14380 Oregon Rd, Cutchogue, NY, 11935
About This Home
Set amid more than 48 breathtaking acres along coveted Oregon Road, this exceptional North Fork estate offers a rare blend of equestrian excellence, privacy, and timeless country sophistication. Featuring a 7-stall barn, heated grooming and wash stalls, a tack room, a geotextile all-weather riding ring, jumping field, cross-country course, and turnout paddocks, the property presents an unparalleled setting for horse enthusiasts. The orchard, featuring cherry, apple, peach, and pear trees, is bordered by mature gardens and encompasses a greenhouse for year-round planting or as a secluded retreat. Privately situated on nearly five buildable acres, the charming farmhouse residence offers two bedrooms and two full baths, blending historic character with modern comforts. Surrounded by mature landscaping, the outdoor spaces are equally inviting, with a gunite pool, outdoor shower, and sweeping vineyard views that embody the essence of North Fork living. Perfectly positioned among the region's award-winning wineries, acclaimed restaurants, farm stands, marinas, and boutique shopping, this is a truly rare offering in the heart of North Fork wine country.
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1925
Type & Style
- Home type: SingleFamily
- Property subType: Single Family Residence
Interior
Basement
- Basement: No
Bedrooms & Bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Cooling
- Cooling features: Central Air
Interior Area
- Total structure area: 1,400
- Total interior livable area: 1,400 sqft
Property
Features
- Stories: 2
- Private pool: Yes
- Pool features: Heated
Lot
- Lot size: 48.70 Acres
Parking
- Parking features: None
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Coastal Flooding
- Hurricane
- Winter Weather
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters in Suffolk County and New York
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $23,639 | $283,668 |
| Home Insurance * | $2,251 | $27,012 |
| Property Taxes | $6,311 | $75,732 |
| Electricity | $246 | $2,954 |
| Total | $32,447 | $389,364 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-06-24 | Listed for sale | $4,675,000 |
| 2018-09-04 | Sold | $1,950,000 |
| 2018-05-01 | Price change | $2,199,999 |
| 2017-10-02 | Listed for sale | $2,595,000 |
| 2017-07-19 | Listing removed | $2,595,000 |
| 2016-07-18 | Listed for sale | $2,595,000 |
| 2016-01-01 | Listing removed | $2,395,000 |
| 2015-06-20 | Price change | $2,395,000 |
| 2013-11-19 | Listed for sale | $2,500,000 |
For Sale by Agent
View on Zillow