You are viewing all listings Homes between $250000 and $500000 dollars.
Under Contract
$349,900 $234 per sq.ft. Westmoreland NH Home »
2 Beds | 2 Baths | Total Sq. Ft. 1494 | Acres: 2Listed on Friday Jul 3, 2026
Description: Opportunity awaits in desirable Westmoreland, NH! Set on a picturesque 2-acre lot with westerly exposure, this 1,430-square-foot ranch offers beautiful sunset views along with the perfect blend of location, value, and potential. Conveniently located between Keene and Walpole, this home features built-in shelving in many rooms and custom cabinetry in many areas, a spacious bonus room over the garage provides endless possibilities create a home office, family room, guest space, or convert it into a private primary suite, two bedrooms, 1.5 baths, hardwood floors, vinyl siding, a durable standing seam metal roof, and a one-car garage under. While some cosmetic updates will enhance the home, its solid construction, desirable setting, and flexible floor plan make it a worthwhile investment. Bring your vision and make this property your own in one of Cheshire County's most sought-after communities! More pictures to come in the near future. Showings will begin at open house on 7/11/26 10am to 12pm & 7/12/26 11am to 1pm. See Listing Details & 17 images.
Under Contract
$499,000 $287 per sq.ft. Westmoreland NH Home »
3 Beds | 2 Baths | Total Sq. Ft. 1740 | Acres: 12.44Listed on Tuesday Jun 9, 2026
Description: Tucked away on approximately 12.44 +/- private acres in one of New Hampshire's most picturesque towns, this lovingly maintained custom-built home offers a rare opportunity to embrace the lifestyle you've always imagined. Thoughtfully designed to celebrate nature, gardening, and year-round beauty, every corner of this property reflects a deep appreciation for the land it occupies. Awaken each morning to the soothing sounds of the stream flowing behind the home as sunlight filters through the trees. Step directly from the primary bedroom onto your private deck overlooking the water, coffee in hand, and begin your day surrounded by the sights and sounds of nature. Inside, abundant natural light and inviting living spaces create the perfect environment for thriving houseplants, while established gardens outdoors provide endless opportunities for those with a passion for cultivating beauty. Currently configured as a two-family residence, the home offers exceptional flexibility for today's lifestyles. Continue using it as an income-producing property, create a private space for multi-generational living, accommodate a live-in caretaker, or easily convert it back to a spacious single-family home. Adding to the property's unique appeal, the Cheshire Rail Trail abuts the property, offering direct access to miles of scenic recreation right from your backyard. With ample acreage, complete privacy, and room to expand, the possibilities are limited only by your imagination. Rich in history and New England charm, Westmoreland provides the backdrop for a life well lived. Whether you're seeking a peaceful retreat, a homestead, a family compound, or simply a place to put down roots, this remarkable property invites you to write the next chapter of your story here. This is more than a home--it's a lifestyle. And it just may check every box, including the ones you didn't even know you had. See Listing Details & 56 images.
$299,000 $399 per sq.ft. Weston VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 750 | Acres: 0.61Listed on Monday Nov 10, 2025
Description: This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally owned shops. Enjoy easy access to nearby ski areas, including Bromley, Magic, Okemo and Stratton as well as the scenic town green, and all that this vibrant village has to offer. Weston is a short drive to Manchester Center for outlet shopping and dining as well as other outdoor activities including hiking, horseback riding and tubing on the Battenkill. The current owners have installed a new electrical panel, new flooring with the exception of the kitchen and updated the bathroom. Whether you're seeking a year-round residence or a weekend getaway, this charming Weston cottage provides the perfect blend of history, convenience, and small-town beauty. See Listing Details & 36 images.
$465,000 $323 per sq.ft. Weston VT Home »
Waterfront on Pond _Unnamed2 Beds | 2 Baths | Total Sq. Ft. 1440 | Acres: 10.5
Listed on Wednesday Jul 1, 2026
Description: This Weston gem, expanded and rebuilt by the seller in 2003, has been loved and cared for and is now ready for its next lucky owner. Set on a south facing hill on a quiet country road, it promises sunlight and mountain views all year long. Protected on 10 wooded acres, it borders the National Forest while benefitting from a rolling lawn, small pond and decorative gardens. Designed for one floor living, the home has a surprising amount of space, from the open concept kitchen, dining room and living room with wood burning fireplace to the 2 bedrooms and baths, a year round sunroom with wet bar, and a home office. A welcoming mudroom, a large front deck with a retractable awning, and a lower level garage and abundant basement storage complete the picture. Suitable for year-round living yet easily maintained for seasonal use, the property is convenient to the vibrant village of Weston with its Vermont Country Store, Weston Theater, and fine cafes, and a short drive to Okemo, Bromley, Magic and Stratton. Hike the back roads and hills, enjoy recreation at nearby Hapgood Pond, Lowell Lake, and the Weston Recreation Area, then return to relax in your cozy Green Mountain retreat. The house is empty; select photos have been virtually staged. Property being sold "As Is." See Listing Details & 36 images. Includes a Virtual Tour
New Listing!
$475,000 $353 per sq.ft. Weston VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1344 | Acres: 1.3Listed on Wednesday Jul 29, 2026
Description: Find your new home in the heart of Weston, VT with this inviting and comfortable three-bedroom home with one-level living in one of southern Vermont's prettiest small villages. From your entrance into the house by way of the new mudroom and entry area, you'll find a small but highly-functional layout with an eat-in kitchen offering tons of cabinets and storage, a spacious sun-filled living room, and the bedrooms and full bath off the rear hall. During the warmer months, the long, wide, covered side porch is the perfect place to unwind with your morning coffee, cocktails, summer dining, or relaxing with friends after a day well spent. A full, unfinished basement with laundry and mechanicals offers space for storage or could be finished for additional living space. Outside, enjoy the beautifully maintained grounds with stunning stonework including the large stone fire pit with stone benches and seating for outside gatherings. Located just a few hundred yards from the beautiful Weston Village Green, you'll enjoy easy access to the renowned Weston Theater Company, local shops, several great restaurants, and the newly rebuilt and expanded Wilder Memorial Library. Mere minutes away, the town of Londonderry offers a popular seasonal farmers market, grocery shopping, dining, and everyday conveniences and Ludlow, Chester and Manchester are 15-30 minutes' drive. Spend winters skiing and riding at Magic Mountain, Bromley, Stratton, Okemo, or Viking Nordic Center - all approximately 20 to 30 minutes away - and summer months will bring endless opportunities for hiking, mountain biking, kayaking, fishing, golf, and more as you explore Weston and the Green Mountain State. Whether you're seeking a primary residence, a second home, or a four-season Vermont retreat, this well-maintained Weston property offers an exceptional combination of village convenience, comfortable one-level living, and easy access to everything that makes southern Vermont such a special place to call home. See Listing Details & 40 images. Includes a Virtual Tour
Under Contract
$325,000 $147 per sq.ft. Weybridge VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2214 | Acres: 1.5Listed on Tuesday Jul 14, 2026
Description: Located at the end of the road, an affordable home with a welcoming front porch and garage awaits. Wood floors in the living areas and a propane stove in the living room for chilly nights. A first-floor office could serve as a bedroom, and a bath with laundry is convenient. Upstairs are four bedrooms and two bathrooms. The one-car garage is extra deep, with a back space for great storage. Located just 4.5 miles from downtown Middlebury for all of the conveniences of town. Close to the trail around Middlebury for great walking and biking trails. Being sold as is. Offer deadline is Friday, July 17th at 3pm. See Listing Details & 32 images.
$275,000 $182 per sq.ft. Wheelock VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 2234 | Acres: 2.43Listed on Thursday Jun 11, 2026
Description: This versatile property offers the perfect blend of comfort, recreation, and room to roam. Whether you're searching for a year-round residence, a Vermont getaway, or a basecamp for outdoor adventures, you'll appreciate the easy access to VAST and VASA trails and the abundance of space for all your gear and hobbies. The main level features a bright, open-concept layout centered around an updated kitchen with modern countertops, a stylish tile backsplash, open shelving, and newer appliances. Just beyond, the sunroom provides a welcoming space to relax and leads directly to the back deck--perfect for summer barbecues, entertaining, or simply taking in the peaceful surroundings. The spacious primary bedroom includes a large walk-in closet, direct access to the full bath, and a cozy sitting area near the back entry. The mostly finished walk-out lower level offers excellent flexibility with multiple bonus rooms, a laundry area, and a utility room with extensive built-in storage. Storage and workspace are abundant. In addition to the garage under the home, the detached barn/garage features two bays, workshop space, and a large overhead storage area. A separate four-bay enclosed pole barn provides even more room for vehicles, recreational equipment, tools, and projects. Outside, you'll find open yard space, room for gardens, and a charming hilltop pond that adds to the property's peaceful setting. Combining thoughtful updates, exceptional storage, and endless possibilities both indoors and out, this Wheelock property is ready for its next chapter. See Listing Details & 41 images.
$299,000 $117 per sq.ft. Wheelock VT Home »
Waterfront on River Miller Run4 Beds | 3 Baths | Total Sq. Ft. 2559 | Acres: 4
Listed on Tuesday May 5, 2026
Description: This lush and level four acre compound along Miller's Run River in Wheelock has more going for it than most properties twice the size. The 2020 Commodore mobile home is the primary residence, with serious mudroom and bedroom additions built for the way Vermonters actually live. With 3 bedrooms and 2 full bathrooms the home feels spacious and full of natural light. Next door a one bedroom guesthouse handles family and friends, or generates rental income with ease. Both homes come simply and elegantly furnished. The newly built 17x32 barn is ready for equipment, livestock, or whatever the next owner has in mind. The insulated 20x42 Quonset hut has power, water, and has previously seen commercial use as a take-out restaurant. Permits are also in place for a third dwelling utilizing existing water and septic. And then there's Miller's Run itself, bordering the entire property with a small rocky cascade before pooling into a deep cold swimming hole that will be the centerpiece of every summer. See Listing Details & 60 images.
$355,000 $192 per sq.ft. Wheelock VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 2632 | Acres: 10.5Listed on Friday Jul 10, 2026
Description: Nestled on just over 10 wooded acres with old logging roads ideal for walking and exploring, this Saltbox-style home offers the privacy and space you have been seeking. Relax in the three-season sun porch. Inside, you'll find a mudroom, spacious living room, and an open-concept kitchen, dining room, and family room with a cozy wood stove; perfect for entertaining and gathering with family and friends year round. Directly off of the dining room area, step onto your back deck to unwind; views of Burke Mountain and Bald Hill Mountain during the spring and winter. The first floor also features a full bathroom with convenient laundry. Upstairs are two generously sized bedrooms, including one that was previously configured as two bedrooms, offering the potential to recreate back into a two bedroom if desired. The full, partially finished walk-out basement includes two bonus rooms and direct access to the one-car under garage. Outside, the property is well-equipped for hobbies, storage, or a home-based business with a 30' x 60' workshop with electricity, additional outbuilding with electricity, and a storage trailer. Wheelock residents enjoy the exceptional benefit of tuition-free attendance at Dartmouth once accepted. Conveniently located minutes from Vermont State University, Burke Mountain, Kingdom Trails and even closer to I-91N/I-91S for ease of commuting and everyday amenities in Lyndon, all while still enjoying the peace and privacy of country living. Property being sold in "as-is" condition. Some fixes/upgrades needed. Tenant occupied; 48 hours notice. Assisted showings. See Listing Details & 58 images.
$299,000 $277 per sq.ft. Whitingham VT Home »
Price Change! Reduced by $13,900 down 5% on July 8th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1080 | Acres: 4
Listed on Tuesday May 26, 2026
Description: Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary bedroom, 2 guest bedrooms, and a half bath. There is a full unfinished basement with great storage space, laundry, and a full walkup staircase. A tremendous primary home or Vermont retreat. See Listing Details & 17 images.
Under Contract
$299,000 $230 per sq.ft. Whitingham VT Home »
Price Change! Reduced by $41,000 down 14% on July 1st 2026
2 Beds | 1 Baths | Total Sq. Ft. 1300 | Acres: 3.33
Listed on Monday Jun 15, 2026
Description: Escape to the beauty of Southern Vermont with this newly built chalet, offering comfort, flexibility, and year-round recreation. Situated just minutes from Lake Sadawga and Town Hill Park, this property is ideal as a full-time residence, vacation home, or investment getaway. The well and septic system were installed in Spring 2026, providing peace of mind and a strong foundation for future enjoyment. The interior is ready for your personal touch, with the opportunity to build a kitchen tailored to your lifestyle or utilize the thoughtfully designed kitchen plans already created by the builder. Enjoy the warmth and charm of chalet-style living, surrounded by the natural beauty of the area and endless outdoor activities throughout every season. Whether you're boating, fishing, hiking, snowmobiling, skiing, or simply relaxing in a peaceful setting, this property offers something for everyone. Being sold partially furnished, this move-in-ready retreat allows you to start enjoying Vermont living right away while adding your own finishing touches. A rare opportunity to own a newly constructed getaway with major infrastructure already in place and the flexibility to make it uniquely yours. See Listing Details & 26 images.
$319,000 $173 per sq.ft. Whitingham VT Home »
Price Change! Reduced by $56,000 down 18% on July 28th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1840 | Acres: 1
Listed on Monday Aug 25, 2025
Description: Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway. The welcoming lower level features three comfortable bedrooms, a spacious full bath with a jetted soaking tub, tiled floors, and a glass-enclosed shower, along with a convenient utility room. Upstairs, abundant natural light fills the open-concept living area where the kitchen, dining, and living spaces flow seamlessly together. A cozy wood-burning fireplace creates the perfect gathering place after a day of skiing, hiking, snowmobiling, or exploring the surrounding lakes and trails. A second full bath on the main level adds convenience for both everyday living and entertaining guests. Step outside to enjoy multiple outdoor living spaces, including a sunny second-floor deck, covered patio, established perennial gardens, and a storage shed. The mostly open lot offers space to relax, entertain, and enjoy the peaceful surroundings. Ideally located just 8 minutes from Jacksonville Village, 10 minutes from Harriman Reservoir (Lake Whitingham), 8 minutes from Lake Sadawga, and 17 minutes from Wilmington, this property provides convenient access to some of Southern Vermont's most sought-after recreation destinations. Enjoy skiing at Mount Snow and Berkshire East, boating and fishing on nearby lakes, hiking the Catamount Trail, paddling the Deerfield River, and exploring the VAST snowmobile trail network. With high-speed fiber internet available and all furnishings included, this distinctive home offers the perfect combination of comfort, character, and year-round adventure. Whether you're seeking a mountain getaway, recreational base camp, investment opportunity, or full-time residence, this turnkey Vermont property is ready to enjoy from day one. See Listing Details & 58 images.
$324,000 Whitingham VT Home »
Price Change! Reduced by $145,000 down 45% on July 19th 2026
4 Beds | 2 Baths | Total Sq. Ft. 0 | Acres: 10.9
Listed on Monday Jul 21, 2025
Description: New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels. Planned for a stone fireplace. Prepped for decks on the east and west sides of the House. Septic plan is designed by a Vermont Licensed Engineer to be built, area is cleared for the system. There is Timber on the property estimated at 15,000 board feet of volume. Close to Wilmington and Dover, Lake Whitingham, Burrington Brook. Deerfield River, North River, Burrington Brook, Haystack Club Golf and Ski and Mount Snow Resort. See Listing Details & 12 images.
$349,000 $149 per sq.ft. Whitingham VT Home »
Price Change! Reduced by $31,000 down 9% on July 15th 2026
5 Beds | 3 Baths | Total Sq. Ft. 2336 | Acres: 12.8
Listed on Tuesday Feb 3, 2026
Description: Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat, ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property's timeless rural appeal. See Listing Details & 57 images. Includes a Virtual Tour
Under Contract
$349,000 $134 per sq.ft. Whitingham VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2596 | Acres: 1Listed on Tuesday May 26, 2026
Description: This charming chalet on one acre is surrounded by enchanting gardens, with a peaceful stream providing a soothing natural backdrop. Over the years, the seller has lovingly planted thousands of daffodils and day lilies, along with a beautiful mix of perennials, annuals, flowering shrubs, and potted plants that line the walkways, gazebo, and hillside below the home. The original chalet has been expanded with two substantial additions, creating a flexible floor plan featuring a spacious main-level living room with a woodstove and a private primary bedroom or study above, plus a separate dining nook (good for expanding the kitchen). Enter through the welcoming kitchen and dining area, where oak flooring and a wood-burning fireplace create warmth and character. Glass patio doors fill the space with natural light and open to an expansive deck overlooking the lush gardens--an ideal setting for relaxing or entertaining. Located on a town-maintained gravel road, Chapel Hill Road is home to a mix of year-round residences and vacation getaways. Enjoy nearby Lake Sadawga for kayaking, canoeing, and fishing, or head to Lake Whitingham for swimming, sailing, waterskiing, and more. Conveniently located within easy driving distance of MASS MoCA. See Listing Details & 30 images.
