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Pending
  • $269,900

    158 Skyline Trl, Middlefield, MA 01243

    3beds
    3,576sqft
    : 
    $1,973/mo
    Get pre-qualified
    Single Family Residence
    Built in 1837
    1 Acres Lot
    $281,000 Zestimate®
    $75/sqft
    $-- HOA

    What's special

    Mature landscapingBlueberry bushesGenerously sized roomsSpacious lawnPear treesFlexible floor plan
    Attention investors, cash buyers, and those ready to bring their vision to life—this charming 1837 Colonial-style farmhouse offers a unique opportunity in the heart of beautiful Middlefield. With approximately 3,576 square feet of bright, sun-filled living space, the home features generously sized rooms, a flexible floor plan, up to 5+ possible bedrooms, and 3 full bathrooms. The attached red carriage barn/workshop adds valuable versatility, providing ample space for hobbies, storage, a workshop, or creative pursuits. Set on a full acre, the property features mature landscaping, pear trees, blueberry bushes, and a spacious lawn that creates a peaceful country retreat.Enjoy the best of small-town living with the Middlefield Fairgrounds just a short walk away, plus easy access to area trails for hiking, snow sports, and exploring the outdoors. For those seeking recreational or investment potential, this Berkshire location is ideally situated near Jacob’s Pillow Dance Festival, Otis Reservoir, Otis Ridge Ski Area, Butternut, Stockbridge, Northampton, Pittsfield, Lee, Lenox, and many other popular cultural and recreational destinations.With its character, generous living space, acreage, carriage barn, and desirable Berkshire location, this property offers exciting possibilities as a primary residence, vacation getaway, or investment property, including potential Airbnb/vacation rental use. Property is being sold as-is. Buyers are responsible for their own due diligence. Shared well serves 6 homes and has a semi-annual water system maintenance fee of $168.
    23 days
    1,456
    235

    Zillow last checked:

    Listing updated:

    Listed by:

    Dennis LeClair 413-841-1863,

    RE/MAX Compass 413-568-0040

    Source: MLS PIN,MLS#: 73567550

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Level: Second
      Bedroom 5
      • Level: Second
      Bathroom 1
      • Level: First
      Bathroom 2
      • Level: Second
      Bathroom 3
      • Level: Second
      Heating
      • Forced Air, Electric Baseboard, Oil, Electric, Wood
      Cooling
      • None
      Appliances
      • Included: Electric Water Heater, Refrigerator, Washer
      • Laundry: In Basement, Washer Hookup
      Features
      • Basement: Full,Crawl Space,Sump Pump,Dirt Floor,Concrete
      • Has fireplace: No
      Interior area
      • Total structure area: 3,576
      • Total interior livable area: 3,576 sqft
      • Finished area above ground: 3,576

      Property

      Parking
      • Total spaces: 4
      • Parking features: Storage, Workshop in Garage, Barn, Off Street
      • Has garage: Yes
      • Uncovered spaces: 4
      Features
      • Patio & porch: Porch
      • Exterior features: Porch, Rain Gutters, Barn/Stable
      • Fencing: Fenced/Enclosed
      Lot
      • Size: 1 Acres
      • Features: Level
      Details
      • Additional structures: Barn/Stable
      • Parcel number: M:406.0 B:0013 L:0000.0,4082131
      • Zoning: R1

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial,Farmhouse
      • Property subtype: Single Family Residence
      Materials
      • Frame, Brick, Stone
      • Foundation: Stone, Brick/Mortar
      • Roof: Shingle
      Condition
      • Year built: 1837

      Utilities & green energy

      • Electric: Circuit Breakers
      • Sewer: Private Sewer
      • Water: Shared Well
      • Utilities for property: Washer Hookup

      Community & HOA

      Community
      • Features: Walk/Jog Trails, Bike Path, Public School
      HOA
      • Has HOA: No
      Location
      • Region: Middlefield

      Financial & listing details

      • Price per square foot: $75/sqft
      • Tax assessed value: $292,000
      • Annual tax amount: $5,326
      • Date on market: 8/24/2026

        Estimated market value

        $281,000

        $267,000 - $295,000

        $3,862/mo

        Price history

        DateEventPrice
        9/16/2026Pending sale$269,900$75/sqft
        Source: MLS PIN #73567550 Report a problem
        9/2/2026Contingent$269,900$75/sqft
        Source: MLS PIN #73567550 Report a problem
        8/24/2026Listed for sale$269,900+66.9%$75/sqft
        Source: MLS PIN #73567550 Report a problem
        1/12/2007Sold$161,700$45/sqft
        Source: BCMLS #174964 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,326 +0.6%$292,000 +9.4%
        2024$5,293 +19.9%$266,800
        2023$4,416 -2.4%$266,800 +4.9%
        2022$4,526 +3.6%$254,400 +3%
        2021$4,370 -4.4%$246,900 -1%
        2020$4,572 +1.8%$249,300
        2019$4,492 +4.3%$249,300 +2.1%
        2017$4,305 +2.4%$244,200 +3.7%
        2016$4,204 -0.7%$235,500 -3%
        2015$4,233 +0.1%$242,700
        2014$4,228 -5.9%$242,700 -12.8%
        2013$4,492 +2.3%$278,300
        2012$4,392 +4.2%$278,300 -0.1%
        2011$4,214 -2.4%$278,700 +6.7%
        2010$4,319 +6%$261,300
        2009$4,074 +128.7%$261,300 +143.1%
        2008$1,781 $107,500
        2005$1,781 +1.1%$107,500 +17.4%
        2003$1,762 +10.7%$91,600 -1.8%
        2001$1,591 $93,300
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 01243

        Getting around

        15 / 100
        Car-Dependent
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Chester Elementary/Littleville
        • Middle: Gateway Regional School
        • High: Gateway Regional School

        Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.