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24420 Lovers Lane, Isle of Wight - South
$378,000
4 Beds ⋅ 2.1 Baths ⋅ 10605816 MLS
Welcome home to this 4 bedroom 2.5 bath Ranch built in 1968 with various improvments throughout the years. Home is waterfront on a pond that is partially owned by the homes who's properties border it. Roof was replaced in 2015. One heat pump was replaced in late 2013 and the other around 2018 and both have recently been serviced. Water heater was replaced around 2020. Flooring in family room was replaced with tile in 2015. Dock on the pond was completely rebuilt and completed in 2023.

24420 Lovers Lane, Isle of Wight - South
1020 Breakwater Trail, Isle of Wight - North
$377,790
3 Beds ⋅ 2.1 Baths ⋅ 10603638 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.

1020 Breakwater Trail, Isle of Wight - North
1044 Breakwater Trail, Isle of Wight - North
$377,205
3 Beds ⋅ 2.1 Baths ⋅ 10606381 MLS
CAROLINE.SOLD.TBB

1044 Breakwater Trail, Isle of Wight - North
1024 Breakwater Trail, Isle of Wight - North
$376,175
3 Beds ⋅ 2.1 Baths ⋅ 10605952 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.

1024 Breakwater Trail, Isle of Wight - North
2089 Striper Court, Isle of Wight - North
$375,180
3 Beds ⋅ 2.1 Baths ⋅ 10618055 MLS
CAROLINE. SOLD. TBB

2089 Striper Court, Isle of Wight - North
10804 Smiths Neck Road, Isle of Wight - North
$375,000
3 Beds ⋅ 2 Baths ⋅ 10639605 MLS
Charming, updated Historic 1920s Sears Kit Home in Carrollton! This property blends classic character with modern upgrades on a spacious, quiet lot. Enjoy a fully refreshed interior featuring new paint, new flooring, & all season room overlooking the property. The kitchen shines with updated LED lights, new appliances (incl gas line run for gas range). Major systems bring peace of mind, including a brand-new HVAC system (3-ton gas pack & new heat pump coil) & a roof replaced in '23. The massive 30x28 detached garage is a dream feature. It boasts a 12-foot roll-up door, a 30-amp camper plug, & a fully floored attic. Inside, discover a private 18x28 finished bonus room with a window A/C unit & an included pool table. The expansive yard offers room to roam, a garden spot, & a ready setup for an outdoor pool with power & gas lines already run. Enjoy low-cost community well water ($30/month) & a prime location near grocery stores, dining, and the Smithfield Saturday Farmer's Market!

10804 Smiths Neck Road, Isle of Wight - North
119 Bishops Reach, Smithfield
$375,000
4 Beds ⋅ 2.1 Baths ⋅ 10631577 MLS
Just 5 minutes from historic downtown Smithfield, this beautifully updated single-family townhouse is located in a quiet, established neighborhood. Inside, enjoy a bright open layout with durable LVP flooring (2024) and all-new kitchen appliances. Spacious bedrooms and a comfortable primary suite offer flexibility and privacy. Go outside to a newly updated patio (2024) and fully fenced backyard (2024)—perfect for entertaining or relaxing. Major updates include a new roof (2020) and HVAC system (2017), providing added peace of mind. Move-in ready and conveniently located near shopping, dining, and more—this home is a must-see!

119 Bishops Reach, Smithfield
27175 Walters Highway, Isle of Wight - South
$375,000
3 Beds ⋅ 2 Baths ⋅ 10628033 MLS
Private country living on 6.2 acres! This 3-bedroom, 2-bath brick rancher offers 1,632 sq ft with a spacious layout and plenty of room to enjoy the outdoors. Features include a cozy wood-burning fireplace, sunroom perfect for relaxing year-round, and beautifully refinished wood floors (2026). Recent updates also include a new roof in 2026. The detached 1-car garage provides additional storage or workspace. Enjoy peace and privacy with no HOA while still having plenty of space for hobbies, gardening, or simply unwinding in your own secluded setting.

27175 Walters Highway, Isle of Wight - South
1119 Breakwater Trail, Isle of Wight - North
$374,655
3 Beds ⋅ 2.1 Baths ⋅ 10609950 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.

1119 Breakwater Trail, Isle of Wight - North
1023 Breakwater Trail, Isle of Wight - North
$372,270
3 Beds ⋅ 2.1 Baths ⋅ 10607105 MLS
CAROLINE.SOLD.TBB

1023 Breakwater Trail, Isle of Wight - North
201 Cathedral Street, Smithfield
$372,000
2 Beds ⋅ 2 Baths ⋅ 10643563 MLS
Welcome to easy, low-maintenance living in Church Square, a sought-after 55+ community just minutes from downtown Smithfield! This corner-lot home offers a spacious one-level floor plan designed for comfort and convenience. Relax on the front porch or entertain on the enclosed side patio. Inside, you'll find an open layout featuring granite countertops, a large center island, oversized walk-in pantry, and seamless flow between the kitchen, dining area, and great room. The primary suite includes a private bath and large walk-in closet, while a second bedroom and full bath provide ideal space for guests or a home office. A rear-loading two-car garage adds convenience. Community amenities include a clubhouse, swimming pool, fitness center, grilling patio, and gathering spaces. Conveniently located near shopping, restaurants, medical facilities, and everyday essentials, this move-in-ready Smithfield home offers the perfect blend of style, comfort, and carefree 55+ living.

201 Cathedral Street, Smithfield
2054 Striper Court, Isle of Wight - North
$371,885
3 Beds ⋅ 2.1 Baths ⋅ 10627521 MLS
CAROLINE. SOLD. TBB.

2054 Striper Court, Isle of Wight - North
208 Edgewood Drive, Smithfield
$370,000
3 Beds ⋅ 1.1 Baths ⋅ 10635045 MLS
Stop scrolling — this is the one you’ve been waiting for! This beautifully maintained brick ranch is packed with updates, extra space & tons of personality in a location you’ll absolutely love. Freshly painted & move-in ready, it features a new front door, updated kitchen with stainless steel appliances, stylish LVT flooring, pantry storage & beautifully renovated bathrooms that make everyday living feel fresh & modern. Outside you’ll find a patio & fenced-in backyard with plenty of room for outdoor activities. The HUGE 570SF detached finished workshop is a total game changer! With water & electric, the possibilities are endless - home gym, workshop, art studio, game room, potential ADU… you name it! Plus, you’re just minutes from all the charm of historic downtown Smithfield, Windsor Castle Park, community events, local restaurants, boutique shopping, & waterfront attractions. Homes like this don’t come around often. Come see this one in person before someone else falls in love first!

208 Edgewood Drive, Smithfield
24 N Court Street, Isle of Wight - South
$370,000
3 Beds ⋅ 1.1 Baths ⋅ 10624428 MLS
This well-maintained home blends classic charm, full of character, and thoughtful updates offering plenty of space both inside and out right in the heart of Windsor! You’ll find a gorgeous interior featuring a dedicated dining room, three generous bedrooms, and an additional versatile room perfect for a home office, playroom, or flex space. A large living space also leads to an updated kitchen showcasing beautiful soapstone countertops that add timeless style and durability. Outside, the spacious, fully fenced backyard provides plenty of room to relax, entertain, or play. A long driveway offers parking for at least five vehicles and leads to a huge two-car detached garage. The rear half was beautifully redone into a workshop in 2022—perfect for hobbies, projects, or extra storage. Major improvements also include a new roof, crawl space work, gutters, and a brand-new back deck all completed in 2025. Don’t miss the opportunity to make this phenomenal property your next home!

24 N Court Street, Isle of Wight - South
31016 Walters Highway, Isle of Wight - South
$370,000
4 Beds ⋅ 4.1 Baths ⋅ 10613799 MLS
Nestled on a beautiful corner lot just over an acre, this spacious brick ranch offers 4 bedrooms and 4.5 baths, along with an additional living space that could serve as a 5th bedroom. The large kitchen features generous counter space and two cooktops, perfect for meal prep and entertaining. Enjoy both a sizable living room and a comfortable family room, giving you plenty of space to spread out with more than 2,800 square feet of living area. Outside, relax on the large back deck overlooking the in-ground pool and fenced backyard. A storage shed adds convenience for yard tools and pool accessories. This property is an ideal blend of space, comfort, and outdoor enjoyment. Carrsville and Windsor School district!

31016 Walters Highway, Isle of Wight - South
1115 Breakwater Trail, Isle of Wight - North
$369,990
3 Beds ⋅ 2.1 Baths ⋅ 10621518 MLS
READY IN APRIL! This beautiful end-unit Caroline floorplan comes with exceptional features including all appliances included, quartz countertops, upgraded lighting, stylish black fixtures throughout, and a covered rear porch—ready for spring enjoyment. 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, 2 car garages, and multi million dollar amenities. The Caroline offers 1,775 sq ft of open living space with a luxurious main level owner’s suite featuring dual vanities, shower, linen closet, and private water closet. The gourmet kitchen boasts a 10-foot island that flows into the great room and dining area, ideal for entertaining. Maintenance free backyards offer relaxation without the upkeep. Upstairs provides two additional bedrooms, a full bath, and a large storage room. Ready to experience South Harbor Towns? Schedule your tour today

1115 Breakwater Trail, Isle of Wight - North
301 Cathedral Street, Smithfield
$369,900
2 Beds ⋅ 2 Baths ⋅ 10634463 MLS
Welcome to easy living in one of Smithfield’s sought after 55+ communities! Situated on a desirable corner lot, this beautifully maintained home offers low maintenance living with fantastic amenities including a pool, clubhouse, fitness room, outdoor activities and more. Inside you’ll find an open concept layout connecting the living, dining and kitchen spaces, perfect for entertaining or everyday comfort. The kitchen features a large walk in pantry with plenty of storage. Home offers 2 spacious bedrooms and 2 full baths, including a generous primary suite with walk in closet and ensuite bath complete with double sinks, a walk in shower and grab bars for added convenience. Enjoy relaxing on the side patio and the ease of a rear entry 2 car garage. Conveniently located just minutes from downtown Smithfield, Windsor Castle Park, the new hospital, shopping, restaurants, interstates and more!

301 Cathedral Street, Smithfield
1040 Breakwater Trail, Isle of Wight - North
$369,425
3 Beds ⋅ 2.1 Baths ⋅ 10604436 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, no maintenance 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 no maintenance 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.

1040 Breakwater Trail, Isle of Wight - North
31165 Walters Highway, Isle of Wight - South
$369,000
4 Beds ⋅ 2 Baths ⋅ 10615865 MLS
Welcome home to this thoughtfully updated classic 2464 sq ft 4 bedroom 2 full bath tri-level, perfectly situated on a full 1-acre lot. This home offers space, flexibility, and timeless appeal with the right mix of traditional charm and modern updates — truly move-in ready. Interior Highlights include Updated kitchen with soft-close Shaker cabinets, granite countertops, stainless steel appliances & subway-tile backsplash, Fresh interior paint (2026), New carpet padding & luxury vinyl plank flooring (2026), Upgraded lighting & fixtures, Updated electrical & plumbing (2020), New windows (2020), NewRoof (2020), New HVAC (2020) Living Spaces include Flexible floor plan with a family room/ separate den; Separate dining room ; Comfortable owner’s retreat. Step onto the rear deck overlooking an expansive one-acre yard — a place for play, pets, gardening, or simply enjoying that peaceful country feel, while still being convenient to local amenities.

31165 Walters Highway, Isle of Wight - South
200 Durham Street, Smithfield
$369,000
2 Beds ⋅ 2 Baths ⋅ 10612026 MLS
Free, Free, Free! Wish you could have electric power for FREE? This beautiful ranch style, 2 BR, 2BA, + flex rm ( perfect for Den/office/DR/Guest rm) features PAID-for Solar Panels that provide you with free electric power & may also provide you a quarterly rebate! The one level living open floor plan features a spacious living area w/double French doors which open to the patio & provide tons of natural light, a galley style-kitchen w/a huge island, SS appliances, granite countertops & cozy breakfast nook, all with 9ft ceilings & gorgeous LVP flooring. Not only can you save on utilities, but you can enjoy the low maintenance life style of this 55+ community - enjoy in the 3,000 sq ft clubhouse, pool & fitness center while your exterior maintenance & lawn care are done for you! Built in 2021 & situated on a corner lot with a 2 car garage, this home is ready for you.

200 Durham Street, Smithfield
1032 Breakwater Trail, Isle of Wight - North
$367,345
3 Beds ⋅ 2.1 Baths ⋅ 10609422 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 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 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.

1032 Breakwater Trail, Isle of Wight - North
1139 Breakwater Trail, Isle of Wight - North
$367,115
3 Beds ⋅ 2.1 Baths ⋅ 10616896 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.

1139 Breakwater Trail, Isle of Wight - North
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
2078 Striper Court, Isle of Wight - North
$366,065
3 Beds ⋅ 2.1 Baths ⋅ 10621103 MLS
CAROLINE. SOLD. TBB.

2078 Striper Court, Isle of Wight - North
1028 Breakwater Trail, Isle of Wight - North
$365,685
3 Beds ⋅ 2.1 Baths ⋅ 10606469 MLS
CAROLINE.SOLD.TBB

1028 Breakwater Trail, Isle of Wight - North
1036 Breakwater Trail, Isle of Wight - North
$365,565
3 Beds ⋅ 2.1 Baths ⋅ 10603895 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, no maintenance 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 no maintenance 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.

1036 Breakwater Trail, Isle of Wight - North
22392 Barrett Town Road, Isle of Wight - South
$365,000
3 Beds ⋅ 2.1 Baths ⋅ 10654613 MLS

22392 Barrett Town Road, Isle of Wight - South
208 Monticello Court, Smithfield
$365,000
4 Beds ⋅ 2.1 Baths ⋅ 10637125 MLS
Beautiful 4-Bedroom, 2.5 bath end unit townhome featuring a spacious loft and oversized upgraded paver patio perfect for relaxing outdoors. Bright, open kitchen with granite countertops, ample cabinetry and natural light throughout. Spacious Great Room with a corner Fireplace and Newer LVP flooring adds modern style and durability. Gorgeous finishes and a desirable layout make this home move-in ready and a must see! Situated in the Charming town of Smithfield and convenient to all areas of Hampton Roads.

208 Monticello Court, Smithfield
11670 Magnet Drive, Isle of Wight - North
$365,000
3 Beds ⋅ 2 Baths ⋅ 10617691 MLS
Very well maintained 3 bedroom, 2 bath home built in 2016 with approximately 1,512 square feet of living space on a private 2-acre parcel in Smithfield. Featuring a functional layout with comfortable living area and outdoor space for relaxing or entertaining. Enjoy country living while still being able to shop and dine. Don’t miss this opportunity to own a well cared for home in Isle of Wight County.

11670 Magnet Drive, Isle of Wight - North
210 Azalea Drive, Smithfield
$365,000
3 Beds ⋅ 2 Baths ⋅ 10612379 MLS
Tucked away on a generous 1/2 acre lot in the waterfront community of Moonefield Estates, this beautifully maintained home offers the perfect blend of charm & modern updates. The fully fenced yard provides privacy/space for outdoor living/gardening/pets to roam. Inside, you're greeted by LVP flooring thru out, offering durability w/a high-end look. The kitchen is a showstopper, featuring stunning fantasy brown granite countertops that bring natural elegance & drama, w/new stainless steel appliances. Both bathrooms have been thoughtfully renovated, contemporary tile showers w/glass doors that create a spa-like feel. A detached storage shed is perfect for tools, hobbies, or seasonal storage. Updates: fresh paint thruout 2025, updated light fixtures 2025, LVP floors 2023, stainless steel appliances 2025, fantasy brown granite countertops 2025, door hardware (knobs/hinges) 2024, & electrical outlets/light switches 2025. Roof/siding/windows/water heater all replaced in the past 6 years.

210 Azalea Drive, Smithfield

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.