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For sale
  • Price cut: $50K (6/26)
    $1,745,000

    2 Longwood Drive, Redding, CT 06896

    4beds
    6,259sqft
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    Single Family Residence
    Built in 1998
    2.72 Acres Lot
    $1,704,200 Zestimate®
    $279/sqft
    $-- HOA

    What's special

    Classic new england charmPrivate sanctuarySoaring nine foot ceilingsGenerously proportioned roomsExpansive lawnsPremium sub-zero refrigerationSurrounded by mature trees
    ***Rare turn-key opportunity at an unbeatable price point*** For buyers seeking exceptional craftmanship, serenity, a strong sense of community, award winning schools and uncompromised value. 2 Longwood Drive is a rare opportunity to purchase a 6,200+ square foot luxury home in southern Redding below recent comparable sales. Experience the exceptional lifestyle that has made Redding one of Fairfield County's most desirable towns for discerning buyers. Known for its scenic landscapes, extensive open space, award-winning parks, the Redding Country Club, and highly regarded public schools, Redding offers an unmatched quality of life just over an hour from Manhattan. With convenient access to Metro-North stations in Westport, Wilton, and West Redding, commuting and weekend travel are effortless. This 6,259 square foot custom built and meticulously maintained colonial is a must see, perfectly positioned on 2.72 professionally landscaped acres in one of Redding's most sought-after neighborhoods. Surrounded by mature trees, rolling lawns, and classic New England charm, the property provides a peaceful retreat while remaining just minutes from Redding schools, hiking trails, top-rated restaurants, shopping, cultural attractions, and the neighboring towns of Ridgefield, Westport, and Wilton. Families will appreciate Redding's highly acclaimed public schools, consistently recognized for small class sizes, dedicated educators, and strong academic achievement. The town's commitment to education, combined with its welcoming community and abundant recreational opportunities, makes it one of the area's most desirable places to call home. This exceptional residence was designed for today's lifestyle, the home features an open, light-filled floor plan with soaring nine foot ceilings, rich hardwood floors, generously proportioned rooms, and seamless spaces for both everyday living and elegant entertaining. The beautifully updated chef's kitchen showcases premium Sub-Zero refrigeration, Thermador double ovens, a six-burner Wolf gas cooktop, an oversized center island, butler's pantry, and wet bar. It flows effortlessly into the spacious family room with a gas fireplace, while formal living and dining rooms provide sophisticated settings for holidays and special occasions. Whether working remotely, hosting extended family, or simply enjoying the luxury of extra space, the home's thoughtful design offers exceptional flexibility and comfort. Step outside to your own private sanctuary where expansive lawns, mature landscaping, and peaceful outdoor living spaces capture the beauty and tranquility that define Redding. For added confidence, the home includes a brand new HVAC unit and a comprehensive full home warranty, providing valuable coverage for many major home systems and appliances during your first year of ownership. Offering over 6,200 square feet of exceptional craftsmanship, a premier Redding location, access to outstanding schools, and compelling value compared with recent luxury home sales, 2 Longwood Drive presents a rare opportunity to enjoy the very best of Connecticut country living, whether as a full-time residence or an elegant weekend retreat.
    60 days
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    1,068
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    63
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    Zillow last checked:

    Listing updated:

    Listed by:

    Jeffrey Kaplan (203)505-3375,

    William Raveis Real Estate 203-847-6633

    Source: Smart MLS,MLS#: 24177771MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Bedroom Suite, Ceiling Fan(s), Full Bath, Whirlpool Tub, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 503.93 Square Feet
      • Dimensions: 16.1 x 31.3
      Bedroom
      • Features: Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 208 Square Feet
      • Dimensions: 16 x 13
      Bedroom
      • Features: Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 208 Square Feet
      • Dimensions: 16 x 13
      Bedroom
      • Features: Ceiling Fan(s), Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 212.8 Square Feet
      • Dimensions: 16 x 13.3
      Dining room
      • Features: High Ceilings, Hardwood Floor
      • Level: Main
      • Area: 248.4 Square Feet
      • Dimensions: 13.8 x 18
      Kitchen
      • Features: High Ceilings, Granite Counters, Wet Bar, Kitchen Island, Patio/Terrace, Hardwood Floor
      • Level: Main
      • Area: 451.04 Square Feet
      • Dimensions: 22.11 x 20.4
      Living room
      • Features: High Ceilings, Wet Bar, Gas Log Fireplace, Patio/Terrace, Hardwood Floor
      • Level: Main
      • Area: 445.2 Square Feet
      • Dimensions: 15.9 x 28
      Office
      • Features: High Ceilings, Bookcases, Built-in Features, Hardwood Floor
      • Level: Main
      • Area: 248.4 Square Feet
      • Dimensions: 13.8 x 18
      Rec play room
      • Features: Skylight, Cathedral Ceiling(s), Ceiling Fan(s), Hardwood Floor
      • Level: Upper
      • Area: 602.14 Square Feet
      • Dimensions: 38.11 x 15.8
      Rec play room
      • Features: High Ceilings, Ceiling Fan(s), Full Bath, Steam/Sauna, Hardwood Floor
      • Level: Upper
      • Area: 1334.04 Square Feet
      • Dimensions: 39.11 x 34.11
      Heating
      • Forced Air, Oil
      Cooling
      • Ceiling Fan(s), Central Air, Zoned
      Appliances
      • Included: Gas Cooktop, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Ice Maker, Dishwasher, Disposal, Washer, Dryer, Wine Cooler, Water Heater
      • Laundry: Upper Level
      Features
      • Wired for Data, Central Vacuum, Open Floorplan, In-Law Floorplan, Smart Thermostat
      • Doors: French Doors
      • Windows: Thermopane Windows
      • Basement: Full,Unfinished,Storage Space,Interior Entry,Concrete
      • Attic: Crawl Space,Access Via Hatch
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 6,259
      • Total interior livable area: 6,259 sqft
      • Finished area above ground: 6,259
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 3
      • Parking features: Attached, Garage Door Opener
      • Attached garage spaces: 3
      Features
      • Patio & porch: Covered, Patio
      • Exterior features: Garden, Lighting, Stone Wall
      Lot
      • Size: 2.72 Acres
      • Features: Secluded, Few Trees, Dry, Sloped, Cul-De-Sac, Landscaped
      Details
      • Parcel number: 269523
      • Zoning: R-2
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1998
      Details
      • Warranty included: Yes

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      Green energy
      • Energy efficient items: Windows

      Community & HOA

      Community
      • Features: Golf, Library, Medical Facilities, Paddle Tennis, Public Rec Facilities, Tennis Court(s)
      • Security: Security System
      • Subdivision: Gallows Hill
      HOA
      • Has HOA: No
      Location
      • Region: Redding

      Financial & listing details

      • Price per square foot: $279/sqft
      • Tax assessed value: $1,036,500
      • Annual tax amount: $30,618
      • Date on market: 5/22/2026

        Estimated market value

        $1,704,200

        $1.62M - $1.79M

        $7,665/mo

        Price history

        DateEventPrice
        6/26/2026Price change$1,745,000-2.8%$279/sqft
        Source: Smart MLS #24177771 Report a problem
        5/22/2026Listed for sale$1,795,000-2.9%$287/sqft
        Source: Smart MLS #24177771 Report a problem
        5/22/2026Listing removed$1,849,000$295/sqft
        Source: Smart MLS #24147905 Report a problem
        1/29/2026Listed for sale$1,849,000$295/sqft
        Source: Smart MLS #24147905 Report a problem
        12/23/2025Listing removed$1,849,000$295/sqft
        Source: Smart MLS #24116027 Report a problem
        11/13/2025Price change$1,849,000-7.3%$295/sqft
        Source: Smart MLS #24116027 Report a problem
        8/22/2025Listed for sale$1,995,000+117.6%$319/sqft
        Source: Smart MLS #24116027 Report a problem
        7/16/1998Sold$916,775$146/sqft
        Source: Smart MLS #97028080 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$30,618 +2.9%$1,036,500
        2024$29,768 -0.1%$1,036,500 -3.7%
        2023$29,808 +0.4%$1,076,500 +20.9%
        2022$29,686 -1.2%$890,400 -2.7%
        2021$30,042 $914,800
        2020$30,042 $914,800
        2019$30,042 +3.5%$914,800
        2018$29,017 -0.1%$914,800 -6.7%
        2017$29,042 +1.3%$980,500
        2016$28,670 +1.1%$980,500
        2015$28,346 $980,500
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 06896

        Getting around

        2 / 100
        Car-Dependent
        8 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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