You are viewing all listings Homes between $250000 and $500000 dollars.
Under Contract
$425,000 $345 per sq.ft. Winchester NH Home »
1 Beds | 2 Baths | Total Sq. Ft. 1232 | Acres: 7.53Listed on Tuesday Jun 9, 2026
Description: 2007 EXPANDABLE CAPE! A lovely, lovely home to begin with, plus the entire 2nd floor open to expansion, already plumbed and wired with layout for 2BR's and full bath with full shed dormer. On 7.5 acres with privacy and views to distant hills, you will not want to leave this serene home. It is a sanctuary. Plenty of wildlife viewing in your front yard. Inside is a welcoming single level layout with 2 baths, open concept LR/DR/KIT area and a main bedroom with walk-in closet. Hickory cabinetry in the cooks kitchen with a Viking gas range anchoring the space is ready for all your cooking adventures. A walk-in pantry makes meal prep easy and has plenty of room for canned goods and your seldom used appliances. The full basement is high and dry with ample room for workshop, family room or storage. There really is nothing not to like about this home! Close to state park, snow mobile and walking trails. See Listing Details & 31 images.
$425,000 $329 per sq.ft. Winchester NH Home »
Price Change! Reduced by $25,000 down 6% on July 4th 2026
199 Ft. of Waterfront on River Ashuelot River
1 Beds | 1 Baths | Total Sq. Ft. 1290 | Acres: 1.5
Listed on Tuesday Jun 16, 2026
Description: Presently a contractor who has experience with caring for log homes is applying a special power wash to the main home here. Are you a company boss, family or a fun loving person or one who just wants to relax and enjoy your own RIVERFRONT? These 2 buildings & the open yard can provide room for MANY to stay overnight & enjoy dinners & indoor & outdoor fun. You have been putting in key words as you search for a special property. "log home, my own river waterfront, kayaking, fishing, privacy, guest house or art studio, garage, garden areas, nearby hiking and snowmobiling,year round fun" ...Well here you are! This delightful log home has an open concept first floor with many windows to the yard , beautiful pine floors, a spacious bathroom with a large shower a large bedroom on the second floor. the water view side of the first floor could be enclosed for a bedroom. It has BBHW oil heat. NH Fish and Game stocks the river with fish. Close by are hiking and snowmobile trails (Ashuelot) bridge . Pisgah Park is nearby. You can kayak to Town from your yard along the Ashuelot River.. Enjoy the pavilion picnic place overlooking the river. Across the lawn is the guest house (cabin or art studio) built in 2012. The first floor is open concept and the second floor has a bathroom, the walls have been insulated, there is electric heat but one might add a mini-split for winter use. You can sit on the deck and relish the river view. The river side front yard gets lots of afternoon sun on a good day. The paved driveway leads to the 2 car garage for vehicles and boat storage, a newer roof and just a few steps to the 8x6 mudroom into the kitchen/living area. If you want privacy but still want a few friendly area neighbors the Back Ashuelot Rd. area is for you! Just off Rte.10 it is a short drive to Rte. 91 and picturesque routes to Eastern Massachusetts, and sbout 30 minutes to Keene,NH or Brattleboro,Vt. less than a half hour to Keene and to Brattleboro. See Listing Details & 53 images. Includes a Virtual Tour
$445,000 $417 per sq.ft. Winchester NH Home »
Price Change! Reduced by $50,000 down 11% on July 14th 2026
100 Ft. of Waterfront on Lake Forest
3 Beds | 2 Baths | Total Sq. Ft. 1066 | Acres: 0.39
Listed on Friday Jun 26, 2026
Description: This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living. See Listing Details & 42 images.
$479,900 $265 per sq.ft. Winchester NH Home »
Price Change! Reduced by $20,000 down 4% on July 19th 2026
465 Ft. of Waterfront on River Ashuelot River
3 Beds | 2 Baths | Total Sq. Ft. 1808 | Acres: 4.3
Listed on Wednesday Jun 3, 2026
Description: ** OPEN HOUSE SATURDAY, JULY 25 FROM 10AM-12PM** Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home, or hosting friends. Outside, enjoy the benefits of outdoor living from the rear deck or wrap around front porch, perfect for summer barbecues, morning coffee, or simply relaxing while taking in the surroundings. The solar system helps reduce energy costs while adding long-term value and sustainability. 465' of frontage on Ashuelot River. Conveniently located with easy access to local amenities, schools, shopping, dining, and recreational opportunities, this property offers the perfect balance of small-town New Hampshire living and modern convenience. Easy commute to Keene, Mass, Brattleboro and Interstate 91. See Listing Details & 60 images.
New Listing!
$499,900 $579 per sq.ft. Winchester NH Home »
103 Ft. of Waterfront on Lake Forest2 Beds | 2 Baths | Total Sq. Ft. 1392 | Acres: 0.4
Listed on Friday Jul 24, 2026
Description: Set back from the road at the end of a well-maintained driveway sits this adorable waterfront home with gorgeous views over Forest Lake! The property features an open concept kitchen/dining/living area overlooking the water, a large deck, screened in porch, 2 ample sized bedrooms plus a full bath to complete the first level. Downstairs offers a bonus bunk room, sitting area, plus bath and laundry. Add in the handy storage shed, plenty of available parking spaces, large .40 acre lot, private dock and beach area on your 103 feet of lake frontage, and you have the total package! See Listing Details & 42 images.
Under Contract
$250,000 $166 per sq.ft. Windham VT Home »
5 Beds | 2 Baths | Total Sq. Ft. 1504 | Acres: 2.6Listed on Tuesday Dec 17, 2024
Description: Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor. Home is ready for your improvements. Close to ski resorts! See Listing Details & 18 images.
$253,000 $293 per sq.ft. Windham VT Home »
Price Change! Reduced by $6,000 down 2% on July 27th 2026
2 Beds | 1 Baths | Total Sq. Ft. 864 | Acres: 4
Listed on Saturday Apr 25, 2026
Description: Tucked away on a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in a clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Price increase reflects work done to reinforce roof structure. If you have been looking for a true Vermont getaway, this property delivers! See Listing Details & 31 images.
$344,000 $202 per sq.ft. Windham VT Home »
Price Change! Reduced by $5,000 down 1% on July 23rd 2026
2 Beds | 2 Baths | Total Sq. Ft. 1700 | Acres: 4
Listed on Saturday Jul 11, 2026
Description: Set in the quaint village of South Windham, this charming Vermont home offers a warm, comfortable lifestyle with ski areas, outdoor recreation, and four-season adventure all close at hand. Known locally as the "old dance hall," the property is believed to date to around 1900, possibly reflecting an earlier community use that adds an interesting layer to its history. Lovely pine floors bring warmth and character throughout the home, while a Jøtul wood stove in the living room creates a cozy gathering place. A second wood stove in the basement provides efficient whole-house heat during the colder months. The flexible floor plan includes three bedrooms, with two on the main level and one upstairs, making the home well suited as a starter property, retirement home, or peaceful Vermont getaway. The living spaces open to an expansive deck overlooking a generous backyard with a beautiful backdrop of the surrounding hills. A gentle stream meanders through the property, enhancing the quiet setting and creating a wonderful sense of peace. There is ample room for gardens, outdoor projects, or the makings of a small homestead. With 1.5 baths and approximately 1000+ square feet of unfinished attic space offering potential for additional living area, office space, or storage, the home has room to grow and adapt. Full of charm, history, and practical comfort, this is a special opportunity in one of Vermont's most peaceful village settings. See Listing Details & 29 images.
$395,000 $113 per sq.ft. Windham VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 3502 | Acres: 1.3Listed on Monday Jul 13, 2026
Description: In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here. See Listing Details & 31 images.
$442,999 $226 per sq.ft. Windsor VT Home »
Waterfront on Lake Runnenede3 Beds | 2 Baths | Total Sq. Ft. 1961 | Acres: 0.16
Listed on Friday Jul 17, 2026
Description: Open House Sunday July 26th 10a.m. - 12 p.m.! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current setup as two separate 1 bedroom units, each with its own utilities. That kind of flexibility is hard to find, whether you're thinking multigenerational living, rental income, or just extra breathing room. And then there's the view. Gorgeous lake views greet you from inside this home, the kind that make you stop and appreciate where you live every single day. This is a true Victorian, full of the character and detail that newer homes just can't replicate. The full basement includes a bonus room, perfect for a home office, workshop, or extra storage. A detached garage adds even more convenience for parking and yard equipment. Tucked into charming Windsor, you're close to 91 and just minutes from local shops and restaurants downtown. Homes with this much versatility and this kind of view don't come along often. See Listing Details & 45 images.
$430,000 $517 per sq.ft. Winhall VT Home »
5 Beds | 2 Baths | Total Sq. Ft. 1664 | Acres: 1Listed on Thursday Jun 11, 2026
Description: The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a delightful retreat. See Listing Details & 22 images.
Under Contract
$449,000 $460 per sq.ft. Winhall VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 1460 | Acres: 0.47Listed on Thursday May 14, 2026
Description: A Sanctuary for Every Season: Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you're here to chase the morning light on the slopes of nearby Stratton Resort or to spend a slow summer afternoon exploring the local swimming holes, this home serves as the perfect basecamp for your Green Mountain adventures. Inside, the vibe is cozy. On crisp autumn evenings, the pellet stove becomes the heart of the home, casting a steady warmth that invites long conversations and board game marathons. When the Vermont summer hits its peak, you'll stay perfectly cool thanks to the modern mini-split system--a rare and welcome comfort in a mountain retreat. The expansive deck is your private outdoor dining room, ideal for long weekend brunches or stargazing after a day of hiking. With four bedrooms and 2.5 baths, there is plenty of space for everyone to find their own corner of peace without feeling crowded. A dedicated storage shed means your paddleboards, skis, canoes, and fishing gear are always organized and ready for the next excursion. You can feel the care that has gone into this property. It has been kept in peak condition so that your only job upon arrival is to drop your bags and head outside. From the gear storage to the effortless climate control, every detail has been managed to make your mountain getaways seamless. The mountains are calling, and this chalet is the perfect place to answer. Contact us today to see this Winhall gem in person and start planning your first weekend away. See Listing Details & 32 images. Includes a Virtual Tour
Under Contract
$495,000 $271 per sq.ft. Winhall VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1824 | Acres: 0.4Listed on Thursday May 28, 2026
Description: Quintessential Vermont charm meets modern comfort in this beautifully updated New England farmhouse just minutes from Stratton Mountain. Ideally located only 1 mile from the Stratton Mountain Access Road and just 1/10 mile to the VAST snowmobile trail, this 4-bedroom, 2-bath home offers the perfect four-season retreat. Rich with character, the home features exposed beams, warm hardwood floors, and a classic cast iron wood stove that creates the ultimate cozy Vermont atmosphere. Thoughtfully modernized while preserving its historic charm, this inviting property blends timeless farmhouse appeal with everyday comfort. Once a gathering place for legendary folk singer Arlo Guthrie, the home carries a unique sense of history and soul. Enjoy easy access to skiing, snowmobiling, hiking, and The Mountain School at Winhall, embracing the classic placement of historic Vermont farmhouses, originally built close to the road for practical year-round access during harsh New England winters. Today, that timeless design translates into effortless convenience with easy in-and-out access and no long driveway to maintain or plow, all while enjoying the beauty and charm of Vermont living. Whether you're searching for a primary residence, weekend getaway, or investment opportunity, this special property captures the very best of Vermont living. See Listing Details & 39 images.
Under Contract
$325,000 $343 per sq.ft. Wolfeboro NH Home »
Price Change! Reduced by $50,000 down 15% on July 8th 2026
3 Beds | 1 Baths | Total Sq. Ft. 948 | Acres: 0.5
Listed on Monday Apr 27, 2026
Description: Beautifully renovated and full of character, this 3-bedroom, 1 bath home has been thoughtfully updated in recent years with charming modern touches throughout. Highlights include cathedral ceilings, exposed beams, custom barn doors, gleaming wood floors, and a full daylight basement offering excellent additional potential. Set back from the road for added privacy, the property features a lovely fenced-in backyard complete with an outdoor shower, firepit, and storage shed, perfect for relaxing or entertaining. Ideally located just over a mile from Lake Wentworth's beach and close to Nick Recreation Park, Abenaki Ski Area, Pop Whalen Ice Arena, and all the shops and dining downtown has to offer. See Listing Details & 28 images.
$329,000 $264 per sq.ft. Wolfeboro NH Home »
Price Change! Reduced by $20,500 down 6% on June 22nd 2026
2 Beds | 2 Baths | Total Sq. Ft. 1248 | Acres: 0
Listed on Monday Mar 30, 2026
Description: Welcome to 1 Harvey Brook! Located in the desirable Birch Hill over 55 Co-Op community, this home is on a spacious corner lot with an oversized one car garage. The home features two bedrooms and two full bathrooms. Arched doorway in the Foyer, high ceilings and large windows create a bright and airy atmosphere. It offers comfortable living for residents seeking a peaceful environment. The location provides convenient access to a variety of amenities, including dining options, shops, lakes, walking trails, and museums in Wolfeboro and the surrounding area. Residents can enjoy both natural beauty and cultural attractions just a short distance from their doorstep. This is an Estate Sale and Trustee would pefer a quick sale. Park Approval is required. See Listing Details & 51 images.
