Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a primary suite, all have water views. The private bay beach is a short stroll away. Easy access to renowned North Fork wineries, farmstands, restaurants and shops. Memorial Day-Labor Day $45,000; May $6000; June $8000; July $18,000; August not available, September after LD $8000; winter $6000/mo.
Listing by Marianne Collins• Brown Harris Stevens N Fork
North Fork, located between Riverhead and Greenport, is a coastal and agricultural Calverton neighborhood with working vineyards and wide-open bayfront views. The mood concentrates around the Sound Avenue corridor near the Calverton hamlet center, where farm stands, tasting rooms, and low-key eateries set a weekend rhythm. Architectural character leans to shingled cottages, ranch homes, and barn-like outbuildings tied to the area’s farming roots. Macari Vineyards, Jamesport Farm Brewery, and Harbes Family Farm act as local pillars for tastings, seasonal events, and market-style shopping. Peconic Bay and the Long Island Sound frame the landscape with beaches, marinas, and long, flat roads made for cycling. The pace stays rural, with small clusters of storefronts separated by fields and rows of vines.
Provided by Walk Score and Local Logic
Historical weather
Southold, NY • 11971
Average low and high temperatures (°F)
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74
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52
54
43
42
31
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Climate risks
7/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 90° expected this year, 19 days in 30 years
8/10 Wind Factor
80% chance of strong winds in next 30 years
3/10 Air Factor
2 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Sun exposure
In this area, properties receive around 9 hours in
June and 4.6 hours in December, which is comparable to the
U.S. average for solar exposure.
This property is priced $3,788 above the rental estimate.
Asking rent
$8,000
Rental estimate
$4,212
Nearby comparable rentals
The Rental Estimate uses 0 recent nearby rental.
Sale and tax history for 355 Midway Rd
Sale History
Tax History
Date
Event
Price
ONEKEY #L3389441
Apr 22, 2026
Price Changed
$8,000
Mar 18, 2026
Listed for Rent
$18,000
Mar 11, 2026
Rental Removed
$18,000
Jul 31, 2025
Listed for Rent
$18,000
Jul 25, 2025
Rental Removed
$20,000
Nov 26, 2024
Listed for Rent
$20,000
ZUMPER1 #3
Jul 31, 2025
Rental Removed
$18,000
Jul 26, 2025
Listed for Rent
$18,000
ONEKEY #3389441
Nov 26, 2024
Rental Removed
$20,000
Nov 9, 2024
Price Changed
$20,000
Mar 27, 2024
Listed for Rent
$6,000
Feb 24, 2024
Rental Removed
$6,000
Oct 28, 2023
Price Changed
$6,000
Jul 12, 2023
Listed for Rent
—
Public Records
Jul 18, 2019
Sold
$850,000
OneKey® MLS as Distributed by MLS Grid #L2802247
Feb 19, 2016
Sold
$700,000
Oct 8, 2015
Listed
$785,000
Just Now Completed By Renowned Designer Nanjoo Joung, This Home Features A Gigantic Granite And S/S Gourmet Kitchen, Tile Baths, Oak Floors Throughout, F P, Expansive Den/Study, Second Floor Laundry. It Offers Water Views From Nearly Every Room, Excellent Privacy, And A Sandy Private Beach. This Is Truly A Turn-Key Home--Many Furnishings And Decor Items Are Included!, Additional information: Appearance:Ravishing!
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Listing provided courtesy of: Brown Harris Stevens N Fork
Listing agent: Marianne Collins (6317342957)
Based on information submitted to the MLS GRID as of Thu Sep 03 2026. 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.
Last Updated: 2026-06-27T12:38:25.589Z
We estimate that 355 Midway Rd would rent between $4,212 / mo.355 Midway Rd is located in Southold, the 11971 zipcode, and the Southold Union Free School District.