• Primary Photo - 28 Windermere Dr
  • Building Photo - 28 Windermere Dr
    Building Photo - 28 Windermere Dr
  • Building Photo - 28 Windermere Dr
    Building Photo - 28 Windermere Dr
$7,000 / Month

28 Windermere Dr

,

Sag Harbor, NY 11963

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631-725-0200

  • Bedrooms

    4

  • Bathrooms

    3

  • Square Feet

    1,360 sq ft

  • Available

    Available Jan 1, 2027

Highlights

  • Open Floorplan
  • Traditional Architecture
  • Cathedral Ceiling
  • Main Floor Primary Bedroom
  • Farmhouse Sink
  • Fireplace
28 Windermere Dr
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About This Home

Available Jan 1, 2027

Spend your summer in style in this beautifully updated 4 bedroom 3 bath rental in the coveted waterfront community of Bay Point in Sag Harbor offered at $132,000 for Year Round,$95,000 for MD-LD,$27,500 for June,$40,000 for July and $45,000 for August for the 2027 season and $40,000 for winter 2026/2027. Just minutes from the village and moments from Foster Memorial Beach this tastefully appointed home offers the perfect blend of modern comfort and Hamptons charm. Inside you will find an open concept living area with cathedral ceilings skylights and great natural light. The gourmet kitchen features top tier stainless steel appliances including a Bertazzoni range white quartz countertops a farmhouse sink and soft grey beige and white tones throughout. The main level primary suite offers a private entrance and barn doors for added seclusion. Upstairs two guest bedrooms share a full bath with elegant finishes and raindrop showerheads. The lower level is ideal for entertaining with a spacious media lounge wet bar fourth bedroom and an additional full bath with a glass walk in shower and designer tile. Outside enjoy a beautifully landscaped private setting with a heated in ground pool outdoor shower and multiple areas for lounging or dining alfresco. Located just 1.5 miles from Sag Harbor Village and minutes from Serene Green Organic Farmstand this home offers convenience tranquility and easy access to everything the Hamptons has to offer including unforgettable west facing sunsets at nearby Long Beach. MLS ID KEY1000970 Based on information submitted to the MLS GRID as of [see last changed date above]. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Prices displayed on all Sold listings are the Last Known Listing Price and may not be the actual selling price.

28 Windermere Dr is a house located in Suffolk County and the 11963 ZIP Code. This area is served by the Sag Harbor Union Free School District attendance zone.

* Price shown is base rent. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Home Details

Home Type

Single Family Detached Home

Year Built

Built in 2006

Bedrooms and Bathrooms

Primary Bedroom on Main Bathroom on Main Level En-Suite Primary Bedroom 3 Full Bathrooms 4 Bedrooms

Home Design

Traditional Architecture Entry on the 1st floor

Interior Spaces

Open Floorplan Cathedral Ceiling Fireplace 1,360 Sq Ft Home

Kitchen

Farmhouse Sink Breakfast Bar Oven Microwave Dishwasher

Listing and Financial Details

12-Month Minimum Lease Term Assessor Parcel Number 0900-009-00-02-00-052-000

Lot Details

13,068 Sq Ft Lot No Common Walls

Parking

Driveway

Schools

Sag Harbor Elementary School Pierson Middle/High School

Utilities

Central Air

Community Details

Pet Policy

Call for details about the types of pets allowed

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified. Use the Cost Calculator to determine costs based on your needs.

  • One-Time Basics
    • Due at Move-In
      • Security Deposit - Refundable
        Charged per unit.
        $25

Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

Contact

  • Listed by Thomas R. Cavallo | Douglas Elliman Real Estate
  • Phone Number
  • Contact
  • Source
    OneKey® MLS
Information Copyright 2026, OneKey® MLS. All Rights Reserved. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.
Location Get Directions
| Edit
Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
City - Sag Harbor

Sag Harbor sits at the edge of the Hamptons where whaling history and waterfront life shape every corner of this small but storied Long Island village. The entire business district along Main Street holds a spot on the National Register of Historic Places, giving everyday errands a backdrop of 19th-century architecture and seafaring heritage. Strolling to the harbor, browsing independent boutiques, and catching a show at the historic Bay Street Theater are all part of the routine here. Sag Harbor Village sits within easy reach of East Hampton and Southampton, so the dining and recreation options extend well beyond the village limits.

The rental landscape here leans toward character-filled cottages, historic homes converted into apartment communities, and waterfront townhomes that put Gardiners Bay practically in your backyard. Inventory is limited given the village spans just two square miles, so available rentals tend to move quickly.

Learn more about living in Sag Harbor 
Amenities
  • Air Conditioning
Education
Colleges & Universities Distance
Colleges & Universities Distance
SUNY Suffolk Co., Eastern
Drive: 52 min 29.9 mi
Connecticut College
Drive: 157 min 37.6 mi
University of Connecticut
Drive: 165 min 41.3 mi
28 Windermere Dr is within 52 minutes or 29.9 miles from SUNY Suffolk Co., Eastern. It is also near Connecticut College and University of Connecticut.
Schools
Sag Harbor Elementary School
Public Elementary School
Grades PK-5
431 Students
Attendance Zone
GreatSchools rating: 6 out of 10
Pierson Middle High School
Public Middle & High School
Grades 6-12
502 Students
Attendance Zone
GreatSchools rating: 7 out of 10
Ross School
Private Elementary, Middle & High School
Grades PK-12
362 Students
Nearby
The Hayground School
Private Elementary & Middle School
Grades PK-8
87 Students
Nearby
HARBOR WALDORF SCHOOL
Private Elementary School
Grades PK-5
30 Students
Nearby
School data provided by GreatSchools The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

28 Windermere Dr is near Tweed/New Haven, located 89.3 miles or 197 minutes away.

Commuter Rail Distance
Commuter Rail Distance
Bridgehampton
Drive: 14 min 6.1 mi
Greenport
Drive: 46 min 8.9 mi
East Hampton
Drive: 19 min 8.9 mi
Southampton
Drive: 23 min 11.0 mi
Southold
Drive: 54 min 13.2 mi
Airports Distance
Airports Distance
Tweed/New Haven
 Drive: 197 min 89.3 mi
Getting Around
Somewhat Walkable
Walkability
20 / 100
Minimal Public Transit
Transit
0 / 100
Exceptionally Drivable
Drivability
90 / 100
Fairly Bikeable
Bikeability
50 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
Active
Soundscore™
78 / 100

Traffic

Busy

Airport

Calm

Businesses

Calm

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 28 Windermere Dr.

Shopping Centers Distance
Shopping Centers Distance
Bridgehampton Village
Drive: 14 min 6.0 mi
Bridgehampton Commons
Drive: 15 min 6.6 mi
Wainescott Village
Drive: 18 min 7.8 mi
28 Windermere Dr has 3 shopping centers within 7.8 miles, which is about a 18-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Elizabeth A. Morton National Wildlife Refuge
 Drive: 9 min 3.7 mi
South Fork Natural History Museum & Nature Center
 Drive: 12 min 5.8 mi
LongHouse Reserve
 Drive: 20 min 9.0 mi
Cedar Point County Park
 Drive: 29 min 10.1 mi
Custer Institute Observatory
 Drive: 56 min 14.2 mi
28 Windermere Dr has 5 parks within 14.2 miles, including Elizabeth A. Morton National Wildlife Refuge, South Fork Natural History Museum & Nature Center, and LongHouse Reserve.
Hospitals Distance
Hospitals Distance
Stony Brook Eastern Long Island Hospital
Drive: 48 min 9.5 mi
28 Windermere Dr is 9.5 miles and a 48 minute drive from Stony Brook Eastern Long Island Hospital.
Military Bases Distance
Military Bases Distance
Fort Trumbell US Navy
Drive: 157 min 37.2 mi
New London Naval Sub Base
Drive: 165 min 41.1 mi
Naval & Marine Reserve Center
Drive: 222 min 83.3 mi
28 Windermere Dr has 3 military bases within 83.3 miles, the nearest is Fort Trumbell US Navy which is 37.2 miles away and a 157 minute drive.

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