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$1,720,000

  • Sold
  • Closed
  • Single Family
  • 6 Beds
  • 5 Full Baths
  • 2 Partial Baths
  • 9,296 Sq. Ft.
  • 3 Car Garage
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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.

Full Property Details for 59 Hillside Rd

General

  • Sold For: $1,720,000
  • Taxes: (July 2024-June 2025)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24084150
  • Added to Site: 391 day(s) ago

Interior

  • Number of Rooms: 17
  • Fireplace: Yes
  • Number of Fireplaces: 5
  • Appliances: Gas Cooktop, Wall Oven, Refrigerator, Freezer, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 5
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 6
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper
  • Bedroom 4: Bedroom, Upper
  • Bedroom 5: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Dining Room: Dining Room, Main
  • Laundry: Main Level, Upper Level
  • In-Law/Au Pair Suite: Yes

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Infinity Edge, In Ground Pool

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Litchfield
  • Driving Directions: 59 Hillside Road Extension, Woodbury, CT 06798

School Information

  • Elementary School: Mitchell
  • High School: Nonnewaug

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Radiant, Geothermal
  • Heating Fuel: Geothermal
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Stone, Stucco
  • Basement Desc.: Full
  • Roof: Fiberglass Shingle, Slate
  • Attic: Yes
  • Square Feet: 9,296
  • Above Ground: 9,296 Sq. Ft.
  • Year Built: 2006

Lot Features

  • Lot Size (Acres): 3.49
  • Zoning: OS80
  • Lot Description: Secluded, Lightly Wooded, Borders Open Space, On Cul-De-Sac, Open Lot

Financial Considerations

  • Assessment Amount: $1,448,160
  • Tax Year: July 2024-June 2025

Disclosures and Reports

  • Bank-owned: Yes
  • Property ID: 932938

Listed by Tranzon Auction Properties, Samantha Kelley
Sold by Epique Realty LLC, Marc Nieto

Listing agent

— 59 Hillside Rd —

  • Samantha Kelley

    Tranzon Auction Properties

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 59 Hillside Rd

School District:Regional School District 14
NameGradesDistance
Mitchell Elementary School
14 School Street, Woodbury, CT 06798
PK-52.4 mi
Bethlehem Elementary School
92 East Street, Bethlehem, CT 06751
PK-58.3 mi
Woodbury Middle School
67 Washington Avenue, Woodbury, CT 06798
6-82.6 mi
Nonnewaug High School
5 Minortown Road, Woodbury, CT 06798
9-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 59 Hillside Rd

Date
Details
Price
Change
Source
5/21/2025
Sold
$1,720,000
25.09%
MLS
4/30/2025
Price Increased
$1,375,000
27.91%
MLS
4/29/2025
Price Increased
$1,075,000
4.88%
MLS
4/28/2025
Price Increased
$1,025,000
2.5%
MLS
4/27/2025
Price Increased
$1,000,000
4.17%
MLS
4/26/2025
Price Increased
$960,000
60%
MLS
4/25/2025
Price Increased
$600,000
14.29%
MLS
4/24/2025
Price Increased
$525,000
5%
MLS
3/31/2025
Listed
$500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Tranzon Auction Properties, Samantha Kelley
Sold by Epique Realty LLC, Marc Nieto

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59 Hillside Road, Woodbury, CT 06798 (MLS# 24084150) is a Single Family property that was sold at $1,720,000 on May 21, 2025. Want to learn more about 59 Hillside Road? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.