5+ Days Ago
Highlights
- Open floor plan
- Two car garage attached, one detached
Location
380 Private Road 27, Southold, New York 11971, United States
Tour 380 Private Road 27
Contact
Douglas Elliman Real Estate
Nearby rentals
Renter hub
Property management
Apartments for rent East HamptonApartments for rent New HavenApartments for rent SouthamptonApartments for rent West HavenApartments for rent Sag HarborApartments for rent AmagansettApartments for rent DwightApartments for rent East RockApartments for rent Downtown New HavenApartments for rent BridgehamptonApartments for rent SagaponackApartments for rent WainscottApartments for rent BridgeportApartments for rent WaterfordApartments for rent New SuffolkApartments Near Me
Houses for rent Westhampton BeachHouses for rent East MorichesHouses for rent East HamptonHouses for rent WoodburyHouses for rent New HavenHouses for rent BridgeportHouses for rent WaterburyHouses for rent Hampton BaysHouses for rent New BritainHouses for rent New LondonHouses for rent BristolHouses for rent WoodmontHouses for rent North EndHouses for rent Milford cityHouses for rent Beaver HillsHouses for rent near me
Amenities for 380 Private Road 27
Apartment Amenities
| Hardwood Floor |
Building
| Exterior Type: Cedar |
Grounds
| Garage Parking | Swimming Pool |
Other
| Ductless | Eight Rooms |
| Exterior Type: Log | Hot Water Heating |
| Oil | View Type: Panorama |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
Advertisement
About 380 Private Road 27
Property Status: Active Southold Town Rental Permit #1016. Cozy Northern White Cedar Log Style Chalet With Heated Saltwater Pool. It is the juxtaposition between the rustic qualities and the elegant essence of this home that makes it so unique! Covered Wrap Around Porch. 2 Car Garage Attached, 1 Detached. Open Floor Plan. Two Spacious Bedrooms, The Primary Is En-Suite. Extra Loft Style Bedroom With Two Single Beds. Two Full Baths. Unique Smoke House. Appointed Details Inside This Home Were Skillfully Created By The Hands Of A Master Craftsman. Tucked Away On An Acre Property With Ample Privacy. The Perfect Home For Those Seeking A Secluded Vacation On The North Fork. Close Proximity To A Private Beach(Cedar Beach), Easy Access To The Water For Kayak Enthusiasts And A Ramp For Launching Small Crafts. Very Close To Goose Creek & Peconic Bay. Be Part Of What The North Fork Has To Offer: Pristine Beaches, Delectable Restaurants, Local Produce & A Burgeoning Wine Country. May = $3000 per 2 week stay) (June = $4000 per 2 week stay) (July = $5000 per 2 week stay) (August = $6,000 per 2 week stay) (September = $3500 per 2 weeks) (October Through April = $2000 per 2 week stay). Southold Town Rental Permit #: 1016 Office Phone: (631) 354-8100 Copyright © 2025 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 380 Private Road 27 compares to other nearby properties.
Positives
- More space
- The 2-bedroom is 300 sqft larger than other listings nearby
- Images Available
- There are at least 10 photos of this address
Considerations
- No in-unit dishwasher
- Dishwashers aren't available
Address details
| Zip code | 11971 |
|---|---|
| Type | House for rent |
Get the latest listings anytime, anywhere
Receive similar listings in the area, download our app, and more.
Rent trends in Southold
2-bedroom apartments at 380 Private Road 27 cost about 7% more than the average rent price for 2-bedroom apartments in Southold.
Median rents as of Feb 21 2026.
Southold
| Month | Median Rent |
|---|---|
| March 2024 | $6,625 |
| April 2024 | $6,750 |
| May 2024 | $6,333 |
| June 2024 | $7,000 |
| July 2024 | $7,000 |
| August 2024 | $7,150 |
| September 2024 | $7,125 |
| October 2024 | $6,750 |
| November 2024 | $6,200 |
| December 2024 | $7,000 |
| January 2025 | $7,000 |
| February 2025 | $5,125 |
| March 2025 | $4,500 |
| April 2025 | $3,750 |
| May 2025 | $3,900 |
| June 2025 | $4,000 |
| July 2025 | $4,000 |
| August 2025 | $4,000 |
| September 2025 | $4,000 |
| October 2025 | $4,000 |
| November 2025 | $3,750 |
| December 2025 | $3,562 |
| January 2026 | $3,500 |
| February 2026 | $3,650 |
Affordability calculator
Can I afford to live at 380 Private Road 27?
Bedrooms
2 bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$160,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $160,000 annually to afford this 2-bedrooms monthly rent price of $4,000.
For more information on rent affordability, visit our rent calculator.
Schools near 380 Private Road 27
Southold Elementary School
420 oaklawn ave
southold, NY, 11971
K-6Public
B-
Oysterponds Elementary School
23405 main rd
orient, NY, 11957
PK, K-6Public
B
Tuckahoe School
468 magee st
southampton, NY, 11968
PK, K-8Public
B-
Wainscott School
47 main st
wainscott, NY, 11975
K-3Public
Springs School
48 school st
east hampton, NY, 11937
PK, K-8Public
B
Advertisement
Internet available near 380 Private Road 27
Neighborhood
NEIGHBORHOOD VIBE
Peaceful and quiet
Noise-canceling headphones not required in this mostly noise free area.
Getting around Southold near 380 Private Road 27
Walking
2/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Driving
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Cycling
3/10
This is semi-bikeable, but you’ll need another way of getting around.
Transit
0/10
FYI, there are little to no public transit options within walking distance.
Points of interest for 380 Private Road 27, Southold
Groceries
0/10
Closest supermarket further than a 30-minute walk
Shopping
2/10
Some shops within walking distance
Cafes
1/10
Few or no cafés within walking distance
Restaurants
3/10
Some restaurants within walking distance
Primary schools
0/10
Closest elementary school further than a 30-minute walk
High schools
0/10
Closest high school further than a 30-minute walk
Nightlife
0/10
Few or no bars within walking distance
Compare similar properties nearby
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
- hardwood floor
- in-unit laundry
- dishwasher
Check availability
Advertisement