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

$122,000

1 Beds ⋅ 1 Baths ⋅ 5104998 MLS

Welcome to easy, low-maintenance living in this renovated condo on the lower level. Thoughtfully laid out to make the most of its space, this inviting unit offers a comfortable living area, functional kitchen, and all the essentials in a manageable footprint. Sliding glass doors provide an abundance of sunlight which leads out to a patio area and an open grass yard perfect for pets overlooking mountain view. Whether you're looking for a primary residence, weekend getaway, or an easy-to-maintain Vermont home base, this condo offers simplicity and convenience without the upkeep of a larger property. This condo offers a private heated entrance leading to the unit and acts as a mudroom, a private heated storage room and coin-op laundry. A great opportunity to make a space your own and enjoy carefree condo living.

21 Old Colony Way Unit B2, 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

$290,000

3 Beds ⋅ 2 Baths ⋅ 5101279 MLS

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. 9/4 New Roof!

126 Shadow Ln, Pittsford

$262,000

3 Beds ⋅ 2 Baths ⋅ 5100006 MLS

Come see 5190 Whipple Hollow Road and discover your opportunity to own a beautiful Vermont country retreat at an attractive price. If you’ve been waiting for the right home, the time to see this one is now! Open House: Saturday, September 5th, 2026 from 12pm-1pm. Set on a picturesque country lot, this inviting, move-in-ready property offers the perfect blend of comfort, privacy, and Vermont charm. The open and airy floor plan is filled with natural light, while the updated kitchen flows seamlessly into the dining and living areas—perfect for entertaining or simply enjoying everyday life. Step outside onto the wrap-around deck overlooking the beautiful yard, an ideal setting for morning coffee, summer gatherings, and relaxing evenings surrounded by nature. All improvements made since 2023 include a brand new kitchen, plus both the primary and secondary bathrooms, updated light fixtures, new appliances, updated exterior doors, fresh paint, new flooring, and a new septic tank replaced in August, 2026. A new oil tank, plus all mechanics of the home have 2026 annual service tags. Whether you're searching for your first home, a peaceful getaway, or a place to enjoy everything Vermont has to offer, this property delivers country living with convenient access to Rutland, skiing, golf, lakes, hiking, and year-round outdoor recreation. OPEN HOUSE — COME TAKE A LOOK BEFORE IT’S GONE! With an attractive price and so many recent updates, this is an opportunity you won’t want to miss. Come see it, fall in love with the setting, make your offer, and move in before the last of the foliage falls!

5190 Whipple Hollow Rd, Pittsford

$249,500

3 Beds ⋅ 2 Baths ⋅ 5097502 MLS

Classic Vermont charm meets everyday comfort in this inviting Pittsford Village home, where original character, thoughtful updates, and a spacious backyard come together at an exceptional value. A welcoming covered front porch offers the perfect place to enjoy your morning coffee or unwind after a busy day. Step inside to discover original hardwood floors that add warmth and timeless appeal throughout much of the home. The comfortable living room is centered around a cozy wood stove, creating an inviting atmosphere during Vermont's colder months. The eat-in kitchen and formal dining room provide flexibility for both everyday living and entertaining, while a full bath with first-floor laundry adds convenience. Upstairs, three comfortable bedrooms and a second full bath offer space for family, guests, or a home office. The .38-acre lot features a spacious backyard with room for gardening, pets, play, or outdoor gatherings. Replacement windows, low-maintenance vinyl siding, and a standing-seam metal roof provide lasting durability and reduced maintenance. A detached garage and ample driveway parking complete the property. Ideally located in the heart of Pittsford Village, you'll enjoy walking to the Pittsford Recreation Area and Lothrop Elementary School, with local shops and amenities just minutes away. Rutland is only 15 minutes away, and Burlington International Airport is less than 90 minutes from home. Blending character, functionality, and value, this home offers an opportunity that's becoming increasingly difficult to find in today's market. Sale is subject to the sellers securing suitable housing. Relocation options have been identified, and a flexible closing timeline is available.

268 Furnace Rd, 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

$589,000

4 Beds ⋅ 3 Baths ⋅ 5095511 MLS

Stately Colonial with 10 Private Acres and Spectacular Western Mountain Views. Perched atop a beautiful knoll and privately situated on 10 acres, this exceptional four-bedroom, three-bath home offers timeless charm, warmth, and breathtaking western sunsets. A winding driveway leads to the residence, creating a wonderful sense of arrival and complete privacy. Offering approximately 2,700 square feet of living space, this home is filled with character, including rustic wide-plank pine flooring, exposed brick walls, beautiful beams, and three wood-burning fireplaces that create an inviting atmosphere throughout. The spacious kitchen and family room combination is the heart of the home, featuring wide pine floors, exposed beams, and a handsome brick fireplace. A separate dining room, ideal for entertaining, is highlighted by a large window overlooking the meadow beyond. The generously sized living room also showcases wide pine flooring and a warming fireplace, creating a wonderful gathering space. Mini-split systems add year-round comfort, providing efficient air conditioning during the warmer months. The first floor also offers a nicely sized office, mudroom, full bath, and a delightful sunroom just off the kitchen, providing the perfect place to relax and enjoy the peaceful surroundings. The second level features four oversized bedrooms, including a spacious primary suite with its own private bath, plus an additional family bath. The finished lower level features the home's third fireplace and offers flexible space for a recreation room, media room, exercise area, or hobby space. Pittsford is known for its scenic walking trails, beautiful rural landscapes, and strong sense of community. Residents enjoy the town's community swimming pond and the iconic Kamuda's Market, a local favorite for generations. Conveniently located between Rutland and Middlebury, with easy access to world-class ski areas, pristine lakes, shopping, dining, and year-round recreation. LIVE VT.

5876 Rte 7, Pittsford

$524,600

3 Beds ⋅ 3 Baths ⋅ 5095139 MLS

Set along desirable Orchard Hill in Pittsford, this distinctive Tudor-inspired home offers timeless curb appeal, comfortable living space, and a beautiful 1.3-acre setting. The exterior blends brick, stucco-style accents, dark trim, mature landscaping, and a welcoming front entry, creating a property with warmth and character from the moment you arrive. Inside, the home features an inviting kitchen with abundant cabinetry, generous counter space, stainless appliances, a gas range, and a charming windowed sink area overlooking the backyard. The floor plan provides comfortable everyday living, with 3 bedrooms, 3 baths, and approximately 2,070 sq. ft. of space. The expansive primary bedroom boast a large sitting area that would be great space for a quite sitting area, an exercise space or an office and an enormous walk-in closet. Add to that a bath which offers dual vanities, an oversized walk-in tiled shower and a relaxing jetted shower panel. Outside, you will enjoy both a sun-drenched side porch that extends the already spacious living room as well as a rear deck with access to the back yard and fenced in area. This space is ideal for relaxing, entertaining, pets, or gardening. An attached 2-car garage adds convenience, while the Pittsford location offers a peaceful residential feel with easy access to Rutland, Brandon, area recreation, schools, and local amenities. A wonderful opportunity to own a character-filled Vermont home in a well-established neighborhood. Welcome home!

608 Orchard Hl, Pittsford

$299,000

5074851 MLS

Discover the potential that savvy investors dream about with this remarkable multi-family property. This four-bedroom, three-and-a-half-bathroom gem offers a rare chance to build substantial passive income while enjoying the charm of rural New England living. What makes this property truly shine is its impressive rental income potential. Current rents are positioned below market rates, presenting an immediate opportunity to increase your return on investment. Each unit comes equipped with its own washer and dryer, a highly sought-after amenity that today's tenants prioritize and willingly pay premium prices to secure. Convenience defines daily life here. Residents enjoy effortless access to local markets, quality schools, and an abundance of recreational opportunities that make this region so desirable. Nature enthusiasts will appreciate the proximity to Cadwell Trail, perfect for hiking adventures and outdoor exploration just minutes away. The property's location along a well-traveled route ensures excellent visibility and accessibility, making it attractive to prospective tenants. Schedule your private showing today and see firsthand why this multi-family property deserves a place in your portfolio

3880 Us Rte 7, Pittsford

$525,000

4 Beds ⋅ 3 Baths ⋅ 5064746 MLS

Welcome to your peaceful mountain retreat in the heart of Vermont's premiere ski country. Only minutes from Killington and Pico Mountains, this spacious 2.5-story, 4 bedroom, 3 bathroom home offers the perfect blend of rustic charm and modern comforts. All surrounded by Vermont’s natural beauty and stunning views of Killington Mountain. Step inside to a bright and open living space where the vaulted ceiling, exposed beams, and the large multi-floor windows frame the tranquil forest setting. The inviting great room features a grand stone hearth and wood stove, creating a cozy atmosphere after a day on the slopes. The adjoining dining area and kitchen make entertaining easy, with warm wood cabinetry, ample counter space, and a breakfast bar that’s perfect for gatherings. Off of this space is a wonderful wrap-around deck that offers unobstructed mountain views. Completing this level are two guest bedrooms with each offering its own sense of privacy and relaxation, highlighted by natural light and peaceful woodland or mountain views. The primary suite is located just above this space and has a private entrance overlooking the great room below. Downstairs, a finished walkout lower level provides flexible space for a media room, home office, or guest suite complete with a recessed ceiling, built-in shelving and an additional full bathroom. So if you are into skiing, snowmobiling, hiking, swimming or anything outdoors then this home is a must see. Welcome Home!

1724 Sangamon 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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