221 Smith Clove Road

Off Market

221 Smith Clove Road

Woodbury NY 10930

5142 sq. ft.

283140 sq. ft.

Single-Family

Last sold for $1,075,000

Jamie Aisenstat, last sold this property on 02 September 2026 after 481 days on market.

Overview

Introducing one of Highland Mills’ most impressive estates—an architectural statement set on 6.5 private acres in the Monroe–Woodbury School District. Built by a seasoned general contractor for his own family, this 5,140+ sq ft residence pairs exceptional craftsmanship with the scale and sophistication of a true luxury home. A sun-filled two-story foyer welcomes you with a sweeping handcrafted staircase and a dramatic Palladian window that frames the outdoors. The great room rises with towering ceilings and centers on a striking floor-to-ceiling stone fireplace, surrounded by oversized windows and multiple sets of Andersen doors that bathe the space in natural light. The kitchen is a standout—a 12' marble island, full-size Sub-Zero refrigerator and freezer, 8-burner Wolf range, beverage station, and custom cabinetry combine to create a space built for serious cooking and effortless entertaining. It flows seamlessly into the dining and living areas, creating an ideal environment for gatherings of any size. A first-floor flex space is conveniently located adjacent to a full bath and den with its own fireplace. This offers versatility for guests, multi-generational living, or a private office. Additional conveniences include a mudroom off the three-car garage and a stylish powder room. Upstairs, the primary suite provides a true retreat with tray ceilings, hardwood floors, and a spa bathroom featuring travertine tile, a jacuzzi tub, rain shower, and marble finishes. Three additional bedrooms, two well-appointed full baths, and a second-floor laundry complete the level. The home’s construction reflects quality at every turn: 2x6 Douglas fir framing, 12" concrete foundation, spray foam insulation, Buderus boiler, 300-amp underground electric, owned propane tank, central vacuum, built-in speakers, and automatic lighting throughout. Designed for efficiency, comfort, and longevity, this is a home engineered to outperform others in its class. Outside, a 20' x 25' bluestone patio overlooks two cleared acres with wooded surroundings—offering privacy, space for recreation, and the potential for future enhancements such as a pool or guest cottage. Located minutes from highways, trains, and Woodbury’s private lake, pool, and recreation complex, this property offers a rare blend of convenience, seclusion, and true custom construction. A standout luxury offering rarely available at this level in Orange County

Features

4 bedrooms

5 bathrooms

3 carspaces

3 garage spaces

5142 sq. ft. floor area

283140 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Woodbury over the last 12 months, the estimated median property value of 221 Smith Clove Road is $615k.

Median value

$615k

Estimated value range

$390k - $1.07m

Median days on market

Estimated value trend

-5%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Woodbury. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 221 Smith Clove Road

2026

Sold

$1,075,000

02 Sep 2026 by Jamie Aisenstat, of Serhant LLC

Happy sellers in Woodbury

We have insufficient information to provide an overview of customer satisfaction for Woodbury. Viewing the agent profiles, reviews and sales for Woodbury can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Woodbury

In the last 12 months, 30 four-bedroom single-family properties similar to 221 Smith Clove Road, have been sold.

This represents a 18% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Woodbury for a market analysis.

Dionne Harris-Jackman

at eXp Realty, LLC (E - TR12 - New York - White Plains)

(31 reviews)

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Rosemarie Franzese

at Howard Hanna | Rand Realty

(7 reviews)

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Antoinette Gundersen

at HomeSmart Homes & Estates

(16 reviews)

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Helene Spear

at Keller Williams Realty

(1 review)

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Woodbury

Dionne Harris-Jackman

Sellers who recommend Dionne Harris-Jackman have praised them for being local expert, patient, clear communication, reliable, supportive, responsive, and dedicated