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225 Old Sherman Hill Road, Woodbury CT 06798

Current Price: $2,100,000

4 beds 5 baths 4517 sq. ft

Last Update: 7/19/2025

Property Type: Single Family For Sale

Public Remarks

A long winding drive leads you to Four Winds Farm. Perched on the hill, this remarkable 33.98-acre property includes a 4,500 sq ft, 11 room, 4 bedrooms, 4.1 bath residence as well as a home for your horses. The contemporary house has many updates throughout, cathedral ceilings, tall windows, multiple sliders to exterior entertainment areas and spacious deck. There is central air, a security system, central vac, generator, and 4-bay heated garage. The spectacular grounds include the inground gunite saltwater pool, spacious composite deck, mature professional landscaping, and amazing views of distant hills. For the horses there is a two-story 8 stall stable, 14 paddocks with aisle ways, 120 x 200 riding ring with Atwood Equestrian Surface (re-surfaced 4 years ago), 7 run-in sheds, 20 x 20 tractor barn and trail. Woodbury designated as Connecticuts Most charming small town, by Readers Digest offers tree-lined Main St, parks, playgrounds, hiking trails and streams to dip your toes in on those hot summer days. Also known as the Antiques Capital of CT, theres no shortage of shops, boutiques and antiques homes lining the historic district. Woodbury is home to a half dozen fun and diverse restaurants and a brewery with music. Just twenty minutes to the historic Palace Theater for concerts, comedy and much more. Forty minutes to Mohawk Mountain for winter fun. 35 minutes to Brewster Train Station and 90 minutes to NYC. Come see what Litchfield Hills has to offer!

Map to Property at 225 Old Sherman Hill Road, Woodbury CT 06798


Rte 6 to Rte 64 towards Middlebury. Take right on Old Sherman Hill. Property on the left.

Residential Property Information for 225 Old Sherman Hill Road, Woodbury CT 06798

MLS #: 24072926

Style: Contemporary

Color:

Total Rooms:

Bedrooms: 4

Bathrooms: 5

Acres: 33.98

Year Built: 1969 (Public Records)

New Construction: No/Resale

Home Warranty Offered:

Property Tax: $15,888

Zoning: OS80

Mil Rate:

Assessed Value: $672,630 

Potential Short Sale:

Square Footage: Estimated HEATED Sq.Ft. above grade is 4057; below grade sq feet total is 460; total sq ft is 4517

Features
Appliances Incl.: Electric Cooktop,Wall Oven,Microwave,Refrigerator,Dishwasher,Washer,Dryer
Laundry Location & Info: Main Level  Off Kitchen
Fireplaces: 2
Energy Features: Generator,Programmable Thermostat
Interior Features: Auto Garage Door Opener,Cable - Available,Central Vacuum,Security System
Energy Features: Generator,Programmable Thermostat
Basement Desc.: Full,Partially Finished
Exterior Siding: Vertical Siding,Wood
Exterior Features: Shed,Barn,Deck,Gutters,Stable,Stone Wall,Paddock,Patio
Foundation: Concrete
Roof: Asphalt Shingle
Parking Spaces: 4
Garage/Parking Type: Attached Garage
Swimming Pool: 1
Waterfront Feat.: Not Applicable
Lot Description: Lightly Wooded,Borders Open Space,Level Lot,Professionally Landscaped,Rolling,Open Lot
Nearby Amenities: Basketball Court,Library,Park,Playground/Tot Lot,Private School(s),Tennis Courts
Occupied: Owner
Utility Information

Hot Water System

Heat Type:

Fueled By: Hot Air.

Cooling: Central Air

Fuel Tank Location: In Basement

Water Service: Private Well

Sewage System: Septic

School Information

Elementary: Per Board of Ed

Intermediate:

Middle: Woodbury

High School: Nonnewaug

Marketing History

Current List Price: $2,100,000

Original List Price: $2,100,000

DOM: 163

Listing Date: 2/6/2025

Last Updated: 3/19/2025 11:07:05 PM

Listing Agent and Broker

List Agent Name: Maria Taylor

List Office Name: Klemm Real Estate Inc