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Off market
  • $3,433,600

    238 Painter Hill Rd, Roxbury, CT 06783

    5beds
    3,428sqft
    SingleFamily
    Built in 1872
    11.36 Acres Lot
    $3,433,600 Zestimate®
    $1,002/sqft
    $5,285 Estimated rent

    Home value

    $3,433,600

    $2.99M - $3.98M

    $5,285/mo

    Zestimate® history
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    $5,285/mo

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    Rent Zestimate®

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    $23,253/mo

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    $23,253/mo

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    What's special

    Picture-perfect essence of NE. c.1872. 5 BR main residence, guest house, gunite pool, screened porches, brick dining patio w/ pergola. Fully renovated in 2015 while maintaining all of its charm. Quiet setting w/ western exposure at the top of Painter Hill. Ideally sited on 12+/- AC of level lawn w/ antique canopied trees, flowering perennials, rebuilt stone walls, pond, bocci court & orchard. Interior w/ period details. Oak flooring & exposed hand-hewn beams. Country kitchen w/ glass-faced cabinetry, soapstone counters & designer appliances - Subzero refrigerator, Wolf stove + walk-in pantry, butler closet. Formal dining room w/ 8-over-8 windows, sunset views & direct access to outdoor dining patio. Adjacent are the formal LR w/ views of the grounds, FP & cozy family room/media nook. Main floor master suite, private screened porch, walk-in closet/dressing room, marble BA, dbl sinks, soaking tub & separate shower. Also on main floor, office, laundry rm w/ dbl set of Miele washer/dryers. On 2nd floor, 4 guest BRs, 2 w/ sleeping coves & built-in storage, 2 full baths. Partially finished lower level w/ temperature-controlled wine cellar & pantry. Guesthouse/ home office w/ full eat-in kit w/ the quality of the main house. Main level en-suite BR & 1/2 BA. Upper level w/ media room & sleeping alcoves. Full house generator & irrigation system. Plans are avail for barns/garage. Orig antique barnwood avail for construction - inquire on pricing. 90 minutes from NYC. Further History: Information from a survey of Roxbury by Rachel Carley. This 19th-century farmstead is significant as one of few Roxbury properties remaining in the family of the original owners. An Irish immigrant, Thomas OBrien (b. 1845) came to America in 1848 as a child and became a citizen in 1872. In 1924 he deeded his home lot to his son Edward J. OBrien, who then owned the property at 277 Painter Hill. In 1970, this property at 238 Painter Hill Road was distributed from Edwards estate to his son Joseph OBrien, who grew up on his fathers farm at 277 Painter Hill Road. Here at 238 Painter Hill Road, Joe OBrien maintained a herd of about 85 head of cattle and also raised pigs and poultry. The family owned 222 acres on Painter Hill and Painter Ridge Roads and another 20 acres on Booth Road. Crops included tobacco, hay and corn to provide silage for the dairy herd and the workhorses.

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 4
    • Full bathrooms: 3
    • 1/2 bathrooms: 1
    Heating
    • Other, Other
    Cooling
    • Central
    Appliances
    • Included: Dishwasher, Dryer, Washer
    Features
    • Flooring: Hardwood
    • Basement: Residence
    • Has fireplace: Yes
    Interior area
    • Total interior livable area: 3,428 sqft

    Property

    Parking
    • Total spaces: 2
    Features
    • Exterior features: Other
    Lot
    • Size: 11.36 Acres
    Details
    • Parcel number: ROXBM30L20

    Construction

    Type & style
    • Home type: SingleFamily
    Materials
    • Roof: Other
    Condition
    • Year built: 1872

    Community & neighborhood

    Location
    • Region: Roxbury

    Price history

    DateEventPrice
    6/23/2021Sold$2,750,000$802/sqft
    Source: Smart MLS #170388180
    4/16/2021Contingent$2,750,000$802/sqft
    Source: Smart MLS #170388180
    4/9/2021Listed for sale$2,750,000+12.2%$802/sqft
    Source: Smart MLS #170388180
    6/9/2020Sold$2,450,000$715/sqft
    Source: Smart MLS #170241553
    5/6/2020Pending sale$2,450,000$715/sqft
    Source: William Pitt Sotheby's International Realty #170241553

    Public tax history

    YearProperty taxesTax assessment
    2025$28,506 +3.2%$2,192,750
    2024$27,629 +81.2%$2,192,750 +81.2%
    2023$15,251 +12.9%$1,210,370 +36.6%

    Find assessor info on the county website

    Neighborhood: 06783

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Booth Free

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

    Sell for more on Zillow
    Get a free Zillow Showcase℠ listing and you could sell for .
    $3,433,600
    2% more+ $68,672
    With Zillow Showcase(estimated)
    $3,502,272