Pittsford Homes for Sale

Welcome to Pittsford, a charming town nestled in the heart of Rutland County, Vermont. Known for its picturesque landscapes and friendly community, Pittsford offers a peaceful retreat from the hustle and bustle of city life.

In Pittsford, you'll find a variety of homes for sale to suit every lifestyle. Whether you're looking for a cozy cottage, a historic farmhouse, or a modern family home, Pittsford has something for everyone. With its tree-lined streets and well-maintained properties, Pittsford is the perfect place to put down roots and call home.

From outdoor enthusiasts to history buffs, Pittsford has something to offer everyone. Explore the nearby hiking trails, take a leisurely stroll through the town's historic district, or simply relax and enjoy the beauty of Vermont's countryside.

If you're looking for a place to settle down and enjoy the peace and tranquility of small-town living, Pittsford is the perfect place for you. Come and discover all that this charming town has to offer - you may just find your dream home here in Pittsford, Vermont.

Newest Pittsford Homes for Sale

$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

$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

$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

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