$2,750,000
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36 Chestnut Woods Road, Redding, CT 06896

4 Beds
7 Baths
5,562 Sq Ft

Most spectacular country estate on 11.58 acres with scenic pond in prestigious West Redding location. This breathtaking country compound includes the gracious main home with 5,562 sf including 1,003 sf in the dramatic lower level media/bar/billiard room; total 4 bedrooms, 5/2 fully remodeled baths; additional studio or guest quarters with private entry, bedroom & full bath; legal rental cottage with living room, kitchen & full bath (additional 741 sf); & state of the art pool house (additional 504 sf). Highest attention to detail both inside & out w/apprx $500K in recent improvements by current owner including brand new slate roof; stunning kitchen & baths; new a/c; new lighting; full studio renovation; new pool house; updates in cottage including hardwood installation; full interior painting; fit out of main garage as a catering kitchen; hardwood installation in lower level; sun porch w/retractable screen; & so many other tasteful touches which have polished this home to exquisite perfection. Casual elegance abounds w/6 fireplaces including the LR w/exposed beams, dining room, paneled library, MBR suite, 2nd ensuite BR, & lower level billiards room. Picturesque grounds w/heated gunite pool; private pond; outbuildings including detached garage & barn/shed; plus potential to subdivide & permits in place to build a new large barn if desired. Bucolic privacy adjoining the 54 acre Connecticut Audubon Society's Edward Steichen Memorial Wildlife Preserve & just 61 miles to Midtown!

  • MLS# 170375137
  • Date Listed02/25/2021
  • Bedrooms 4
  • Bathrooms 5 Full baths, 2 Half baths
  • Lot Size 11.58 acres (504,425 sq. ft)
  • Sewer Septic Tank
  • Property Type Single Family
  • County Fairfield
  • Year Built 1942
  • Water Well
  • Square Feet 5,562 sq. ft
  • Price Per Sq. Ft $494.43

Interior Features

  • Appliances Dishwasher, Dryer, Gas Range, Refrigerator, Washer
  • Cooling Central Air
  • Heating Oil, Propane, Forced Air, Hot Water

Exterior / Lot Features

  • Exterior Balcony, Garden, Barn(s), Guest House, Pool House
  • Roof -
  • Lot Size Acres 11.58
  • Lot Size SQFT 504,424.80
  • Lot Features Level, Waterfront

Financial Considerations

  • Tax Amount $43,158
  • Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in CT / 06896

Source: Walkscore

8/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 6/100, Transit Score: 0/100, Bike Score: 11/100.

Points of Interest near 36 Chestnut Woods Road, Redding, CT 06896

Frequently Asked Questions for 36 Chestnut Woods Road

Source: Realty.com

36 Chestnut Woods Road, Redding, CT 06896 is a Single Family 5,562 sq. ft. home listed for sale. Realty.com has 40 photos available of this 4 bed, 7 bath house, listed at $2,750,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 40 photos of 36 Chestnut Woods Road.

Our records indicate that 36 Chestnut Woods Road was built in 1942.

The full address for this home is 36 Chestnut Woods Road, Redding, CT 06896.

36 Chestnut Woods Road has been listed on Realty.com since Thu February 25, 2021

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 6/100, Transit Score: 0/100, Bike Score: 11/100.

There are 3 schools assigned to this home. Check out the schools near 36 Chestnut Woods Road. Redding Elementary School (Grades: PK - 4), John Read Middle School (Grades: 5 - 8), Ridgefield High School (Grades: 9 - 12)

Listing provided courtesy of: William Pitt Sotheby's Int'l (tel: 203-438-9531)
Listing agent: Laura Ancona (tel: 203-438-9531) (#7789)

This content last refreshed on 2025-12-07 02:29:20. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 36 Chestnut Woods Road, Redding, CT 06896 : MLS# 170375137