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New construction
  • $2,299,000

    41-B Whippoorwill Road, Old Lyme, CT 06371

    5beds
    4,694sqft
    : 
    $13,127/mo
    Get pre-qualified
    Single Family Residence
    Built in 2026
    12.78 Acres Lot
    $2,234,700 Zestimate®
    $490/sqft
    $100/mo HOA

    What's special

    Striking fireplaceVaulted ceilingsWelcoming front paver patioBeautifully appointed guest suiteStunning natural rock formationsCustom millworkExpansive windows
    Set on more than 12 private acres in one of Old Lyme's most desirable locations, this exceptional new construction residence offers a rare combination of luxury, flexibility, and space to grow. Thoughtfully designed for today's lifestyle, the home features four bedrooms, including a spacious primary suite on the main level, and a beautifully appointed guest suite ideal for extended family, visiting guests, or a private home office. Inside, vaulted ceilings, custom millwork, rich hardwood floors, and a striking fireplace create an atmosphere of timeless elegance and warmth. The open concept design seamlessly blends sophisticated living with everyday comfort, while expansive windows invite natural light and frame picturesque views of the surrounding landscape. The property's expansive grounds are enhanced by stunning natural rock formations and thoughtfully designed outdoor living spaces, including a welcoming front paver patio and a large rear paver patio ideal for entertaining, dining al fresco, or simply enjoying the peaceful setting. With ample room for a pool, pool house, gardens, or additional recreational amenities, the possibilities are endless. Surrounded by natural beauty yet just minutes from the historic village of Old Lyme, beaches, marinas, and major commuting routes, this is a rare opportunity to enjoy the privacy of a country estate with the convenience of shoreline living. A truly exceptional property where luxury, craftsmanship, and nature come together. Beyond the property itself, 41-2 Whippoorwill Road offers the opportunity to experience the unparalleled lifestyle that has made Old Lyme one of Connecticut's most cherished shoreline communities. Rich in history, culture, and natural beauty, Old Lyme is known for its picturesque village center, renowned art heritage, preserved open spaces, beautiful beaches, marinas, and miles of scenic trails. Residents enjoy a relaxed coastal lifestyle with convenient access to everyday amenities while remaining connected to major metropolitan areas. Positioned between New York City and Boston, Old Lyme offers easy access via Interstate 95 and Amtrak rail service, making weekend escapes and business travel remarkably convenient. Boston is approximately two hours away, while New York City can be reached in just over two hours. The property's location also places you within easy reach of some of New England's most desirable destinations. Explore the vibrant waterfront, boutique shopping, acclaimed restaurants, and maritime charm of downtown Mystic. Spend afternoons enjoying the beautiful beaches, boutiques, and renowned dining scene of Westerly and Watch Hill, Rhode Island, home to some of the region's most spectacular coastal vistas. Whether boating on Long Island Sound, enjoying a sunset dinner overlooking the water, or strolling through charming seaside villages, the best of the Connecticut and Rhode Island coastlines is at your doorstep. Offering exceptional privacy without sacrificing convenience, 41-2 Whippoorwill Road represents a rare opportunity to embrace the quintessential New England coastal lifestyle in one of the shoreline's most sought after communities.
    42 days
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    525
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    14
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    Zillow last checked:

    Listing updated:

    Listed by:

    Tammy J. Tinnerello (860)867-6120,

    William Pitt Sotheby's Int'l 860-434-2400

    Source: Smart MLS,MLS#: 24183457MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Exercise Room, Laundry
      Primary bedroom
      • Features: High Ceilings, French Doors, Walk-In Closet(s), Hardwood Floor
      • Level: Main
      • Area: 345.72 Square Feet
      • Dimensions: 20.1 x 17.2
      Primary bedroom
      • Features: Bedroom Suite, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 265.6 Square Feet
      • Dimensions: 16 x 16.6
      Bedroom
      • Features: High Ceilings, Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Main
      • Area: 196.5 Square Feet
      • Dimensions: 15 x 13.1
      Bedroom
      • Features: High Ceilings, Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Main
      • Area: 216.46 Square Feet
      • Dimensions: 15.8 x 13.7
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 276 Square Feet
      • Dimensions: 23 x 12
      Den
      • Features: Gas Log Fireplace, Hardwood Floor
      • Level: Main
      • Area: 402.75 Square Feet
      • Dimensions: 22.5 x 17.9
      Dining room
      • Features: High Ceilings, French Doors, Hardwood Floor
      • Level: Main
      • Area: 182.71 Square Feet
      • Dimensions: 15.1 x 12.1
      Kitchen
      • Features: High Ceilings, Breakfast Bar, Kitchen Island, Pantry, Hardwood Floor
      • Level: Main
      • Area: 257.4 Square Feet
      • Dimensions: 13.2 x 19.5
      Living room
      • Features: Cathedral Ceiling(s), Fireplace, Hardwood Floor
      • Level: Main
      • Area: 504 Square Feet
      • Dimensions: 24 x 21
      Office
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 107.1 Square Feet
      • Dimensions: 10.5 x 10.2
      Heating
      • Hydro Air, Zoned, Propane
      Cooling
      • Central Air
      Appliances
      • Included: Allowance, Water Heater, Tankless Water Heater
      • Laundry: Main Level, Mud Room
      Features
      • Open Floorplan, In-Law Floorplan
      • Doors: French Doors
      • Basement: Full,Unfinished,Concrete
      • Attic: Storage
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,694
      • Total interior livable area: 4,694 sqft
      • Finished area above ground: 4,694

      Property

      Parking
      • Total spaces: 6
      • Parking features: Attached, Driveway, Garage Door Opener, Private, Circular Driveway
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Patio
      Lot
      • Size: 12.78 Acres
      • Features: Subdivided, Few Trees, Borders Open Space
      Details
      • Parcel number: 2524483
      • Zoning: RU-80

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch,Farm House
      • Property subtype: Single Family Residence
      Materials
      • HardiPlank Type
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • Under Construction
      • New construction: Yes
      • Year built: 2026
      Details
      • Warranty included: Yes

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Underground Utilities

      Community & HOA

      Community
      • Features: Basketball Court, Lake, Library, Medical Facilities, Playground
      • Security: Security System
      • Subdivision: The Woods At Whippoorwill
      HOA
      • Has HOA: Yes
      • Services included: Maintenance Grounds, Snow Removal, Road Maintenance, Insurance
      • HOA fee: $100 monthly
      Location
      • Region: Old Lyme

      Financial & listing details

      • Price per square foot: $490/sqft
      • Tax assessed value: $147,290
      • Annual tax amount: $2,391
      • Date on market: 6/26/2026

        Estimated market value

        $2,234,700

        $2.12M - $2.35M

        $7,643/mo

        Price history

        DateEventPrice
        6/26/2026Listed for sale$2,299,000+21%$490/sqft
        Source: Smart MLS #24183457 Report a problem
        10/23/2025Listing removed$1,899,999$405/sqft
        Source: Smart MLS #24100300 Report a problem
        9/23/2025Listed for sale$1,899,999$405/sqft
        Source: Smart MLS #24100300 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$2,391 -7.3%$147,290 +39.4%
        2024$2,579 +3.8%$105,690
        2023$2,484 $105,690
        2022$2,484 +0.9%$105,690
        2021$2,463 +0.4%$105,690
        2020$2,452 -1.7%$105,690 -5%
        2019$2,494 +2.3%$111,270
        2018$2,438 +0.7%$111,270
        2017$2,420 +2.6%$111,270
        2016$2,359 +2.8%$111,270
        2015$2,294 $111,270
        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: 06371

        Getting around

        1 / 100
        Car-Dependent
        2 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Middle: Lyme-Old Lyme
        • High: Lyme-Old Lyme

        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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