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308 Early Station Trail, Isle of Wight - North
$444,960
4 Beds ⋅ 2.1 Baths ⋅ 10603632 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! This beautifully designed Allegheny, a 4-bedroom, 2.5-bath home, offers the perfect blend of style and function, with the flexibility to convert one bedroom into a cozy loft—ideal for a playroom, media space, or home office. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating an ideal space for entertaining or everyday living. Upstairs, you’ll find a convenient laundry room so you aren't carrying laundry up and down stairs, and a private owner’s suite complete with a spacious ensuite bath with double sinks. A 2-car garage, generous backyard, and thoughtful details throughout make this home a modern haven for your lifestyle.

308 Early Station Trail, Isle of Wight - North
20277 N Cherry Grove Road, Smithfield
$340,000
3 Beds ⋅ 2.1 Baths ⋅ 10618131 MLS
Welcome home to this charming 3 bedroom, 2.5 bath country home featuring a spacious kitchen and living room, for everyday living and entertaining. Start your mornings with coffee on the large front porch, then step out back to see the fenced-in backyard that’s a blank canvas for all your outdoor dreams. Attached garage and plenty of yard space complete the package. This home is full of potential and needs some cosmetic updates to make it your own. Sellers are open to buyer concessions- use towards closing costs or upgrade allowance. Experience small-town living with quick access to Downtown Smithfield, Suffolk, JRB, and major commuter routes.

20277 N Cherry Grove Road, Smithfield
105 Cathedral Street, Smithfield
$395,000
2 Beds ⋅ 2 Baths ⋅ 10618638 MLS
Beautiful ranch-style like-new condo featuring an open living, dining, and kitchen area with custom cabinetry, granite countertops, and stainless steel appliances. LVP Flooring and abundant storage throughout this condo. The spacious primary suite offers an oversized closet and a luxurious ensuite bath with dual vanities, tiled floor and tiled shower with bench. A second bedroom includes hall bath access and another oversized closet. Enjoy a large 2-car garage and a fenced patio perfect for outdoor relaxation. Low-maintenance living with exceptional community amenities including a clubhouse, exercise room, pool, grounds maintenance, and trash service.

105 Cathedral Street, Smithfield
1704 Kathy Ann Way, Isle of Wight - North
$289,593
1 Beds ⋅ 2 Baths ⋅ 10618352 MLS
Our Beechwood plan is one floor living at its best. Beautiful choices for cabinets, countertops, and flooring, etc. The neighborhood includes a 2-story club house equipped with a private gym, kitchen, arcade room, and party areas. Enjoy the pool, bark park, and nature trails and a multi fun park including volleyball, pickle ball, horseshoes, and bocci ball. Never worry about lawn care or exterior maintenance again. Just enjoy your resort style living here.

1704 Kathy Ann Way, Isle of Wight - North
12387 Old Suffolk Road, Isle of Wight - South
$330,000
4 Beds ⋅ 2 Baths ⋅ 10619973 MLS
Welcome home to this beautiful ranch-style home perfectly situated on 1.30+ acres, offering exceptional space to spread out, entertain, and enjoy peaceful outdoor living. Inside this well maintained home, you’ll find 4 good sized bedrooms and 2 full bathrooms, along with bright and welcoming living and dining areas designed for both comfortable everyday living and entertaining. The home features a tasteful blend of carpet and laminate flooring, a spacious primary owner’s suite with a double vanity, and a separate laundry room for added functionality. Step outside to a huge backyard with endless possibilities—great for hosting gatherings, gardening, or simply unwinding in your own private retreat. Conveniently located just 5 minutes from downtown Windsor, 10 minutes from the interstate, and centrally positioned near Smithfield, Suffolk, Franklin and Chesapeake. Land, space, and location—this home has it all. Schedule your private showing today and don’t miss this great opportunity!

12387 Old Suffolk Road, Isle of Wight - South
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
13414 High Gate Mews, Isle of Wight - North
$320,000
3 Beds ⋅ 2 Baths ⋅ 10608093 MLS
Come See this Lovely 3 Bedroom 2 Bath Home in the Woodbridge Community with Attached 2 Car Garage. One Level Living with All New Luxury Vinyl Plank Flooring. Living Room has a Cozy Fireplace next to the Formal Dining Area Both with High Ceilings. The Primary Suite has an Ensuite Bath and Large Walk In Closet. Plenty of Cabinets Space in the Kitchen with Breakfast Area. Screened Porch and Fenced Backyard. Upgraded AC Unit with an Oxyquantum UV Light System and a Micropower Guard Electronic Air Cleaner! The Eagle Harbor Community Amenities include a Pool, Tennis Courts, Clubhouse, Walking Trails, and Grounds Maintenance. Welcome Home!

13414 High Gate Mews, 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
24401 John Henry Street, Isle of Wight - South
$445,000
4 Beds ⋅ 3.1 Baths ⋅ 10613338 MLS
Lovely 4 bedroom 3.5 bathroom home located in the Holland Meadows neighborhood of Windsor. IN-Ground Swimming pool / Salt water / located in a cup-de-sac / white vinyl back yard. You will love the home and the neighborhood! Items to convey - all items to include all appliances to include the washer and dryer, 8'/8' garden shed . Tile showers / Granite island and vanities. electric fire place in great room. Windsor school system.

24401 John Henry Street, Isle of Wight - South
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
16348 Smithfield Heights Drive, Smithfield
$485,000
4 Beds ⋅ 2.1 Baths ⋅ 10620112 MLS
Welcome to this GORGEOUS home in Smithfield Heights, where modern updates and thoughtful renovations truly take this property to the next level! NEW windows, NEW carpet, fresh paint, a NEW front door (with storm door), and NEW back door—all creating a fresh, move-in-ready feel. The NEW garage door (2023) adds even more curb appeal and convenience. A completely renovated kitchen (2021) featuring stunning quartz countertops, updated finishes, and a layout perfect for cooking and gathering. Retreat to the wonderful primary ensuite, complete with: A spacious walk-in closet, a beautifully updated bath, A HUGE walk-in designer shower. Three additional large bedrooms provide ample space for family, guests, or a home office. Step outside to your private backyard OASIS! Enjoy an AMAZING stone fireplace and grilling station, perfect for entertaining year-round. Relax in the serene in-ground pool featuring a new pump and salt cell. Large wooden playset, RainSoft softner & pellet stove convey.

16348 Smithfield Heights Drive, Smithfield
24232 Sugar Hill Road, Isle of Wight - North
$335,000
3 Beds ⋅ 2 Baths ⋅ 10617471 MLS
Welcome to 24232 Sugar Hill Rd in Carrollton, a fantastic opportunity in an exceptional location offering the perfect balance of convenience, privacy, and small-town charm. Built in 2010, this 3 bedroom, and office could be 4 bedroom, 2-bath home with approximately 1,742 square feet provides a solid layout and great potential for the next owner to make it their own. Its needs TLC (major cosmetic work) The home could benefit from some updating, making it an ideal option for buyers looking to add personal touches and build equity. Situated in one of Carrollton’s most desirable areas with quick access to Smithfield, Suffolk, and major commuter routes, this location is hard to beat. A rare chance to get a well-located property with strong upside in a sought-after area.

24232 Sugar Hill Road, 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
1047 Breakwater Trail, Isle of Wight - North
$351,765
3 Beds ⋅ 2.1 Baths ⋅ 10607887 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.

1047 Breakwater Trail, Isle of Wight - North
1027 Breakwater Trail, Isle of Wight - North
$332,450
3 Beds ⋅ 2.1 Baths ⋅ 10606383 MLS
CAROLINE. SOLD. TBB

1027 Breakwater Trail, Isle of Wight - North
Lot 23 Lovers Lane, Isle of Wight - South
$60,000
10622931 MLS
This vacant residential lot offers the perfect opportunity to create a custom home in an established neighborhood with a peaceful, small-town atmosphere. Enjoy paved road frontage and convenient access to local schools, shopping and commuter routes to the greater Hampton Roads area. Whether you're ready to build now or planning for the future, this property provides the ideal setting to bring vision to life.

Lot 23 Lovers Lane, Isle of Wight - South
13428 Harbor Drive, Isle of Wight - North
$475,000
3 Beds ⋅ 2.1 Baths ⋅ 10616236 MLS
Beautiful Florence model in highly sought after Eagle Harbor. This spacious home features a formal living room and a large family room with a cozy fireplace that opens to an expansive kitchen with granite countertop, quality cabinetry, pantry, island and a bright breakfast area. Downstairs includes a convenient laundry room and a half bath. Upstairs offers a generous loft currently used as a 4th bedroom, plus 3 well sized bedrooms all with ceiling fans. The primary suite impresses with a huge walk in closet, dual sinks, separate shower, and soaking tub. An additional full bath completes the second floor. Enjoy a nicely sized backyard and the convenience of being close to shopping, dining, and community amenities. A brand new tankless water heater. Don't Delay, get in Today!

13428 Harbor Drive, Isle of Wight - North
12189 Smiths Neck Road, Isle of Wight - North
$284,900
3 Beds ⋅ 1 Baths ⋅ 10615507 MLS
Enjoy rural living just minutes from the James River Bridge. This home sits on over 1/2 acre lot and is in excellent condition. Large living room with LVP flooring open dining/kitchen area with newer ceramic flooring. Three good sized bedrooms, renovated bath room and large utility room. The exterior features a nice deck, patio and a oversized 2 car garage with electricity. Washer, dryer, refrigerator conveys and A/C is 2 years old and the water heater is 1 year old.

12189 Smiths Neck Road, Isle of Wight - North
211 Red Oak Court, Isle of Wight - North
$344,500
3 Beds ⋅ 2 Baths ⋅ 10614338 MLS
Welcome to the highly sought after neighborhood of Wrenns Mill Estates. This well-maintained ranch is on a quiet cul-de-sac lot that’s just under one acre. Inside, you will find three spacious bedrooms, two bathrooms, and a large open living room and kitchen. Through the kitchen is the garage, which leads to a large sunroom, ideal for year-round entertainment. Seller is offering $5000 towards closing cost assistance! Don’t wait, call today to schedule a private showing.

211 Red Oak Court, Isle of Wight - North
103 Barcroft Drive, Smithfield
$450,000
4 Beds ⋅ 3.1 Baths ⋅ 10613781 MLS
Welcome to 103 Barcroft Drive — a beautifully maintained 4-bedroom, 3-bath home offering over 2,800 square feet of spacious living in one of Smithfield’s most desirable neighborhoods. From the moment you enter, you’ll notice the thoughtful layout designed for both comfort and functionality. A large open kitchen, and generously sized bedrooms, this home is for growing families or those who love to entertain. The primary suite includes a private en-suite bath, while the additional bedrooms offer flexibility for guests, home offices, or playrooms. Step outside to enjoy a spacious backyard is for relaxing, grilling, or gathering around a fire pit. Located just minutes from historic downtown Smithfield, local shops, dining, and top-rated schools — this home truly has it all!

103 Barcroft Drive, Smithfield
1059 Breakwater Trail, Isle of Wight - North
$384,745
3 Beds ⋅ 2.1 Baths ⋅ 10607785 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.

1059 Breakwater Trail, Isle of Wight - North
1051 Breakwater Trail, Isle of Wight - North
$336,195
3 Beds ⋅ 2.1 Baths ⋅ 10606384 MLS
CAROLINE.SOLD.TBB

1051 Breakwater Trail, Isle of Wight - North
1055 Breakwater Trail, Isle of Wight - North
$342,115
3 Beds ⋅ 2.1 Baths ⋅ 10603639 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.

1055 Breakwater Trail, Isle of Wight - North
103 Sandpiper Drive, Isle of Wight - North
$125,000
3 Beds ⋅ 2 Baths ⋅ 10625091 MLS
SOLD AS IS WHERE IS.

103 Sandpiper Drive, Isle of Wight - North
109 Spinnaker Run Court, Smithfield
$503,000
4 Beds ⋅ 2.1 Baths ⋅ 10616640 MLS
BRAND NEW ROOF! Roof completed January 20, 2026! Assumable 2.7% loan (subject to approval) Tucked away on a quiet cul-de-sac beneath a canopy of mature trees, this private retreat offers refined living with a semi-rural feel just minutes from downtown Smithfield. This 4-bedroom, 2.5-bath home has been thoughtfully updated with an enhanced kitchen featuring a farmhouse sink, fresh interior and exterior paint, and a new roof with transferable warranty to be completed within a week. Upstairs HVAC was replaced in 2021 and downstairs in 2025, and the home received a clear termite inspection in November. The expansive, wooded backyard creates a peaceful, park-like escape great for unwinding or entertaining. Located in the sought-after Gatling Pointe community, enjoy access to the Yacht Club lifestyle with riverfront dining, pool, tennis courts, playground, and boat slips. Conveniently positioned near major military bases, this home perfectly balances privacy, lifestyle, and accessibility.

109 Spinnaker Run Court, Smithfield
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
2217 Mainsail Drive, Isle of Wight - North
$510,305
3 Beds ⋅ 2 Baths ⋅ 10601278 MLS
Welcome to South Harbor Single! The Palladio Ranch.SOLD.TBB

2217 Mainsail Drive, Isle of Wight - North
307 Early Station Trail, Isle of Wight - North
$559,950
4 Beds ⋅ 2.1 Baths ⋅ 10601135 MLS
LEHIGH. SOLD. TBB.

307 Early Station Trail, Isle of Wight - North
Trail, Isle of Wight - North
$360,340
3 Beds ⋅ 2.1 Baths ⋅ 10612661 MLS
MOVE IN MARCH 2026! 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.

Trail, Isle of Wight - North
222 Richmond Avenue Unit 20-1, Smithfield
$406,743
2 Beds ⋅ 2 Baths ⋅ 10605526 MLS
Now offering $10,000 use as you choose - Rate buy-down, closing costs, or options/upgrades. This beautiful home is ready and waiting for you! The popular Newport model has everything most 55+ are looking for: one-level living, a large, spacious kitchen with an entertaining island, lots of natural light, a private outdoor courtyard, a well-appointed owner's suite, a generous guest suite, a flex space, and storage galore in and over the very large 2-car garage! You won't want to miss this one. Please call to schedule your appointment with our on-site sales manager to learn more about this home and the wonderful Church Square community! At Church Square, neighbors are friends, and life is never boring. Join in the fun or relax in your home.

222 Richmond Avenue Unit 20-1, 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.

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