating an inviting space for everyday living or gathering with friends. The primary suite offers a relaxing retreat with a private bath and walk-in closet, while additional bedrooms provide room for guests, hobbies, or a home office. Enjoy low-maintenance living with HOA amenities including a pool, dock, and dog parks, creating opportunities to relax, connect, and enjoy the outdoors. Conveniently located near shopping, dining, and interstates. Welcome HOME!

1719 Ark Royal Rd, South Chesapeake

409 Torre Pine Court, South Chesapeake
$935,000
6 Beds ⋅ 3.1 Baths ⋅ 10642291 MLS
Welcome to luxury living in Chesapeake's coveted Cahoon Plantation community! This custom brick home was built in 2012. The stunning 6-bedroom home showcases a spacious open-concept design that works for both everyday living & entertaining. The beautifully appointed kitchen flows seamlessly into the main living and dining areas, creating a bright, inviting space filled with natural light & modern elegance. The kitchen offers maple cabinets, range hood, backsplash granite countertops & brand-new matte black Kitchen Aid appliances. The first-floor primary bedroom has an ensuite bathroom w/ shower, soaking tub, dual vanities and large walk-in closet. Upstairs the generously sized bedrooms provide flexibility for family, guests, or a home office. Step outside to your backyard retreat featuring a large, heated saltwater in-ground pool, play area, gas fire pit all while overlooking the woods. This home has been meticulously maintained and is ready for its new owners. Just minutes from interstates, restaurants & shopping.

409 Torre Pine Court, South Chesapeake

1905 Lancing Crest Lane, South Chesapeake
$1,207,500
5 Beds ⋅ 4 Baths ⋅ 10641173 MLS
A beautiful brick waterfront home located in Mariners Pointe! This 4 bedroom plus flex home has been completely upgraded. Some of the highlights include -a complete kitchen renovation including new cabinets, quartz countertops, GE Cafe stainless steel appliances and a full downstairs bathroom renovation. Other upgrades include a new roof ('25), windows ('23), water heater ('24), a dock upgrade ('24), 1st floor HVAC ('24), 2nd Fl. HVAC ('25), Gutters and French drains ('25). This home is made for outdoor entertaining -featuring a screened-in porch with outdoor heaters, in-ground pool -pump and filter('22), pool liner ('25), large backyard, children's playset, and dock. Solar panels ('24) ($40,000. -power averages $9/mo). This house has it all! Please call for a tour!

1905 Lancing Crest Lane, South Chesapeake

1013 Stern Way, South Chesapeake
$396,000
3 Beds ⋅ 2.1 Baths ⋅ 10635810 MLS
The Mendelssohn lower-level features 2-car garage & massive rec room w/ access to private back yard that backs up to woods! Nest thermostat & wi-fi enabled garage opener! The main living level kitchen includes granite island, dining area, pantry & access to 8'x18' composite deck. The kitchen opens onto a bright/airy living room w/ a conveniently placed powder room. Upstairs are 2 guest bedrooms w/ ample closet space, a hall bath & convenient 2nd floor laundry room along with the generous owner’s bedroom which features a tray ceiling & walk in closet. A separate owner’s bath features a double-bowl vanity & oversized shower. No flood insurance required. A private marina club, docks, boat tie-off. POOL, CLUBHOUSE, FITNESS CENTER, PLAYGROUND & DOG PARK.

1013 Stern Way, South Chesapeake

1904 Ballahack Road, South Chesapeake
$1,000,000
5 Beds ⋅ 3 Baths ⋅ 10635362 MLS
Custom-built brick home nestled on 23+ acres in a rural setting within Grassfield. This 5-bed, 3-full bath residence blends timeless character with spacious design, feat. hardwood flrs, full-length casement windows, and a durable slate-style metal roof. The 1st flr primary suite offers a tray ceiling, generous bath, and space for relaxation, while the home theater is designed for memorable experiences. The eat-in kitchen is thoughtfully appointed with stainless steel appliances, a gas range, and premium Corian countertops. The formal dining and living rooms are accented by custom built-ins, elegant crown molding, and graceful curved entryways. The expansive family room showcases a marble hearth fireplace and overlooks a French-style sunroom, which opens to the backyard gardens. Approx 4 cleared acres are enhanced by a 2-car att. garage w/ bonus rm above, a det. 3-car garage w/ upstairs workshop, plus a fully enclosed RV garage w/ abundant storage. Don’t miss the garden storage room!

1904 Ballahack Road, South Chesapeake

1002 Midway Drive, South Chesapeake
$545,000
4 Beds ⋅ 2.1 Baths ⋅ 10632354 MLS
HEY BUYERS, would an interest rate buy down or closing cost assistance be helpful? Then don't miss out on this bonus. with an acceptable offer, the seller will give a $7500 credit! Welcome to 1002 Midway Drive—a rare nearly half-acre find in the sought-after Grassfield High School district! This 4-bedroom, 2.5-bath home boasts a bright, open floor plan. The spacious kitchen with custom cabinetry, granite counters, breakfast bar, and stainless appliances overlooks the living room—ideal for entertaining. Modern light fixtures and a custom accent wall add style to the dining area.Upstairs, the master suite offers space for an office or sitting area, 2 walk-in closets, and a double vanity the bath. A 2nd-floor laundry room (washer/dryer convey) and 3 spacious bedrooms complete the upper level. Bonus perks: NO water bills thanks to well water, plus a water filtration/softening system (2020) and Leaf Filter gutters (2022). Double garage is fully finished and insulated. The huge fenced yard features a deck with overhead string lights and a chicken coop- chickens can convey, so fresh eggs daily! Country charm minutes from shopping, dining & highways. Plus with an acceptable offer, the seller will give the buyer a $7500 credit to be used as needed. So if an interest rate buy down or loan closing cost assistance is helpful to a buyer, they can take advantage of this additional bonus!

1002 Midway Drive, South Chesapeake

450 Abelia Way, South Chesapeake
$380,000
3 Beds ⋅ 2.1 Baths ⋅ 10626053 MLS
Welcome to the good life!  An exceptional home, meticulously maintained & move-in ready is waiting for you! This inviting home has honey colored hardwood floors, stainless steel appliances, & a large breakfast bar w/granite countertops. The open floorplan is perfect for entertaining & has a private/fenced patio The major upgrades have been made! Brand new carpet, r oversized HVAC system replaced w/new Nest 3 thermostat. New high-end lighting & ceiling fans, newer stainless-steel refrigerator, microwave, and disposal, Replaced vanity in upstairs bath and downstairs bathroom flooring. New storm door, garage opener & more. Ask me for addl. list of upgrades.  A turnkey home that boasts pride of ownership in a fantastic location.

450 Abelia Way, South Chesapeake

705 Pleasant Ridge Court, South Chesapeake
$780,000
4 Beds ⋅ 2.2 Baths ⋅ 10644986 MLS
Welcome Home to this newly remodeled from top to bottom classic Home in Hickory's Pleasant Ridge neighborhood. Nestled back on this 3+ acre lot is this elegant and stylish two-story residence with new siding, windows, trim, fascia - the ultimate facelift. Enter into your foyer with new floors and fresh paint, new hardware, finishes, and lighting flow through this ideal layout. Formal living or dining off the left of foyer and to the right is large great room. Half bath for guests. Kitchen is spacious and feat. breakfast area and access to rear FROG stairs and garage. Second level feat. large primary suite with ensuite bath, two secondary bedrooms, hall bath, and FROG with half bath for convenience. Large newly installed deck leads to massive backyard waiting for you to put your stamp on. Call this Home Today!

705 Pleasant Ridge Court, South Chesapeake

2708 Horseshoe Drive, South Chesapeake
$485,000
4 Beds ⋅ 2 Baths ⋅ 10640735 MLS
Completely renovated all-brick ranch offering timeless charm & modern updates throughout! Recent improvements include a new roof, HVAC system, gutters, carpet, interior & exterior paint, shutters, well pump & sealed crawlspace w/dehumidifier, providing peace of mind for years to come. The updated kitchen features modern cabinetry, countertops & appliances, while both bathrooms have been tastefully renovated with stylish tile, vanities, toilets & fixtures. Bright, inviting living spaces showcase fresh paint, updated flooring & a functional layout designed for comfortable everyday living. The durable brick exterior offers lasting curb appeal & low-maintenance ownership. With major system upgrades & cosmetic improvements already completed, this move-in-ready home is the perfect blend of quality, comfort, & convenience. Simply unpack & enjoy all this beautifully updated property has to offer!

2708 Horseshoe Drive, South Chesapeake

1068 Scenic Boulevard, South Chesapeake
$1,089,000
4 Beds ⋅ 3.1 Baths ⋅ 10639310 MLS
This incredible all-brick, nearly 5,000SF custom-built home is the kind of home dreams are made of. 4 bedrooms PLUS a FROG(finished room over garage), and 3.5 baths in the main house alone! Thoughtfully renovated in recent years with exceptional attention to comfort, craftsmanship, and the way life is actually lived. 4bedrooms each offer their own private retreat w/ ensuite baths. The primary suite bath is a true retreat, with heated tile floors, a soaking tub, and a dual-head shower. Kitchen was made not just for cooking but for gathering: double ovens, gas range, pot filler, under-cabinet lighting, and custom Closet Factory pantry that makes Home Edit dreams come to life. Set on 0.73 acres and no HOA, the outdoors is an extension of the home. Heated saltwater pool, covered patio, lush landscaping, irrigation& room for boats, RVs, and whatever comes next. Detached garage has fully equipped apt wonderful for guests, extended living, creative pursuits, and even rental income. It makes a wonderful private inlaw suite and already has a chair lift installed. There are truly too many features to list. Every detail has been considered! This one is a must see!

1068 Scenic Boulevard, South Chesapeake

1436 Paul Eason Drive, South Chesapeake
$1,740,000
6 Beds ⋅ 5.2 Baths ⋅ 10634528 MLS
Experience luxury country living at its finest in the heart of Chesapeake. Situated on over 4 private acres with its own pond, this stunning all-brick estate offers over 6,000 sqft of refined living space with 6 bedrooms and 7 bathrooms, including 5 bedrooms with private full baths. Every bedroom features oversized closets large enough to rival bedrooms in many homes. The fully remodeled designer kitchen blends modern elegance with timeless charm, while grand Chandeliers create a breathtaking first impression. Step outside to your private resort featuring an inground heated pool, pool house with kitchenette and half bath, outdoor grilling area, and a custom Italian pizza oven perfect for entertaining. Attached double garage plus detached double garage with finished room above. Too many exceptional features to list-this is a property that truly must be seen in person to be fully appreciated.

1436 Paul Eason Drive, South Chesapeake

2907 Seven Eleven Road, South Chesapeake
$170,000
10572124 MLS
Your Canvas Awaits in the Trees. Tucked in sought-after Pleasant Grove this rare three-acre wooded parcel offers the kind of privacy and potential that's becoming increasingly hard to find. Whether you're ready to break ground today or prefer to hold a premium piece of land until the time is right, this property adapts to your plans not the other way around. The site has been approved by the Health Department for a four-bedroom home, giving you the confidence to move forward with your custom build without the uncertainty. Bring your own builder and design a home that's truly yours from the footprint to the finishes. The mature wooded setting creates a natural buffer of seclusion, meaning your future home will feel like a retreat even as Chesapeake's amenities remain conveniently close. Privacy and community, all on one parcel. Pleasant Grove is known for its character and quality of life. Parcels of this size and caliber in this location rarely come to market — and for good reason.

2907 Seven Eleven Road, South Chesapeake

408 Mallet Way, South Chesapeake
$550,000
5 Beds ⋅ 2.1 Baths ⋅ 10638618 MLS
This charming, Two-story, Traditional home in the highly sought-after Sawyer’s Mill community offers spacious & functional living throughout. Nestled on a wooded lot that backs to the lake, the home is situated on a cul-de-sac with scenic water views & a fully, fenced-in backyard. The 1st floor features an open-concept floor plan consisting of a spacious Foyer, Living Room w/custom built-ins, Formal Dining Room, First Floor Bedroom or Home Office, Family Room w/cozy wood burning fireplace that opens to the Kitchen w/eat-in Breakfast area, SS appliances, granite countertops, pantry & access to the backyard. The 2nd floor features the Primary Bedroom w/ensuite Bathroom, dual vanity sinks, jetted tub, large walk-in closet, 3 additional Bedrooms, another Full Bathroom off the main hallway & a utility room w/washer & dryer. Highlights include: vinyl siding-2020, TREX deck-2021, water heater-2025 & MORE! Neighborhood amenities include: a community pool, clubhouse & playground. Welcome Home!

408 Mallet Way, South Chesapeake

621 Wood Nymph Lane, South Chesapeake
$675,000
5 Beds ⋅ 2.1 Baths ⋅ 10633577 MLS
Situated in a well-established community in Chesapeake, this well-maintained home offers comfortable living areas and natural light throughout. The layout includes a blend of open and defined spaces for everyday living and entertaining. In addition to five bedrooms, the home features dedicated office space, an enclosed screened-in all-seasons room, and additional flexible space suitable for a playroom, guest area, second office, creative space, or home gym. The oversized primary suite includes a double walk-through closet, offering ample storage and functionality. Conveniently located near shopping, dining, and major roadways, the property provides a practical balance of comfort, location, and usability. Sellers are open to considering reasonable concessions with a strong offer.

621 Wood Nymph Lane, 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.

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