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Sold for $2,200,000
  • $2,200,000

    299 Main St, Sag Harbor, NY 11963

    4beds
    2,000sqft
    MultiFamily
    Built in 1840
    -- sqft lot
    $2,405,800 Zestimate®
    $1,100/sqft
    $5,192 Estimated rent

    Home value

    $2,405,800

    $2.17M - $2.69M

    $5,192/mo

    Zestimate® history
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    $5,192/mo

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    $15,142/mo

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    $15,142/mo

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    What's special

    Newly landscaped gardenBright foyerSpacious ground floor spaceBay windowsOriginal glass window panesOriginal fir floorsFormal dining room
    Rental Registration #: R-25-0020 Looking for a spacious rental in the village of Sag Harbor? Experience Sag Harbor Cove sunset views from this versatile village home and legal guest cottage filled with character and comfort. Situated on Main Street, just moments from the heart of Sag Harbor, this spacious home is convenient to shopping, restaurants and the Hampton Jitney. Inside the main house, a bright foyer opens to a classic double parlor living/dining room with bay windows, moldings, and original glass window panes-details that nod to the home's 1840 roots. This beautifully restored village gem combines classic charm with modern convenience. The spacious ground floor space is spectacularly decorated with all the modern comforts while maintaining its historical charm. Enjoy original fir floors, and large windows that flood the space with an amazing amount of natural light. There is a large living space, formal dining room, and large, fully equipped chefs' kitchen. French doors off the kitchen and dining area lead to a quaint covered patio insulated by potted evergreens. Two generously sized ground-floor bedrooms provide a perfect mix of elegance and serenity. The updated bathroom features modern fixtures while retaining a vintage feel, complete with a clawfoot tub/shower combo. Upstairs you'll find a modern 1-bedroom apartment that combines comfort and convenience. Enjoy an open-concept layout with large windows and French doors that bring in an abundance of natural light, creating a warm and welcoming atmosphere. There is spacious kitchen, dining area, and ample living room which leads to a private deck where you can grill, dine, and unwind and enjoy elevated living and panoramic views of Otter Pond. Architectural potted evergreen screening for enhanced privacy - grill, dine, and enjoy the warm light of golden hour. A bright and light bedroom and a full bathroom provides a peaceful haven for relaxation. A lovely, newly landscaped garden with brand new heated, saltwater pool offers a peaceful escape to enjoy your morning coffee or evening relaxation. Several seating areas and quiet nooks to find respite or soak in the sun. In the evening, enjoy quiet moments by the modern fire pit under the open sky and stars. A separate, legal one bedroom cottage with kitchenette and full bath sits at the rear of the property; a perfect place for guests or remote work. Off-street parking available. Don't miss the chance to call this piece of history your home! [[Rental Registration # R-25-0020]]

    Zillow last checked:

    Listing updated:

    Source: Zillow Rentals

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 3
    • Full bathrooms: 3
    Cooling
    • Central Air
    Features
    • View
    • Has basement: Yes
    Interior area
    • Total interior livable area: 2,000 sqft

    Property

    Parking
    • Parking features: None
    • Details: Contact manager
    Features
    • Stories: 2
    • Exterior features: Architecture Style: victorian, Broker Exclusive
    • Pool features: Pool
    • Has view: Yes
    • View description: Water View
    Lot
    • Size: 8,712 sqft
    Details
    • Parcel number: 0903006000100005000

    Construction

    Type & style
    • Home type: MultiFamily
    • Property subtype: MultiFamily
    Condition
    • Year built: 1840

    Community & neighborhood

    Community
    • Community features: Pool
    Location
    • Region: Sag Harbor

    Price history

    DateEventPrice
    5/16/2026Listing removed$75,000$38/sqft
    Source: Zillow Rentals Report a problem
    1/21/2026Listed for rent$75,000+36.4%$38/sqft
    Source: Zillow Rentals Report a problem
    9/2/2025Listing removed$55,000$28/sqft
    Source: Zillow Rentals Report a problem
    4/25/2025Listed for rent$55,000$28/sqft
    Source: Zillow Rentals Report a problem
    1/13/2025Sold$2,200,000-13.7%$1,100/sqft
    Source: Public Record Report a problem
    7/19/2024Price change$2,550,000-7.3%$1,275/sqft
    Source: Out East #377471 Report a problem
    4/18/2024Price change$2,750,000-11.3%$1,375/sqft
    Source: Out East #377471 Report a problem
    3/7/2024Price change$3,100,000-11.4%$1,550/sqft
    Source: Out East #377471 Report a problem
    12/8/2023Listed for sale$3,500,000+251.8%$1,750/sqft
    Source: Out East #377471 Report a problem
    4/23/2004Sold$995,000$498/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $1,022,300
    2024-- $1,022,300
    2023-- $1,022,300
    2022-- $1,022,300
    2021-- $1,022,300
    2020-- $1,022,300
    2019-- $1,022,300 +3.2%
    2018-- $990,600
    2017$5,908 $990,600
    2016-- $990,600
    2015-- $990,600
    2014-- $990,600
    2013-- $990,600
    2012-- $990,600
    2011-- $990,600 +0.6%
    2007$4,973 -3.9%$985,000 +25.4%
    2005$5,173 +6.1%$785,366 +6462.2%
    2004$4,875 +8.4%$11,968
    2003$4,498 +10.4%$11,968
    2002$4,075 +7.5%$11,968
    2001$3,789 +8.7%$11,968
    2000$3,485 $11,968

    Find assessor info on the county website

    Neighborhood: 11963

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $2,405,800
    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
    $2,405,800