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905 Calhoun Way, South Chesapeake
$645,840
3 Beds ⋅ 3.1 Baths ⋅ 10629473 MLS
TO BE BUILT - Dreamy Augusta Cottage by coveted local builder w/unmatched architectural detail, from custom arches to soaring 10’ ceilings & stunning hardwood floors. Open-concept 1st floor blends Dining & Great Rm, w/French doors opening to private courtyard & patio, your outdoor oasis. Chef’s kitchen shines w/oversized island, Quartz counters & custom range hood. Generous 1st-floor BR w/en-suite bath offers flexible living. Versatile mudroom w/pantry, powder room & access to 2-car garage make everyday living effortless. Upstairs, sun-filled BR3 features walk-in closet, while BR4 (or loft) adapts to your needs. Also included are a shared dual bath & oversized laundry room. Private Primary retreat boasts spa bath w/ dual sinks, garden tub, large tiled shower & super-sized walk-in closet w/ dual storage areas. Professionally managed grounds offer low-maintenance living. Luxury, comfort & lifestyle in one exceptional home.

905 Calhoun Way, South Chesapeake

2206 Edwin Drive, South Chesapeake
$573,390
3 Beds ⋅ 3 Baths ⋅ 10627394 MLS
Welcome to The Charleston at Retreat at Edinburgh—a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more—all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections.

2206 Edwin Drive, South Chesapeake

1300 Oregon Crossing, South Chesapeake
$555,000
4 Beds ⋅ 2 Baths ⋅ 10654828 MLS
Remarkable brick ranch situated on a corner lot overlooking the community pond! Meticulously maintained and beautifully updated, this home offers exceptional style and comfort throughout. Recent improvements include gorgeous flooring, fresh paint, and updated fixtures that create a warm, inviting atmosphere. The spacious room over the garage serves as a fourth bedroom and offers additional space perfect for a home office, hobby room, or flex area. The well-appointed kitchen features gas appliances, while the cozy gas fireplace adds charm to the living space. Step outside to your private backyard retreat featuring a sparkling in-ground pool, captivating landscaping, and multiple deck areas designed for relaxing and entertaining. Every detail has been thoughtfully maintained, making this home truly move-in ready. A rare opportunity, don't sit on this one

1300 Oregon Crossing, South Chesapeake

515 Sweet Leaf Place, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10654218 MLS
Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, South Chesapeake

604 Colonel Byrd Street, South Chesapeake
$550,000
4 Beds ⋅ 3.1 Baths ⋅ 10653623 MLS
Gorgeous planned community with neighborhood clubhouse, swimming pool, fitness center and recreation spaces. At the center of the home, the chef-inspired kitchen features an oversized prep island, stone countertops, stainless steel appliances, premium soft-close cabinetry, and a walk-in pantry. The primary suite is conveniently situated on the main level, complete with a generous walk-in closet and en-suite bath. Upstairs, you will find two sizable secondary bedrooms, a full bath, and an open loft enhanced with custom built-ins. A private fourth bedroom or versatile bonus suite sits above the garage, featuring its own dedicated full bath and integrated shelving—ideal for guests, a home office, or a media room. Outdoor living is a standout feature, highlighted by a screened porch, an open patio, and a wood-burning firepit overlooking peaceful water views within a fully fenced backyard.

604 Colonel Byrd Street, South Chesapeake

1100 Dane Street, South Chesapeake
$430,000
3 Beds ⋅ 2 Baths ⋅ 10653150 MLS
If you’re looking for a home that feels like a luxurious vacation retreat all year long, this is the one. Beautifully renovated inside and out, this home blends timeless traditional elegance with comfort and resort-style living. Inside, you’ll find two spacious living rooms, each with its own fireplace, creating warm and inviting spaces for relaxing or entertaining. The over sized primary bedroom is a private retreat, complete with a beautifully renovated, spa-inspired bathroom designed to make everyday life feel luxurious. Step outside into your own private backyard oasis, featuring a beautiful in-ground pool, covered pergolas, landscaped surroundings, and inviting outdoor living spaces where you can relax, entertain, and feel like you’re on vacation without leaving home. The property also features a two-car carport and a huge detached two-story workshop/flex storage building, offering exceptional additional space for storage, hobbies, projects, or more. This is more than a home, it's a lifestyle designed to enjoy every day. Extensive improvements completed in 2024 - 2025. A detailed Features & Upgrades, Conveyance/Exclusion, and Seller Information package available upon request. This home is a must-see in person contact your agent to schedule a private showing.

1100 Dane Street, South Chesapeake

1120 Kathleen Lane, South Chesapeake
$1,500,000
5 Beds ⋅ 3.1 Baths ⋅ 10650552 MLS
A builder's own estate — private, impeccable, and set on approximately eight wooded acres at the end of a quiet Chesapeake cul-de-sac. Custom-built by the builder for his own family, this brick-and-stone home reflects a level of care you rarely find. Nothing here has been left untouched; it lives like new construction. A long gravel drive winds past mature trees to the home, where a sweeping front porch offers multiple entries and room to linger. Deer, turkey, and other wildlife are frequent visitors. Inside, a grand open floor plan rises to cathedral ceilings, finished with updated tile flooring, crown molding, and Hunter ceiling fans. The living area anchors around a dramatic stone fireplace and flows into an eat-in kitchen with rustic cabinetry, updated KitchenAid appliances, an electric cooktop, and a large center island with bar seating. The first floor holds a spacious primary suite, generously sized baths, and a well-placed Jack-and-Jill. Upstairs, brand-new carpet runs through bedrooms of exceptional size, and the primary closet is fitted with extensive custom built-ins. The two-story garage apartment is a standout, two bedrooms, 1.5 baths, multiple living areas, and a full eat-in kitchen, great for guests, multigenerational living, or income potential. The garages themselves have been freshly painted white, bright and spotless. Recent improvements include fresh paint throughout, LED lighting, updated kitchen and bath fixtures, two new HVAC units, a mini-split serving the room over the garage, smoke detectors, smart locks, and an on-demand propane water heater. Estate infrastructure is equally serious: 600-amp electrical service, a four-inch private well with pump house, a new water-softening system, hard-ducted HVAC, an illuminated crawl space, and a septic system serviced in 2026. A concrete parking pad completes the property. Privacy, craftsmanship, and acreage — a genuinely distinctive Chesapeake estate.

1120 Kathleen Lane, South Chesapeake

1145 Sunlight Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10655999 MLS
Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, South Chesapeake

313 Holyoke Lane, South Chesapeake
$283,999
2 Beds ⋅ 2.1 Baths ⋅ 10653079 MLS
Turnkey Luxury in Oakbrooke Crossing – Fully Updated & Pre-Inspected!Welcome to this beautifully updated 2-bedroom, 2.5-bathroom townhome-style condo in desirable Oakbrooke Crossing! This move-in-ready home features brand-new LVP flooring, fresh neutral paint, and an updated kitchen with laminate countertops, breakfast bar, and stainless steel appliances. Upstairs, you’ll find two spacious primary suites, each with its own private en-suite bathroom great for guests, roommates, or a home office. Enjoy added peace of mind with a brand-new water heater (2024), recently serviced HVAC, and a professional pre-inspection with the report available upon request.Conveniently located in the heart of Chesapeake, just minutes from Greenbrier shopping, dining, business centers, and interstate access. The low-maintenance condo lifestyle includes ground maintenance, trash service, and community upkeep. Ready for you! Schedule your showing today!

313 Holyoke Lane, South Chesapeake

1070 Mesa Loop, South Chesapeake
$501,763
4 Beds ⋅ 3.1 Baths ⋅ 10631709 MLS
Ready Now: Luxury End Unit townhome condo w/rear load 2 car garage. Luxury LVP floor in select living areas, 2nd floor: Kitchen GE Cafe Matt Black appliances including refrigerator, center island w/shiplap, living room linear fireplace w/shiplap, pantry, living area w/Office/flex room, 1st floorbr/flex room, hall bath & mudroom. 3rd floor Primary w/ceramic shower-2 shower heads, dual sinks, 2 closets, 2 br's - jack & jill bath, linen closet, laundry. Quartz tops kitchen & all baths, covered entry, fenced front yard w/gate to multi trail, 2nd floor Deck off dining area. Wood shelving all closets. Pet Friendly. Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board. 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central Greenbrier location.

1070 Mesa Loop, South Chesapeake

415 Prince Phillip Court, South Chesapeake
$409,000
3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS
Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, South Chesapeake

917 Erie Street, South Chesapeake
$534,000
4 Beds ⋅ 3.1 Baths ⋅ 10650841 MLS
THE perfect blend of modern construction and warm lodge-inspired style in this stunning, nearly new home. Striking black windows add a sophisticated touch and beautifully complement the home’s gorgeous exterior. Featuring four bedrooms, including two bedrooms with full en-suite baths located on each floor, this home offers flexibility and privacy for everyone. The second-floor laundry adds everyday convenience, while the large, beautifully appointed kitchen is designed to be the heart of the home. Step outside to enjoy your morning coffee or unwind in the evening on the private deck just off the kitchen, with additional access from the main-level primary bedroom; perfect for indoor-outdoor living and entertaining. With new appliances, HVAC, roof, and more, this home is truly move-in ready, allowing you to settle in with confidence and enjoy it without the worry of major updates. Stand out from the rest with this exceptional, that combines style and peace of mind!

917 Erie Street, South Chesapeake

2009 Barton Lane, South Chesapeake
$575,000
4 Beds ⋅ 2.1 Baths ⋅ 10647703 MLS
Welcome to the Shenandoah at Retreat at Edinburgh -Chesapeake’s premier 55+ low-maintenance community! Enjoy luxury townhome living with a modern open-concept design, gourmet kitchen with quartz countertops and stainless steel appliances, and a sunlit family room perfect for entertaining. The first-floor primary suite offers a spa-inspired bathroom, featuring a walk-in shower, and oversized walk-in closet, while upstairs features three spacious bedrooms, a loft, and ample storage. Community amenities include a resort-style pool, clubhouse, fitness center, dog park, walking paths, and more. Embrace the ultimate active adult lifestyle near fine dining, shopping, and beautiful parks. Photos and renderings are from builder's library, actual finishes and features may vary.

2009 Barton Lane, South Chesapeake

709 Forest Mills Road, South Chesapeake
$1,240,000
4 Beds ⋅ 4 Baths ⋅ 10637217 MLS
MOTIVATED SELLER!!! Welcome to 709 Forest Mills Road, a stunning private estate nestled on approximately three acres in Chesapeake's highly sought-after Hickory community. This exceptional custom-built residence offers over 5,300 square feet of thoughtfully designed living space, blending timeless elegance with everyday comfort. Featuring four spacious bedrooms and four full bathrooms, the home boasts generous living and entertaining areas, soaring ceilings, abundant natural light, and quality craftsmanship throughout. The expansive floor plan provides flexibility for both formal gatherings and relaxed family living. Outside, the beautifully maintained acreage offers a rare combination of privacy and open space, creating the perfect setting for outdoor entertaining, recreation, gardening, or simply enjoying peaceful country living. Mature landscaping and a picturesque setting enhance the property's impressive curb appeal. Located within the award-winning Hickory school district and just minutes from shopping, dining, and major commuter routes, this remarkable property delivers the ideal balance of luxury, convenience, and tranquility. Experience the space, privacy, and lifestyle that make 709 Forest Mills Road a truly exceptional place to call home.

709 Forest Mills Road, South Chesapeake

2200 Edwin Drive, South Chesapeake
$499,990
2 Beds ⋅ 2 Baths ⋅ 10627377 MLS
The Asheville, one of our quad-style homes, features two bedrooms and 2 full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. $10,000 closing cost incentive with use of preferred lender!

2200 Edwin Drive, South Chesapeake

1108 Kathleen Lane, South Chesapeake
$1,200,000
5 Beds ⋅ 4.1 Baths ⋅ 10655222 MLS
This home truly has it all! Meticulously maintained & beautifully updated, this custom home sits on 3 acres offering space, privacy & versatility. Hardwood floors span the 1st & 2nd floors, complemented by plantation shutters. With 5 bedrooms, PLUS a finished room over the garage, there is room for everyone, including 3 bedrooms with ensuites .The 1st floor primary features a clawfoot tub & separate shower. A gorgeous kitchen with updated appliances & pot filler opens to the family room & bright sunroom with wood stove overlooking the saltwater pool. Outside, enjoy a low maintenance deck, attached 2-car garage, detached 2-car garage with unfinished 2nd floor & extra parking for a boat or RV. Brand new roof, updated HVAC ,remodeled bath & numerous additional improvements make this home truly move-in ready. Assumable 2.25% VA loan. This one is a must see!

1108 Kathleen Lane, South Chesapeake

302 Fairfax Terrace, South Chesapeake
$305,000
3 Beds ⋅ 2.1 Baths ⋅ 10654893 MLS
Largest floor plan in the neighborhood! Lovingly maintained and thoughtfully updated, this spacious brick townhome is tucked away on a quiet cul-de-sac in the heart of Chesapeake. Enjoy a private, fully fenced backyard with no homes directly behind you and no HOA. Inside, you’ll find fresh paint, new carpet and flooring, updated bathrooms, new fixtures and hardware, and gleaming hardwood floors. The brand-new kitchen features granite countertops, stainless-steel appliances, a gas range, and full-size refrigerator. A wood-burning fireplace adds warmth and character, while abundant natural light fills the home. Plenty of indoor and outdoor storage provides added convenience. With a low-maintenance brick exterior, spacious floor plan, thoughtful updates, and a private backyard, this home is truly move-in ready. Pride of ownership is evident throughout—come see it today!

302 Fairfax Terrace, South Chesapeake

2424 Youngman Road, South Chesapeake
$275,000
3 Beds ⋅ 1 Baths ⋅ 10653366 MLS
Seeking a starter home under $300K. We delivered. If you’ve been searching for a home that allows you to become a homeowner without stretching yourself too thin, this may be the one you’ve been waiting for. This 3-bedroom, 1-bath home offers the space & comfort you need to get started without sacrificing the things that make a house feel like home. Inside, you’ll find three bedrooms, a spacious full bathroom featuring a huge shower, & comfortable living spaces ready for you to make your own. 3rd bedroom currently being used as an additional living space. Outside is where this home really shines. Enjoy morning coffee or evening wind-down on the front porch with a swing, or head to the spacious backyard featuring a new deck great for entertaining, relaxing, or enjoying your own outdoor space which includes a detached garage! If you’ve been saying, “I just want a good starter home that I can actually afford,” consider this a sign. Come see what affordable homeownership can look like.

2424 Youngman Road, South Chesapeake

1204 Murray Drive, South Chesapeake
$754,000
5 Beds ⋅ 3 Baths ⋅ 10651816 MLS
Stunning one-owner home on 3 treed acres in the sought-after Hickory High School district, with easy access to Virginia Beach! Custom hardwood floors and trim/woodwork throughout, brand new carpet, and new luxury vinyl in the rec room off the garage. Main floor is 100% hardwood. 5 bedrooms plus two bonus rooms over the garage — great for a teenage suite or mother-in-law suite. Spacious great room with fireplace, formal dining room, and breakfast area off the kitchen. Remodeled kitchen features granite countertops, double oven, double sink, and a generous pantry. First floor offers a shelved library/home office. Florida room with screens and Andersen windows throughout, plus skylights including one in the primary suite. Newer Trex composite deck and storage building in back. Encapsulated crawlspace w/ sump pump & dehumidifier (JES). Well on-site, city water, septic. HVAC serviced annually. Lots of space to grow in this sturdy home!

1204 Murray Drive, South Chesapeake

832 Parapet Road, South Chesapeake
$379,999
4 Beds ⋅ 2 Baths ⋅ 10650851 MLS
Nestled in Chesapeake’s established Camelot neighborhood, this beautifully updated vinyl and brick ranch offers 4 bedrooms, 2 full baths, and 1,762 square feet of comfortable single-level living. Luxury vinyl plank flooring flows throughout the main living areas, while the freestanding wood-burning stove creates a warm focal point for gathering. The kitchen features an oversized island, abundant workspace, and opens to a dedicated laundry/mudroom. Spacious bedrooms, updated finishes, and a functional layout make this home truly move-in ready. Step outside to a privacy fenced backyard on an approximately 72’ x 101’ lot with room to entertain, garden, or unwind beneath mature shade trees. Ideally located near Camelot Elementary and Camelot Park with quick access to George Washington Hwy (US-17), Indian River Rd to I-64, and Military Hwy to I-264 for easy commuting throughout Hampton Roads.

832 Parapet Road, South Chesapeake

705 Turnbuckle Court, South Chesapeake
$605,000
4 Beds ⋅ 2.1 Baths ⋅ 10645717 MLS
BACK ON MARKET, NO FAULT OF SELLER ~ WATERFRONT LIVING IN GREAT BRIDGE! Welcome to “The Lake House,” a waterfront retreat tucked away on a quiet cul-de-sac in the sought-after Great Bridge school district. Offering nearly 3,000 square feet, 4 bedrooms and 2.5 baths, this home was made for enjoying life on the water—with peaceful views from many of the rooms throughout the home. Start your morning overlooking the water from the kitchen and breakfast area, gather in the spacious living areas, or enter the screened porch and simply slow down. The backyard stretches to the water’s edge, creating a beautiful setting for entertaining, relaxing, or enjoying an evening outside. Upstairs, the spacious primary suite feels like a true retreat with vaulted ceilings, a fireplace in the bedroom, water views and a soaking tub—the perfect place to unwind at the end of the day. Inside, fresh paint, LVP flooring throughout the first floor, updated lighting, and a refinished staircase add to the move-in-ready home. Major improvements include HVAC (2023), water heater (2022) and a new dehumidifier in crawlspace. Washer and dryer convey. NO HOA.

705 Turnbuckle Court, South Chesapeake

3209 Dodd Drive, South Chesapeake
$530,000
4 Beds ⋅ 3 Baths ⋅ 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, 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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