Refine Search
Map
Sort by
23082 Retreat Lane, Isle of Wight - North
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10630239 MLS
Elegant Craftsman Condo in Premier 55+ community- packed with Amenities! . Head inside to luxury LPV flooring on the 1st floor enhancing both beauty and durability. A spacious open floor plan seamlessly flows into a screened in back porch/sunroom, great for coffee and morning relaxation. Showstopping kitchen featuring quartz countertops and designer backsplash - a chef's delight with a large center island for entertaining. Upstairs, spacious bedrooms offer ample storage and privacy, while the first floor primary suite includes a well-appointed en suite bath including dual sinks, walk-in closet, tray ceilings and a great view of a wooded backyard. Beyond the home, the neighborhood offers an unmatched lifestyle. Residents enjoy access to resort-style heated pools, hot tubs, clubhouse, shuffleboard, tennis courts, pickleball, and even a koi pond for tranquil moments.

23082 Retreat Lane, Isle of Wight - North
177 Spring Grove Way, Isle of Wight - North
$385,000
4 Beds ⋅ 3.1 Baths ⋅ 10618577 MLS
Awesome 4BR, 3.5 Baths over 2000 Sq Ft. Benns Grant is a great community! Explore lakes, pools, walking trails, clubhouse! You will love the open concept gourmet kitchen, dining and living space. Huge master bedroom with walk in closets. Master bathroom has dual vanities with separate tub and shower. This is a must see!

177 Spring Grove Way, Isle of Wight - North
10176 Bank Street, Isle of Wight - South
$384,999
3 Beds ⋅ 2 Baths ⋅ 10624837 MLS
New construction with premium upgrades by an award-winning builder—move-in ready and built to impress! This modern home offers spacious open living, upgraded LVP flooring, elegant granite countertops, and upgraded cabinetry throughout. A designer lighting package enhances the bright, airy feel of every room. Step outside to a large fenced backyard, ideal for entertaining, or play. Conveniently located with quick access to Route 460, and just minutes from shopping, dining, and commuter routes. Don’t miss this opportunity to own a new construction home in Hampton Roads with high-end finishes and exceptional convenience.

10176 Bank Street, Isle of Wight - South
53 Pine Lane, Isle of Wight - South
$384,900
3 Beds ⋅ 2 Baths ⋅ 10627003 MLS
Sprawling brick ranch in the heart of Windsor sits on .91 AC! Lots of privacy! Convenient to town yet tucked away on a quiet st with no thru traffic. Home has insulated tilt windows, arch shingle roof, thermal sheet insul of entire attic, lg bedrooms, sprawling rear yard to incl wooded areas, central vac, sec sys, whole house attic fan & more. Easy to show! Wood burning fireplace works well but conveys AS-IS. 3 sheds in rear yard. Lg white shed has 100 amp panel, TV & mini fridge that convey!

53 Pine Lane, Isle of Wight - South
3290 Poplar Drive, Isle of Wight - North
$384,000
3 Beds ⋅ 2 Baths ⋅ 10639234 MLS
Welcome home to this charming ranch-style retreat offering 3 bedrooms and 2 full baths, designed for comfortable everyday living. Filled with abundant natural light, the inviting interior creates a warm and welcoming atmosphere throughout. Come outside to enjoy the expansive covered patio, perfect for entertaining guests or relaxing with your morning coffee. The backyard is your own private oasis, featuring a hot tub and above-ground swimming pool—ideal for enjoying summer days and peaceful evenings. With its functional layout and exceptional outdoor amenities, this home is ready for you to move in and make lasting memories. Optional Community Assoc w/ boat ramp, beach access & parking for $35.00 per year!!

3290 Poplar Drive, Isle of Wight - North
2098 Striper Court, Isle of Wight - North
$383,130
3 Beds ⋅ 2.1 Baths ⋅ 10618522 MLS
CAROLINE. SOLD. TBB.

2098 Striper Court, Isle of Wight - North
17155 Riddick Road, Isle of Wight - North
$380,000
3 Beds ⋅ 2 Baths ⋅ 10642039 MLS
Welcome home to peaceful country living on a beautiful 1-acre lot in Smithfield! This immaculate ranch offers the perfect blend of comfort and privacy with a serene wooded backdrop. Inside, you'll find durable LVP flooring throughout and an open, inviting layout filled with abundant natural light. The updated kitchen features quartz countertops, stainless steel appliances, and plenty of space for cooking and gathering. A brand-new roof provides added peace of mind. Step outside to enjoy the spacious yard with plenty of room for gardening, recreation, or simply relaxing, plus a storage shed for all your tools and outdoor equipment. Outdoor enthusiasts will appreciate the dedicated area currently set up as a private gun range. If you're looking for a move-in ready home with room to spread out without sacrificing convenience, this one is a must-see! It is just minutes from major highways, shopping, dining, and local attractions.

17155 Riddick Road, Isle of Wight - North
9269 Whispering Pines Trail, Isle of Wight - South
$380,000
3 Beds ⋅ 2 Baths ⋅ 10641944 MLS
Hunter's paradise on 5.93 private acres! Zoned Rural Residential, this peaceful property offers the perfect blend of privacy, comfort, and country living. Surrounded by abundant wildlife, it's an ideal retreat for hunters, nature lovers, or anyone looking to escape the hustle and bustle. Enjoy your morning coffee on the full-length front porch while watching deer, birds, and other wildlife. The approximately 1-acre fenced yard is perfect for pets, gardening, or outdoor activities. A detached garage/workshop with upper-level storage provides plenty of room for projects, equipment, or recreational gear. Chickens and horses are welcome, making this property well-suited for a rural lifestyle. The nearly 1,500-square-foot ranch features an open-concept living and dining area with vaulted ceilings and a centrally located wood stove, creating a warm and inviting gathering space. Ceiling fans throughout add year-round comfort. The spacious kitchen includes granite countertops, a pantry, and ample cabinet and counter space. Down the hall are three bedrooms, including a first-floor primary suite with a private bath featuring a relaxing jetted tub. Additional features include a 27.5 kW automatic whole-house generator, providing dependable backup power for added peace of mind. If you've been searching for acreage, privacy, abundant wildlife, and the comforts of country living, this exceptional property is ready to welcome you home.

9269 Whispering Pines Trail, Isle of Wight - South
1107 Breakwater Trail, Isle of Wight - North
$379,990
3 Beds ⋅ 2.1 Baths ⋅ 10613852 MLS
Ready in April- This new construction end unit home has started and embellished to feel just like the decorated model. 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. Your New home features nearly 1,800 sq ft of open living space, including a luxurious main-level owner’s suite included with dual vanities, dual shower head walk-in shower with seat. The gourmet kitchen showcases a 10-foot quartz island that flows into the great room with LVP and dining area. Coffee and conversation on your included back 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. Schedule your tour today.

1107 Breakwater Trail, Isle of Wight - North
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
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
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
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
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
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
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
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
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
1147 Breakwater Trail, Isle of Wight - North
$363,275
3 Beds ⋅ 2.1 Baths ⋅ 10612303 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. ALL APPLIANCES INCLUDED THROUGH 12/15/25.

1147 Breakwater Trail, Isle of Wight - North
2085 Striper Court, Isle of Wight - North
$361,740
3 Beds ⋅ 2.1 Baths ⋅ 10621515 MLS
This beautiful home is an end unit and backs up to a serine pond view! 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 floorplan features 1,775 sq ft of open living space, including a luxurious main-level owner’s suite with dual vanities, 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 large storage room. Ready to experience South Harbor Towns? Schedule your tour today.

2085 Striper Court, Isle of Wight - North
1123 Breakwater Trail, Isle of Wight - North
$361,435
3 Beds ⋅ 2.1 Baths ⋅ 10609863 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.

1123 Breakwater Trail, Isle of Wight - North
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
12050 Greenbrier Lane, Smithfield
$360,000
4 Beds ⋅ 2 Baths ⋅ 10639062 MLS
This fully renovated rancher offers privacy, comfort, and peace of mind with major updates including a new roof 2026, brand new HVAC and electrical panel and brand new windows. Inside, brand new LVP floors, welcoming atmosphere, complemented by a timeless neutral color palette. The primary suite with a spacious closet, and a beautifully fully renovated bathroom. Three additional bedrooms and a full hall bath. 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.

12050 Greenbrier Lane, 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.