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

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

Rarely does a property offer both 102 private acres and the convenience of one-level living. Set in the low-tax town of Rowe, this well-maintained home offers peace, privacy, and endless possibilities. The open floor plan features a primary bedroom suite with a private bath and walk-in closet on one side, and two additional bedrooms and a full bath on the other side. First-floor laundry and a versatile mudroom with convenient storage connect to the oversized two-car garage, while a separate shed provides additional space for tools and equipment. The finished lower-level family room adds additional living space. Enjoy the sun-filled enclosed front porch and the 14' x 26' rear deck overlooking a peaceful setting surrounded by nature and wildlife. Just 22 years young, this exceptional property is just minutes from Pelham Lake's resident beach, the Deerfield River, Berkshire East Mountain Resort, and many opportunities for hiking, fishing, skiing, kayak and year-round outdoor recreation

Here's an open concept, post and beam beauty located on a quiet country road just outside West Brattleboro. Walk through the covered porch into the welcome foyer, where there's plenty of closet space for coats and gear, then enter the main home. The post and beam construction highlights the bright and open spaces. The chef's kitchen is complete with ample cabinet areas, granite counter tops, full pantry to hold all your cooking needs, and an island for easy sit downs or work space for entertaining. The kitchen flows to the living-dining room, with windows galore and doors that lead out to the deck. The Jotul woodstove anchors the space and will keep you warm on cold winter nights. On the second floor you'll find spacious bedrooms with a 3/4 bath and the main bedroom suite featuring an extra large bath that includes a shower and spa tub. Then upstairs to the bonus rooms with cathedral ceilings, perhaps a home office or study or just a quiet place to relax. There's a full walkout basemen

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

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

Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field - grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space. A large barn accommodates up to two vehicles and offers excellent additional storage potential. The home features low-maintenance vinyl siding, plenty of off-street parking, and strong investment potential for both owner-occupants and investors alike. Each unit has its own private entrance and separate electric service, adding convenience for tenants and ease of management for owners

Located in one of the area's most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a formal dining room, complemented by a retro-inspired kitchen full of personality. Just off the living room, the enclosed south-facing porch with newer windows may become your favorite place to relax and unwind. Upstairs offers 3 bedrooms, a bright and cheerful bath, and access to an incredible attic space with exciting potential for a studio, yoga room, office, or expanded living area. Outside, the landscaping is a delightful surprise, featuring striking artistic bluestone details and a peaceful water feature that create a private, zen-like setting rarely found in town. This is a wonderful oppor

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

Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the p

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

Price Improvement! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings, cool factory-style windows, slate siding, and 2,000 square feet of sunny living space. The second level has a bedroom and a full bath, and the third level has two spacious private rooms that have been used in the past as bedrooms or office space with a large common/recreation area in between. Beautiful double patio doors open to a private sun-filled deck for outdoor dining. Zoning allows for a multitude of uses. Whether it's a primary residence, an artist studio, or a second home, this is a must-see for those who appreciate in-town offerings with a vibe and the only condo-ized loft on the market.

Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting ro

What will the next life be for this iconic property' From popular and innovative hair salon to successful dental practice to a 4 unit family complex. pick your use! Owner occupied business. roomy apartments. small business complex. this multi use property has been renovated in the last few years with nice kitchens and baths. and has been used essentially as a single family with a huge yard, paved parking and easy access. Some permits may be required but it is a great base to start a new investment

A great fixer-upper find! Solid feeling cape home set on 2 level acres just outside the village of Newfane with long frontage on the Smith Brook. Once a loved local primary home - now it's your opportunity. If you are handy and have cash or pre-qualified for a construction loan this may be your chance to break into the Newfane area at a fraction of what a renovated home will cost. Seller has license to sell and has been diligently working to clean the property out and the grounds up. Full concrete basement with ThermoPride forced hot air furnace, inspected oil tank, newer propane water heater and laundry hookups. A nook was created for a root cellar, great storage space with bulkhead to get outside. Electrical box will need to be updated but is currently servicing the property. All hard wood floors upstairs and down with vinyl in kitchen and baths. Solid wood doors, sweet built-in China cabinet, antique kitchen sink set up, oversized windows and lovely center staircase - all charming f

Set on 5 acres in the scenic hills of Readsboro, this spacious 4-bedroom, 2.5-bath farmhouse offers privacy, mountain views, and plenty of room to enjoy Vermont's natural beauty. The 2,120-square-foot interior features warm wood flooring, abundant natural light, and a welcoming layout designed for everyday living and entertaining. The kitchen offers generous cabinetry, ample workspace, and an island that opens to the dining area, while the comfortable living room is anchored by a stone-surround wood stove. Four bedrooms provide flexibility for family, guests, or home office space. A walk-up attic and unfinished walkout basement offer excellent storage and future possibilities. Outside, relax on the deck, enjoy the expansive lawn, or explore the surrounding acreage. Additional highlights include public water and sewer, fiber-optic internet availability, a gravel driveway, and a peaceful country setting on a dead-end road. Located in southern Vermont, Readsboro offers a quiet, close-knit

69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and WandD hookups in the basement. The second floor apartment has an additional room (office), WandD hookups, decking and a rear staircase. Recent improvements include a new boiler, full attic insulation and new oil tanks. Tenant pays for Heat, Electric, Water and Sewer

So many possibilities await at this recently renovated and affordable 3-bedroom, 2-bath home, featuring two full kitchens, one up and one down. Whether you're envisioning multigenerational living, a home-based business, or simply want to be close to skiing and outdoor adventure, this versatile layout adapts to fit your life. Recent renovations touch nearly every corner of the home, including both kitchens, both bathrooms, and two decks. The furnace is 4 years old, while the roof is just 8 years young and several appliances are only 6 months old. New solar panels keep your electricity bill WAY down. Outside your door, every kind of outdoor adventure is minutes away: ATV and snowmobile trails are close by, skiing at Mount Snow is an easy trip via the MOOver, and both whitewater and flat-water kayaking options are nearby, along with boating on Whitingham and Somerset. Move right in and start living the Vermont life you've been dreaming of

Outstanding investment opportunity! This well-maintained 5-unit apartment building offers strong income in a highly desirable neighborhood close to downtown, shopping, schools, and the hospital. The property features five 1-bedroom apartments and has seen some updates, including some new vinyl replacement windows, one unit fully renovated, recently painted porches, and improvements to portions of the plumbing and electrical systems. Two car garage, off-street parking, and rear yard, adding to the property's long-term appeal and rental demand. With its prime location, valuable updates, and excellent cash-flow, this is a turnkey addition to any investment portfolio or a great opportunity for an owner looking to grow their rental holdings. Don't miss your chance to own this exceptional income-producing property! No interior photos due to tenant privacy

Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser. Seller is doing a 1031 exchange. 48 hour notice to show, mask up please!

What sets this unit apart is not just that it is an end unit, but it is an end unit with a private deck! You are also right next to the path to Memorial Park for swimming, skiing, skating, baseball games, summer theatre, and so much more! Or head to the popular Saturday Farmer's Market just around the corner. This unit features two bedrooms, one and a half bathrooms, single car garage with storage and laundry. The end units are bright with extra windows and this unit has wood floors in the dining room and hall, carpet for the living room and bedrooms, and has also had efficiency upgrades. There is a charming brick patio off the dining area, think summer potted plants and fairy lights! A previous owner had a stairlift installed which could stay or go. This unit is ready to go and could not be easier!

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 beautifully remodeled 2-bedroom, 2-bath modern farmhouse offers the ideal blend of comfort and character, whether you're searching for a full-time residence or a four-season vacation getaway. Move right in and start enjoying everything southern Vermont has to offer. Outdoor enthusiasts will feel right at home here. Skiers are just 30 minutes from Mount Snow, and the property offers direct access to miles of snowmobile and ATV trails connecting towns throughout southern Vermont. You will love the nearby kayaking, boating, and fly fishing, and hiking trails. When it's time to unwind, head into Wilmington or down to North Adams, MA for dinner. Whether you're chasing powder days, riverside adventures, or simply a quiet home base in the mountains, this move-in-ready farmhouse has it all

An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only fully qualified with either proof of funds or a bank rehab loan prequel letter. Pets, so flexibility is needed for showing

Attention Investors and 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a proven portfolio foundational asset. The property features a rock-solid financial track record with an annual net operating income (NOI) of $33,756.41, representing an exceptional 6.25% un-leveraged Cap Rate and a highly competitive 5.86 Gross Rent Multiplier (GRM). All 6 units are currently fully occupied by seasoned tenants, with all security deposits transferring securely to the new owner at closing. The asset stands out for its exceptional location and structural layout. Situated in a prime, highly walkable in-town location, it sits just minutes from vibrant downtown Brattleboro shops, dini

A rare combination of recreation and convenience in one of Brattleboro's most desirable neighborhoods. This home is designed for living and entertaining! The property sits on 1.6 acres of landscaped grounds with sweeping views of Mt. Wantastiquet showcasing spectacular sunrises and front-row views of Brattleboro's 4th of July fireworks. Tucked beside Living Memorial Park on a quiet cul-de-sac where skiing, tennis, baseball, swimming, playgrounds and year-round recreation are just steps away. Inside, oversized windows fill the home with natural light while viewing the spectacular setting. A welcoming foyer with beveled glass doors and three generous closets opens to the elegant living room with hardwood floors, propane fireplace, and expansive windows. The heart of the home is the stunning kitchen / dining area featuring ash flooring, a massive center island, custom Schrock cabinetry, granite countertops, and large sliding doors opening to the patio w/ firepit overlooking the views. Adj