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1016 Breakwater Trail, Isle of Wight - North
$366,765
3 Beds ⋅ 2.1 Baths ⋅ 10605053 MLS
Now selling the next phase at South Harbor Towns—a vibrant 55+ community in Carrollton, VA offering low-maintenance living with first-floor owner’s suites, maintenance free-backyards, 2-car garages, and multi-million-dollar amenities. The Caroline model features nearly 1,800 sq ft of open living space, including a luxurious main-level owner’s suite with dual vanities, walk-in shower, linen closet, and private water closet. The gourmet kitchen showcases a 10-foot island that flows into the great room and dining area. You can enjoy optional rear covered porch upgrades and maintenance-free backyards designed for relaxation without the upkeep. Upstairs includes two bedrooms, a full bath, and a walk-in storage room. Ready to experience South Harbor Towns? Schedule your tour today.

1016 Breakwater Trail, Isle of Wight - North

20517 Madison Court, Smithfield
$605,000
5 Beds ⋅ 2.1 Baths ⋅ 10601312 MLS
A true Southern charmer in the sought-after Gatling Pointe Yacht Club community—no town taxes! This 5-bedroom, 2.5-bath home features gleaming hardwood floors, tall ceilings, and an open floor plan perfect for entertaining and gatherings. The upgraded kitchen ( with tons of counter space) opens to a spacious family room with a soaring cathedral ceiling in the family (amazing for decorating), creating the heart of the home. Enjoy a formal dining room and private office ( on the 1st floor), ideal for today’s lifestyle. The primary suite offers a deep walk-in closet and spa-like ensuite bath. The third floor is great for in-law suite or theater room. Motivated seller allowing for a faster-than-normal closing. Move-in ready for the holidays—host family around the fire pit and start making memories. Residents enjoy resort-style amenities including a private marina, clubhouse, pool, tennis courts, and on-site dining.

20517 Madison Court, Smithfield

2305 James River Trail, Isle of Wight - North
$287,000
3 Beds ⋅ 2 Baths ⋅ 10616447 MLS
Move-in ready condo in the sought-after Eagle Harbor community! This spacious open floor plan offers excellent flow for everyday living and entertaining. Upgrades include stainless steel appliances, granite countertops throughout, ceramic tile flooring, Stainmaster carpet, and modern square-basin sinks with brushed nickel pull-down faucets. Smart-home features include a Google Nest thermostat, security system, and smart-lock doors. The garage features an epoxy-coated floor, power door, and remote for added convenience. Enjoy low-maintenance living with grounds maintenance included, plus access to top-notch amenities including a clubhouse, mini-golf, tennis courts, walking paths, a 5-acre catch-and-release pond, and a swim club with two pools. Ideally located just over the James River Bridge with quick access to Langley AFB, Newport News Shipbuilding, shopping, dining, and more. Schedule your showing today!

2305 James River Trail, Isle of Wight - North

18423 Tomlin Hill Drive, Isle of Wight - South
$300,001
10615182 MLS
Amazing 34 acres of pristine farmland, the perfect site for your custom dream home or a premier equestrian estate. This expansive lot is mostly cleared and ready for development, featuring mature tree lines for natural privacy around the property. Experience the quintessential peace and tranquility of country living without sacrificing convenience; you are less than 10 minutes from Windsor’s schools and shops, and only 20 minutes from the charm of Smithfield. With an easy commute to local military bases and major hubs like Chesapeake, Newport News, and Petersburg in under an hour, this property offers the best of rural serenity and city accessibility. Enjoy starlit nights that surpass planetarium skies and no traffic noise! Welcome home to the country life!

18423 Tomlin Hill Drive, Isle of Wight - South

209 Marshall Lane, Isle of Wight - North
$720,000
4 Beds ⋅ 3.1 Baths ⋅ 10611249 MLS
Decorated with contemporary panache, this home is most impressive! Striking Italian Murano glass lighting fixture graces the foyer. Prominent eat-in kitchen is enhanced by cherry wood cabinets w/ sophisticated gray wash finish, spacious sit-up counter, high-end appliances and granite countertops provide both function and style, custom lighting and hardwood floors throughout the home. Adjacent to kitchen is a keeping area embracing a cozy gas fireplace, perfect for relaxing or casual gatherings; upscale dining room; office; family room w /gas fireplace and stunning views of manicured backyard surrounded by woods ensuring privacy and tranquility; back deck w /gas firepit ideal for entertaining guests. 1st floor primary en-suite is complete with his-and-hers floating vanities and shower w/ rain feature for ultimate relaxation. Additional features include a well for the sprinkler system and whole-house generator. Situated in a cul-de-sac, this home offers both exclusivity and convenience.

209 Marshall Lane, Isle of Wight - North

383 Tributary Lane, Isle of Wight - North
$470,990
3 Beds ⋅ 2 Baths ⋅ 10611712 MLS
Welcome to South Harbor 55+, a vibrant community in Isle of Wight near Smithfield, offering single-family homes with first-floor living, no yard work, and resort-style amenities including a clubhouse, pool, walking trails, and pickleball courts. The Palladio Ranch is a stunning ranch-style home available now for a quick move-in. This home is designed for both elegance and convenience, featuring a cozy gas fireplace, luxury vinyl plank flooring throughout, and a gourmet kitchen with upgraded quartz countertops and premium cabinets. The owner’s suite offers a spa-like retreat with a Roman shower that includes a bench and dual shower heads. Enjoy outdoor living with a full stone front porch and a huge rear covered porch, perfect for relaxing or entertaining. A spacious two-car garage adds practicality, while the single-level layout ensures easy living. This home combines style, comfort, and functionality—ready for you to move in and start enjoying the South Harbor 55+ lifestyle today.

383 Tributary Lane, Isle of Wight - North

10748 Smiths Neck Road, Isle of Wight - North
$265,000
3 Beds ⋅ 2 Baths ⋅ 10596820 MLS
Enjoy the best of both worlds with this room 3-bedroom, 2-bath home nestled on just under 1 acre of cleared land. Located in a peaceful rural setting, this property offers privacy and space while still being conveniently close to major shopping, colleges, universities, and entertainment venues. With easy access to all the major cities in the region, commuting a breeze. The smartly designed floorplan feels larger than its 1,100 square feet, featuring a comfortable flow and a combination of wood, carpet, and vinyl flooring. Relax or entertain on the screened deck overlooking the spacious yard and take advantage of the handy storage shed. A rare opportunity for comfortable, country-style living with modern day conveniences.

10748 Smiths Neck Road, Isle of Wight - North

23068 Andrew Court, Isle of Wight - South
$456,500
5 Beds ⋅ 3 Baths ⋅ 10613459 MLS
Located in the established Windsor Woods community, this spacious 5-bedroom, 3-full-bath home offers a flexible layout and comfortable living with no HOA. The first floor features a primary suite and a guest bedroom, along with soaring cathedral ceilings that fill the home with natural light and create an open, airy feel. Upstairs offers three additional generously sized bedrooms with excellent storage, including a large walk-in attic with potential for future finished living space. Recent updates include brand-new carpet throughout, fresh paint, and many interior doors replaced for a refreshed interior. Enjoy relaxing or entertaining on the back deck overlooking a peaceful pond, complete with an awning perfect for summer BBQs and evenings outdoors. Conveniently located with a toll-free route to nearby military bases and easy access to the charming town of Windsor, Smithfield, and Downtown Suffolk, this home offers space, updates, and a prime location.

23068 Andrew Court, Isle of Wight - South

341 Early Station Trail, Isle of Wight - North
$490,945
4 Beds ⋅ 2.1 Baths ⋅ 10604433 MLS
Discover modern living with small-town charm in Isle of Wight! Spacious new homes near shops, dining, Route 17, and key military bases—from the mid $400s. Your ideal lifestyle starts here! Welcome to a home that redefines comfort and convenience—featuring 4 spacious bedrooms, 2.5 baths, and a versatile flex room perfect for a home office, additional living space, or a playroom. The heart of the home is the open-concept living, dining, and kitchen area, offering a warm, connected space for everyday living and entertaining. But the true showstopper is the owner’s suite—a private retreat featuring a serene ensuite with double vanities and a massive walk-in closet that’s practically a room of its own. Upstairs, the laundry room adds convenience where it’s needed most, close to all bedrooms. A 2-car garage provides plenty of storage, and the spacious backyard is ideal for outdoor dining, gardening, or play. The Columbia home offers both elegance and everyday ease.

341 Early Station Trail, Isle of Wight - North

107 Harrison Drive, Smithfield
$455,000
4 Beds ⋅ 2 Baths ⋅ 10615578 MLS
Tucked away on a quiet cul-de-sac in an established, non-HOA community, this well-maintained rancher offers privacy, comfort, and peace of mind with major updates including a 2017 roof, 2019 HVAC, and 2021 hot water heater. Inside, hardwood floors and a vaulted ceiling create a bright, welcoming atmosphere, complemented by a timeless neutral color palette. The primary suite features custom molding, a spacious closet, and a beautifully tiled shower. Two additional bedrooms and a full hall bath complete the main level. A private fourth bedroom over the garage offers flexible space for a home office, playroom, or guest suite. An attached two-car garage adds convenience. Outdoors, enjoy a fully fenced backyard with a six-foot PVC privacy fence (Can be extended), oversized deck, storage shed, and space for gardening. Conveniently located near military bases and just minutes from downtown Smithfield’s shops and dining, this home offers the perfect blend of lifestyle and location.

107 Harrison Drive, Smithfield

378 Pagan Road, Smithfield
$510,000
3 Beds ⋅ 2.1 Baths ⋅ 10613554 MLS
Welcome home to this beautifully maintained property situated on a spacious .62 acre corner lot with a circular driveway and exceptional outdoor living. Enjoy relaxing on the large front porch or entertaining on the expansive patio just off the sunroom. Inside, the home offers 2,808 sq ft of living space with 3 bedrooms and 2.5 baths. The updated kitchen is open to the family room and features a bar, ample cabinet space, and great flow for everyday living and entertaining. A dedicated dining room sits just off the kitchen, while the large front living room provides additional flexible space. The sunroom is a standout feature, filled with natural light and offering direct access to the patio. Additional highlights include a new HVAC system, washer and dryer, central vacuum, and an irrigation system with a separate well to help keep water costs down. The home has been meticulously maintained throughout. So many great features, you need to see it for yourself!

378 Pagan Road, Smithfield

362 Spring Hill Place, Isle of Wight - North
$343,000
3 Beds ⋅ 2.1 Baths ⋅ 10616816 MLS
Beautifully maintained 3-story townhome in the highly sought-after Benns Grant community! This 3-bedroom, 2.5-bath home features a flexible office/study space and is filled with upgrades throughout. The open-concept main living area showcases granite countertops, stainless steel appliances, a gas range, soft-close cabinetry, and hardwood floors on the first and second levels. Enjoy indoor-outdoor living with a private balcony off the dining/kitchen area—perfect for morning coffee or evening relaxation.The spacious primary suite offers a tray ceiling and en-suite bath, while additional bedrooms provide comfort and versatility. Additional highlights include a tankless water heater and thoughtful finishes throughout.Residents enjoy resort-style amenities including a stunning clubhouse with lake and pool views, a pool with waterslide, stocked lakes, scenic nature trails, and a large playground. Conveniently located with an easy commute to both the Peninsula and Southside.

362 Spring Hill Place, Isle of Wight - North

325 Tributary Lane, Isle of Wight - North
$519,989
3 Beds ⋅ 3 Baths ⋅ 10614441 MLS
Welcome to South Harbor 55+, a vibrant community in Isle of Wight near Smithfield, offering single-family homes with first-floor living, no yard work, and resort-style amenities including a clubhouse, pool, walking trails, and pickleball courts. The Palladio 2-Story offers flexibility and style with 3 bedrooms, 3 bathrooms, and a versatile flex room that can serve as a dining area, sitting room, office — or even be converted into a 4th bedroom. The gourmet kitchen with a large island is the perfect spot for entertaining, flowing seamlessly into the spacious family room. All essential living spaces, including the owner’s suite with en-suite bath and walk-in closet, are on the first floor, along with a covered back porch and the option for a wooded homesite. Upstairs, enjoy a loft, a bedroom and bath, and a temperature controlled walk-in storage room. A 2-car garage completes this thoughtfully designed home. MOVE IN READY BY JANUARY/EARLY FEBRUARY!!!!

325 Tributary Lane, Isle of Wight - North

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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