Pittsford Real Estate

Pittsford Real Estate

Welcome to the charming town of Pittsford, nestled in the picturesque state of Vermont. Located in Rutland County, Pittsford offers a perfect blend of small-town charm and natural beauty.

Pittsford is known for its historic architecture, with many well-preserved buildings dating back to the 18th and 19th centuries. The town's quaint downtown area is lined with local shops, cafes, and restaurants, making it a delightful place to explore on foot.

Outdoor enthusiasts will appreciate Pittsford's proximity to outdoor recreational opportunities. The town is surrounded by lush forests, rolling hills, and pristine lakes, providing ample opportunities for hiking, fishing, and boating. The nearby Green Mountain National Forest offers even more opportunities for outdoor adventure, including camping and wildlife viewing.

Pittsford is also known for its strong sense of community. Residents take pride in their town and come together for various events and festivals throughout the year. The town's schools are highly rated, making it an attractive destination for families looking to settle down in a safe and welcoming community.

Whether you're looking to enjoy the beauty of Vermont's countryside, explore historic New England architecture, or become part of a vibrant community, Pittsford has something to offer everyone. Come and discover the unique charm of this lovely town in the heart of Rutland County.

Newest Listings in Pittsford

1646 Plains Rd, Pittsford
$230,000
2 Beds ⋅ 1 Baths ⋅ 5115634 MLS
*Charming Vermont Cape with Country Appeal!* Discover the charm of Vermont living at 1646 Plains Road in Pittsford! Set on approximately 1.17 acres, this classic New England Cape offers a wonderful opportunity for buyers seeking character, outdoor space, and potential. Built in the late 1800s, this inviting two-bedroom, one-bath home blends traditional charm with modern conveniences, such as the eat-in kitchen, first-floor bedroom, and laundry, plus the second-floor loft and private second bedroom. Enjoy country living with a spacious yard offering raised beds for gardening, outdoor gatherings, pets, a farm stand, or simply relaxing in your own slice of Vermont. A screened back porch provides a welcoming spot to enjoy the fresh air, while the detached two-car garage offers valuable space for vehicles, storage, hobbies, or workshop needs. Whether you're searching for your first home, looking to downsize, or hoping to find a property that maximizes indoor/outdoor living, this home presents an exciting opportunity to make it your own. Conveniently located in Pittsford, you'll appreciate access to nearby amenities, an abundance of community events, and outdoor recreation that makes Vermont such a desirable place to live. On your corner lot, enjoy the beauty of the surrounding countryside while creating your own vision for this classic New England property. Bring your ideas and explore the possibilities at 1646 Plains Road, a home with timeless Vermont character, a generous lot full of potential, and room to make your dreams a reality!

1646 Plains Rd, Pittsford
73 Old Colony Way Unit A4, Pittsford
$225,000
2 Beds ⋅ 2 Baths ⋅ 5114573 MLS
Discover the perfect blend of comfort, style, and low-maintenance living in this beautifully renovated condominium in Pittsford’s Old Colony Way community. Thoughtfully updated throughout and meticulously maintained since its purchase in 2024, this inviting home offers a truly turnkey opportunity. Simply move in and enjoy! Step inside to find warm wood flooring, tasteful finishes, and a welcoming layout that makes everyday living feel effortless. The updated kitchen features crisp white cabinetry, butcher block countertops, black appliances, open shelving, and attractive modern accents. This eat-in kitchen offers a charming space for meals and gatherings, complemented by stylish pendant lighting and a custom shiplap accent wall. The comfortable living room features beautiful wood floors and sliding glass doors leading to a private rear deck, where you can relax and take in the peaceful wooded surroundings and seasonal Vermont foliage. It’s an ideal spot for morning coffee or unwinding at the end of the day. Upstairs, the inviting bedrooms showcases rich natural wood ceilings, warm architectural details, and a cozy retreat-like atmosphere. The home’s updated bathrooms feature thoughtfully selected fixtures, attractive accent walls, and contemporary finishes that carry the home’s cohesive style throughout. Additional highlights include distinctive wood accents, updated lighting, and charming built-in storage. Every space reflects a balance of modern convenience and classic Vermont character. Enjoy the ease of condominium living in a scenic setting, with convenient access to Rutland, Killington, local amenities, outdoor recreation, and everything that makes this part of Vermont so special. Welsome home!

73 Old Colony Way Unit A4, Pittsford
95 Goat Farm Rd, Pittsford
$879,000
4 Beds ⋅ 2 Baths ⋅ 5110885 MLS
Admired by many for years, this classic 1900 Vermont farmhouse is filled with warmth, character, and history. After 50 years of cherished memories, sugaring in the spring, raising sheep, gathering with family and friends, and gazing at the magnificent western views from Adirondack chairs, the time has come for a new owner to love this remarkable property. Set at the corner of Oxbow and Goat Farm Road in Pittsford, Vermont, the home offers a truly special country lifestyle on 48 beautiful acres. Inside, approximately 2,600 square feet of inviting living space includes a classic living room with a beautiful fireplace, a centrally located dining room, and an updated cherry kitchen with granite countertops. A cozy den lined with bookshelves and warmed by a soapstone woodstove provides the perfect retreat on cold Vermont winter nights. Beautiful pine floors add warmth and character throughout, while a wonderful covered porch offers a peaceful place to relax and gaze across the meadow. Upstairs are four bedrooms, with one full and a three quarter bath throughout the home. A standing seam metal roof is another valuable improvement. Over the years, the current owner has carefully strengthened and preserved the barn while completing numerous upgrades throughout the property. Enjoy a peaceful country setting just minutes from Mountain Top Inn and Resort, Chittenden Reservoir, and the renowned skiing and year round recreation of Killington. This is a quintessential Vermont farmhouse in a truly beautiful setting, offering timeless character, an exceptional lifestyle, and a one of a kind place to call home.

95 Goat Farm Rd, Pittsford
3210 W Creek Rd, Pittsford
$160,000
5110096 MLS
Wonderful views to the north, east, and especially south to Killington and Pico from this 4 acre building site. The property also sets up nicely for two x 2 acre sites. Town water and electricity readily available at the street. At one time this land was all in use as part of a family farm, maybe it will be again? Bring your plans and energy!

3210 W Creek Rd, Pittsford
172 Pinewoods Rd, Pittsford
$350,000
3 Beds ⋅ 2 Baths ⋅ 5103574 MLS
Set on 5.7 acres with mountain views, this well-maintained home sits nicely above the sprawling property, with a terrific front deck that’s the perfect spot to sit back, take it all in, and enjoy the sunsets. Inside, you’ll find hardwood floors, a comfortable living room with fireplace, and the convenience of an attached garage. A 16' x 32' shed with electricity makes a great workshop or provides plenty of additional storage. There’s ample room for gardening, with established gardens in place, while the basement offers additional space for a rec room, storage, or casual hangout area. Two separate portions of the property offer frontage along Route 7, with potential for subdivision. Just up the road from Proctor-Pittsford Golf Course and Pico & Killington Ski Areas, with Rutland less than 15 minutes to the south and Brandon just minutes to the north!

172 Pinewoods Rd, Pittsford
126 Shadow Ln, Pittsford
$275,000
3 Beds ⋅ 2 Baths ⋅ 5101279 MLS
Price Reduced! -This private and serene three bedroom, furnished country get-away is located in Pittsford but just minutes to the Chittenden Reservoir and Killington/Pico down hill skiing. The open living room with a dining area greets you at the front door. There is an efficient kitchen with ample counterspace and oak cabinets conveniently located just off the dining area. The first floor has a charming step-down sunroom that provides extra living space for family and friends with a sliding glass door for extra sun light and easy access to the garden. There is a full bathroom and laundry/mudroom area with a door leading to the large covered back porch. From here you can entertain in style or just relax while listening to the babbling brook that passes between the house and back garden path. The stairway to the second level has a generous landing area with three bedrooms off of it. The primary bedroom has a full bathroom with a dressing room that is currently being used as an office. From here you have the luxury of sitting on the second story partially covered porch with an open balcony for sunbathing in the summer and warmer winter days! There is a yard with a patio and paths with bridges to cross the brook to a lovely garden area. The main yard has beautiful perennial gardens. A peaceful location just minutes to recreation, the Mountain Top Inn and Rutland shopping. New Roof was completed on 9/4/26!

126 Shadow Ln, Pittsford
13s 13s Mountain View Dr, Pittsford
$65,000
5096054 MLS
Picture the home you've always sketched in your mind, then imagine the perfect blank canvas to bring it to life. This vacant parcel in Pittsford offers exactly that—an opportunity to build your Vermont vision from the ground up, with mountain views thrown in as a daily bonus. Tucked along a quiet dead-end street shared by just three neighboring homes, this lot delivers the kind of peace that's increasingly hard to find. No through traffic, no crowded cul-de-sac chaos—simply a serene setting where the loudest sound might be the breeze rustling through the trees. It's privacy without isolation, since town conveniences remain refreshingly close at hand. For those who measure a great location by what surrounds it, this spot truly shines. The Proctor-Pittsford Country Club sits less than a mile away, ready to welcome golf enthusiasts and social gatherers alike. Nature lovers can wander the nearby Cadwell Trail, perfect for morning walks or weekend exploration on foot. When winter arrives, you're wonderfully positioned for adventure. Pico Mountain Ski Resort is a short drive down the road, while the legendary slopes of Killington Resort await just beyond—world-class skiing practically in your backyard. This is more than a piece of land; it's the foundation for a lifestyle balancing scenic tranquility with everyday accessibility. Whether you envision a cozy retreat or a forever home, the possibilities here are wide open. Come walk the property and start dreaming today.

13s 13s Mountain View Dr, Pittsford
Off Off Allen Mills Rd, Pittsford
$265,000
5029253 MLS
Town of Pittsford Tax bill uses the address as 40 Allen Mills Road. There is no access to this property from Allen Mills Road. DO NOT use Allen Mills Road to access this property. It is a private Road and has no access to this property. This property is considered "land locked" with no road frontage on any private or public road or any recorded or implied right of way to this property. Property adjoins the West Rutland State Forest which is public lands. There is a steep winding access road to the State Forest off Whipple Hollow Road in Florence. Seller does not represent that there is any right to use State Forest Road to access this property. No vehicles allowed on West Rutland State Forrest. ***There is no trespass authorized or implied by seller or Agent across any adjacent lands or any non public road without prior written consent obtained from the owner of adjacent lands by any interested parties attempting to access this property.***Adjacent landowners are recorded at the Pittsford Town Offices.

Off Off Allen Mills Rd, Pittsford
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