• UNDER CONTRACT

59 Hillside Road

Woodbury, CT 06798

  • $1,375,000
  • 6 Beds
  • 5/2 Baths
  • 9,296 Sqft
  • 3.49 Acres
  • 2006 Built

Auction Opportunity. Please review FAQ and Property Information Package included in the additional documents on MLS (you may have to request these directly from your agent or the auction company). Asking Price is Opening Bid only. Final price will be determined by competitive bidding. All bidding online, opening April 23 at 4pm and ending April 30 at 4pm. Bidding website available upon request. ~ Stunning 6-bedroom, 6 full bath, 2 half-bath, French-inspired estate with over 9, 000 sq. ft. of luxurious living space, set atop one of Woodbury's highest points. This elegant retreat features soaring ceilings, detailed craftsmanship, a chef's kitchen, and grand entertaining areas. The main suite offers a private escape, while 3 additional en-suite bedrooms provide comfort and privacy. Ideal for multi-generational living, the estate includes a 2-bedroom guest house with full kitchen and private entrance, plus an in-law suite above the heated 3-car garage. Outside, enjoy a resort-style infinity pool, hot tub, and expansive decks with breathtaking views. Timeless design meets modern versatility. High bid as of 4/24/25 is $525, 000. High bid as of 4/25/25 at 9:04 AM is $600, 000.High bid as of 4/26/25 at 8:21 AM is 960, 000. High bid as of 4/29/25 is $1, 075, 000. Current high bid as of 12:11 PM on 4/30/25 is $1, 300, 000.

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Property Highlights
  • STYLE : Colonial
  • POOL : Yes
  • PRICE/SQFT : $148
  • DAYS ON MARKET : 31
  • MLS : 24084150

Additional Information

LOT DETAILS
  • ACRES: 3.49
  • ACRES SOURCE: Public Records
  • COUNTY: Litchfield
  • GAS DESCRIPTION: Geothermal
  • LOT DESCRIPTION: Secluded, Lightly Wooded, Borders Open Space, On Cul-De-Sac, Open Lot
  • OCCUPANCY: Vacant
  • WATER DESCRIPTION: Private Well
  • WATER FRONTAGE: Not Applicable
  • WATERFRONT DESCRIPTION: Not Applicable
EXTERIOR FEATURES
  • EXTERIOR SIDING: Stone, Stucco
  • POOL DESCRIPTION: Gunite, Infinity Edge, In Ground Pool
  • ROOF: Fiberglass Shingle, Slate
INTERIOR FEATURES
  • AIR CONDITIONING: Central Air
  • APPLIANCES INCLUDED: Gas Cooktop, Wall Oven, Refrigerator, Freezer, Dishwasher
  • ATTIC: Yes
  • BEDS: 6
  • COOLING: Central Air
  • FIREPLACES: 5
  • FULL BATHS: 5
  • FURNACE TYPE: Geothermal
  • HALF BATHS: 2
  • HEAT: Geothermal
  • HEAT FUEL: Geothermal
  • HOT WATER: Domestic
  • LAUNDRY ROOM: Main Level, Upper Level
  • ROOMS: 17
  • TOTAL BATHS: 7
ADDITIONAL INFORMATION
  • ATTIC DESCRIPTION: Access Via Hatch
  • AVERAGE DAYS ON MARKET: 31
  • BASEMENT DESCRIPTION: Full
  • DAYS ON MARKET: 31
  • ELEMENTARY SCHOOL: Mitchell
  • GARAGE: Attached Garage
  • HAS POOL?: Yes
  • HIGH SCHOOL: Nonnewaug
  • IS OCCUPIED?: Vacant
  • LIVING AREA SQFT: 9,296
  • PROPERTY TAX: $33,554
  • SEWER: Septic
  • STATUS: Under Contract
  • STYLE: Colonial
  • TYPE: Single Family For Sale
  • YEAR BUILT: 2006
  • YEAR BUILT DETAILS: Public Records
  • ZONING: OS80

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Location for 59 Hillside Road, Woodbury, CT

Schools for 59 Hillside Road, Woodbury, CT

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Private Schools
SCHOOL LOCATION GRADE
Creative Arts Studio 122 South Pomperaug Avenue, Woodbury, CT, 06798 PK-K
Brown Tufts Montessori 4 Church Street, Woodbury, CT, 06798 PK-K
Westover School 1237 Whittemore Road, Middlebury, CT, 06762 9-12
Reg 15 Bas Child Care Center-Pomperaug 129 Wheeler Road, Middlebury, CT, 06762 PK-K
Great Expectations Dc-Learning Center 1235 Southford Rd, Southbury, CT, 06488 PK-K
First Steps Learning Center 1486 Seymour Road, Southbury, CT, 06488 PK-K
First Step Pre-School 28 Heritage Crest Drive, Southbury, CT, 06488 PK-K
Generali School Child Care Center-Lit & Arts 1625 Straits Turnpike, Middlebury, CT, 06762 PK-K
Creative Arts Studio 122 South Pomperaug Avenue, Woodbury, CT, 06798 PK-K
Brown Tufts Montessori 4 Church Street, Woodbury, CT, 06798 PK-K
Westover School 1237 Whittemore Road, Middlebury, CT, 06762 9-12
Reg 15 Bas Child Care Center-Pomperaug 129 Wheeler Road, Middlebury, CT, 06762 PK-K
Great Expectations Dc-Learning Center 1235 Southford Rd, Southbury, CT, 06488 PK-K
First Steps Learning Center 1486 Seymour Road, Southbury, CT, 06488 PK-K
First Step Pre-School 28 Heritage Crest Drive, Southbury, CT, 06488 PK-K
Generali School Child Care Center-Lit & Arts 1625 Straits Turnpike, Middlebury, CT, 06762 PK-K
GreatSchools

*UG = ungraded.
Detailed school information provided by GreatSchools.org © 2025. All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

Community

Woodbury>

Woodbury

Litchfield County, Connecticut

The Litchfield County town of Woodbury is known as a prime destination for antiques shoppers, having earned the title of “Antiques Capital of Connecticut.” Its quaint town center hosts numerous antiques...

Market Stats for Woodbury, Connecticut

An exclusive report that informs you of residential real estate sales activity and trends in Woodbury, Connecticut.

Request More Info for 59 Hillside Road, Woodbury, CT

  • Kent Brokerage

    9 Maple Street , PO Box 82
    Kent, CT 06757
    O

Listing Courtesy of Samantha Kelley of Tranzon Auction Properties (207.775.4300).