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

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level offers a fantastic opportunity with a partially finished, extra-large bonus room that can be customized to suit your needs. Additionally, this level includes a convenient laundry/utility room and a small workshop space, offering practical solutions for storage and hobbies.Outdoor living is equally inviting with a private deck off the back of the house, leading to a fenced backyard. This space is ideal for relaxation and entertaining, complete with a firepit perfect for enjoying summer and fall evenings. You'll also appreciate the thoughtful landscape touches, particularly the delightful goldfis

Beautifully cared-for 3 bedroom, 3 bath single family condo in a desirable small association, conveniently located near town, golf course and major road access. This spacious home features a sought after first-floor primary suite with en-suite bath, skylights that fill the home with natural light, and elegant cherry flooring throughout the main living areas. The remodeled kitchen offers modern finishes and functionality, while the family room boasts brand new carpeting for added comfort. a perfect blend of privacy, convenience, and tasteful updates in an exceptional location. Open house Sunday May 31st 11am-2pm

Open House Sunday 7/19 from 11am-1pm* Welcome to a home where everyday living feels just a little more special. Offering three comfortable bedrooms and a functional, inviting layout, this property is designed for everything from quiet evenings at home to hosting family and friends. The true highlight is the incredible backyard, a rare, fully fenced, level oasis that's ready for every season of life. Fire up the grill on the spacious back deck, let the kids and pets roam freely, plant the garden you've always wanted, or gather around a fire pit under the Vermont stars. This is the kind of outdoor space buyers dream about and seldom find. In addition to the incredible yard. A fully paved driveway with room for multiple cars, space for RV's Boats and other recreational items is at your service. Located in one of Brattleboro's most convenient neighborhoods, you'll love being just minutes from vibrant downtown shops, local restaurants, schools, parks, and minutes from I-91 leaving you 30 mi

Presenting an exceptional opportunity at 3 Hog Hollow Rd, Buckland, MA, a single-family residence constructed in 1880, offering 1131 square feet of living space. This property represents a compelling option for investors and discerning handy homeowners seeking a project with significant potential. The living room features elegant hardwood flooring, providing a foundation for sophisticated interior design. One of the bathrooms is equipped with a walk-in shower, offering a contemporary and functional bathing experience. The bedrooms also showcase hardwood flooring, contributing to a cohesive aesthetic throughout the private quarters. Further enhancing the property's appeal are a dedicated laundry room, a covered deck perfect for outdoor enjoyment, and a welcoming porch. This bungalow-style residence offers a distinctive canvas for creating an aspirational living environment

Wonderful, expansive contemporary home set on over 5 acres of land with 2 streams amidst the natural beauty of the hills of Buckland. Featuring over 3500 sq ft,including a finished walkout basement, this 8 room,4 bedroom,2 full and 2 half-bath home with cathedral ceiling and balcony offers a fabulous floor plan for family living as well as a country getaway for seasonal recreation. Enjoy the beauty of your surroundings from a 58x13 deck as well as a spacious and welcoming front porch and patio with firepit. As an additional bonus, the 36x32 garage with high ceilings, water,electric,septic connection and large walkup space offers a terrific opportunity for expansion and creative use such as studio, home office or au pair living. Nearby you'll find Berkshire East and Zoar Outdoor, offering year-round recreational activities and the historic village of Shelburne Falls with its Bridge of Flowers. Schools abound Charlemont,Deerfield, Eaglebrook, Stoneleigh-Burnham are all a short commute

Elegant Post-and-Beam! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls and gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows. Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access. The formal living room features a brick fireplace and is surrounded by classic post and beam architecture and stained glass windows. The open kitchen and dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and

Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident throughout, with the property having been carefully maintained over the years. Whether you're looking to expand your investment portfolio or live in one unit while generating income from the other, this well-kept duplex offers convenience, versatility, and lasting value in a desirable location

Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an exceptional occupancy history with very little vacancy. The building has been well maintained and features newer windows, vinyl siding, two oil tanks, and two boilers. Tenants pay their own electric while the owner covers heat, water, sewer, and taxes. Conveniently located just moments from downtown shopping, restaurants, entertainment, and public transportation, the property is ideally situated to support continued strong rental demand. A unique opportunity to acquire a proven income-producing property with a long track record of stable occupancy and excellent cash flow potential

Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. Offered at an impressive 10% cap rate, the building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term maintenance. Located in vibrant Brattleboro, tenants enjoy easy access to the town's eclectic mix of restaurants, coffee shops, galleries, and local events, along with convenient access to Interstate 91 and nearby outdoor recreation. Known for its strong sense of community and thriving arts scene, Brattleboro continues to attract residents seeking both small-town charm and everyday conveniences. Whether you're expanding an existing portfolio or looking for a high-yield investment in one of Southern Vermont's most dynamic communities, this property offers

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

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

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

Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat, water/sewer, landscaping and more

Spacious and Inviting Home in a Convenient Location! Ideally located just minutes from Brattleboro and I-91, this wonderful home offers the perfect blend of comfort, space, and convenience. The first floor features a bright bedroom with abundant natural light and a handicap-accessible bath complete with a beautiful walk-in tile shower - ideal for single-level living or guests. Enjoy cooking and entertaining in the large eat-in kitchen, featuring generous cabinet and counter space, and direct access to the back deck and yard for outdoor dining or relaxation. The spacious living room offers plenty of room for seating and gathering, while the delightful three-season porch, surrounded by windows, provides a sunny retreat throughout much of the year. Upstairs, you'll find three comfortable bedrooms and a full bath, offering flexibility for family, guests, or a home office. With its versatile layout, natural light, and easy access to area amenities, this move-in ready home is a wonderful opp

Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water heater, spray foam insulation, and new cellulose insulation in the attic. The building offers six rental units, including three efficiency apartments, (2) two-bedroom units, and (1) one-bedroom unit (please note the bedroom does not have a window). Three units are currently occupied by long-term tenants. The two-bedroom and one-bedroom units each have separate electric service, while the three efficiency units are on the owner's electric meter. Heat and hot water are included for all tenants. The property also offers plenty of off-street parking with a convenient location close to shopping, the hos

Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This exceptional estate is now ready to welcome its next owners. Designed with sustainability in mind, this eco-friendly property features numerous green initiatives such as locally sourced materials and renewable energy sources. Thoughtful land management practices further enhance the property's environmental stewardship, making it a sanctuary that harmonizes with its natural surroundings. As you ascend the driveway, you pass grain bins, barns, and pastures, remnants of a once-thriving goat farm. Midway up the drive, near the old foundation of the original homesite, you will discover a serene swimmi

Time to think of the garden! This sweet home has a huge level back yard just right for flowers, veggies and fruit trees. There is still time to get the jump on planting your favorite things! There is a primary suite on the 1st floor including laundry so there is total first floor living if you need/want it. The traditional cape 2 beds and a bath up are private for family or guests. The living room us huge and sports a fireplace at the end (sellers have not used it), the formal dining has great light and can set 6. the kitchen has lovely cherry cabinets and lots and lots of counter top for baking and every day meals. No mud season here! This lovely well cared for home is waiting for a new owner

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

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character and elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has Italian ceramic countertops and butcher block, including a dinette with southern light. With an open concept living/dining arrangement, the living room has lovely radiant wood stove heat. The adjacent dining area is drenched in sunlight. The home affords views of the West River Valley and Green Mountain vistas as far as Hogback Mountain. The first floor offers a fabulous great room, 2 fireplaces, an office, a sun room with hot tub, a laundry room and decks for admiring the sunrises and sunsets. The second floor is exceptional with three expansive primary en suites and two more rooms perfect for st

Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for investors. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. All three units are currently occupied, providing immediate cash flow. Unit 2 also benefits from a recently installed water heater. Enjoy peace of mind with separate utilities, state lead compliance, vinyl siding, and several replacement windows. Located in a highly walkable area-just steps from downtown, grocery stores, the hospital, and public transit-this property combines low maintenance with strong income potential. The spacious 2-bedroom units feature bright living areas and comfortable bedroom sizes, while the 1-bedroom unit offers a cozy, efficient layout. Each unit is thoughtfully designed to maximize natural light and functional living space. Off-street parking inclu

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

First time offered, EVER. built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big bedrooms and full bath up! The full basement has room for a workshop, storage or game room. Drive and carport are paved for easy maintenance. Huge shed in the back for storage or lawn care tools. Just what you have been waiting for!

Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. There are two furnaces and two oil tanks, one for the first floor, one for the second floor, and a propane wall unit for the third floor