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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

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

3712 Sidley Road, West Chesapeake
$420,000
4 Beds ⋅ 2 Baths ⋅ 10646489 MLS
Welcome home to this move-in ready classic ranch! Fresh paint, an open-concept kitchen, and a cozy fireplace create a warm and inviting living space. Step outside to enjoy the fully fenced backyard featuring a patio with a pergola—perfect for relaxing or entertaining family and friends. The spacious primary suite offers plenty of closet and storage space, while two additional bedrooms share a well-appointed hall bath. The converted garage provides incredible flexibility and can be used as a home theater, game room, bonus living area, or a fourth bedroom. You'll also enjoy peace of mind knowing the major updates have already been completed, including the roof, windows, HVAC system, and water heater. Located in the highly sought-after Point Elizabeth neighborhood, this home is just up the street from all Western Branch schools and offers easy access to the scenic Seaboard Coastline Trail, perfect for walking, running, and enjoying the outdoors. Call/text for your private showing!

3712 Sidley Road, West Chesapeake

1920 Ames Circle W, West Chesapeake
$420,000
4 Beds ⋅ 2 Baths ⋅ 10643474 MLS
Look no further than this charming, beautifully remodeled mini-homestead ranch in the middle of the highly sought Dock Landing community in Western Branch. 4 bedroom, all-brick home with hardwood floors throughout. Newly remodeled bathrooms with no expense spared or corners cut. Beautiful designer color palette throughout with upgraded woodwork. An abundance of storage space with 3 closets in the primary suite alone. Step out back through your newly renovated sunroom and into an oasis complete with fencing, a shed, raised garden beds filled with home grown veggies, and your very own chicken coup complete with friendly, egg laying hens. Lush flower beds throughout the front and back. Only minutes away from highways 664 and 64. Close proximity to highly sought schools and the amazing Western Branch shopping corridor. Roof, HVAC, and water heater only a few years young. New dishwasher. Refrigerator and washer/dryer convey (as is)

1920 Ames Circle W, West Chesapeake

3004 Royal Court, West Chesapeake
$420,000
4 Beds ⋅ 2.1 Baths ⋅ 10635476 MLS
FIRST RIGHT OF REFUSAL. Welcome to 3004 Royal Court, a classic brick ranch offering solid bones, timeless curb appeal, and wonderful potential. This home is ideal for buyers looking for a property they can personalize, update, and truly make their own. Featuring a comfortable single-level layout, this home offers practical living space with the charm and durability brick ranch homes are known for. Spaciously designed with 4 bedrooms plus a finished room over the garage, there is plenty of flexibility for a home office, playroom, guest space, hobby room, or additional living area. Heating 2024, Roof 2016. While the home is ready for cosmetic updates, it presents a great opportunity for renovation, investment, or building equity in an established setting. The spacious yard provides room to enjoy outdoor living, gardening, and entertaining.

3004 Royal Court, West 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

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

1001 Gabion Way, South Chesapeake
$419,000
3 Beds ⋅ 2.1 Baths ⋅ 10636926 MLS
Welcome home! Located in the sought-after Bryan’s Cove neighborhood of Chesapeake, this end unit condo is sure to delight! Built in 2022, this three-story townhome boasts an open floor plan with an abundance of natural light throughout. Step inside to discover the large, versatile first-floor flex room along with an attached two-car garage. The open-concept second floor features a very spacious living room that flows into the picture-perfect kitchen complete with granite countertops, stainless steel appliances, a large island, and an eat-in dining area. Sliding glass doors invite you out onto the private balcony, where you can relax and enjoy your morning coffee or afternoon beverage. Upstairs, the third floor offers a spacious primary ensuite featuring a tray ceiling, large walk-in closet, double vanity sinks, and a tiled walk-in shower. Community amenities galore! Enjoy access to the pool, clubhouse, exercise room, two dog parks, pier, docks, playgrounds, and more! Conveniently located near shopping, dining, and interstates! This turnkey, move-in ready condo is waiting for YOU!

1001 Gabion Way, South Chesapeake

1256 Kingsway Drive, South Chesapeake
$417,900
3 Beds ⋅ 2 Baths ⋅ 10632172 MLS
Welcome to 1256 Kingsway Drive, Brick Ranch tucked into one of Greenbrier’s most convenient and sought-after locations. Set on a generous .455-acre lot, this home blends timeless character, creating a property that feels both welcoming and practical. Original hardwood flooring flowing through the main living area, adding warmth and authenticity the moment you enter. The home offers 3 bedrooms and 2 full baths, a large family room, dining room and living room. Improvements including a new roof and gutters (2025) and a new concrete driveway that enhances curb appeal and durability. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the rare combination of a 2-car attached garage plus a detached garage with electric a perfect workshop, studio, or project space. Outdoors, the expansive yard offers room to garden, play, entertain, or simply enjoy the privacy and space that’s increasingly hard to find. Close to Interstate, shopping, restaurants and medical facilities

1256 Kingsway Drive, South Chesapeake

614 Ray Avenue, South Chesapeake
$417,000
4 Beds ⋅ 2.1 Baths ⋅ 10632519 MLS
Welcome to this beautifully 4 bed, 2.5 bath home in the desirable Crestwood community! Renovated in 2025, this home offers peace of mind with a brand new roof and windows, along with stylish updates throughout. Inside you'll find an open and inviting layout featuring a spacious living area with a cozy fireplace. The kitchen is a true standout with newer cabinetry, quartz countertops, updated appliances, a modern backsplash, and a bright breakfast area. Elegant light fixtures and fresh paint throughout the home add a clean, contemporary feel. Upstairs, you’ll find four generously sized bedrooms, including a stunning primary suite with double closets, a beautifully updated bathroom featuring a walk-in tile shower and dual vanity. Outside there's a fenced-in backyard—great for gatherings, pets, or simply unwinding. An attached garage adds convenience and extra storage. This move-in-ready home combines modern upgrades with comfortable living. Don’t miss your opportunity to make it yours!

614 Ray Avenue, 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.