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557 Bright Red Run, South Chesapeake
$424,500
3 Beds ⋅ 2.1 Baths ⋅ 10633316 MLS
Like New Construction! This stunning end-unit townhome-style condo, is only 4 years young. Nestled in the highly sought-after Grassfield area of Chesapeake. This beautifully maintained property offers the perfect blend of comfort and convenience. As you step inside, you’ll be greeted by an abundance of natural light that flows through the open layout. The kitchen features white shaker cabinets, quartz countertops, and a generous island. Upstairs, you’ll find the primary suite includes 2 spacious closets and a private en-suite bathroom. Additional bedrooms offer flexibility for guests, a home office, playroom, etc. Come home to a neighborhood with top-rated schools, parks, walking trails, and easy access to shopping, dining, and major highways. VA assumable loan at 3.125%. Schedule a showing today!

557 Bright Red Run, South Chesapeake

929 Saint Brides Road W, South Chesapeake
$424,000
3 Beds ⋅ 2 Baths ⋅ 10602598 MLS
Escape to the peace of the countryside with this rare opportunity! Nestled on 3 acres, this property offers endless potential for the right buyer. The home, with vision and investment, can be transformed into the perfect retreat, spacious, private, and full of charm. Surrounded by nature and located in a quiet rural setting, you’ll enjoy plenty of room to breathe while still being part of a welcoming neighborhood. Near to 8+ schools, this property is great for those seeking both tranquility and convenience. HUD Case# 541-827201 IN (Insured), Subject to Appraisal. Subject to Appraisal. Property is sold “As-Is,” with seller making no representations or warranties as to condition. Equal Housing Opportunity. Seller may contribute up to 3% toward buyer’s closing costs upon request. Don’t miss the 3D Virtual Tour, allowing you to explore the home on any device, measure rooms, view the 3D dollhouse, and experience both interior and exterior details before stepping inside.

929 Saint Brides Road W, South Chesapeake

1929 Shepherds Gate, South Chesapeake
$423,000
4 Beds ⋅ 2.1 Baths ⋅ 10646343 MLS
Opportunity awaits at 1929 Shepherds Gate, where spacious living, a large corner lot and a convenient Chesapeake location come together! This 4-bedroom, 2.5-bath home offers classic brick curb appeal and an attached garage. Inside, enjoy a bright, open living and dining area with hardwood flooring and crown molding. The kitchen features abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting and plenty of workspace. A separate family room provides additional living space with a cozy fireplace and direct access to the backyard. Upstairs, the generously sized primary bedroom includes a private bath with a walk-in shower. Three additional bedrooms offer flexibility for guests, a home office or playroom. Outside, the fully fenced backyard features a large patio and storage shed, creating an excellent setting for relaxing, entertaining or outdoor activities. Conveniently located near Greenbrier shopping, restaurants, schools, interstate access and Chesapeake attractions. Bring your personal style and make this wonderful home your own!

1929 Shepherds Gate, South Chesapeake

3217 Pryor Court, South Chesapeake
$423,000
4 Beds ⋅ 2 Baths ⋅ 10645625 MLS
Make this your first stop! This well-maintained split-level home in Strawberry Acres offers the perfect blend of space, functionality, and outdoor living—and best of all, NO HOA! Fresh paint throughout and a beautifully updated kitchen featuring all-new cabinets and countertops make this home feel bright and inviting from the moment you walk in. The flexible floor plan includes a versatile front room that can serve as a home office, playroom, guest space, or additional living area. Outside, you'll find an above-ground pool, a large storage shed with electricity, and an oversized fully insulated detached garage that's perfect for a workshop, hobbies, storage, or parking. Situated on a spacious lot in a quiet neighborhood, this home offers plenty of room to relax, entertain, and make it your own. Conveniently located near schools, shopping, dining, and major commuter routes, you'll love the combination of space, updates, and freedom that this property provides!

3217 Pryor Court, South Chesapeake

1013 Port Side Way, South Chesapeake
$422,700
3 Beds ⋅ 2.1 Baths ⋅ 10620981 MLS
Stunning townhouse in the highly desirable Bryan’s Cove. This community offers resort style amenities to elevate everyday living, including a pool, private beach, clubhouse, fitness center, dog park, and playground. This beautifully designed home has been freshly painted with new carpet and offers three spacious bedrooms, including a convenient first-floor bedroom, along with 2.5 baths. The second level features an open concept layout with a bright living room, dining area, and a gorgeous kitchen, all flowing seamlessly to a wide balcony for relaxing or entertaining. The kitchen is a standout with quartz countertops, a large center island, pantry, ample cabinet space, and stainless steel appliances. The primary suite includes a walk-in closet and a private ensuite bath for your own retreat. An attached two-car garage adds both convenience and storage. Ready to enjoy low-maintenance living with exceptional amenities? Schedule your private tour today!

1013 Port Side Way, South Chesapeake

206 Dunn Street, South Chesapeake
$421,000
4 Beds ⋅ 2.1 Baths ⋅ 10626838 MLS
Welcome to this beautifully updated Great Bridge home in one of Chesapeake's most sought-after areas. Designed for comfort and everyday ease, this property offers good-sized bedrooms and a functional layout to fit a variety of lifestyles. The upgraded kitchen features modern finishes and generous prep space which is great for both daily living and entertaining. The renovated bathrooms add a fresh touch and the large tub in the primary bathroom combined with generous counter space makes it appealing to everyone. Enjoy the outdoors in this spacious backyard, offering plenty of room to relax, host, or create your own private retreat. Conveniently located near major communicating routes, shopping, dining, and local amenities, this move-in ready home is an excellent opportunity for buyers seeking both comfort and convenience in Chesapeake.

206 Dunn Street, South Chesapeake

1903 Dawnee Brook Trail S, South Chesapeake
$420,000
4 Beds ⋅ 3 Baths ⋅ 10635369 MLS
Deceptively spacious, this home reveals an interior that offers far more room than the exterior suggests. The front living room is enhanced by cathedral ceilings & a wood-burning fp, creating a striking yet comfortable first impression. The generously sized kitchen offers quartz countertops & abundant cabinet space, providing both function & flexibility for daily living. Separate living & family rooms allow for a variety of uses & lifestyles. Two bedrooms are located on the main level, including a primary suite, w/2 additional bedrooms upstairs. Recent improvements 2026: 30-year architectural roof, LVP flooring, carpet, water heater, vanities, light fixtures, ceiling fans, stove & dishwasher, 2024: HVAC. Positioned in a cul-de-sac with lake views and convenient access to the interstate, this home delivers space, updates & location in one thoughtfully designed package.

1903 Dawnee Brook Trail S, South Chesapeake

541 Bright Red Run, South Chesapeake
$420,000
3 Beds ⋅ 2.1 Baths ⋅ 10631346 MLS
This end unit townhome has been meticulously cared for by the original owners since purchasing it new in 2021. From the welcoming foyer, LVP flooring throughout the 1st floor leads to a stunning great room, which flows nicely into the dinette and gourmet kitchen that provides abundant counter space and large pantry for all your kitchen storage needs. Upstairs, 3 spacious bedrooms and 2 full bathrooms provide privacy and comfort. Your luxurious owner’s suite includes tray ceilings, a generous sized walk-in closet, a double vanity sink and large stand up shower with built-in seating. When you live in Cardinal Meadows, you’ll love the easy access to Route 17, Cedar Road, I-64 and I-464, not to mention being located right off Cahoon Parkway puts you just minutes away from all your shopping needs at Cahoon Commons.

541 Bright Red Run, South Chesapeake

1427 Hawick Terrace, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10625700 MLS
Welcome home to Eagle Pointe, Chesapeake's premier 55+ active adult community! This rare, move-in-ready home offers luxury, low-maintenance, one-level living with fresh paint and new carpet. The open-concept layout features a spacious kitchen that flows seamlessly into the dining room and opens to a private outdoor patio, ideal for everyday living and entertaining. The cathedral-ceiling family room with gas fireplace connects to a bright sunroom, perfect for relaxing year-round. The first-floor primary suite includes a custom walk-in closet and an ensuite bath with ceramic tile shower and split vanities. Two additional bedrooms and a full bath provide flexible space for guests, hobbies, or a home office. Enjoy resort-style amenities at The Bay Club, including indoor and outdoor pools, fitness center, social spaces, and a vibrant calendar of activities. Schedule your private tour today!

1427 Hawick Terrace, South Chesapeake

1436 Scoonie Pointe Drive, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10620257 MLS
Located in Eagle Pointe, Chesapeake’s premier gated 55+ community, this private neighborhood sits alongside the Cahoon Plantation Golf Course. Welcome home to this 3-bedroom, 2-bath end-unit offering a truly low-maintenance lifestyle. Thoughtfully designed, this home features a spacious eat-in kitchen, hardwood and laminate flooring throughout, and cathedral ceilings that flood the space with natural light. Unwind in the beautifully tiled sunroom, complete with a cozy double-sided fireplace—for relaxing year-round. Every detail reflects comfort, care, and ease of living. Residents enjoy exceptional amenities including a stunning clubhouse, fitness center, heated indoor pool, outdoor pool, and hot tub.Resort-style living at its finest—just move in an enjoy!

1436 Scoonie Pointe Drive, South Chesapeake

1733 Fortune Terrace, South Chesapeake
$420,000
3 Beds ⋅ 2.1 Baths ⋅ 10619367 MLS
LIKE-NEW 3-story townhouse in DESIRABLE BRYAN’S COVE neighborhood w/ TOP RATED SCHOOLS. Built in 2022 & still feels brand NEW! 3BR, 2.5 BATH, plus EXTRA 1st FLOOR ROOM (home office, gym, lounge, or a MAN CAVE), spacious 2-car garage. 2nd floor: open, modern kitchen with tall soft-close cabinets, granite countertops, large island, spacious pantry, & access to a wide balcony. Upstairs, you’ll FALL IN LOVE with the MASTER BEDROOM SUITE, thoughtfully designed with large windows, a spacious walk-in closet, and your own private bath with DOUBLE VANITY, OVERSIZED SHOWER, & linen closet. 2 additional BR on the same level & full bath, with convenient laundry - exactly where you want it! Enjoy RESORT-STYLE AMENITIES including a pool, private beach, dock, fitness room, dog park, and ground maintenance. Quiet setting just minutes from shopping, dining, and major routes. Some photos were virtually staged or digitally enhanced for marketing purposes to help visualize property's potential.

1733 Fortune Terrace, South Chesapeake

925 Oklahoma Drive, South Chesapeake
$420,000
4 Beds ⋅ 2.1 Baths ⋅ 10616872 MLS
Welcome home to this beautifully updated 4-bedroom, 2.5 bath home built in 2004. Located in Deep Creek School district. This move in ready home shines with new luxury vinyl wood flooring downstairs, complemented by all new lighting and ceiling fans throughout. The updated kitchen features granite countertops, brand-new stainless-steel appliances and newly stained cabinets. Bathrooms have been thoughtfully updated with new mirrors, fans, faucets and toilets. Entire home has new blinds and curtains throughout. Additional highlights include a new ADT alarm system that comes with the home. Step outside to enjoy a spacious backyard, complete with a brand-new awning covering the patio, a new firepit, new shed and a new backyard gate, great for gatherings, relaxation and outdoor fun.

925 Oklahoma Drive, South Chesapeake

3501 Old Mill Road, South Chesapeake
$420,000
4 Beds ⋅ 3 Baths ⋅ 10614012 MLS
This fully renovated home in Deep Creek sits on an oversized, private lot and blends modern upgrades with comfortable living. The heart of the home is the gorgeous, updated kitchen, featuring stylish finishes and plenty of space for cooking, gathering, and entertaining. Every detail has been refreshed to create a clean, move-in-ready feel, while large windows bring in natural light and highlight the home’s spacious layout.With four bedrooms (plus a bonus room) and three full bathrooms, this home offers flexibility for families, guests, or a home office setup. The massive detached garage provides abundant room for vehicles, storage, or hobbies, making it a standout feature of the property. Surrounded by the space and privacy of a giant lot, this Deep Creek home delivers both functionality and comfort in a beautifully renovated package.

3501 Old Mill Road, South Chesapeake

3307 Firebird Court, South Chesapeake
$420,000
4 Beds ⋅ 2 Baths ⋅ 10611062 MLS
Welcome home to this charming 4-bedroom, 2-bath ranch nestled in the desirable Elmwood Landing community. Thoughtfully updated & impeccably maintained, this home offers modern comfort with timeless appeal. Step inside to find fresh paint throughout the entire home, including the garage, & a wood-burning fireplace at the heart of the living space. The kitchen was renovated in 2023 & showcases finished & sealed butcher block countertops, newly added electrical outlets & appliances that are just 1 year old. In 2020, both bathrooms were updated with new subfloor, tile, & contemporary finishes. Additional upgrades include dedicated circuits & recessed lighting added in the garage, a gas water heater replaced in September 2025, & an HVAC system approximately six years young. The home features an encapsulated crawlspace with 2 tons of sand, vapor barrier, sealed vents, & dehumidifier. Move-in ready & packed with upgrades, this Elmwood Landing gem offers comfort, style, and value!

3307 Firebird Court, South Chesapeake

3625 Weiss Lane, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10608979 MLS
Beautifully updated and move-in ready! This stunning 3-bedroom, 2-bath ranch offers an open floor plan that flows seamlessly into a brand-new kitchen featuring soft-close shaker cabinets, quartz countertops, stainless steel appliances, and a custom tile backsplash. Primary bedroom with ensuite bathroom. Modern updates throughout, including fresh interior paint, plush new carpet, and luxury vinyl plank flooring. Spacious bedrooms and refreshed bathrooms with stylish new fixtures provide comfort and contemporary charm. Detached two-car garage/workshop with power and a generous half-acre backyard offer plenty of space to relax or entertain. The inviting front porch or enclosed sunroom is perfect for your morning coffee. Major updates include a new roof, HVAC system, water heater, and windows. Conveniently located near interstates 64, 664, and 464—close to shopping, military bases, and about 30 minutes to the Virginia Beach Oceanfront. Schedule your showing TODAY before it's gone!

3625 Weiss Lane, South Chesapeake

110 Esplanade Place, South Chesapeake
$420,000
3 Beds ⋅ 2.1 Baths ⋅ 10608261 MLS
METICULOUSLY, STUNNINGLY, Renovated and maintained TURN KEY TOWNHOME. Featuring granite countertops, fabulous oversized renovated PRIMARY BATH with MARBLE tile. Experience the BEST floor plan in this beautiful END-UNIT townhome, just steps from the water. Featuring two oversized bathrooms that have been RENOVATED to the 9’s! ENJOY the screened in porch and back PAVER patio overlooking the water. The SERENE water views are priceless and ready for the Adventure seeker. New Recessed lighting makes it SHINE day or night. Located in a desirable community with amenities including a POOL, clubhouse. Enjoy shopping, restaurants and adventures all within a short distance of the community. Don’t miss this opportunity to own a slice of PARADISE!

110 Esplanade Place, South Chesapeake

1337 King Arthur Drive, South Chesapeake
$420,000
5 Beds ⋅ 3 Baths ⋅ 10606736 MLS
Built just 3 years ago, this stunning 5-bedroom, 3-bath home feels brand new and sits in one of Chesapeake’s most convenient locations. You’ll love the open layout, quality finishes, and thoughtful details throughout. The kitchen features granite countertops, stainless steel appliances (dishwasher, glass-top range, and microwave), and plenty of prep space — great for cooking and entertaining.Each room offers great natural light and generous space, including a spacious primary suite with a double-vanity bathroom and massive walk-in closet. The first-floor bedroom could easily serve as a second primary suite, complete with its own walk-in closet and full bath nearby.Ceiling fans in every bedroom and the family room add comfort year-round. This home blends style, comfort, and functionality — move-in ready and waiting for its next chapter. Schedule your showing today !!!

1337 King Arthur Drive, South Chesapeake

2325 Delwood Road, South Chesapeake
$419,900
3 Beds ⋅ 2.1 Baths ⋅ 10631308 MLS
Fully renovated brick ranch on a quiet, tree-lined street—this is the one you have been waiting for! Every major upgrade has been completed, offering true move-in ready living. The show-stopping kitchen features abundant soft-close cabinetry, a large island, farmhouse sink, and designer finishes that make this space the heart of the home. The spacious primary suite includes a private full bath and overlooks your backyard retreat with an in-ground pool featuring a brand new liner—perfect for summer entertaining. Two additional generously sized bedrooms, including one with its own half bath, offer ideal flexibility for guests or multi-generational living. Enjoy all new flooring, fresh paint, updated fixtures, and beautifully renovated bathrooms with custom tile. Big-ticket updates include upgraded plumbing and electrical, newer roof and windows, and a 2-year-old HVAC. Detached garage with workshop. Convenient to interstates, bases, and Greenbrier.shopping and dining!

2325 Delwood Road, South Chesapeake

2736 Benefit Road, South Chesapeake
$419,900
4 Beds ⋅ 2 Baths ⋅ 10629260 MLS
Built in 1933 and maintained by only 2 owners, this 4-bedroom, 2-bath home offers timeless character and flexible living space on nearly 2 acres of fully usable land. The 1st floor features 3 bedrooms 2 full baths, including a spacious primary suite with a walk-in closet. A traditional layout includes a living room, dining room, and a spacious kitchen with separate pantry, plus an enclosed porch/utility room for added convenience. Recent updates include fresh interior paint, refinished hardwood floors, and durable waterproof laminate flooring. Upstairs offers a bedroom, flexible living space, and a bonus nook good for an office or reading area, along with a large walk-in attic for storage or future expansion. Enjoy the fully cleared 1.9-acre lot with mature landscaping, room for outdoor activities, and a rear patio for relaxing or entertaining. Conveniently located near interstates, shopping, and amenities while offering a private, country-style setting.

2736 Benefit Road, 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.