Pittsfield VT Homes

Learn more about Pittsfield homes from KillingtonPicoRealty.com, the best source for real-time information about property for sale in Killington’s nearest neighborhood to the north, Pittsfield, Vermont. Conveniently located in the Route 100 corridor, Pittsfield is the classic ski town, offering a balance of vacation and primary residential homes. From affordable chalets to gentleman’s farms, Killington Pico Realty can help you find a Pittsfield property that is right for you. Start here to browse all the homes currently for sale in the town of Pittsfield, VT.

* Magnificent 5BR Residence with Exceptional Views in Pittsfield, VT

239 Silver Spring Hill Road Pittsfield VT 05762

MLS Number 5024887

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

Experience breathtaking mountain views from nearly every room in this magnificent, architecturally compelling Pittsfield, VT residence. As you enter the generous, airlock mudroom with built-in cubbies, storage benches, shelves and coat racks, the thoughtful design integral to this masterful build is immediately evident. The easy flowing open floor plan features a living room with vaulted, knotty pine ceilings, a striking stone fireplace crafted from locally quarried natural granite, new hardwood floors and a wall of custom windows offering majestic views of the Green Mountains. Graceful curvilinear design components on each level provide the perfect counterpoint to the steep roof lines and contemporary exterior styling. The deck from the living room is the perfect place to relax with friends and take in evening sunsets. With cabinets and counters on three sides, a massive walk-in pantry, and generous breakfast bar, the spacious kitchen is a chef's delight, making this home perfect for entertaining. The dining area is surrounded by windows, bringing the natural environment indoors, while the the two-stage deck offers a covered area for grilling and an elegant open space for al fresco dining. With five bedrooms there is room for all your friends and family. Two guest bedrooms share a Jack and Jill bathroom, the main floor bedroom suite features private elevator access - ideal for family or guests with mobility challenges, while the primary bedroom suite on the upper level is an oasis of privacy, offering views, a covered three-season screened porch, dressing room and graceful architectural components. In addition to guest bedrooms, the walkout lower level features a beautiful family room with a second stone fireplace and magnificent natural slate floors, a generous laundry room with built-in shelves, cabinets, and folding table, two bathrooms and walkout access to the fabulous new 9-person hot tub, where you can indulge yourself in luxury after a day of exciting outdoor lifestyle activities in the surrounding mountain community. A new roof, completely rebuilt chimney, new floors, many new windows, a rebuilt elevator, new furnishings, dual-stage, high-efficiency heating comprising both radiant floor and baseboard hot water systems, a standby automatic backup generator, and updated security systems, ensure your comfort today and promise trouble-free living for years to come. Don't miss this opportunity to own this exceptional mountain getaway in the heart of the Green Mountains. Call today for a private showing of this magnificent residence.  Click here for an immersive 3-D virtual tour.

Listed by Killington Pico Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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-Family compound with views and sunny southern exposure

121 Jenny Pond Road Pittsfield VT 05762

Pittsfield, VT121 Jenny Pond Road

Price$749,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5013389

  • Residential Single Family
  • Full Bath 3
  • Address 121 Jenny Pond Road
  • Construction Existing
  • Bedrooms 4

Charming four-bedroom home on 3.247 acres with seasonal guest cottage, sunny southern exposure, and mountain views is perfect to host your extended family. The main house features an expansive master suite, two fireplaces, wrap-around deck, an in-law suite with second kitchen, lots of storage space, and an attached two car garage. The private setting provides breathtaking views and the magnificent grounds include beautiful stonework walls, blue stone patio, mature perennial gardens, nice gently sloping lawns and an outdoor hot tub gazebo. The gambrel-style cottage features a second two car garage below and a rustic, adorable guest suite on the upper level, ideal for summertime visitors. The property is on a quiet end of road location near the Green Mountain National Forest, close to skiing, mountain biking, hiking, the VAST trail, and offers direct access to a shared, private swimming pond. Net rental income in 2023 was $38,000 with owner usage.

Listed by Killington Pico Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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* Log Home with Soaring Vaulted Ceilings on 11 Private Acres - Close to Killington!

853 South Hill Road Pittsfield VT 05762

Pittsfield, VT853 South Hill Road

Price$689,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5015634

  • Residential Single Family
  • Full Bath 2
  • Address 853 South Hill Road
  • Construction Existing
  • Bedrooms 3

Discover your perfect mountain retreat in this stunning traditional log cabin, nestled on 11 private acres in the heart of the Green Mountains, just minutes from Killington, Vermont. As you enter the home, the soaring cathedral ceilings will take your breath away, while the wood and timber surfaces evoke a uniquely rustic, yet sophisticated ambiance. The open floor plan, beautifully crafted with knotty pine ceilings, hand-scraped natural log posts, gleaming hardwood floors and a striking fieldstone fireplace, make this home ideal for après-ski entertaining. The main level features a well-designed kitchen with center island and breakfast bar, a sunny dining area with lovely views, two gracious guest bedrooms and a full bathroom. The upper level comprises the private primary bedroom suite, including a spacious loft overlooking the great room, and an ensuite bathroom complete with jetted tub for the ultimate in relaxation. The finished walkout level offers a generous rec-room, two bonus rooms, half bath and a classic Vermont Castings woodstove for extra warmth on those cold Vermont winter nights. Step outside to enjoy the covered porch or soak up the sun on the south-facing deck, where you can take in the natural beauty of the surrounding landscape while sipping your morning coffee or enjoying an afternoon cocktail. With many recent upgrades and offered fully furnished, this home is truly turn-key, just in time for ski season! Don’t miss your chance to own this one-of-a-kind property. Call today for more information and to schedule your private showing. View 3-D Virtual Tour Here

Listed by Killington Pico Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3631 Route 100 Pittsfield VT 05762

Pittsfield, VT3631 Route 100

Price$390,000

Est. Mortgage: $/month

MLS Number 4970732

  • Multifamily
  • Address 3631 Route 100
  • Units 2
  • Bathroom 2
  • Acreage 0.7

Investment property with good rental opportunity. Located in bucolic Pittsfield and just minutes to the Killington Ski Area, this is a 2-unit commercial property consisting of a 2-bedroom apartment, a spacious main floor office unit with a 1/2 bath and a former studio with a 1/2 baht and a separate shower room. The basement has been used as a personal gym. The property has flat, easy access with plenty of parking and great sight lines. Good opportunity as this property has previously been a successful country store, butcher shop and yoga studio. Could be converted into residential units...may need Act 250 permission.

Listed by Walter Findeisen of Killington Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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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. Data last updated January 21, 2025 7:07 PM EST