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For sale
  • $1,749,500

    220 Bailey Ave, Greenport, NY 11944

    4beds
    3,389sqft
    Single Family Residence
    Built in 1925
    0.25 Acres Lot
    $1,701,100 Zestimate®
    $516/sqft
    $-- HOA

    What's special

    Private backyardTimeless charmNew mahogany deckSun-drenched bedroomStunning ensuite bathroomOversized islandSpacious walk-in closet
    Originally built in the early 1900s, this farmhouse has been thoughtfully reimagined in 2024 with a full-scale, design-forward renovation that honors its storied past while embracing modern luxury. Featuring 4 bedrooms and 2.5 baths, every inch of this home has been meticulously updated with custom finishes, high-end fixtures, and timeless charm. Original elements such as reclaimed wood flooring, solid wood doors, and vintage crystal doorknobs have been beautifully preserved, blending seamlessly with contemporary additions. The first floor welcomes you with a cozy living room centered around a wood-burning fireplace, a stylish study or home office, a sun-drenched bedroom currently styled as a tranquil zen room, bright and airy dining room, and a chic half bath. The heart of the home is the chef's kitchen—designed to impress—with custom cabinetry, Thor appliances, an oversized island, wine fridge, bar, desk nook, and expansive entertaining space with gliding bifold door to the backyard. Upstairs, two guest bedrooms share a well-appointed full bath, while the primary suite boasts cathedral ceilings, a spacious walk-in closet and a stunning ensuite bathroom. Indoor-outdoor living is effortless here. Slide open the custom bi-panel doors from the kitchen to access a new mahogany deck and private backyard—perfect for relaxing or entertaining. Room for a pool! The property also includes a garage and full basement for additional storage or future potential. Sellers are open to discussing the sale of furnishings separately, offering a turnkey opportunity for buyers seeking a fully styled home. Enjoy picturesque views of the neighboring Kontokosta Vineyard from both your front porch and bedroom. Ideally located just half a mile from Greenport Village's restaurants, shops, wineries, and all! Perfectly situated between both 67 Steps and Norman Klipp beaches, each about .5 mile away. This home is a rare blend of history, character, and modern elegance. For buyers seeking classic charm without compromising on luxury—this is where the past and present come beautifully together!
    4 days
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    Zillow last checked: 7 hours ago

    Listing by:

    Daniel Gale Sotheby's International Realty 631-298-4130,

    Erica Kelly - Real Estate Sales Person 516-527-7589

    Source: Out East,MLS#: 390608
    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 220 Bailey Ave.

    Next available tour time:Today at 11am

    Open house

    • Sat, Aug 23

      12:00 PM - 2:00 PM

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 3
    • Full bathrooms: 2
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Office
    Cooling
    • Central Air
    Features
    • Has fireplace: Yes
    Interior area
    • Total structure area: 3,389
    • Total interior livable area: 3,389 sqft

    Property

    Parking
    • Parking features: GarageDetached
    • Has garage: Yes
    Features
    • Stories: 2
    Lot
    • Size: 0.25 Acres
    Details
    • Parcel number: 1000034000200005000

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Condition
    • New construction: No
    • Year built: 1925

    Community & HOA

    Location
    • Region: Greenport

    Financial & listing details

    • Price per square foot: $516/sqft
    • Tax assessed value: $1,181,818
    • Date on market: 8/18/2025
    • Lease term: Contact For Details
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