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$2,100,000

225 Old Sherman Hill Rd Woodbury, CT 06798

4 beds
4 full, 1 partial
4,517 sqft
34.0 acres
$465 / sqft
House

Property details

About 225 Old Sherman Hill Rd

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 Connecticut's "Most charming small town," by Reader's 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," there's 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!

Highlights

Home typeOther
HeatingForced Air
StatusActive
CoolingCentral Air
Size4,517 sqft
BasementYes
Lot size33.98 Acres
Year built1969
ParkingAttached Garage
MLS #24072926
Attached garage4 spaces
ViewTrees/Woods
Private poolYes

Summary

  • Partial Bathrooms: 1
  • Full Bathrooms: 4
  • Appliances: Electric Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Basement: Yes
  • Interior: Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
  • Total Bedroom Count: 4
  • Garage Space: 4 spaces
  • Attached Garage: Yes
  • Private Pool: Yes
  • Parking: Attached Garage
  • View: Trees/Woods
  • Exterior: Shed, Barn, Deck, Gutters, Stable, Stone Wall, Paddock, Patio
  • Architectural Style: Contemporary
  • Heating: Forced Air
  • Cooling: Central Air
  • List Price: $2,100,000
  • Price/SqFt: $464
  • Annual Tax Amount: $15,413
  • Tax Year: 2024
  • Lot: Wooded, Level, Landscaped, Rolling/Hilly, Open Lot
  • Directions: Rte 6 to Rte 64 towards Middlebury. Take right on Old Sherman Hill. Property on the left.
  • Year Built: 1969
  • Living Area: 4,517 SqFt
  • Lot Size: 33.98 Acres
  • MLS Number: 24072926
  • Office Name: Klemm Real Estate Inc
  • Office Phone: (860) 868-7313
  • Office Email: mtaylor1800@aol.com
  • Listing Agent: Maria Taylor

IDXCopyright © 2025 Smart MLS. The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/8/2025, 4:45:31 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

Price information

Property sales

DateEventPrice
Aug 08, 2006
Home Sold
$2,525,000
Sep 25, 2000
Home Sold
$2,225,000

Tax history

YearAssessmentProperty Tax
2024$665,210$15,413
2023$526,020$15,286
2022$526,020$15,344
2021$526,020$15,344
2020$526,020$15,344
2019$526,020$15,344

History based on county public records data.

Nearby schools

7

Mitchell Elementary School

Public District PK-5

1.9 mi

14 School St

8

Long Meadow Elementary School

Public District PK-5

2.3 mi

65 N Benson Rd

7

Gainfield Elementary School

Public District KG-5

3.8 mi

307 Old Field Rd

School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $74,643. The majority of Woodbury, CT residents have income between $35k-100k annually. Most families are single, no kids. Residents of this area typically have post secondary degree education.

How much money do the neighbors make?

24%
<35k
38%
35k-100k
25%
100k-200k
13%
200k+

What level of education do the neighbors have?

No High School
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate

What types of families live nearby?

51%
Single, No Kids
5%
Single, with Kids
28%
Married, No Kids
16%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

10%
<11 yrs old
7%
12-17 yrs old
14%
18-34 yrs old
46%
35-64 yrs old
23%
65+ yrs old

What do the neighbors do for fun?

  • Skiing/snowboardingSkiing/snowboarding
  • PGA/LPGAPGA/LPGA
  • Figure SkatingFigure Skating

Where do the neighbors shop?

  • BJs Wholesale ClubBJs Wholesale Club
  • Stein MartStein Mart
  • KmartKmart

Where do the neighbors go to eat?

  • PaneraPanera
  • Cracker BarrelCracker Barrel
  • Bob EvansBob Evans

What do the neighbors drive?

  • InfinitiInfiniti
  • LexusLexus
  • LincolnLincoln

What do the neighbors listen to?

  • Adult HitsAdult Hits
  • OldiesOldies
  • News/Talk/InformationNews/Talk/Information
All data provided by Home Junction and Claritas

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Frequently asked questions

About 225 Old Sherman Hill Rd

The listing price of 225 Old Sherman Hill Rd property is $2,100,000.

The property 225 Old Sherman Hill Rd is a house located in Woodbury, Connecticut, 06798.

Active Listing: 225 Old Sherman Hill Rd is For Sale (Active/New) which means the seller is accepting offers.

The nearby schools for 225 Old Sherman Hill Rd are: Mitchell Elementary School (GreatSchools Rating 7/10), Long Meadow Elementary School (GreatSchools Rating 8/10), Gainfield Elementary School (GreatSchools Rating 7/10), Woodbury Middle School (GreatSchools Rating 8/10), Rochambeau Middle School (GreatSchools Rating 5/10), Memorial Middle School (GreatSchools Rating 5/10), Nonnewaug High School (GreatSchools Rating 7/10), Pomperaug Regional High School (GreatSchools Rating 8/10), Watertown High School (GreatSchools Rating 4/10).

According to the records, the last property tax for 2024 is $15,413 (source: MLS/based on county public records data).

The last sale was on August 8, 2006 for $2,525,000 (source: MLS/tax record).

The property at 225 Old Sherman Hill Rd has 4 bedrooms and 4 full and 1 half bathrooms.

The property 225 Old Sherman Hill Rd is 4,517 SqFt (source: MLS/tax record).

The year of construction for 225 Old Sherman Hill Rd is 1969.

This home is located at 225 Old Sherman Hill Rd in Woodbury, CT and zip code 06798. This 4,517 square foot home, which was built in 1969, sits on a 33.98 acre lot. Features: 4 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since February 6, 2025 and is currently priced at $2,100,000.

In June 2025 more than 3 listings in Woodbury, CT were sold above the asking price. During the same period more than 1 listings were sold at asking price, while more than 1 were sold below. The inventory of homes for sale in Woodbury, CT between May and June 2025 increased by 13.1%.

From Rocket Homes Real Estate and based on county public records data.

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