Windham, VT Classified Ad Listings

152 Main St. Beautifully updated 4 bedroom, 2 bathroom home located in the heart of Grafton along Main Street. Brand new kitchen with all new cabinetry, appliances and quartz countertops. All new windows throughout, 2 brand new bathrooms, new paint both interior and exterior, and newly sanded floors. Old world charm with the amenities of today. Very easy to maintain home. Airbnb Rental Income o...

430 Fenn Rd. Set on a scenic knoll in a picturesque farm setting, just 10 minutes from Okemo's Jackson Gore base and Ludlow village, this remarkable 6-bedroom, 4-bathroom property offers a rare combination of privacy, convenience and truly majestic Vermont views. Encompassing 9.7 acres, the setting is nothing short of magical, with sweeping vistas toward the backside of Okemo, Mount Ascutney, K...

427 Depot St. Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are availab...

6 Juniper Hill Rd. Perched on a hill in one of Springfield's most desirable neighborhoods, this well-maintained home offers a peaceful setting just minutes from downtown amenities. Tucked away from the hustle and bustle, 6 Juniper Hill Road has been lovingly cared for over the years and is ready for its next chapter. The flexible layout offers four bedrooms and two bathrooms, making it ideal fo...

4669 Vermont Route 100. Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burnin...

494 W River Rd. Lucky for the next Buyer that this home is back on market because last buyer could not secure financing! This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the...

3531 Route 5. There is an immense amount of space in this home. With one bedroom downstairs, 4 bedrooms upstairs, plus a family/bonus room, everyone has space of their own. The space carries over to the 2 story attached barn where both floors offer workshop and creative space. Even the basement is sprawling and usable. Enjoy Fiber internet and the most pure well water from the Westminster Aquif...

66 Duttonsville School Dr. Where History Meets Possibility. An 1862 Schoolhouse Reimagined. Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use. Since 1973, the building has served as the home of a thriving distribution business, pro...

Household pet. Breeding allowed. Not registered. Starter food, favorite toy. Adorable brother and sister purebred sealpoint Siamese kittens available now, separately or together. They are 12 weeks old and eager to settle into your lap and a new home. Both are loving and cuddly but the boy is exceptionally affectionate. $700 for one or $650 each for the pair. The new owner will be responsible fo...

295 Hotel Rd #18. This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Lots of storage and closet space. Step out onto your private deck overlooking the tubing trail. This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including mountai...

364 Houghtonville Rd. At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an ...

1189 Cole Pond Rd. Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, c...

56 River Bend Dr. Riverfront properties rarely come on the market, but this gem is in a sweet cul-de-sac, with stunning views from the house and deck and with access to the river. Put your canoe in and enjoy a lazy day on the water. This one level home features an open concept living, kitchen, dining space, beautifully designed and updated. The large family room features a beautiful stone firep...

30 Fieldstone Way. Set in the peaceful Vermont countryside of Londonderry, this contemporary home offers the perfect blend of spacious living, natural beauty, and convenient access to some of Southern Vermont's ski areas. Situated on 1.58 acres between Magic Mountain, Bromley, and Stratton, the property is ideally positioned for year-round recreation and relaxation. Built in 2004, the 4,094-squ...

284 Kirk Meadow Rd. Investor special with strong value add potential! This property already has key improvements underway, including sections of new sheetrock and refinished hardwood floors saving time and upfront renovation costs. The layout includes a desirable three-season porch, adding usable space and storage. The property features a drilled well and private septic, with a nice lot offerin...

14 Cemetary Road. Lots and Land for sale in Springfield, VT for $110,000. The lot size is 1.47.. Sunshine, open skies, and peaceful country living! This beautiful, completely open lot on Cemetery Road in North Springfield offers an inviting setting with wide-open views, abundant sunshine, and plenty of possibilities. With level, open ground, the property offers an appealing opportunity to build...

3668 VT Route 103 N. Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured ...

566 Patch Hill Rd. PRICE IMPROVEMENT...AN AMAZING VALUE! Experience the charm and tranquility of Vermont living in this beautifully maintained log home, privately situated on 10.77 wooded acres. The property offers an exceptional blend of comfort, functionality, and outdoor enjoyment, featuring a one car tuck-under garage, three-stall pole barn, 30-panel solar array, and a private stocked pond....

2940 Route 103 Unit 158. A Rare Find...1 bedroom condominium at Castle Point, only 3 miles to Okemo Mountain Resort. This condo can be rented out or used whenever you like, it is a full ownership property and fully furnished. It is located in the back away from the hotel lobbies, but has access to the pool and gym facilities. On the first floor the condo has an open living room with a gas firep...

289 Putnam Rd. Welcome to a home that truly has it all! Perfectly positioned off a quiet road, this property is a seamless blend of privacy while offering easily accessible town amenities. This well-maintained property offers the rare and coveted convenience of first-floor living with all three bedrooms and a full bathroom on the main level. The home features beautiful hardwood floors, a pellet...