Pittsfield Vermont Real Estate
Rutland County
Chartered: July 29, 1781
Area: 13,418 Acres = 20.97 Square Miles
Population (US Census, 2000): 427
Population Density (persons per square mile): 20.4
Pittsfield is found in the heart of the Green Mountains, with access to the Long Trail and extensive hiking and cross-country skiing trails in the Green Mountain National Forest. The town is smack in Central Vermont, along RT 100, north of Killington. Residents don’t have to drive far to get to Killington Resort and Pico Ski Area. The nearby Tweed River is a great location to fish. In under an hour one can drive from Pittsfield Vermont real estate to Vermont’s best ski resorts, like Killington Resort, Pico Ski Area, Suicide Six Ski Area, and Okemo Mountain Resort.
![]() |
Hawk Mountain Road Pittsfield
[ Photos: 8 ]
Listing Price: $36,000
Parcel is not part of Hawk Mountain Association. Short private shared Road to PAVED driveway (aprox 500') to Lot 3. Survey pins are well marked. This 1.7 acre parcel includes an additional 10,000sq.ft. parcel that is authorized for subservice waste water disposal. This building site is priced for a quick sale and was on the market in 2006 for $49,500. Land Use permit EC-0638 dated 1979 as well as Septic design by Bruno Assoc dated Jan 1979 on file. MLS #: 4019301 [View Property] |
![]() |
Listing Price: $39,000
No other opportunity exists at this price. Wooded 1.06 acre lot in Pittsfield, located in the exclusive Highwood Community. Close proximity to Killington. Come build your dream home. Enjoy skiing, kayaking, swimming, fishing and the peace and serenity of the Vermont Mountains. MLS #: 4000646 [View Property] |
![]() |
50 Dove Drive; Lot 90 Pittsfield
[ Photos: 4 ]
Listing Price: $49,000
Beautiful 1 acre building site with views of mountains to the west. Country setting yet less than a mile to the village of Pittsfield. Located in Our World/Highwood, a community of mostly vacation homes. Septic permit approves a 3 bedroom house. On-site septic plans include an Ecoflow Biofilter. Also permitted for an on-site well. MLS #: 2705181 [View Property] |
![]() |
Rte. 100 Pittsfield
[ Photos: 4 ]
Listing Price: $59,000
Great spot! On scenic Rte.100; close to Killington ski areas, restaurants and shopping MLS #: 4015720 [View Property] |
![]() |
7 SOUTH HILL RD 7C (lot#3) Pittsfield
[ Photos: 2 ]
Listing Price: $60,000
Pittsfield, VT: High terrain, 10.8 acres with 3-bedroom in-ground septic sys design. Elec at road. Great location for vacation home near skiing, rivers, snowmobiling, hiking, fishing, etc. MLS #: 2601728 [View Property] |
![]() |
7 SOUTH HILL RD 7A (lot#1) Pittsfield
[ Photos: 2 ]
Listing Price: $60,000
PITTFIELD, VT: HIGH TERRAIN - 10.2 AC W/ 3BR IN-GROUND SEPTIC SYS DESIGN. ELEC AT RD. PERFECT LOCATION FOR VACATION HOME -NEAR SKIING, RIVERS, SNOWMOBILING, HIKING, FISHING, ETC. WINTER VIEWS MLS #: 2601531 [View Property] |
![]() |
7 SOUTH HILL RD 7B (lot#2) Pittsfield
[ Photos: 2 ]
Listing Price: $60,000
Pittsfield, VT: High terrain, 10.1Acres w 3-BR in-ground septic sys design. Elec at road. Great location for vacation home near skiing, rivers, snowmobiling, hiking, fishing, etc. Adj.lots (A&C aka 1&3) have septic ROW's on this parcel known as Lot B, #2. MLS #: 2601727 [View Property] |
![]() |
232 Route 100 Pittsfield
[ Photos: 3 ]
Listing Price: $65,000
20-acre wooded parcel with 4-bedroom State WW Permit, located just north of Killington/Pittsfield town line. Great location for ski house or hunting camp. Timber contract in place, with additional logging potential. MLS #: 4009890 [View Property] |
![]() |
2358 Route 100 Pittsfield
[ Photos: 21 ]
Listing Price: $68,500
This Wintergreen condo offers high ceilings, updated appliances, brand new carpeting, and park at your front door access. Fees include firewood, trash, laundry facility, hot tub, plowing, shoveling. Perfect for someone who needs a cozy home close to skiing and golf with no weekend projects! MLS #: 2816283 [View Property] |
![]() |
14 Graysville Drive Pittsfield
[ Photos: 12 ]
Listing Price: $144,000
This home is a quintessential Log Cabin in a picturesque country setting. The spacious 4 Bedroom/2 Bath home has a huge living room with wood burning fireplace & cathedral ceilings, an open dining area, sunny eat-in-kitchen, tons of windows throughout, ample storage, mud room with room for all your gear, a massive porch, mountain views & more. MLS #: 2835776 [View Property] |
One-Click Searches
- » Rutland Vermont Homes (257)
- » Castleton Vermont Homes (62)
- » Ludlow Vermont Homes (44)
- » Lots and Acreage (17)
- » Vermont Foreclosures (133)
- » Open Houses (3)
182 Woodstock Avenue
Rutland, Vermont 05701
Telephone: 802-773-3500
Fax: 802-773-2837
Toll Free: 800-639-0022
Email: rutland@cbwatson.net
» more contact info
194 Main Street
Ludlow, Vermont 05149
Telephone: 802-228-5678
Fax: 802-228-4100
Toll Free: 866-318-5678
Email: ludlow@cbwatson.net
» more contact info
15 Route 4A, P.O. Box 493
Castleton Corners
Bomoseen, Vermont 05732
Telephone: 802-468-2222
Fax: 802-468-5666
Toll Free: 800-489-6955
Email: castleton@cbwatson.net
» more contact info









