Single Family

860 Hillcrest Drive

Active · Southold · Suffolk County, NY 11957

Asking price$2,350,000Estimate monthly payment Request a Showing

Bedrooms: 3 Beds
Bathrooms: 4 Baths
Year built: 2001
Est. monthly taxes: $900

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About this home

Set on a spacious, shy acre with open field views, this renovated cedar-shingled farmhouse pairs classic North Fork character with a comprehensive renovation and addition. An expansive wrap-around porch drenched in light and enveloped in beautiful mature hydrangeas gives the home an inviting presence, while the pool and surrounding grounds make the most of its peaceful Orient setting. Inside, the three-bedroom, three-bath home features an open, light-filled floor plan designed for easy living and entertaining. Multiple sets of doors open directly to the deck and porch, creating a natural connection between the interior spaces, outdoor seating areas, pool, and landscape beyond. A bonus loft and finished lower level add valuable flexibility for guests, recreation, or work-from-home space. The property offers a comfortable sense of space, privacy, and connection to its surroundings in one of Orient’s most desirable pastoral locations.

Listing snapshot

Days on site: 28 days
Listed on MLS: Sep 30, 2026
Full baths: 3
Half baths: 1
Annual property tax (MLS): $10,800
Tax year: 2026
Area source (MLS): Other
Listing brokerage: Compass Greater NY LLC
MLS ID: KEY1056455
Last updated: Oct 10, 2026

General features

Property type: Single Family
Property subtype: Single Family Residence
Year built: 2001
Garage: No
Parking: Driveway
Water source: Well
Sewer: Septic Tank
Utilities: Electricity Connected

Interior features

Basement: Finished, Full, Walk-Out Access
Heating: Electric, Forced Air
Cooling: Central Air
Interior: First Floor Bedroom, First Floor Full Bath, Formal Dining, High Ceilings, Kitchen Island, Open Kitchen, Primary Bathroom, Walk-In Closet(s)
Appliances: Dishwasher, Dryer, Oven, Range, Refrigerator, Washer
Flooring: Hardwood
Fireplace: Yes
Fireplaces: 2

Exterior features

Architectural style: Cape Cod
Construction materials: Frame
Private pool: Yes

Schools (MLS)

Elementary school: Oysterponds Elementary School
Elementary school district: Oysterponds
Middle school: Greenport High School
Middle school district: Greenport
High school: Greenport High School
High school district: Greenport

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

Oct 10, 2026Listing updated from MLS
Sep 30, 2026First seen on this site
Sep 30, 2026MLS status changed

Location

Southold · Suffolk County, NY 11957Show interactive map

860 Hillcrest Drive

Southold · Suffolk County, NY 11957

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Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.

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Property expenses (USD)

Annual property taxMonthly association / maintenance fees

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Listing data is supplied by the MLS and may change without notice.

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