Property Description
2026 Rates: $45,000 for Memorial Day Weekend-Labor Day: Welcome to 619 Bailey Avenue, a fully restored and turnkey farmhouse ideally located on the fringe of Greenport Village. Once part of a historic North Fork farm and estate, this circa 1900 residence has been thoughtfully reimagined to offer the perfect blend of classic charm and modern comfort for a summer escape. Original details-including hardwood floors, custom millwork, and timeless architectural elements-have been beautifully preserved, while stylish updates throughout create a relaxed and functional living environment. The custom chef's kitchen is a true centerpiece, featuring a 48 range, oversized island, bespoke cabinetry, and an 8-foot bi-fold glass door that opens to the backyard for effortless indoor-outdoor living. The first floor offers a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, you'll find two guest bedrooms and a full bath, along with a sun-filled primary suite featuring vaulted ceilings, a large walk-in closet, and a spa-like en-suite bath with double vanity and dual-head walk-in shower. Set on a generous and private lot, the backyard provides ample space to relax and entertain, complemented by a detached one-car garage. Enjoy close proximity to Greenport Village, Kontokosta Winery, nearby bay and Sound beaches, and local favorites like Sep's Farm Stand-making this an exceptional North Fork summer retreat.
619 Bailey Avenue | MLS# 992636
This property located at 619 Bailey Avenue , Greenport, NY 11944 is currently listed for rent with an asking price of $45,000 / Monthly. Bailey Avenue is located within the Greenport school district. Search Greenport real estate on sean-oshaughnessy.timberlandproperties.com today.
Gallery
Property Features
Property Type: Rental - Single Family
Basement: Yes
Basement: Bilco Door(s), Finished, Full
Cooling: Central Air
Fireplaces: 1
Garage: 1
Heating: Hot Water
Home Style: Craftsman
Lot Size: 0.25 Acres
Year Built: 1925
Amenities
First Floor Bedroom
Breakfast Bar
Built-in Features
Chefs Kitchen
Double Vanity
Eat-in Kitchen
Formal Dining
High Speed Internet
Kitchen Island
Original Details
Primary Bathroom
Recessed Lighting
Smart Thermostat
Stone Counters
Walk-In Closet(s)
Feature Descriptions
Appliances: Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Range, Microwave, Range, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Attic: Partial
Days on Site: 1
Exterior: Clapboard, Fiberglass Insulation, Frame
Fencing: Back Yard
Fireplace Features: Wood Burning
Fireplace Y/N: Yes
Flooring: Hardwood, Tile
Formal Dining: Yes
GarageY/N: Yes
Heating Zones: 2
House Faces: East
Laundry: In Basement
Lot Features: Back Yard, Front Yard, Landscaped, Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Sprinklers In Front, Sprinklers In Rear
On Market Date: 2026-04-29
Parcel Number: 1000-034-00-02-00-005-000
Parking Features: Driveway, Garage
Pets Allowed: No
Rental Term: Monthly
Rooms Total: 10
Sewer: Septic Tank
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Water Connected
Water: Public
Window Features: ENERGY STAR Qualified Windows
Local Schools
High School: Greenport High School
Middle School: Greenport High School
Elementary School: Greenport Elementary School
School District: Greenport
Demographics
Listed By / Shown By
Listing By
Agency Name: Daniel Gale Sothebys Intl Rlty
Agency Contact: 631-477-0013
Shown By
Agent Name: Sean O'Shaughnessy
Agent Phone: Cell: (607) 287-0030
Agency Title: Timberland Properties
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619 Bailey Avenue , Greenport, NY 11944
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Sean O'Shaughnessy Licensed Real Estate Salesperson
Cell: (607) 287-0030
Main: (845) 586-3321
Office: (845) 586-3321
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