Windham County

MLS Number 5078084

• Residential Single Family
• Address 29 Pikes Falls Road
• Bedrooms 4
• Bathroom 2
• Square Feet 2,520

MOTIVATED SELLERS! Bring your offers! Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living. Ideally situated just 15 minutes from Stratton Mountain and 25 minutes to Mount Snow, the location balances village convenience with premier access to Southern Vermont's ski resorts and outdoor recreation. From the covered porch to the deck and veranda, the property invites relaxed outdoor living amid established gardens and peaceful surroundings. Jamaica State Park, River & Rye, the West River, the village library, and the local general store are all within easy walking distance. Inside, generous proportions define the layout. The expansive primary suite is complemented by three additional well-sized bedrooms, providing flexibility for guests or remote work. A well-appointed kitchen with a center island opens seamlessly to a formal dining room designed for memorable gatherings. The spacious living room offers a warm and welcoming setting, while the back porch and veranda create additional spaces to unwind. Blending historic character, modern comfort, and an exceptional village location, this property represents a rare opportunity to own a quintessential Vermont home-equally suited as a primary residence, seasonal retreat, or investment opportunity.

Listed by Carrie Mathews of Winhall Real Estate

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5086998

• Residential Single Family
• Full Bath 1
• Address 12 Autumn Gem Drive
• Bedrooms 3
• Bathroom 2

This affordable Dummerston home is tucked away on 11 private acres. Built with personal privacy in mind, the primary bedroom is on one end and the other 2 bedrooms and bath are at the other, eliminating hallways and adding to the living area. Warm yourself and save on fuel with the large pellet stove in the living room. Abundant light with the picture window in the front and skylight over the work area in the kitchen. Huge eat in kitchen with tons of cabinets and good baking space. School is right around the corner, minutes to the Coop! Seller must find a place to move and is actively searching. Schedule showing the house is 10 am till 130 pm Monday-Thursday. Saturday morning 9 to 1. No Sundays. 24 hours notice!

Listed by Christine Lewis of Brattleboro Area Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5092011

• Residential Single Family
• Full Bath 1
• Address 7 Academy Avenue
• Village Saxtons River
• Bedrooms 3

This charming village home combines a bright, spacious interior with a large fenced yard, making it an especially attractive property. An inviting front porch opens to a wide entry hall leading to the principal rooms. Wood floors, high ceilings, and easy flow create a welcoming setting for both everyday living and entertaining. The first floor includes a living room with wood stove, family room/den, dining room, and kitchen, along with a half bath, bead-board details, marble countertops, and a walk-in pantry. Upstairs are three bedrooms, a full bath, and a combined laundry and ¾ bath. Most of the home features updated windows, and a deck just off the kitchen, surrounded by shrubbery, provides a pleasant space for outdoor dining and relaxation. A two-story, attached shed offers access from the driveway to the kitchen and is a practical space for boots, gear, firewood and other items, while a detached two-car garage adds even more convenience along with overhead storage. Established plantings and a level open area for gardens enhance the charm and flexibility of this village property. Conveniently located near the Village Market, Main Street Arts, VT Academy School, Elementary School and nearby Bellows Falls Village. Saxtons River is a great place to call home.

Listed by Heidi Bernier of Berkley & Veller Greenwood Country

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 7 Academy Avenue Rockingham VT 05154 (#5092011).

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MLS Number 5087976

• Residential Single Family
• Full Bath 1
• Address 1329 Newfane Road
• Bedrooms 3
• Bathroom 1

Nature lovers rejoice! Escape to the charm of rural Vermont with this rustic cottage retreat, privately set on a secluded 1-acre lot surrounded by woods and nature. Tucked away in a peaceful setting, this inviting home offers warmth, character, and the simple beauty of country living. The first floor features an open floor plan with hardwood floors and natural woodwork throughout, a cozy livingroom with a beautiful fireplace, a small den leading to a bedroom with a knotty pine ceiling, plus a spacious rebuilt (2018) 400 sqft. Primary bedroom with wide pine floors, laundry, ample closet/storage space, and a wood stove perfect for snowy Vermont evenings. Upstairs, you'll find a third bedroom and an additional bonus room for guests, office space, or hobbies. Step outside onto the large deck, built in 2022, and take in the summer breezes and colorful fall foliage while surrounded by the peaceful beauty of rural Vermont. A loose-laid stone wall elegantly frames the garden and established plantings, evoking the timeless appeal of a classic country setting. Property improvements include an upgraded 3-bedroom septic system (2017), a metal roof (approx. 2013), a new well pump (2020), A new Sure Pack driveway (2018), 200-amp electrical service, two outbuildings, vinyl replacement windows, and a generator hookup. Conveniently located near some of southern Vermont's best skiing and outdoor recreation, it's approximately 25 minutes to Mount Snow and 45 minutes to Stratton and Bromley Mountains. Whether you're searching for a cozy year-round home, a rustic Vermont getaway, or a peaceful escape from city life, this charming country cottage is the perfect place to slow down and reconnect with nature.

Listed by Matt Waddington of Hoffman Real Estate

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 1329 Newfane Road Wardsboro VT 05355 (#5087976).

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MLS Number 5078951

• Residential Single Family
• Full Bath 2
• Bedrooms 2
• Bathroom 2
• Square Feet 1,164

Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you'll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a comfortable layout designed for easy living. High-speed Fidium Fiber internet adds modern convenience, making this home ideal as a full-time residence, weekend getaway, or investment opportunity.

Listed by Grayson VanHendrick of Flex Realty, Flex Realty Group of Flex Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 3185 Higley Hill Road Marlboro VT 05363 (#5078951).

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MLS Number 5090926

• Residential Single Family
• Full Bath 1
• Bedrooms 3
• Bathroom 2
• Square Feet 1,080

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.

Listed by Michael Purcell of Berkley & Veller Greenwood/Dover

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 2448 Burrington Hill Road Whitingham VT 05361 (#5090926).

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MLS Number 5091529

• Residential Single Family
• Full Bath 1
• Address 461 South Road
• Bedrooms 2
• Bathroom 2

This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the back side, and new owners can imagine all sorts of outside projects to make this property their own!

Listed by Susan Bellville and A.j. Bellville of Bellville Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 461 South Road Marlboro VT 05344 (#5091529).

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MLS Number 5054419

• Residential Single Family
• Full Bath 2
• Address 109 Central Street
• Bedrooms 4
• Bathroom 2

Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to care for. Near down town,, MOOVER route, hospital and all the other good stuff. Quite, level short street, with easy access. Come join the neighborhood! Only the first floor is available to show on first showing. Please have all buyers qualified before requesting an appointment.

Listed by Christine Lewis of Brattleboro Area Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 109 Central Street Brattleboro VT 05301 (#5054419).

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