295 properties for sale in Jacksonville village, Whitingham town Windham County Vermont

Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. Offered at an impressive 10% cap rate, the building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the property offers exciting upside with attic space that may provide opportunities for additional living area or future expansion, subject to local approvals. Ideally located in Brattleboro, tenants enjoy the convenience of a thriving downtown known for its eclectic shops, restaurants, arts scene, and year-round community events, as well as easy access to Interstate 91 and the outdoor recreation that Southern Vermont is known for. Whether you're seeking stable cash flow or long-term value-add potential, this property delivers both in one of Vermont's most desirable communities. 3D Virtual Tours Availabl

DESIRABLE END UNIT! Why rent when you can buy- giving you peace of mind, an opportunity for stability and building equity. Maybe you are a first-time homebuyer' Or someone who wants to downsize from a bigger house and time-consuming yard chores and projects to a simpler life. An investor' Enjoy easy, affordable, and low-maintenance living in this sweet two-bedroom, 1.5 bath townhouse. Storage space in the attic! Conveniently located 1/2 mile to downtown Brattleboro's Main Street, the food Co-op, the new Brattleboro train station and museum, and lots of fun shops and diverse restaurants. Association amenities: a fabulous in-grown pool, pickleball/tennis court. HOA dues include lovely landscaping, master insurance policy, plowing, snow-removal, and trash. A delightful community of neighbors in a very pretty setting. is contingent on Sellers finding suitable housing/closing within 90 days of contract

Wonderful little getaway for some 'EZ' living-be one with nature with all the essentials in place! It's common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you'll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a propane stove and lighting adds both convenience and comfort, letting you unwind in rustic charm. The solar system provides extra illumination and powers a ceiling fan, ensuring the cabin stays bright and comfortable even on warmer days. The wood stove heats the cabin, you have everything you need for a comfortable stay, and there's an outhouse out back for added convenience. This property is perfectly positioned for Vermont country enjoyment. The shed has enough storage for those toys, making it easy to bring along your favorite outdoor gear. The queen-size Murphy bed in the front nook offers a co

Built with love and offered for the first time ever, 26 Oak Hill Road is a rare opportunity to own a home filled with character and unique workmanship. Lovingly hand built by a local craftsman for his own family in 1964, this 3-bedroom, 2-bath Cape is tucked away in a highly desirable nature-filled Greenfield neighborhood. A picturesque stone wall leads the way to a welcoming stone patio and screened porch perfect for morning coffee or quiet evenings. Inside, hardwood floors, exposed beams, custom cabinetry, handcrafted touches, Dutch doors and a wood-burning fireplace create warmth and timeless charm. The flexible floor plan includes a first-floor bedroom, full bath, and an additional room ideal for an office, den, hobby room, or guest space. Upstairs showcases 2 bedrooms and another full bathroom. From relaxing on the rear deck to gathering by the fire, this a home that becomes the backdrop for life's most meaningful moments. Come see why you'll feel at home the moment you arrive!

Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world' Now is the time to write your own story. and live in your own Hundred Acre Wood. only this one is grown up with 103 acres, rolling meadows, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location. minutes to town, the interstate and all you need for any lifestyle. you are tucked away in the gentle rolling meadows of home. High speed internet is available for home workers or streamers. The small touches are amazing, marble sink toppers from Dartmouth College and dramatic imported faucets tipping the scale of lovely. Delicate adz work in the original wing is amazing and a rarity and the slate floor entry with an inlaid heart to greet you every time you come home is a warm gift from the owner. A huge real cook kitchen with professional Garland range, commercial fridge and soapstone tops galore will tease you i

Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog, the side yard pops off the kitchen deck for easy pet access. Gardens and a small rivulet in the back complete this special setting. In-town corner lot, ready to go!

Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting benign neglect-where nature and romance intertwine to create a storybook setting that will capture your heart from the moment you arrive. Inside, you will find a spacious layout featuring 4 bedrooms and 2 full baths spread across 2,250 square feet of versatile living space. The home has been thoroughly cleaned out and deep-cleaned, presenting a pristine, blank canvas with exceptional, rock-solid bones ready for its next chapter. Fine historic details anchor the home, from rich wood floors to timeless built-ins. At the heart of the home sits a magnificent centerpiece: a vintage Vermont Iron Stov

Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment has another two. You could live in the apartment while you work on updating the house. You'll need to budget for insulating the walls, extensive rewiring, renovating 2 bathrooms plus cosmetics. If you have a business or need storage, there is a 24' x 34' barn with electricity and a large concrete parking lot. Once you see all that's here, you'll quickly realize your investment will yield a spacious and comfortable home with reliable income potential in a convenient Guilford location

Beautifully maintained, 1880s, in-town Victorian blends timeless elegance with modern comfort. The large, light-filled kitchen combines with an open, cathedral ceiling dining area inviting the gathering of family and friends. The renovated kitchen has granite, stainless steel appliances, and laundry area. Soaring, 9 ft ceilings create light-filled rooms. Elegance of timeless design and detailed wood trimmed finishes are throughout with crafted moldings framing arched and stain glass windows, custom fireplace mantles and functionally flexible built-ins. Enjoy the old-world charm of two covered porches. The expansive first floor has lovely potential for those wanting first floor accommodations. An ornately crafted staircase rises gracefully to the second floor with four bedrooms, two full baths and the continuation of flooding sunlight. The outdoors offers gorgeous stonework, lush perennial plantings and a magical patio. So close to downtown's Brattleboro Museum, Art Center, Galleries, C

Neighborhood home! Living in a sweet neighborhood is a lifestyle choice. Walk to schools, playgrounds, and shopping. This vintage home has an added features of roof top solar, 2 car direct entry garage, a fenced-in yard, and lots and lots of gardens. The classic front porch is on everyone's list of must haves. The neighborhood is perfect for long evening strolls or a brisk walk at dawn. Inside there is a huge living room for hanging out with friends, entertaining or movie night. Work at home' You will love the corner office, age in place with first floor bedroom and bath. So nice, just the right location and just the right home

Timeless Character on Coveted Oak Grove Avenue! There's something special about an American Foursquare. Built for comfort and designed to stand the test of time, this quintessential early 20th-century home welcomes you with classic architecture, generous room sizes, and the warmth of original craftsmanship. Set on a desirable in-town lot along Oak Grove Avenue, this 3-bedroom home showcases beautiful hardwood floors, rich natural woodwork, and a cozy fireplace that anchors the inviting living room. The screened front porch is the perfect place to enjoy your morning coffee, greet neighbors, or unwind on warm summer evenings. Upstairs, you'll find three comfortable bedrooms and a full bath, while the unfinished attic offers exciting possibilities - whether you envision a studio, home office, playroom, or additional living space. Outside, there's room to garden, entertain, or simply enjoy the yard, along with the convenience of a one-car garage. Combining timeless character with everyday

BLACK MOUNTAIN ESTATES where your next chapter begins! Welcome to Brattleboro's premier 55+ active lifestyle community, where nature, connection, and comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, and open green space, residents enjoy a serene setting just 1 mile from I-91, with ease of access to cultural and recreational opportunities, shopping, dining, and medical care. Nestled on 33 acres of pristine Vermont landscape, this premier neighborhood is thoughtfully designed, offering a vibrant community center w/ library, fireplace lounge, fitness center, full kitchen, and outdoor patio w/ fire pit. Outdoor recreational amenities incl. pickleball, bocce, shuffleboard, and horseshoes-perfect for staying active and social. Enjoy the ease of HOA-managed services and a lifestyle designed for freedom and fulfillment. Each home is single-story and ADA-compl

Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard-perfect for relaxing, gardening, or outdoor gatherings. Upstairs, the bedrooms offer comfortable accommodations with the opportunity to add a full bathroom in the future, allowing the home to grow with your needs. The lower level includes a separate in-law suite complete with its own private entrance and laundry area, offering flexibility for guests, multi-generational living, a home office, or potential rental income. Conveniently located, the property is less than a block from the Vermont Country Deli and within walking distance of the Brattleboro Farmers' Market, Memorial Park, and recreation fields. Easy

This fun and stylish gem was built and lived in by one family. Now, it is time to pass the torch! A surprise package with the look of a Gambrel but is really a raised ranch, waiting for a finish in the lower level! Cared for lovingly, and ready to move in, you will appreciate the manicured lawn, nice deck on the back, and lower level walk out and garage. The road is dead end, so little traffic. Tucked away in West Brattleboro, you are close to shopping, hospitals, with direct routes north to south on I91 and east to west on RT 9. Bring magic to this home and sweet neighborhood and continue the legacy

Welcome to this lovingly maintained 3-bedroom, 1-bath ranch located in the sought-after Carriage Hill neighborhood of West Brattleboro. Where affordability and opportunity come together in this move-in ready home. Whether you're taking the exciting step into homeownership or searching for a home that lets you spend less time on upkeep and more time enjoying life. The open-concept, light filled living room and eat-in kitchen create a comfortable, welcoming space that feels like home the moment you walk in. South facing windows fill the living room with an abundance of natural light, creating a bright and inviting atmosphere throughout the day. Just off the kitchen, step onto the back deck overlooking the spacious, fenced-in backyard. Mature trees provide natural shade and privacy, while the property extends well into the woods with established walking trails, offering a setting to explore and enjoy nature right from your own backyard. Back inside, you'll find three comfortable bedrooms

Discover the perfect blend of privacy, comfort, and modern living in picturesque Rowe. Set on 1.17 peaceful acres, this beautifully renovated ranch offers easy one-level living with a bright open floor plan, spacious sun-filled living room, and stunning updated kitchen. Step outside to a large deck overlooking your private backyard - perfect for relaxing, entertaining, or enjoying the natural beauty surrounding you. High-speed fiber internet makes working from home effortless while still enjoying the serenity of country living. Ideally located near hiking trails, Mount Snow, and Berkshire East Mountain Resort, this home is a year-round retreat with low Rowe taxes and access to beautiful Pelham Lake Park. Perfect as a full-time home or weekend escape! LOW TAXES

Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef's kitchen with ample counter space and a spacious pantry with an integrated dining area-perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living is elevated by a light-filled sunroom overlooking a lush backyard complete with raised garden beds and blueberry bushes. Unique features include a former garage transformed into a private guest studio with a Murphy bed, and a new, oversized two-car garage with a clever drive-through door for garden access. There is a 40x10' attic space, perfect for tons of storage, or if more living space is needed, it may be finished. Hot water pipes are already located there. Complete with an array of solar panels,{owned}, heat pumps, a whole-house generator, and the potential for single-level living, this B

Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural light, and generous storage. For ease of ownership there is an automatic propane generator and the septic was redesigned in 2022. In addition to all of this is a beautifully crafted timber frame barn that utilized reclaimed beams from the original structure on the property. Rich in authentic New England character, the home showcases exposed hand-hewn beams, a stunning chef's kitchen with custom cabinetry, a massive stone hearth with a traditional beehive oven, and a unique gardener's foyer complete with workspace and cast-iron wash sink. The spacious first-floor primary suite offers cathedral-

Wonderful little getaway for some 'EZ' living-be one with nature with all the essentials in place! It's common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you'll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a propane stove and lighting adds both convenience and comfort, letting you unwind in rustic charm. The solar system provides extra illumination and powers a ceiling fan, ensuring the cabin stays bright and comfortable even on warmer days. The wood stove heats the cabin, you have everything you need for a comfortable stay, and there's an outhouse out back for added convenience. This property is perfectly positioned for Vermont country enjoyment. The shed has enough storage for those toys, making it easy to bring along your favorite outdoor gear. The queen-size Murphy bed in the front nook offers a co

This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2 bedrooms with vaulted ceilings. Just next door is the Living Memorial Park offering swimming, baseball games, pickleball, skiing, skating and annual events, The popular Farmer's Market is also within walking distances. Close to 1-91 this convenient property can be your next. home sweet home

Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of room for everyone in five bedrooms (and of course 7 bathrooms), a choice of large or cozy living rooms and an office to work from home. Toast your toes at either fireplace or soap stone wood stove. Invite your circle of friends to yoga, parties or create a media room in the huge, finished walk-out basement family room, plumbed and wired for a second kitchen, with 1/2 bath, easily converted to extended family suite. 47x21 bonus room with skylights and ample windows overlooking the grounds is perfect for play/gym space, artist studio, etc. 3 car detached heated, finished garage/workshop with storage

Sweet ranch home with 2 car attached garage. A lovely and level lot for gardening or outdoor entertaining, this location provides a country feel but only minutes from vibrant West Brattleboro events and businesses and a short trip brings you into downtown Brattleboro with lots of opportunities. This home with a generous living/dining space, good sized kitchen, 2 bedrooms and 1 full bathroom is great for a starter home or people looking to down size. The attached two car garage has automatic garage doors and an attached breezeway provides direct entry into the house and makes a great mud room with storage. The full basement has storage, the washer and dryer, the pellet stove and an oil hot air furnace. There is also a place to install a bathroom if you want. Use some of the basement as a workshop for projects and fix-it shop. Recent upgrades include new windows and a standing seam metal roof and hot water heater

Rare to find an in-town condo with a waterfront view like this! Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the tranquil Whetstone Brook. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement with washer/dryer hookup and extra storage. The entire interior has been freshly painted, new kitchen cabinets, countertop and appliances, new bathroom vanity, bathtub surround, updated light fixtures and new flooring throughout. This condo is located in a prime location with quick, easy access to I91, Farmers Market and Living Memorial Park. Association fees include heat, water/sewer, landscaping and more

Welcome to a bright, airy home that blends comfort, character, and convenience! Set on 1.26 acres of sunny lawn and wooded privacy, this four-bedroom, two-bath property offers inviting, freshly painted living spaces, central air, and efficient baseboard radiant heat. The living room features a welcoming fireplace, while the kitchen includes a woodstove setup and comes fully applianced with a dishwasher, refrigerator, gas stove, microwave, washer, and dryer. Upstairs, the primary bedroom makes a memorable impression with its vaulted ceiling and exposed brick chimney, adding warmth and architectural charm. Floors are easy to maintain light-toned vinyl planks with carpeted stairs for quiet. Practical features include a drilled well and town sewer, offering ease of ownership in a desirable setting. The location is especially convenient, just a short distance to Exit 1, making it easy to access nearby services, commuting routes, and local amenities. With character-filled details and a 1.26-