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For sale
    • $779,000

    44 Chamberlain Hill Road, Middletown, CT 06457

    6beds
    3,199sqft
    : 
    $5,397/mo
    Get pre-qualified
    Single Family Residence
    Built in 1980
    7.02 Acres Lot
    $-- Zestimate®
    $244/sqft
    $-- HOA

    What's special

    Two striking stone fireplacesThoughtfully designed spacesFabulous loftWalls of windowsDramatic focal pointsGenerous proportionsMeticulous details
    A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to the surrounding landscape. The beautifully designed kitchen features quartz countertops, stainless steel appliances, double ovens, and generous space for gathering and entertaining. Two striking stone fireplaces serve as dramatic focal points, adding warmth, texture and character to the home's expansive living spaces. Offering six bedrooms and three-and-a-half beautifully renovated baths, the versatile floor plan provides exceptional flexibility for today's lifestyle. With its generous proportions and abundance of private and flexible spaces, the home is ideally suited for multigenerational living, extended family, guests, or those seeking dedicated space for a home office or home-based business. A fabulous loft provides yet another versatile area for a family room, office or game room. The spacious primary suite offers a walk-in closet, beautifully updated bath and private patio overlooking the peaceful surroundings. Throughout the home, meticulous details, interesting architectural elements and thoughtfully designed spaces create a sense of character rarely found in today's homes. Expansive windows invite sunlight throughout while showcasing the property's serene and remarkably private setting. Sophisticated yet inviting, spacious yet warm, this hidden gem offers a rare combination of privacy, versatility, character and modern luxury. 44 Chamberlain Hill Road is not simply a home - it is a one-of-a-kind retreat that truly must be experienced to be appreciated
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    Zillow last checked:

    Listing updated:

    Listed by:

    Sharon Linder (860)460-8862,

    Berkshire Hathaway NE Prop. 860-388-3411

    Source: Smart MLS,MLS#: 24199581MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Remodeled, Balcony/Deck, Full Bath, Sliders, Walk-In Closet(s), Engineered Wood Floor
      • Level: Lower
      • Area: 345 Square Feet
      • Dimensions: 15 x 23
      Bedroom
      • Features: Remodeled, Hardwood Floor
      • Level: Main
      • Area: 168 Square Feet
      • Dimensions: 14 x 12
      Bedroom
      • Features: Remodeled, Engineered Wood Floor
      • Level: Lower
      • Area: 224 Square Feet
      • Dimensions: 14 x 16
      Bedroom
      • Features: Remodeled, Hardwood Floor
      • Level: Main
      • Area: 195 Square Feet
      • Dimensions: 13 x 15
      Bedroom
      • Features: Remodeled, Palladian Window(s), Full Bath, Engineered Wood Floor
      • Level: Lower
      • Area: 224 Square Feet
      • Dimensions: 14 x 16
      Bedroom
      • Features: Remodeled, Engineered Wood Floor
      • Level: Lower
      • Area: 224 Square Feet
      • Dimensions: 14 x 16
      Dining room
      • Features: Remodeled, Fireplace
      • Level: Main
      • Area: 240 Square Feet
      • Dimensions: 16 x 15
      Family room
      • Features: Remodeled, Engineered Wood Floor
      • Level: Lower
      • Area: 160 Square Feet
      • Dimensions: 8 x 20
      Kitchen
      • Features: Remodeled, High Ceilings, Quartz Counters, Kitchen Island, Sliders, Tile Floor
      • Level: Main
      • Area: 288 Square Feet
      • Dimensions: 16 x 18
      Living room
      • Features: Remodeled, Skylight, Vaulted Ceiling(s), Ceiling Fan(s), Fireplace, Hardwood Floor
      • Level: Main
      • Area: 580 Square Feet
      • Dimensions: 20 x 29
      Loft
      • Features: Remodeled, Vaulted Ceiling(s), Ceiling Fan(s), Engineered Wood Floor
      • Level: Upper
      • Area: 304 Square Feet
      • Dimensions: 16 x 19
      Office
      • Features: Remodeled, Vaulted Ceiling(s), Ceiling Fan(s), Hardwood Floor
      • Level: Main
      • Area: 192 Square Feet
      • Dimensions: 16 x 12
      Other
      • Features: Remodeled, Hardwood Floor
      • Level: Main
      • Area: 320 Square Feet
      • Dimensions: 20 x 16
      Study
      • Features: Remodeled, Engineered Wood Floor
      • Level: Lower
      • Area: 144 Square Feet
      • Dimensions: 12 x 12
      Study
      • Features: Remodeled, Vaulted Ceiling(s), Hardwood Floor
      • Level: Main
      • Area: 192 Square Feet
      • Dimensions: 16 x 12
      Heating
      • Forced Air, Electric
      Cooling
      • Ceiling Fan(s), Central Air, Ductless
      Appliances
      • Included: Oven/Range, Refrigerator, Freezer, Dishwasher, Water Heater
      • Laundry: Lower Level
      Features
      • Open Floorplan
      • Basement: Full,Interior Entry,Partially Finished,Walk-Out Access,Liveable Space
      • Attic: None
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 3,199
      • Total interior livable area: 3,199 sqft
      • Finished area above ground: 3,199

      Property

      Parking
      • Total spaces: 1
      • Parking features: Attached
      • Attached garage spaces: 1
      Features
      • Patio & porch: Deck, Patio
      • Exterior features: Balcony, Rain Gutters, Lighting
      Lot
      • Size: 7.02 Acres
      • Features: Few Trees, Dry, Sloped
      Details
      • Parcel number: 1011350
      • Zoning: R-60

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Wood Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1980

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Available

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Middletown

      Financial & listing details

      • Price per square foot: $244/sqft
      • Tax assessed value: $486,480
      • Annual tax amount: $18,783
      • Date on market: 8/20/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $5,520/mo

        Price history

        DateEventPrice
        8/20/2026Listed for sale$779,000-6%$244/sqft
        Source: Smart MLS #24199581 Report a problem
        8/7/2026Listing removed$829,000$259/sqft
        Source: Smart MLS #24148860 Report a problem
        7/26/2026Price change$829,000-2.4%$259/sqft
        Source: Smart MLS #24148860 Report a problem
        6/14/2026Price change$849,000-2.3%$265/sqft
        Source: Smart MLS #24148860 Report a problem
        5/19/2026Price change$869,000-3.3%$272/sqft
        Source: Smart MLS #24148860 Report a problem
        4/17/2026Price change$899,000-2.8%$281/sqft
        Source: Smart MLS #24148860 Report a problem
        2/24/2026Listed for sale$925,000+781%$289/sqft
        Source: Smart MLS #24148860 Report a problem
        12/23/2025Sold$105,000-70%$33/sqft
        Source: Public Record Report a problem
        9/13/2024Sold$350,000+0.3%$109/sqft
        Source: Smart MLS #24035388 Report a problem
        8/1/2024Listed for sale$349,000-41.8%$109/sqft
        Source: Smart MLS #24035388 Report a problem
        3/23/2023Listing removed--
        Source: Smart MLS #170508567 Report a problem
        1/16/2023Listed for sale$599,900$188/sqft
        Source: Smart MLS #170508567 Report a problem
        12/23/2022Contingent$599,900$188/sqft
        Source: Smart MLS #170508567 Report a problem
        10/1/2022Price change$599,900-4.8%$188/sqft
        Source: Smart MLS #170508567 Report a problem
        7/14/2022Listed for sale$629,900+270.5%$197/sqft
        Source: Smart MLS #170508567 Report a problem
        4/30/2020Sold$170,000+6.3%$53/sqft
        Source: Smart MLS #170109631 Report a problem
        2/12/2020Pending sale$160,000$50/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        1/28/2020Price change$160,000-11.1%$50/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        12/19/2019Listed for sale$180,000$56/sqft
        Source: Coldwell Banker #170109631 Report a problem
        8/27/2019Listing removed$180,000$56/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        5/3/2019Price change$180,000-10%$56/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        4/23/2019Price change$200,000-4.7%$63/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        1/8/2019Price change$209,900-4.5%$66/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        12/7/2018Price change$219,900-7.2%$69/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        11/30/2018Listed for sale$236,900$74/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        9/17/2018Listing removed$236,900$74/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem
        8/30/2018Pending sale$236,900$74/sqft
        Source: Coldwell Banker Residential Brokerage - Old Saybrook Office #170109631 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$15,016 +2.8%$405,720 -1.6%
        2024$14,601 +5.4%$412,320
        2023$13,858 +9.6%$412,320 +34.6%
        2022$12,639 +0.4%$306,360
        2021$12,583 +0.2%$306,360
        2020$12,562 -0.5%$306,360
        2019$12,623 +3.6%$306,360
        2018$12,188 +1.5%$306,360 -1.3%
        2017$12,010 +2.1%$310,490 +0%
        2016$11,768 $310,460
        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: 06457

        Getting around

        0 / 100
        Car-Dependent
        9 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Middletown

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

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