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253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo
253 Lookout Road, Pittsfield, VT 05762 Photo

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  • Listing Provided by:
    Killington Pico Realty
    Phone: 802-422-3600
    Agent: Kyle Kershner IDX logo

  • 3
    Beds
  • 3
    Baths
  • 1,518
    Square Feet
  • 5105259
    MLS#
$479,000
Status: Active
253 Lookout Road Pittsfield, VT 05762

Property Description

Nestled among the woods of Pittsfield's coveted Townsend Brook area, this beautifully maintained and thoughtfully updated chalet captures the essence of the quintessential Vermont mountain getaway. Designed in the tradition of a European alpine chalet, the main living level occupies the second floor, maximizing natural light and creating a warm, inviting space for après-ski gatherings or quiet evenings by the fire. Recent improvements include an upper-level bump-out with a charming reading nook and convenient powder room, beautiful maple hardwood floors, modern lighting and ceiling fans, and beautifully remodeled bathrooms. An enclosed former storage shed has been transformed into a generous mudroom and first-floor laundry, complete with a wall of built-in cabinetry for skis, bikes, boots, and outdoor gear. A spacious wraparound deck extends the living space outdoors, offering both sunny and shaded spots for morning coffee, al fresco dining, or gathering with friends. Surrounded by the Green Mountains, miles of mountain biking and snowmobile trails are practically at your doorstep, while world-class skiing at Killington and Pico is just minutes away. With easy access from Montreal, Boston, and New York City, this turnkey retreat offers an appealing combination of comfort, recreation, and value - equally suited to weekend escapes, investment income, or year-round living.

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Property Features

MLS Number: 5105259
Subdivision:
County: Rutland
Bedrooms: 3
Full Baths: 1
3/4 Baths: 1
Total Square Feet: 1,518
Style: Chalet
New Constuction: No
Construction: Wood Frame,Vertical Siding,Wood Siding
Outdoor Features: Deck, Shed
Waterfront: No
Property Type: Residential - Single Family
Basement: Crawl Space
Cooling: Wall AC Units, Mini Split
Garage: 1
Heating: Baseboard, Electric
Lot Size: 1.80 Acres
Road Frontage: 197
Roof Type: Architectural Shingle, Standing Seam
Stories: 1.5
Taxes: $5,734
Year Built: 1975

Amenities

Ceiling Fan
Dining Area
Gas Fireplace
Natural Woodwork
Vaulted Ceiling
Deck
Shed

Feature Descriptions

Appliances: Dishwasher, Dryer, ENERGY STAR Qual Dryer, Electric Range, Refrigerator, ENERGY STAR Qual Washer
Baths 1/2: 1
Baths 3/4: 1
Baths Full: 1
Color: Brown
Construction: Wood Frame, Vertical Siding, Wood Siding
Days on Market: 81
Driveway: Gravel
Electric: Circuit Breaker(s)
Equipment: Standby Generator
Exterior: Wood Frame, Vertical Siding, Wood Siding
Flood Zone: No
Flooring: Carpet, Combination, Hardwood, Tile
Foundation: Block
Home Style: Chalet
Lot: Wooded, Neighborhood
Number of Rooms: 8
Parking: Driveway, Garage
Roads: Gravel, Public
Sewer: Private, Septic
Sq. Ft. Above Grade Finished: 1518
Sq. Ft. Total Finished: 1518
Total Stories: 1.5
Water: Drilled Well, Private

Location

Listed By / Shown By

Listed By

Broker Name: Killington Pico Realty
Agent Name: Kyle Kershner
Broker Phone: 802-422-3600

agent picture

Shown By

Agent Name: Keegan Rice
Agent Phone: Cell: (603) 348-7261
Broker Title: Badger Peabody & Smith Realty

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Estimate Your Payment

Estimated Payment

$ 3,197.94 per month $2,580.40 Principal & Interest $477.83 Property Tax $139.71 Homeowner's Insurance

Source: Delta Media Group, Inc.

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 11/14/2026. The listing information on this page last changed on 11/14/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 11/14/2026 8:18:26 AM EST) or Prime MLS (last updated Fri 11/13/2026 2:36:24 PM EST) or MREIS (last updated Sat 11/14/2026 7:22:10 AM EST). Real estate listings held by brokerage firms other than Badger Peabody & Smith Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 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 2026-11-13 14:36:24

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