Pittsford Homes under $350,000

Welcome to Pittsford, Vermont—a charming town nestled in the heart of Rutland County, where picturesque landscapes and a strong sense of community blend seamlessly. Known for its stunning natural beauty, Pittsford is a haven for outdoor enthusiasts, offering a variety of recreational activities including hiking, fishing, and skiing at nearby resorts. With its rich history and quaint New England charm, Pittsford boasts a welcoming atmosphere that makes it an ideal place to call home.

For those seeking an affordable slice of this idyllic lifestyle, Pittsford offers an array of homes priced under $350,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, you’ll find a diverse selection of properties that cater to various needs and preferences. From cozy single-family homes with inviting yards to charming cottages that exude character, the real estate market here is brimming with opportunities.

Living in Pittsford means enjoying the best of both worlds—small-town tranquility with convenient access to larger urban amenities in nearby Rutland. Residents benefit from excellent local schools, community events, and a strong sense of camaraderie among neighbors. Imagine sipping your morning coffee while taking in the breathtaking views of the Green Mountains or exploring the scenic trails that surround your new home.

Don’t miss your chance to discover the charm of Pittsford and the affordable housing options that await you. Embrace the opportunity to create lasting memories in this delightful Vermont town, where every day feels like a breath of fresh air. Your dream home in Pittsford is just a visit away!

Newest Pittsford Homes under $350,000

$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

$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

$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

$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

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