4100 Oregon Road
About This Property
An exceptional North Fork opportunity with scale, pedigree, and a clear path forward. 4100 Oregon Road spans approximately 33 acres in the heart of Cutchogue, combining established viticulture with a rare, rights-retained parcel on a prime stretch of Oregon Road. The estate includes approximately 31 acres with development rights sold to the Town of Southold (preserved), plus 2 acres with retained rights. The rights-retained parcel measures approximately 200'x400' and fronts Oregon Road-an ideal setting for a high-visibility retail tasting room concept and/or a private residential build. A substantial vineyard footprint is already in place, with approximately 24.3 acres planted across key varietals: Chardonnay (10.4 acres), Cabernet (4 acres), Merlot (3.75 acres), Sauvignon Blanc (2.2 acres), Pinot Gris (2.2 acres), Petit Verdot (.75 acre), and Malbec (1 acre). The grapes from these vineyards have historically been used exclusively to make wine at Lenz Winery in nearby Peconic, with those wines consistently acclaimed by leading wine industry professionals such as Robert Parker's 'The Wine Advocate'. Supporting infrastructure includes deep irrigation well (recently refitted), partial irrigation lines in the vineyard, deer fencing, irrigation mains/tubing, and bird netting. A large barn offers on-site storage for equipment and vineyard nets (in need of repair). Dorset Farms is available to provide vineyard management for one to two years post-closing at commercial rates (approximately $8,000 per vineyard acre) and select vineyard management equipment may be available separately. This is a compelling offering for a buyer seeking a true North Fork footprint-preserved acreage, established plantings, and the flexibility of a road-front rights-retained parcel to bring a vision to life.
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Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
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Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
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Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| May 29, 2026 | Sold | ||
| Sold | |||
| Apr 30, 2026 | In contract | - | |
| In contract | |||
| Mar 27, 2026 | Listed by Corcoran | $2,350,000 | |
| Listed by Corcoran | |||
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About Cutchogue
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Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017