Off market may 2025 for $1.7M

$1,338,850

•

9,296

sq ft

59 Hillside Rd, Woodbury, CT 06798

About this home

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.

Single-familyProperty Type

2006Year Built

3.49 acresLot Size

$144Est. Price/Sq.Ft.

3 car garageParking

Listed by Samantha Kelley • Tranzon Auction Properties

Bought with Marc Nieto • Epique Realty LLC

Source:Smart MLS #24084150

Redfin Estimate

$1,338,850

$381K since sold in May 2025$30K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.9% higher than the average sale price ($1.11M) of 5 comparable homes.

SOLD OCT 29, 2026
$840,000
A
4 beds4 baths3,865 sq ft
8 Curtiss Mdws, Woodbury, CT 06798
SOLD OCT 9, 2026
$1,000,000
B
4 beds4 baths3,808 sq ft
31 Cedar Grove Rd, Southbury, CT 06488
SOLD JUN 10, 2026
$950,000
C
4 beds3.5 baths4,861 sq ft
112 Southridge Rd, Southbury, CT 06488
SOLD JUN 30, 2026
$995,214
D
5 beds3 baths4,163 sq ft
445 Dublin Rd, Southbury, CT 06488
SOLD JAN 30, 2026
$1,752,500
E
6 beds7 baths6,357 sq ft
509 Main St N, Woodbury, CT 06798

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Earn from this home

Sell

−$81,085

Est. take-home

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Rent

$4,223/mo

Redfin rental estimate

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Market trends in 06798, CT

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

100.7%

+1.3% MoM

Median sale price

$477K

$61K MoM

Avg. days on market

53d

2 days MoM

Recently sold homes

10 MoM

New listings for sale

OPEN SAT, 1PM TO 3PM
$279,900
2 beds2 baths1,712 sq ft
5 Wintergreen Ct #5, Woodbury, CT 06798
$299,999
3 beds2.5 baths1,467 sq ft
15 Woods Way, Woodbury, CT 06789
$999,000
3 beds4 baths2,280 sq ft
770 Washington Rd, Woodbury, CT 06798
$500,000
4 beds2 baths1,509 sq ft
47 Atwood Rd, Woodbury, CT 06798
$849,900
5 beds4 baths3,657 sq ft
34 Quail Run Rd, Woodbury, CT 06798
$595,000
3 beds2.5 baths1,909 sq ft
36 Main St S, Woodbury, CT 06798
OPEN NOV 21, 1PM TO 3PM
$359,900
2 beds1 bath990 sq ft
555 Middle Road Tpke, Woodbury, CT 06798
See all

Provided by Redfin

Redfin agents who toured

Stunning home with beautiful hardwood floors throughout, infinity inground pool with jacuzzi over looking the mountains, inlaw attached state of the art kitchen and more.
2 years ago• May not reflect the current state of the home
Mary Ellen Wisneski
Redfin agent

Sale history for 59 Hillside Rd

Date

Event

Price

Smart MLS #24084150

May 21, 2025

Sold

$1,720,000

$185/sq ft

May 1, 2025

Pending

—

Apr 30, 2025

Price Changed

$1,375,000

$148/sq ft

Apr 30, 2025

Price Changed

$1,300,000

$140/sq ft

Apr 29, 2025

Price Changed

$1,075,000

$116/sq ft

Apr 28, 2025

Price Changed

$1,025,000

$110/sq ft

Apr 27, 2025

Price Changed

$1,000,000

$108/sq ft

Apr 26, 2025

Price Changed

$960,000

$103/sq ft

Apr 25, 2025

Price Changed

$600,000

$65/sq ft

Apr 24, 2025

Price Changed

$525,000

$56/sq ft

Mar 31, 2025

Listed

$500,000

$54/sq ft

Smart MLS #170625749

Mar 10, 2025

Listing Removed

—

Nov 20, 2024

Contingent

—

Oct 28, 2024

Price Changed

$1,499,000

$161/sq ft

Sep 16, 2024

Contingent

—

Aug 28, 2024

Price Changed

$1,575,000

$169/sq ft

Aug 8, 2024

Price Changed

$1,599,000

$172/sq ft

Jul 3, 2024

Price Changed

$1,660,000

$179/sq ft

Jul 2, 2024

Listing Removed

—

Feb 21, 2024

Listed

$1,745,000

$188/sq ft

Smart MLS #170566868

Dec 1, 2023

Listing Removed

—

May 2, 2023

Listed

$1,995,000

$215/sq ft

Smart MLS #170534856

Mar 31, 2023

Listing Removed

—

Jan 9, 2023

Price Changed

$2,380,000

$256/sq ft

Nov 7, 2022

Listed

$2,600,000

$280/sq ft

Smart MLS #170207963

Mar 19, 2020

Listing Removed

—

Oct 22, 2019

Price Changed

$3,000,000

$323/sq ft

Aug 28, 2019

Price Changed

$1,649,000

$177/sq ft

Aug 2, 2019

Price Changed

$1,749,000

$188/sq ft

Jun 19, 2019

Listed

$1,899,000

$204/sq ft

OneKey® MLS as Distributed by MLS Grid #H4963068

Mar 20, 2020

Listing Removed

—

Oct 22, 2019

Price Changed

$3,000,000

$323/sq ft

Aug 28, 2019

Price Changed

$1,649,000

$177/sq ft

Aug 2, 2019

Price Changed

$1,749,000

$188/sq ft

Jun 19, 2019

Listed

$1,899,000

$204/sq ft

GMLS #107058

Oct 31, 2019

Price Changed

$3,000,000

$323/sq ft

Aug 29, 2019

Price Changed

$1,649,000

$177/sq ft

Jun 20, 2019

Listed

$1,899,000

$204/sq ft

Smart MLS #170032891

Aug 14, 2018

Listing Removed

—

Nov 17, 2017

Listed

$2,495,000

$268/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$38,784 (−0.4%)

$98,320 + $1,236,300

$1,334,620

2022

$38,931

$98,320 + $1,236,300

$1,334,620

2021

$38,931

$98,320 + $1,236,300

$1,334,620

2020

$38,931

$98,320 + $1,236,300

$1,334,620

2019

$38,931 (+4.7%)

$98,320 + $1,236,300

$1,334,620

2018

$37,201 (−2.1%)

$114,360 + $1,285,240

$1,399,600

2017

$38,013 (+3.3%)

$114,360 + $1,285,240

$1,399,600

2016

$36,795 (+2.3%)

$114,360 + $1,285,240

$1,399,600

2014

$35,956

$114,360 + $1,285,240

$1,399,600

Tax history for 59 Hillside Rd

Year

Property tax

Land + Additions

Assessment*

2023

$38,784 (−0.4%)

$98,320 + $1,236,300

$1,334,620

2022

$38,931

$98,320 + $1,236,300

$1,334,620

2021

$38,931

$98,320 + $1,236,300

$1,334,620

2020

$38,931

$98,320 + $1,236,300

$1,334,620

2019

$38,931 (+4.7%)

$98,320 + $1,236,300

$1,334,620

2018

$37,201 (−2.1%)

$114,360 + $1,285,240

$1,399,600

2017

$38,013 (+3.3%)

$114,360 + $1,285,240

$1,399,600

2016

$36,795 (+2.3%)

$114,360 + $1,285,240

$1,399,600

2014

$35,956

$114,360 + $1,285,240

$1,399,600

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

152,024

Year renovated

—

Sq. Ft.

9,296

Year built

2006

Style

Single Family Residential

County

Litchfield County

APN

932938

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

Pool

Last updated by owner on May 23, 2025.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 17
Laundry Room Info: Main Level, Upper Level
In-Law Apartment: Yes
In-Law Access: Second Floor
Fireplaces Total: 5
Cooling System: Central Air
Appliances Included: Gas Cooktop, Wall Oven, Refrigerator, Freezer, Dishwasher

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 2

Bedroom Information
Beds Total: 6

Room Information
Basement Description: Full
Has Attic
Attic Description: Access Via Hatch

Exterior

Exterior Features
Roof Information: Fiberglass Shingle, Slate
Exterior Siding: Stone, Stucco

Lot Information
Lot Description: Secluded, Lightly Wooded, Borders Open Space, On Cul-De-Sac, Open Lot

Pool Information
Swimming Pool
Pool Description: Gunite, Infinity Edge, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 9296

Financial

Assessments Information
Assessed Value: $1,448,160

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Domestic
Heat Type: Radiant
Heat Fuel Type: Geothermal

Location

School Information
High School: Nonnewaug
Elementary School: Mitchell

Location Information
State: Connecticut
Directions: 59 Hillside Road Extension, Woodbury, CT 06798
County: Litchfield

Public facts

Beds: 6
Baths: 6.0
Sq. Ft.: 9,296
Stories: 2.0
Parking Spaces: 3
Basement: Yes
Accessible: No
Lot Size: 3.49 acres
Style: Single Family Residential
Year Built: 2006
Year Renovated: —
County: Litchfield County
APN: 932938
HOA Dues: —
Garage: Yes
Features: Pool

Home facts updated by owner on May 23, 2025

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

K - 12
Preschool & daycare

Mitchell Elementary School

Public PreK-5 • Assigned • 2.4mi

8/10

Woodbury Middle School

Public 6-8 • Assigned • 2.5mi

7/10

Nonnewaug High School

Public 9-12 • Assigned • 2.8mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

6 days above 97° expected this year, 13 days in 30 years

5/10 Wind Factor

26% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Woodbury, CT • 06798

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.27M – $1.54M

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New listings for sale in 06798

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Bright kitchen • Tiled backsplash • Remodeled half bath

OPEN NOV 21, 1PM TO 3PM

$359,900

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Oversized back deck • 0.44 acre lot • Garage

Home values near 59 Hillside Rd

Data from public records.

Address	Redfin Estimate
61 Hillside Rd, Woodbury, CT 3 Beds \| 4.5 Baths \| 3654 Sq. Ft.	$806,911
23 Hillside Rd, Woodbury, CT 4 Beds \| 2.5 Baths \| 2861 Sq. Ft.	$718,790
50 Hillside Rd, Woodbury, CT 4 Beds \| 4 Baths \| 2925 Sq. Ft.	$563,008
46 Hillside Rd, Woodbury, CT 4 Beds \| 3.5 Baths \| 3449 Sq. Ft.	$762,843
47 Hillside Rd, Woodbury, CT 4 Beds \| 2.5 Baths \| 2804 Sq. Ft.	$668,911
20 Hurds Hill Rd, Woodbury, CT 5 Beds \| 2.5 Baths \| 2816 Sq. Ft.	$628,064
14 Hurds Hill Rd, Woodbury, CT 4 Beds \| 4.5 Baths \| 2976 Sq. Ft.	$650,651

Address	Redfin Estimate
60 Hillside Rd, Woodbury, CT 4 Beds \| 2.5 Baths \| 2960 Sq. Ft.	$700,712
64 Hillside Rd, Woodbury, CT 4 Beds \| 6.5 Baths \| 6965 Sq. Ft.	$1,258,603
56 Hillside Rd, Woodbury, CT 5 Beds \| 3.5 Baths \| 4486 Sq. Ft.	$1,127,985
14 Hillside Rd, Woodbury, CT 4 Beds \| 3 Baths \| 1364 Sq. Ft.	$525,785
22 Hillside Rd, Woodbury, CT 4 Beds \| 2 Baths \| 1755 Sq. Ft.	$555,017
321 Old Sherman Hill Rd, Woodbury, CT 4 Beds \| 3 Baths \| 2758 Sq. Ft.	$594,270
294 Old Sherman Hill Rd, Woodbury, CT 3 Beds \| 3 Baths \| 2042 Sq. Ft.	$532,456

Address	Redfin Estimate
53 Hillside Rd, Woodbury, CT 4 Beds \| 2.5 Baths \| 2336 Sq. Ft.	$570,141
31 Hillside Rd, Woodbury, CT 5 Beds \| 3.5 Baths \| 3434 Sq. Ft.	$720,505
40 Hillside Rd, Woodbury, CT 4 Beds \| 4 Baths \| 3284 Sq. Ft.	$704,027
11 Hillside Rd, Woodbury, CT 3 Beds \| 4 Baths \| 2240 Sq. Ft.	$660,036
302 Old Sherman Hill Rd, Woodbury, CT 3 Beds \| 1 Baths \| 1498 Sq. Ft.	$432,130
21 Hurds Hill Rd, Woodbury, CT 3 Beds \| 2 Baths \| 1244 Sq. Ft.	$436,616
32 Hurds Hill Rd, Woodbury, CT 4 Beds \| 2.5 Baths \| 2560 Sq. Ft.	$613,481

Property information provided by Smart MLS when last listed in 2025. This data may not show owner updates. Learn more.

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