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$2,100,000

Listing Price

4beds

5baths

4,057sqft

1,480,169sqft lot

225 Old Sherman Hill Rd, Woodbury, CT 06798

Member Features

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  • Full foreclosure details

  • Home value, equity and ownership info

  • Find homes priced below market

  • Get full access with a FREE Account

Already a member?

For Sale

Off Market

Single Family

Home type

428.41

Price / sqft

1969

Year built

Home Details

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!

Interior Details

Square Feet
  • 4057

Bedrooms
  • 4

Bathrooms
  • 5

Heating
  • Has Heating:

    Yes

  • Heating Type:

    Forced Air With Air Conditioning

Cooling
  • Has Cooling:

    Yes

  • Cooling Type:

    N/A

Fuel
  • Has Fuel:

    Yes

  • Fuel Type:

    Oil

Basement
  • Has Basement:

    No

  • Basement Type:

    Unfinished

Flooring
  • Has Flooring:

    No

  • Flooring Type:

    N/A

Fireplace
  • Has Fireplace:

    Yes

  • Fireplace Type:

    N/A

Property Details

Lot Size
  • 1480169

Water
  • Yes

Sewer
  • Yes

Parking
  • Type:

    Garage, Detached

  • Location:

    N/A

  • Status:

    N/A

  • Number of Spaces:

    0

Deck
  • N/A

Patio
  • N/A

Fence
  • N/A

Pool
  • N/A

Porch
  • N/A

Stoop
  • N/A

Breezeway
  • N/A

Construction Details

Number of Stories
  • 2

Style
  • Contemporary

Exterior
  • Wood Siding

Foundation
  • N/A

Roof
  • Gable

Roofing Material
  • Shingle

Tax History

Year

Amount

Land

Improvement

Percent Change

Assessment

2020

$15,344

$123,420

$402,600

--%

$526,020

2019

$15,344

$123,420

$402,600

--%

$526,020

2018

$15,163

$95,050

$475,410

--%

$570,460

2017

$15,494

$95,050

$475,410

--%

$570,460

2016

$14,997

$95,050

$475,410

--%

$570,460

2014

$14,723

$95,040

$478,050

--%

$573,090

2011

$12,522

$119,650

$415,460

--%

$535,110

percent-home-icon

Average Home Price in 06798

Nearby Properties

Zip Code

Price

Bed

Bath

Sqft

Lot

Sold Date

$2,100,000

4 Beds

5 Baths

4,057 Sqft

1,480,169 Lot (sqft)

Sold 09/29/2026

$1,200,000

4 Beds

4 Baths

3,968 Sqft

174,240 Lot (sqft)

Sold 10/06/2026

percent-home-icon

Calculators

Mortgage

Mortgage Calculator

Calculate your monthly mortgage payments.
Household Income
70,000
$
Home price
2,100,000
$
Down payment
420,000
$
Mortgage Rate
6.5
%
Loan Term
Property Tax Rate
1.1
%
Homeowner's Insurance (Annual)
12,600
$
HOA (Monthly)
0
$
PMI
0
$
$13,594
Your Payment
Total Monthly Payment:$13,594
Percent of Income:233%
Affordable:No

Details for 225 OLD SHERMAN HILL RD

Property Debt

Foreclosure Contact Details

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