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2058 Striper Court, Isle of Wight - North
$334,020
3 Beds ⋅ 2.1 Baths ⋅ 10627512 MLS
CAROLINE. SOLD. TBB.

2058 Striper Court, Isle of Wight - North
21418 Tan Road, Isle of Wight - South
$735,000
4 Beds ⋅ 3.1 Baths ⋅ 10642761 MLS
Welcome to your own private retreat in the heart of Smithfield! Nestled on 3.2 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of country living and modern convenience. Featuring two true primary suites. One on the first floor and one upstairs, this home is ideal for multi-generational living, guests, or added flexibility. Need to work from home? You’ll love the dedicated office, while the enclosed sunroom provides the perfect space to relax and enjoy peaceful views year-round. The location is hard to beat. Enjoy the privacy and tranquility of the countryside while being just 4 miles from Riverside Hospital, shopping, dining, and all that Smithfield has to offer. If you’ve been searching for space, versatility, and an unbeatable location, this is the one you’ve been waiting for.

21418 Tan Road, Isle of Wight - South
879 Maple Court, Smithfield
$360,000
3 Beds ⋅ 2.1 Baths ⋅ 10640718 MLS
Welcome to your new home! Nestled on a quiet culdesac, this home has been lovingly maintained and comes with many new fixtures to help give it a modern look. Enjoy the serenity of your expansive backyard from your deck, or make use of all the space by entertaining friends and family. Worried about mowing your new huge backyard? No problem! A new remote self-driven lawn mower conveys with the property. **Seller to offer new carpet to be installed in the bedrooms with a full price offer** Many recent updates and upgrades including: New roof 2022, New windows in garage and laundry 2026, Replace boards on deck & railing & waterproof stain 2023, Dishwasher 2023

879 Maple Court, Smithfield
328 Main Street, Smithfield
$412,800
3 Beds ⋅ 2.1 Baths ⋅ 10638528 MLS
Historic charm meets opportunity at 328 Main Street! This updated 3BR/2.5BA, 1,816 sqft home is zoned residential & commercial and has an approved special variance as a short-term rental from the town of Smithfield. Features include first-floor primary suite, electric fireplace, walk-in closet, patio, partial fenced yard, and more. Furnishings available for purchase! Whether you want to live here, run a business, or earn income right away, situated in historic downtown Smithfield, this location delivers.

328 Main Street, Smithfield
2062 Striper Court, Isle of Wight - North
$364,925
3 Beds ⋅ 2.1 Baths ⋅ 10629329 MLS
CAROLINE. SOLD. TBB.

2062 Striper Court, Isle of Wight - North
2907 James River Trail, Isle of Wight - North
$285,000
2 Beds ⋅ 2 Baths ⋅ 10646435 MLS
Here is your opportunity to purchase a meticulously maintained & tastefully renovated one level, corner unit in the Bridgewater community of Eagle Harbor! This welcoming home offers many updates to include quartz countertops in the kitchen, a walk-in shower with new surround in the primary bathroom, all new flooring throughout the home to include the stunning hardwood floors, and elegant shutter blinds in every room. You will love the spacious living room, eat-in kitchen with bar area, crown molding, trayed ceiling in primary bedroom, functional layout, and the scenic view from the concrete patio! As an added bonus, this property is located at the end of a dead-end street. The community amenities include multiple pools, a clubhouse, playground, volleyball, putt-putt course, 5 acre lake, ground maintenance, and trash pick up. If you're looking for low maintenance living, look no more! Call today to make this gem your new HOME!

2907 James River Trail, Isle of Wight - North
24129 Johnson Avenue, Isle of Wight - South
$315,000
3 Beds ⋅ 2 Baths ⋅ 10639118 MLS
Come and make your new home in Windsor Virginia, voted the friendliest community by Nextdoor for 2026. For Sale is this approximately 1250 square foot 3 bedroom two bath Ranch home. This home sits on a .34 acre corner lot in a quite established non-HOA neighborhood. The home sits on a crawl space and has had plumbing, electrical and HVAC upgrades in the past. The property had a 16x20 one car oversized metal garage which has power and HVAC. It also has a 12x10 shed that has electricity. This home is in close proximity to retail establishments, library, and parks in town. Two Isle of Wight County schools, Windsor High and Windsor Middle, are also nearby to this home.

24129 Johnson Avenue, Isle of Wight - South
1322 Wharf Hill Drive, Isle of Wight - North
$595,840
5 Beds ⋅ 3 Baths ⋅ 10631411 MLS
This Wescott is a 5 bedroom, 3 bath home. This home features a first floor primary along with a first floor laundry room! Home is on a wooded lot with water views. This home features a designer kitchen with upgraded cabinets and countertops along with an oversized island. Upstairs you will find 2 additional bedrooms and a full bathroom.

1322 Wharf Hill Drive, Isle of Wight - North
300 East Street, Smithfield
$400,000
5 Beds ⋅ 3 Baths ⋅ 10615927 MLS
NEW CONSTRUCTION | 5 BEDS | 2,200+ SQ FT Stop dreaming and start packing! This Smithfield gem offers the perfect blend of open-concept design and high-end finishes. THE HIGHLIGHTS: * Open Floor Plan: Modern layout with durable LVP flooring throughout the main level. * Gourmet Kitchen: Soft-close cabinetry, sleek Granite counters, stainless appliances, and a large social island. * Flexible Layout: 5 spacious bedrooms, including a main-floor guest room/office with full bath access. * Suite Life: Primary bedroom features an oversized en-suite with dual vanity and spa-inspired walk-in shower. * Outdoor Living: Enjoy a fully fenced rear yard, perfect for pets, play, or relaxing. * Ultimate Convenience: Dedicated upstairs laundry room saves you the heavy lifting. * Prime Location: Easy access to everything Smithfield. Call TODAY!

300 East Street, Smithfield
LOT11 Fort Huger Dr, Isle of Wight - North
$75,000
10644674 MLS
Beautiful 5.1-acre wooded corner lot in the desirable Rushmere area, offering the perfect setting to build your dream home. Enjoy a peaceful, private location with the convenience of easy access to both Smithfield and the Jamestown Ferry. Situated at the corner of Fort Huger Drive and Lawnes Creek Road, this spacious property provides endless possibilities for your custom home while surrounded by the natural beauty of Isle of Wight County. Don't miss this opportunity to own a beautiful piece of land in a sought-after location!

LOT11 Fort Huger Dr, Isle of Wight - North
12348 Ava Lane, Isle of Wight - South
$602,902
4 Beds ⋅ 3 Baths ⋅ 10629546 MLS
The Caldwell is a ranch-style home with three bedrooms, two full baths, a first-floor primary bedroom with two closets, a convenient pocket office for a dedicated work or study-from-home space, a formal dining room, a spacious family room, and a kitchen with an island and pantry. Options available to personalize this home include an office instead of the formal dining room or bedroom two, a powder room, an additional storage area instead of the pocket office, primary bath options, several kitchen layout options, a covered porch, sunroom, or screen porch options, and an optional second floor with loft, bedroom four and five, and storage options.

12348 Ava Lane, Isle of Wight - South
181 Cedar Crest Drive, Isle of Wight - North
$385,000
4 Beds ⋅ 3.1 Baths ⋅ 10639854 MLS
Resort-style living awaits in the highly sought-after Benns Grant community! This beautifully maintained 3-level end- unit townhome offers 4 bedrooms, 3.5 baths, and a flexible floor plan designed for today's lifestyle. The first level features a private bedroom/flex space with a full bath, great for guests, a home office, or multigenerational living, along with access to the attached 2-car garage. The spacious second level is great for entertaining, showcasing an open-concept layout with a large kitchen, dining area, and inviting living space. Upstairs, you'll find three additional bedrooms, including a spacious primary suite with an en-suite bath and walk-in closet. Enjoy low-maintenance living with community amenities that include a stunning clubhouse with lake views, pool, stocked lakes, playgrounds, scenic walking and biking trails, and access to a beautiful nature preserve. Conveniently located with easy access to both the Peninsula and Southside, shopping, dining, and more.

181 Cedar Crest Drive, Isle of Wight - North
227 Manor Drive, Isle of Wight - North
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10632560 MLS
This beautiful 4 bedroom 2.5-bath home is located in the desirable community of Briarmeade Estates in Carrollton! Higher end finishes throughout including a tankless water heater, contemporary kitchen featuring two-toned cabinets, granite countertops and island with new light fixtures, stainless steel appliances, and a walk-in pantry. The primary bedroom has a stunning ensuite with a double vanity, granite countertops, all glass shower and a spacious soaking tub. Built-in cabinetry in the sunroom and loft convey. The large fully fenced back yard is great for pets & children. Also, it has a sweet Cabana - perfect for entertaining.*Tesla electric car charger in the two-car garage conveys with this home. Close to military bases, shopping, restaurants; Easy access to good schools; and the JRB for quick trips to the Peninsula. OPEN HOUSE SATURDAY MAY 9th from 12-2PM.

227 Manor Drive, Isle of Wight - North
180 Spring Grove Way, Isle of Wight - North
$355,000
3 Beds ⋅ 2.2 Baths ⋅ 10625217 MLS
Welcome to 180 Spring Grove Way, a beautifully maintained three-story townhome in the sought-after Benns Grant community of Smithfield—just minutes from the new Riverside Smithfield Hospital. This spacious home offers the ideal blend of modern design and comfortable living. The main level features an open-concept layout seamlessly connecting the kitchen, dining, and living areas — works well for entertaining or everyday living. With 3 bedrooms and nicely sized closets, it allows for flexibility of use. Let's not forget the first level bonus space that can be used for workout space, or media room. And yes, the land adjacent to the home comes with the property! Residents of Benns Grant enjoy beautifully maintained surroundings, walking trails, and convenient access to shopping, dining, and major routes. The county is planning a new building for the elementary school just a short distance away! Moving into the area, this home is located within commuting distance of several military bases and government installations!

180 Spring Grove Way, Isle of Wight - North
2158 Mainsail Drive, Isle of Wight - North
$479,975
3 Beds ⋅ 2 Baths ⋅ 10622947 MLS
PALLADIO RANCH. SOLD. TBB.

2158 Mainsail Drive, Isle of Wight - North
216 Monticello Court, Smithfield
$360,000
4 Beds ⋅ 2.1 Baths ⋅ 10638252 MLS
WELCOME TO THIS IMMACULATE 4 BEDROOM, 2 1/2 BATHROOM TOWNHOME WITH 2,124 SQUARE FET OF LIVING SPACE. THIS HOME PAIRS MODERN COMFORT WITH LOW MAINTENANCE LIVING. FEATURING AN ATTACHED GARAGE, A BRIGHT OPEN CONCEPT LAYOUT , A BEAUTIFUL FENCED BACKYARD AND A PRIME LOCATION NEAR LOCAL AMENITIES. CALL TODAY TO SCHEDULE YOUR TOUR!

216 Monticello Court, Smithfield
121 Alexandria Way, Isle of Wight - North
$706,000
4 Beds ⋅ 3.1 Baths ⋅ 10641566 MLS
Beautifully maintained home in the highly sought after community of Founders Pointe, offering modern design, spacious living areas and a comfortable layout with a first floor office and a butlers pantry . The open-concept main level creates an inviting atmosphere for daily living and entertaining, while the upper level provides generous sized bedrooms and a relaxing primary suite. With a spacious yard with recently done concrete patio and fire-pit to add fun to your outdoor activities. The driveway recently expanded, ideal for your guests! The community pool was recently fully re done as well as the entire pier! live in a community that feels like vacation!

121 Alexandria Way, Isle of Wight - North
8 Ventnor View, Smithfield
$717,000
4 Beds ⋅ 3 Baths ⋅ 10639175 MLS
Escape to your own private waterfront sanctuary! Nestled on a sprawling 2.17-acre lot in the desirable Carisbrooke community, this stunning 4-bedroom, 3-bathroom transitional home offers the perfect blend of coastal serenity and functional living. Inside, you'll find over 2,900 square feet of inviting space designed for both comfort and entertaining. The thoughtful layout features gorgeous hardwood floors throughout much of the main level and a cozy sunroom that serves as the perfect spot to enjoy the view. The spacious primary suite offers a true retreat, complete with a jetted tub for ultimate relaxation. The exterior is a nature lover's dream, offering sweeping marsh with water views and the peaceful river breeze. Relax on the expansive deck, host summer gatherings in the gazebo, or utilize the additional storage shed for all your outdoor gear. Don't miss this rare opportunity to own a piece of Carrollton's waterfront paradise. Schedule your private tour today! Some photos virtually staged.

8 Ventnor View, Smithfield
415 Tributary Lane, Isle of Wight - North
$434,520
3 Beds ⋅ 2 Baths ⋅ 10620088 MLS
BRAMANTE RANCH. SOLD. TBB.

415 Tributary Lane, Isle of Wight - North
107 Oxford Avenue, Smithfield
$405,000
4 Beds ⋅ 3 Baths ⋅ 10642407 MLS
Why Build? This stunning villa in Church Square is one of the largest units this community has to offer & is ready for you to move in today. With a charming sunroom, soaring vaulted ceilings, a cozy gas fireplace, swing on the patio, all appliances included, & a whole-home generator— this is turnkey with a few extras. The large eat-in kitchen, with breakfast bar & island, plus open floor plan & two private patios, make everyday living & entertaining effortless. Upstairs, 2 oversized bedrooms share a thoughtfully designed bath with separate individual vanities. Perched with gorgeous views overlooking the clubhouse, you'll have front-row access to a lifestyle most people only dream of: resort-style pool & sundeck, fully-equipped fitness center, catering kitchen for hosting in style, outdoor fireplace, & grilling station made for warm evenings with neighbors. Just minutes from the boutique shops, charming eateries, & picturesque waterfront parks of historic downtown Smithfield.

107 Oxford Avenue, Smithfield
23492 Sugar Hill Road, Isle of Wight - North
$75,000
3 Beds ⋅ 1 Baths ⋅ 10636474 MLS
CONTRACT ACCEPTED, NO SHOWINGS. Do NOT approach this home - Sellers do NOT want anyone visiting the home and will contact the police if anyone approaches the house!!!

23492 Sugar Hill Road, Isle of Wight - North
17403 Carroll Bridge Road, Isle of Wight - North
$549,000
4 Beds ⋅ 3.1 Baths ⋅ 10640852 MLS
Looking for the serenity and privacy of country living with the convenience and amenities of the suburbs? Look no further! This home boasts 1.94 acres, but is only minutes from Historical Downtown Smithfield's restaurants and shopping. Step inside and you will notice an open floor plan and a large eat in kitchen which are perfect for entertaining. The entire 2nd floor consists of a spacious bedroom, expansive walk in closet and a full bath. Your backyard offers endless possibilities with a deck, above ground pool, storage shed, and plenty of wide open space to make it your own. Schedule your showing today!

17403 Carroll Bridge Road, Isle of Wight - North
14151 Foursquare Road, Isle of Wight - North
$645,000
3 Beds ⋅ 2 Baths ⋅ 10640048 MLS
Escape to your own private retreat with this unique wooded property offering peace, privacy, and endless possibilities. The home features spacious first-floor living, a large primary suite with sitting area, expansive kitchen, wood-burning fireplace, and a beautiful atrium with a water feature. Outside, enjoy a detached two-car garage with bonus rooms, a barn with stalls, paddocks, and fenced pasture, plus open fields, trails, streams, and abundant wildlife. All of this is conveniently located just minutes from Historic Smithfield, shopping, dining, and the marina.

14151 Foursquare Road, Isle of Wight - North
203 Winterberry Lane, Smithfield
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10625828 MLS
You are going to love the open and airy feel of this unique home located in the award winning community of Gatling Pointe. A formal dining room has beautiful hardwood floors and elegant trim. The living room can be a home office or music area. The kitchen is open to the family room across the back of the home. Lots of glass lets in plenty of light. Family room has a gas log fireplace and soaring ceilings. A walk out bay window at the kitchen eat in area provides a view of the nicely landscaped yard. The primary bedroom features a tray ceiling and has a five piece bath attached. Three more generous bedrooms all have great closet space. There is plenty of storage with a two car garage and pull down attic. This home is near the yacht club which is a great place to make new friends.

203 Winterberry Lane, Smithfield
103 Chrisfield Circle, Isle of Wight - North
$480,000
3 Beds ⋅ 3 Baths ⋅ 10643195 MLS
Beautiful brick 3 bedroom, 3 bath with warm wood accents. Peaceful neighborhood, with over an acre, on a cul-de-sac, that is minutes from historic downtown Smithfield. Enjoy the sunsets on the front porch. Beautiful hardwood floors in the living room with cathedral ceilings and skylights and a gas fireplace. There is a dining room and a formal living room or office. Updated kitchen with stainless steel appliances and granite counters and pocket doors. Room over garage could be used for 4th bedroom, man cave, or game room. Primary bedroom has walk in closet and quartz double vanity.. Deck has built-in seating to enjoy the wooded views. Detached 20'x12' workshop is powered, with attic space for extra storage. There is plenty of parking, even for a boat or RV. 40A hookup for RV. Whole house generator. No HOA.

103 Chrisfield Circle, Isle of Wight - North
244 Grandville Arch, Smithfield
$513,999
6 Beds ⋅ 3 Baths ⋅ 10641813 MLS
Smithfield 6 bedroom home with 3 full bathrooms. Outside features a fenced backyard, large deck, storage shed, and fire pit. Solar panels reduce utility cost. Located in the pleasant neighborhood of Wellington Estates. Welcome home!

244 Grandville Arch, Smithfield
13177 Harbor Drive, Isle of Wight - North
$505,000
4 Beds ⋅ 2.1 Baths ⋅ 10640950 MLS
Welcome to life in Eagle Harbor—one of Carrollton’s most loved community developments, known for its resort-style amenities, neighborhood feel, and easy everyday living. This warm and inviting home offers comfortable living spaces, a cozy gas fireplace, formal dining room, and a great flow for both everyday life and entertaining. The expansive primary suite is filled with natural light and features two oversized walk-in closets plus a spa-like ensuite with soaking tub, separate shower, double vanity, and linen closet. Three additional bedrooms and a versatile loft offer space for an office, playroom, media room, or second lounge. Out back, enjoy a fully fenced yard and multi-level deck overlooking a protected nature preserve for added privacy and tranquility. New HVAC 2026 and new LVP in kitchen and living room 2026. Enjoy Eagle Harbor’s pool, trails, recreation areas, and amenities. Some photos virtually staged.

13177 Harbor Drive, Isle of Wight - North
132 Riley Way, Isle of Wight - North
$350,000
3 Beds ⋅ 2.1 Baths ⋅ 10638563 MLS
PRICE JUST REDUCED!! OPEN HOUSE SATURDAY JUNE 27, 1PM-3PM. Why wait for a "new build" when you can move into a home just a few years old? The Calvert Model has an open floorplan. This 3 bedroom home has a modern chefs kitchen W/all appliances, granite counters & ample room to store all your culinary gear. An open dining room/family room will accommodate room for those get togethers & holiday gatherings. Off the family room a door leads to the outdoor patio for good times overlooking the community lake. A spacious 1st floor primary bedroom, an on-suite w/double sink vanities, stall shower & a large walk-in closet. Laundry Upstairs you will find two more spacious bedrooms w/ a shared hall bathroom & tub/shower. There are sidewalks for your daily exercise, playgrounds, clubhouse, or enjoy a day at the pool! The yards are maintained by the association. Close proximity to shopping, schools, interstate & more! Some photos may be virtually enhanced or staged to highlight features. Call today to see!

132 Riley Way, Isle of Wight - North
703 Marsh Elder Trail, Isle of Wight - North
$225,000
2 Beds ⋅ 2 Baths ⋅ 10624238 MLS
Consider this 2BR/2BA condo for location, style, and comfort. Close to major hubs including the JR bridge, and Suffolk area. Full kitchen appliance pkg. Walk in tub/shower. See this one today.

703 Marsh Elder Trail, Isle of Wight - North
31397 Lelia Lane, Isle of Wight - South
$219,800
3 Beds ⋅ 2 Baths ⋅ 10641867 MLS
Country Living with Endless Potential! Nestled in a rural setting, this single-story mobile home offers the perfect opportunity for homeowners looking to create their own country retreat. Situated on a spacious lot surrounded by open skies and natural beauty, this property provides a little privacy, tranquility, and room to grow. Inside, you’ll find a functional floor plan ready for your personal touches and updates. Whether you’re looking for a starter home, rental investment, or weekend getaway, this property presents endless possibilities to make it your own. Enjoy the freedom of rural living with outdoor space for gardening, hobbies, pets, recreational vehicles, or future improvements. If you’ve been searching for an affordable property with character, space, and unlimited potential, this is an opportunity you won’t want to miss. Schedule your showing today and imagine the possibilities!

31397 Lelia Lane, Isle of Wight - South

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.