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.
For sale
$4,675,000
14380 Oregon Rd, Cutchogue, NY 11935
2beds
1,400sqft
Single Family Residence
Built in 1925
48.7 Acres Lot
$4,710,000 Zestimate®
$3,339/sqft
$-- HOA
What's special
Gunite poolCross-country courseSweeping vineyard viewsJumping fieldCharming farmhouse residenceSurrounded by mature landscapingMature gardens
- 4 days |
- 399 |
- 34 |
Zillow last checked:
Listed by:
Corcoran Group,
Rolanda Blue Doolan - Real Estate Sales Person 631-766-3376
Source: Out East,MLS#: 396537
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Family Room, Office
Cooling
- Central Air
Features
- Basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,400
- Total interior livable area: 1,400 sqft
Property
Parking
- Parking features: None
Features
- Stories: 2
- Has private pool: Yes
- Pool features: Heated
Lot
- Size: 48.7 Acres
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 1925
Community & HOA
Community
- Features: Room for a Tennis Court
Location
- Region: Cutchogue
Financial & listing details
- Price per square foot: $3,339/sqft
- Date on market: 6/24/2026
- Lease term: Contact For Details
Estimated market value
$4,710,000
$4.47M - $4.95M
$3,559/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/24/2026 | Listed for sale | $4,675,000+139.7%$3,339/sqft |
Source: Out East #396537 Report a problem | ||
| 9/4/2018 | Sold | $1,950,000-11.4%$1,393/sqft |
Source: | ||
| 5/1/2018 | Price change | $2,199,999-15.2%$1,571/sqft |
Source: Bagshaw Real Estate L.L.C #2975387 Report a problem | ||
| 10/2/2017 | Listed for sale | $2,595,000$1,854/sqft |
Source: Bagshaw Real Estate L.L.C #2975387 Report a problem | ||
| 7/19/2017 | Listing removed | $2,595,000$1,854/sqft |
Source: Daniel Gale Sotheby's International Realty #2869691 Report a problem | ||
| 7/18/2016 | Listed for sale | $2,595,000+8.4%$1,854/sqft |
Source: Daniel Gale Sothebys Intl #2869691 Report a problem | ||
| 1/1/2016 | Listing removed | $2,395,000$1,711/sqft |
Source: Daniel Gale Sothebys Intl #2630756 Report a problem | ||
| 6/20/2015 | Price change | $2,395,000-4.2%$1,711/sqft |
Source: Daniel Gale Sotheby's International Realty #2630753 Report a problem | ||
| 11/19/2013 | Listed for sale | $2,500,000$1,786/sqft |
Source: Daniel Gale Agency Inc #2630753 Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 11935
Nearby schools
GreatSchools rating
- 6/10Mattituck Cutchogue Elementary SchoolGrades: K-6Distance: 1.8 mi
- 7/10Mattituck Junior Senior High SchoolGrades: 7-12Distance: 3.2 mi
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Suffolk County
- Cutchogue
- 11935
- 14380 Oregon Rd




