Skip main navigation
Off market
  • $1,854,200

    5 Osprey Ln, Shelter Island, NY 11964

    4beds
    --sqft
    Single Family Residence
    Built in 1974
    0.75 Acres Lot
    $1,854,200 Zestimate®
    $--/sqft
    $7,633 Estimated rent

    Home value

    $1,854,200

    $1.76M - $1.95M

    $7,633/mo

    Zestimate® history
    Loading
    Loading...

    Owner options

    List your home for rent

    $7,633/mo

    Rent Zestimate®

    Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.

    Learn more

    $7,633/mo

    Rent Zestimate®

    Refinance and save

    $12,964/mo

    Est. payment

    Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.

    See today's rates

    $12,964/mo

    Est. payment

    Explore your selling options

    Work with a Zillow partner agent

    Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.

    Get started

    List with your own agent

    Get your home in front of millions of buyers by listing it on Zillow.

    Learn how to do it

    Sell it yourself

    Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).

    List your home

    What's special

    Flexible bonus roomSeparate laundry roomTwo-and-a-half bathsInviting primary suiteRenovated kitchenMature plantingsGenerous grounds

    Tucked away on Shelter Island's coveted southern peninsula, 5 Osprey Lane offers a rare combination of privacy, flexibility, and natural beauty within the sought-after Shorewood Farm enclave. Set on approximately 0.78 acres of beautifully landscaped grounds with room to add a pool, the property is designed for relaxed island living and effortless entertaining.Surrounded by the waters of Peconic Bay, Shorewood Farm is known for its exceptional waterfront setting and outdoor lifestyle. Residents enjoy access to a private association beach, community tennis courts, nearby boat launches at Wade's Beach, and convenient proximity to the South Ferry. Just moments away, the protected 2,350-acre Mashomack Preserve offers miles of scenic trails, tidal creeks, and old-growth forest, preserving the area's natural beauty for generations to come.The approximately 1,750-square-foot main residence features three bedrooms, two-and-a-half baths, a flexible bonus room, and a separate laundry room. Thoughtfully updated, the home is highlighted by a renovated kitchen and an inviting primary suite, blending modern comfort with timeless Shelter Island charm.Complementing the main house is a separate one-bedroom triplex studio offering approximately 1,390 square feet of additional living space. With multiple levels of wraparound decking overlooking the surrounding landscape, the studio provides exceptional versatility and privacy, making it ideal as a guest house, home office, artist's studio, or wellness retreat.Mature plantings and thoughtfully designed outdoor living spaces create a seamless connection between the homes and their natural surroundings. A wraparound bluestone patio anchors the outdoor setting, while the generous grounds provide ample opportunity for future enhancements, including the addition of a pool. Offering two distinct structures, exceptional privacy, and access to one of Shelter Island's most desirable waterfront communities, 5 Osprey Lane presents a unique opportunity to create a lasting island retreat.

    This property is not currently displayed as for sale or rent on Zillow. This may be different from what's on other websites or public sources.

    Zillow last checked:

    Source: Out East,MLS#: 394707

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 5
    • Full bathrooms: 4
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Laundry
    Cooling
    • Central Air
    Features
    • Basement: Yes
    • Has fireplace: Yes
    Interior area
    • Total structure area: 0

    Property

    Parking
    • Parking features: None
    Features
    • Stories: 2
    • Exterior features: Tennis Court(s)
    • Pool features: Room for a Pool
    Lot
    • Size: 0.75 Acres
    Details
    • Parcel number: 0700023000200068001

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Condition
    • New construction: No
    • Year built: 1974

    Community & HOA

    Location
    • Region: Shelter Island

    Financial & listing details

    • Tax assessed value: $1,350,000
    • Date on market: 5/12/2026
    • Lease term: Contact For Details

    Price history

    DateEventPrice
    7/28/2026Listing removed$1,850,000
    Source: Out East #394707 Report a problem
    7/7/2026Price change$1,850,000-5.1%
    Source: Out East #394707 Report a problem
    5/12/2026Listed for sale$1,950,000+56%
    Source: Out East #394707 Report a problem
    11/26/2021Sold$1,250,000-2.8%
    Source: Public Record Report a problem
    6/18/2021Pending sale$1,286,300
    Source: Out East #352544 Report a problem
    3/19/2021Listed for sale$1,286,300+7.3%
    Source: Out East #352544 Report a problem
    12/30/2020Listing removed$1,199,000
    Source: Out East #352544 Report a problem
    10/5/2020Price change$1,199,000-7.8%
    Source: Georgiana B. Ketcham, Lic. RE Broker #352544 Report a problem
    6/22/2020Listed for sale$1,300,000
    Source: Georgiana B. Ketcham, Lic. RE Broker #352544 Report a problem
    1/27/2019Listing removed$30,000
    Source: Town & Country Real Estate Greenport Office #108218 Report a problem
    10/1/2018Listed for rent$30,000
    Source: Town & Country Real Estate Greenport Office #108218 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $1,350,000 +58.8%
    2024-- $850,000 +3.8%
    2023-- $819,000
    2022-- $819,000
    2021-- $819,000 +1%
    2020-- $811,000 +0.2%
    2019-- $809,000 +0.4%
    2018-- $806,000 +2.9%
    2017$4,460 $783,000 +8%
    2016-- $725,000 +8.2%
    2015-- $670,000 +0.9%
    2014-- $664,000 +2.9%
    2013-- $645,000 -0.6%
    2012-- $649,000 -4.6%
    2011-- $680,000 +1.5%
    2010-- $670,000 -10.4%
    2009-- $748,000 -1.8%
    2008-- $762,000 +5.5%
    2007$3,475 +29.9%$722,300 +66.9%
    2005$2,675 +16.1%$432,700 +23.6%
    2004$2,303 +7.8%$350,000 +10.3%
    2003$2,137 -32.2%$317,200 +7.9%
    2002$3,152 $294,100
    2001-- $294,100 +8.7%
    2000$2,783 $270,500
    Find assessor info on the county website

    Neighborhood: 11964

    Nearby schools

    GreatSchools rating
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $1,854,200
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $1,854,200