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$734,900
5 Beds 3 Baths 10646525 MLS
There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first floor, PLUS an office/flex room AND loft-style second living area. Crown molding, hardwood stairs, custom window treatments, a gas fireplace, quartz countertops, stainless appliances, gas cooking, under-cabinet lighting, upstairs laundry, walk-in attic, tankless water heater, smart garage opener, security system, and a custom 36-foot patio add comfort and refinement. Trusted lender Steve Hawley, NMLS #1813927, with Southern Trust Mortgage, NMLS #2921, will provide a 1% lender-paid buydown on this listing. Ask the listing agent for details. Subject to borrower qualification and lender approval.

1741 Watershed Court, South Chesapeake

$849,900
5 Beds 4.1 Baths 10646141 MLS
Under Construction – Luxury New Construction with Timeless Coastal Farmhouse Style! This stunning 3-level home blends classic board-and-batten architecture, clean lines, black-framed windows, and thougthful accents to create exceptional appeal. Inside, an open-concept first floor is designed for modern living, featuring a spacious family room, dining area, and a designer kitchen with a large center island, custom cabinetry, and premium finishes. The second level offers four generously sized bedrooms, including an impressive owner's suite with a spa-inspired bath, plus two full bathrooms to comfortably accommodate family and guests. The third floor provides incredible flexibility with a spacious bonus room or fifth bedroom, a full bath, and convenient walk-in attic storage. With 5 bedrooms, 4.5 baths, thoughtful craftsmanship, and stylish finishes throughout, this exceptional new home offers the perfect blend of luxury, comfort, and functionality for today's lifestyle.

1833 Shillelagh Road, South Chesapeake

$610,000
5 Beds 2.1 Baths 10646157 MLS
Tucked away on a quiet cul-de-sac and sitting pretty on a corner lot, this updated 5-bedroom, 2.5-bath home has room for everyone & everything. From the moment you walk in, you'll feel the perfect blend of comfort and function this home was designed for. Cozy up in the den by the fireplace, host holidays in the separate dining room, or get work done in the private office—there's a space for every part of your life. The kitchen shines with recessed lighting and a pantry, while the living room offers even more room to gather. Retreat to the primary suite, your own private escape complete with a second fireplace, a sitting area, and a spacious walk-in closet. The spa-like primary bath doesn't disappoint either, featuring a walk-in shower, soaking tub, dual sinks, and a linen closet for extra storage. Step outside onto your deck—ideal for weekend BBQs,or just soaking up some sunshine in your own private space. 2-car garage & shed means storage is never an issue.

807 Gresham Way, South Chesapeake

$629,000
6 Beds 3 Baths 10645483 MLS
Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, South Chesapeake

$674,000
5 Beds 2.1 Baths 10645285 MLS
Welcome home to a beautiful one owner home in the highly sought after neighborhood of Dominion Meadows, and Grassfield High School District. Built in 2020, this home offers a bright open-concept design, with 5 spacious bedrooms, and 2.5 baths. Versatile living room or home office, formal dining room, gourmet kitchen with large island, custom cabinetry, granite countertops, stainless appliances, and pantry flows into the spacious family room. Upstairs you will find a laundry room, and generously sized bedrooms. Luxurious primary suite with tray ceiling, spa bath, oversized custom closet. Outside unwind in the screen porch, or the large patio enjoying privacy in the fenced backyard while spending time with family or entertaining with friends. Easy commute to all military bases, and a few minutes away from shopping, restaurants, and entertainment.

815 Angel Wing Drive, South Chesapeake

$765,000
5 Beds 2.1 Baths 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake

$815,000
5 Beds 4 Baths 10644739 MLS
This home has it all! Tall ceilings,recessed lighting throughout,custom built ins, ship lap walls, a high end kitchen with a built in area with electrical for a wine or beer fridge, frosted glass barn doors, a mud room, a primary suite like no other with a cool room off it that could be turned into a secret room for fun or games. The open floor plan and large lot invites entertaining or relaxation while spending time with friends or loved ones. The property line goes back into the woods beyond the large fenced in area. There is an extended drive way for plenty of parking, a large professionally built and installed shed that replicates a small home. Plush grass with installed drainage.There is so much more to tell but seeing is believing don't wait to take a tour of this magnificent home located on a small culdesac.

2504 Calabria Dr Drive, South Chesapeake

$599,000
5 Beds 3 Baths 10644309 MLS
Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

785 Caddie Street, South Chesapeake

$649,999
5 Beds 3 Baths 10643675 MLS
Rare find on Cedar Road! This multi-generational 5-bed, 3-bath home features two primary bedrooms one downstairs and a larger one upstairs deal for multigenerational, extended family or flexible living. The Open Living Format seamlessly connects the kitchen, dining, and great room for effortless entertaining. Enjoy LVP flooring, quartz counters, tile backsplash, pendant lighting, and a first-floor bedroom with full bath. Set on 2.5 acres with a wooded backyard, it offers a true mini wilderness escape while still near to everything. The upstairs primary suite includes a garden tub, tile shower, and generous closet space. Modern finishes, private acreage, and a two-car garage make this a standout home that will not last!

2116 Cedar Road, South Chesapeake

$755,000
5 Beds 3.2 Baths 10642808 MLS
A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Motivated sellers! Renovated 5-bedroom home on a full acre in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today.

1833 Benefit Road, South Chesapeake

$589,000
5 Beds 3 Baths 10642362 MLS
Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by a local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

789 Caddie Street, 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

$899,999
6 Beds 3.1 Baths 10641499 MLS
Welcome to your own private retreat in the heart of Grassfield! Nestled on approximately 5 acres, this beautifully maintained 6-bedroom, 3.5-bath home offers more than 4,200 square feet of space designed for both everyday living and unforgettable entertaining. Inside, you'll find generous living areas with room for everyone—whether you're hosting holiday gatherings, working from home, or simply enjoying quiet evenings with family. Go outside to enjoy the peaceful surroundings, then unwind in the hot tub, which conveys with the home, making it easy to relax under the stars after a long day. Now offered at an improved price, this exceptional property also includes a seller-paid carpet allowance with an acceptable offer, giving you the opportunity to add your own personal style before moving in. If you've been dreaming of acreage, privacy, and a home that offers the perfect blend of comfort, flexibility, and room to grow, this Grassfield gem is ready to welcome you home. Schedule your private tour today and experience everything this incredible property has to offer.

2536 Seven Eleven Road, South Chesapeake

$649,900
6 Beds 2.1 Baths 10641222 MLS
Located in Chesapeake's sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and modern updates. The open floor plan is anchored by a spacious kitchen featuring Samsung Bespoke appliances, generous cabinet and counter space, and a pantry, creating a natural gathering place for everyday living and entertaining. The third floor was expanded in 2021 to include two finished rooms, providing flexible space for a home office, media room, playroom, hobbies, guests, or additional bedrooms. Major improvements include a new 1st floor HVAC in 2024 and 2nd/3rd floor HVAC installed in 2021. Outside, you'll find an expanded extra-wide driveway, EV charger, fully fenced backyard, and a spacious deck ready for cookouts, relaxing evenings, or weekend gatherings. Conveniently located near shopping, dining, major highways, and everyday conveniences, this home combines space, function, and updates in one of Chesapeake's most desirable locations. Some photos are virtually staged.

568 Waters Road, South Chesapeake

$674,000
5 Beds 2.1 Baths 10640526 MLS
Upgrade your lifestyle in highly sought-after Grassfield with this move-in ready home offering nearly 3,000 sq ft of relaxed, coastal living space. Impeccably maintained, it features open gathering areas and oversized bedrooms. The chef's kitchen showcases granite countertops, custom cabinetry, and a built-in pet station. A dedicated library with custom bookshelves makes an ideal space for reading, relaxing or a home office. The spacious primary retreat boasts double doors, tray ceilings, a spa-inspired en suite, and a custom walk-in closet. Step outside to a fenced backyard with dual patios, a built-in firepit, and raised garden beds. Relax on the screened-in porch and enjoy the rare privacy of a protected, undeveloped nature preserve. Buyer may choose between a flooring allowance or significant ***Rate Buy Down** with acceptable offer, allowing buyers to personalize select finishes. Seller wishes 3 televisions to convey to buyer.

952 Checkerspot Way, South Chesapeake

$609,900
5 Beds 3 Baths 10639976 MLS
Welcome home to this spacious & beautifully maintained residence located in a highly sought-after neighborhood. Offering a versatile floor plan & generous living spaces, this home is designed to accommodate a variety of lifestyles.The main level features dining room & living room w/built ins, providing the perfect setting for entertaining, hardwood flooring flows throughout downstairs living areas, newer carpet adds comfort throughout the upper level. A rare & desirable feature, this home offers spacious first floor bedroom w/full bath. The upstairs primary retreat boasts an elegant tray ceiling & two closets. All 5 bedrooms include walk-in closets & ceiling fans, providing ample storage & comfort for everyone! The updated kitchen is a chef's dream with SS appliances, gas range,granite countertops,new microwave & refrigerator. It flows seamlessly to a breakfast nook & sunroom! Private backyard oasis, featuring stamped concrete patio & firepit to enjoy peacful evenings!!!

712 Creekwood Drive, South Chesapeake

$669,000
5 Beds 3.1 Baths 10639977 MLS
Beautifully appointed transitional style home offers the perfect balance of comfort, style & privacy. Nestled in cul-de-sac w/ no HOA, the home welcomes you w/ elegant natural stone accents that frame the covered front porch and enhance its timeless curb appeal. Inside, hardwood floors & ceramic tile complement a bright, thoughtfully designed layout. A versatile first-floor room provides an ideal space for a private office, guest suite, or flex room. The open-concept great room flows seamlessly into a well-equipped kitchen featuring granite countertops, stainless steel appliances, and generous workspace. Formal living and dining rooms offer inviting spaces for entertaining or everyday gatherings. Go outside to enjoy a private backyard retreat complete w/ an elevated Trex deck, saltwater pool, hot tub, gazebo & det. garage—creating an ideal setting for relaxing, entertaining & making the most of life at home. VA assumable loan.

803 Gresham Way, South Chesapeake

$699,000
5 Beds 2.1 Baths 10638474 MLS
Welcome home to 2209 Beeblossom Lane located in the sought-after Grassfield High School well-known for its STEM Academy! Built in 2016, this move-in ready 5-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and energy efficiency. Inside, you’ll find wood flooring, a kitchen with sunny eat in nook open to a den w/ cozy gas fireplace ready for the Fall& Winter holidays. Enjoy living , dining & extra office flex space room , ideal for entertaining or everyday living. The expansive primary suite is a true retreat, featuring a dual-entry oversized walk-in closet and a private en suite bath complete with a soaking tub and separate shower. Upstairs, the dedicated theater room with a big-screen setup is ready for unforgettable movie nights, game days, or family gatherings. Step outside to your own backyard oasis! Relax or entertain around the inground saltwater pool, all within a fully fenced backyard designed for privacy and fun. Additional highlights include a Rinnai tankless water heater and paid-off solar panels, providing energy savings and peace of mind. Dominion Meadows offers planned community events throughout the year, scenic sidewalks, & beautiful fountains that make every stroll through the neighborhood enjoyable. Convenient to interstates to bases, shopping , dining & more. Schedule a showing today & start making new memories in your new home!

2209 Beeblossom Lane, South Chesapeake

$550,000
5 Beds 2.1 Baths 10638238 MLS
Welcome to your ultimate retreat in the heart of Grassfield! Situated in a 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. The large open kitchen is equipped with granite countertops, white shaker soft-close cabinets and drawers, stainless steel appliances, kitchen island and tile backsplash. Step through the relaxing sunroom onto a sprawling backyard deck serving as an outdoor oasis designed for grand-scale entertaining, summer barbecues, or peaceful evenings under the stars. The bedrooms are spacious, while the primary bedroom features tray ceilings, big walk-in closet, a large & elegantly designed en-suite bathroom. Conveniently located near shopping, dining, and major commuter routes while still enjoying the privacy of a cul-de-sac setting. This home offers interior comfort, plenty of outdoor entertaining space, privacy, modern updates, & community. This is a must see!

402 Undershot Court, South Chesapeake

$685,000
5 Beds 3.1 Baths 10637618 MLS
Built in 2021, the home welcomes you with a covered front porch, an inviting entryway, and a formal dining room. Just off the large living room, highlighted by a gas fireplace with tile surround the chef’s kitchen features a large center island with sink, granite countertops, built-in double ovens, white shaker cabinets, tiled backsplash, pantry, eat-in area, and Frigidaire appliances. Luxury vinyl plank flooring spans the main living areas, mudroom, first-floor bedroom, and secondary baths. Upstairs, the spacious primary suite showcases tray ceilings, recessed lighting, and a spa-inspired bath with ceramic tile floors, double vanity, freestanding soaking tub, full tile shower, and private water closet. The four large bedrooms share a huge bathroom with double vanity. The finished room over the garage is complete with a large closet and access to the walk-in attic with additional storage. Custom upgrades include board-and-batten gables, craftsman-style trim, 220 fast charging station and well pump in the garage, and oversized windows that flood the home with natural light. Outside, enjoy a covered patio overlooking the expansive backyard and side yard, complete with a basketball court and storage shed. Come tour your next home!

200 Heron Bay Lane, South Chesapeake

$1,089,000
5 Beds 3.1 Baths 10635945 MLS
NEW CONSTRUCTION HOME SITUATED ON 3 ACRE PRIVATE LOT. TRANSITIONAL STYLE HOME OFFERS AN OPEN FLOOR PLAN, 5 BEDROOMS, 3.5 BATHS & LOFT. KITCHEN WITH LARGE ISLAND, SPACE FOR SEATING AND OPENS TO THE GREAT ROOM AND FEATURES GRANITE COUNTERS, TILE BACKSPLASH, PANTRY AND GE CAFE STAINLESS APPLIANCES TO INCLUDE A REFRIGERATOR, GAS COOKTOP. FIRST FLOOR PRIMARY SUITE FEATURES A LARGE WALK IN CLOSET, WOOD SHELVING, FULL BATH, SHOWER, TILE SURROUND, SOAKING TUB, TILE FLOORING, DOUBLE VANITY, QUARTZ COUNTERS, SEPARATE WATER CLOSET. UPSTAIRS JACK & JILL BATH, AND A HALL BATH. LOFT CAN BE UTILIZED FOR TV/OFFICE/PLAYROOM THE CHOICE IS YOURS. COVERED SCREENED PORCH OFFERS A RETREAT-LIKE SETTING FOR HOMEOWNERS TO ENJOY. 3 CAR ATTACHED GARAGE, TANKLESS GAS WATER HEATER, LVP FLOORING ON 1ST FLOOR, CARPETING IN UPSTAIRS BEDROOMS, WOOD SHELVING FOR ALL BEDROOM CLOSETS, GRANITE COUNTERTOPS IN BATHS, ARCHITECTURAL SHINGLE/METAL ROOF.

2624 Ballahack Road, South Chesapeake

$1,550,000
5 Beds 4.1 Baths 10632068 MLS
Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath! HUGE primary suite complete with fireplace, fantastic walk-in closet and beautiful new bath. The detached 3.5 car garage includes a garage apartment with kitchenette and full bath. New windows, roof, gutters, soffits and pool liner. Absolutely amazing opportunity to secure this gorgeous, move-in ready property. Awesome enclosed patio with hot tub as well as an outdoor kitchen/bar area. This is an entertainer's dream! See it today before it is SOLD!

641 Ravenwoods Drive, South Chesapeake

$999,900
5 Beds 3.1 Baths 10628432 MLS
Introducing The Grassfield, a beautifully crafted new construction home designed with both style and everyday livability in mind. This well-planned floor design offers a natural flow, anchored by a chef-inspired kitchen that serves as the heart of the home, great l for gathering, entertaining, and daily living. The private primary suite is thoughtfully positioned to provide a comfortable and quiet retreat. Additional highlights include the option for a three-car garage, offering added flexibility for storage, hobbies, or multiple vehicles. Designed with versatility in mind, buyers can personalize selections to suit their style or take it a step further and collaborate with the builder to create a fully custom home. A standout opportunity to build something truly your own.

MM Carley (The Grassfield) Court, South Chesapeake

$1,250,000
6 Beds 5 Baths 10611669 MLS
Welcome to this stunning 6-bedroom, 5-bath, 4,726 sq ft brick estate set on nearly 6 acres of serene countryside. This two-story residence offers an amazing blend of luxury, comfort, and functionality. Inside, you’ll find expansive living spaces, a well-appointed kitchen, and generously sized bedrooms designed for both privacy and togetherness. The home is ideal for entertaining, featuring an in-ground heated pool for year-round enjoyment. A land-mounted solar system adds modern efficiency, keeping energy costs low while supporting sustainable living. With plenty of room to spread out, both indoors and out, this property is a rare opportunity to enjoy refined living on a private, spacious retreat.

2700 Ballahack 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.