Pittsfield, VT Houses for Sale

/60
$2,150,000
- 3 Beds
- 4.5 Baths
- 4,671 Sq Ft
681 S Hill Rd, Pittsfield, VT 05762

Welcome to your private sanctuary in the heart of Vermont—this exceptional three bedroom, five bath property blends high-end craftsmanship with unmatched access to outdoor adventure. Offered fully furnished and meticulously equipped, this log-home masterpiece is defined by its stunning views of neighboring mountains and the valley below. Situated on 31 secluded acres encompassing three

Bret Williamson Killington Valley Real Estate

681 S Hill Rd, Pittsfield, VT 05762
/50
$599,999
- 3 Beds
- 1.5 Baths
- 1,512 Sq Ft
26 Fiddlehead Ln, Pittsfield, VT 05762

Completely renovated, furnished, and equipped 3+ bedroom home offers immediate relaxation. Nestled on 1.8 acres in a highly desirable neighborhood. The large porch-way with storage leads you to a foyer with a laundry area, closet, bench seating, and shelving for travel totes. The primary bedroom boasts vaulted ceilings and large windows which bring in natural light. Upstairs, you'll find an open

Jessica Posch Killington Pico Realty

26 Fiddlehead Ln, Pittsfield, VT 05762
/50
$715,000
- 3 Beds
- 2 Baths
- 1,882 Sq Ft
162 Campbell Rd, Rochester, VT 05767

This classic Vermont farmhouse has been lovingly renewed from the studs out, preserving its 19th-century charm while adding the comfort and convenience of modern living. Step inside and you’ll find warm hardwood floors crafted from ash, birch and cherry harvested right from the property, exposed beams, and a central brick hearth with a soapstone woodstove that invites you to gather around on

Kyle Kershner Killington Pico Realty

162 Campbell Rd, Rochester, VT 05767
/43
$679,000
- 3 Beds
- 2 Baths
- 1,424 Sq Ft
108 Heritage Heights, Stockbridge, VT 05772

Welcome to your dream home in the heart of Vermont! ONLY MINUTES TO KILLINGTON MOUNTAIN RESORT. This stunning 3 bedroom, 2 bath home offers breathtaking views from many of the rooms of the house and the expansive deck allowing you to soak up the beauty of every season. The bright and airy open floor plan is perfect for both relaxing and entertaining. Walk into the spacious tiled mudroom, ideal

Katie McFadden RE/MAX North Professionals

108 Heritage Heights, Stockbridge, VT 05772

Vermont Rutland County Pittsfield

Why Live in Pittsfield

Pittsfield, Vermont, is a small community nestled in the Green Mountains, offering year-round outdoor activities. Located about 13 miles from Killington Resort, residents have easy access to skiing and snowboarding in winter, as well as hiking and mountain biking in the warmer months. The Green Mountain National Forest surrounds the area, providing numerous trails, including the Long Trail. Homes in Pittsfield range from turn-of-the-century farmhouses to contemporary cabins, with unique architectural designs by Robert Carl Williams featuring stone fireplaces and large windows. The community has a mix of Victorian and Craftsman styles along Route 100, while more modern homes are found in the mountainous areas. Local amenities include The Original General Store, which offers groceries, gifts, and a deli, and The Backroom, a seasonal restaurant serving upscale American cuisine. Nearby, Wild Fern in Stockbridge provides casual dining with live music. Annual events like the Snow Devil Snowshoe Race and Memorial Day parade bring the community together. For education, Killington Elementary School and Woodstock Union High School and Middle School are highly rated, offering a range of academic and extracurricular opportunities. Pittsfield is conveniently located with Route 100 running through it, and Rutland, with its larger shopping options, is about 20 miles away. The area is known for its lower taxes compared to neighboring Killington and offers a quiet countryside retreat with a variety of things to do.

Learn more about living in Pittsfield

Home Trends in Pittsfield, VT

On average, homes in Pittsfield, VT sell after 81 days on the market compared to the national average of 52 days. The median sale price for homes in Pittsfield, VT over the last 12 months is $660,000, up 25% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$660,000

Median Single Family Sale Price

$629,999

Average Price Per Sq Ft

$392

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

8.00

Median List Price

$699,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

25%

How to Buy a Home How to Finance a Home How to Sell a Home

In Pittsfield, there are currently 4 houses for sale, offering an array of options for potential buyers. With houses priced between $599,999 to $2,150,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Pittsfield is $699,000, while the average sale price is $671,833, offering insights into the local housing market. On average, houses spend 81 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Pittsfield, VT and find the perfect place to call home.

Pittsfield Types of Homes for Sale

Pittsfield Homes for Sale

More About Living in Pittsfield

Homes in Nearby Cities

Homes in Nearby Counties

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.