Off market jun 2015 for $990K

$1,699,356

Est. refi paymentEst. refi $8,135/mo

•

3,536

sq ft

66 Rucuum Road Ext, Woodbury, CT 06798

About this home

Country estate with the finest quality & craftsmanship throughout! A builders own home with many reproduction features including cedar shake roof, 12 over 12 sdl windows, wideboard flooring, copper gutters, center fp & beamed ceiling. A pristine home! Saltbox style with many special reproduction features; hand hewn beams, textured walls, paneling, wide board pine and oak flooring, wood doors with bead, brick fireplace with pizza oven, 12 over 12 marvin windows, granite and oak counters and master suite with private stone terrace. The lower level offers great space with brick fireplace, home office with full bath, walkout area with 8' slider and high ceilings.

Single-familyProperty Type

2005Year Built

25 acresLot Size

$481Est. Price/Sq.Ft.

4 car garageParking

Listed by Timothy Drakeley • Drakeley Real Estate, Inc.

Bought with Marguerite Starr • William Raveis Real Estate

Source:Smart MLS #W1077165

Redfin Estimate

$1,699,356

$709K since sold in June 2015$71K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 39.7% higher than the average sale price ($1.22M) of 5 comparable homes.

SOLD JUL 31, 2026
$1,275,000
A
4 beds3.5 baths3,480 sq ft
46 Grassy Hill Rd, Woodbury, CT 06798
SOLD JUL 30, 2026
$885,000
B
4 beds3.5 baths3,784 sq ft
557 Upper Grassy Hill Rd, Woodbury, CT 06798
SOLD FEB 9, 2026
$1,200,000
C
4 beds4.5 baths4,676 sq ft
101 Old Grassy Hill Rd, Woodbury, CT 06798
SOLD MAR 30, 2026
$959,000
D
4 beds4 baths3,686 sq ft
34 Bacon Rd, Roxbury, CT 06783
SOLD JUL 20, 2026
$1,764,000
E
4 beds4.5 baths3,566 sq ft
176 Apple Ln, Roxbury, CT 06783

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,004,728

Est. take-home

List your home with Redfin and save $16,994

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,411/mo

Redfin rental estimate

List your home for rent

Market trends in 06798, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.0%

+0.5% MoM

Median sale price

$500K

$216 MoM

Avg. days on market

60d

6 days MoM

Recently sold homes

16 MoM

New listings for sale

3D WALKTHROUGH
$290,000
2 beds1.5 baths1,430 sq ft
74 Washington Rd #40, Woodbury, CT 06798
$2,149,900
6 beds4.5 baths5,973 sq ft
348 Weekeepeemee Rd, Woodbury, CT 06798
OPEN SUN, 12PM TO 2PM
$849,900
4 beds2 baths2,662 sq ft
63 Main St N, Woodbury, CT 06798
$550,000
3 beds2.5 baths2,796 sq ft
164 Quanopaug Trl, Woodbury, CT 06798
OPEN SUN, 10AM TO 12PM
$875,000
3 beds2.5 baths2,480 sq ft
2 Pomperaug Rd, Woodbury, CT 06798
$990,000
6 beds3.5 baths3,842 sq ft
92 Quail Run Rd, Woodbury, CT 06798
$199,900
2 beds1 bath913 sq ft
229 Bacon Pond Rd #312, Woodbury, CT 06798
OPEN SUN, 12PM TO 2PM
$299,900
2 beds2 baths1,182 sq ft
47 Woods Way #47, Woodbury, CT 06798
$550,000
3 beds2 baths1,550 sq ft
578 Old Sherman Hill Rd, Woodbury, CT 06798
OPEN SUN, 10AM TO 12PM
$925,000
4 beds2.5 baths2,568 sq ft
69 Nonnewaug Rd, Woodbury, CT 06798
See all

Provided by Redfin

Sale history for 66 Rucuum Road Ext

Tax history for 66 Rucuum Road Ext

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

25 Acres

Year renovated

—

Sq. Ft.

3,788

Year built

2005

Style

Single Family Residential

County

Litchfield County

APN

2491082

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 20, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage
Garages Number: 4

Interior

Interior Information
Total Rooms: 11
Laundry Room Location: First Floor
Interior Features: Cable - Available, Open Floor Plan, Security System
In-Law Apartment: Possible
In-Law Access: Lower Level
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Dishwasher, Microwave, Oven/Range, Refrigerator

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Workshop
Room Count: 9
Basement Description: Full With Walk-Out, Partially Finished
Has Attic
Attic Description: Finished

Exterior

Exterior Features
Exterior Siding: Clapboard
Exterior Features: Fruit Trees, Patio, Stone Wall, Underground Utilities

Lot Information
Lot Description: Level Lot, Open Lot, Secluded, Sloping Lot, Treed, Professionally Landscaped

Property Information
Property Type: Single Family For Sale
Property Info: Horse Property
Driveway Type: Crushed Stone

Financial

Assessments Information
Assessed Value: $432,430

Rental Information
Lease Purchase YN: No

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Domestic
Heat Type: Hydro Air
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground
Energy Features: Thermopane Windows

Location

School Information
Intermediate School: Wms
High School: Nonnewaug
Elementary School: Mitchell

Location Information
State: Connecticut
Directions: 6 To 317 to grassy to laurel woods left onto rucuum continue straight onto rucuum rd ext (gravel road) right onto driveway
County: Litchfield

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 3,788
Stories: 3.0
Lot Size: 25 acres
Style: Single Family Residential
Year Built: 2005
Year Renovated: —
County: Litchfield County
APN: 2491082

Home facts updated by county records on Jun 20, 2023

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

Mitchell Elementary School

Public PreK-5 • Assigned • 2.2mi

5/10

Woodbury Middle School

Public 6-8 • Assigned • 2.0mi

6/10

Nonnewaug High School

Public 9-12 • Assigned • 3.2mi

9/10

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

7 days above 96° expected this year, 15 days in 30 years

5/10 Wind Factor

23% 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

$1.62M – $1.96M

Reach more buyers when you sell with Redfin. Save up to $16,994 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$599,900

4 beds2.5 baths2,972 sq ft

348 Hoop Pole Hill Rd, Woodbury, CT 06798

$3,950,000

4 beds6 baths6,139 sq ft

297 Painter Hill Rd, Roxbury, CT 06783

OPEN SAT, 11AM TO 1PM

$709,000

4 beds3.5 baths2,425 sq ft

4 Fleetwood Ln, Brookfield, CT 06804

$1,269,000

3 beds2.5 baths2,440 sq ft

85 Good Hill Rd, Roxbury, CT 06783

$525,000

2 beds2.5 baths1,388 sq ft

33 Old Field Hill Rd #18, Southbury, CT 06488

OPEN SUN, 11AM TO 1PM

$875,000

5 beds3.5 baths4,180 sq ft

132 Good Hill Rd, Woodbury, CT 06798

New listings for sale in 06798

3D WALKTHROUGH

$290,000

2 beds1.5 baths1,430 sq ft

74 Washington Rd #40, Woodbury, CT 06798

$2,149,900

6 beds4.5 baths5,973 sq ft

348 Weekeepeemee Rd, Woodbury, CT 06798

OPEN SUN, 12PM TO 2PM

$849,900

4 beds2 baths2,662 sq ft

63 Main St N, Woodbury, CT 06798

$550,000

3 beds2.5 baths2,796 sq ft

164 Quanopaug Trl, Woodbury, CT 06798

OPEN SUN, 10AM TO 12PM

$875,000

3 beds2.5 baths2,480 sq ft

2 Pomperaug Rd, Woodbury, CT 06798

$990,000

6 beds3.5 baths3,842 sq ft

92 Quail Run Rd, Woodbury, CT 06798

$199,900

2 beds1 bath913 sq ft

229 Bacon Pond Rd #312, Woodbury, CT 06798

OPEN SUN, 12PM TO 2PM

$299,900

2 beds2 baths1,182 sq ft

47 Woods Way #47, Woodbury, CT 06798

$550,000

3 beds2 baths1,550 sq ft

578 Old Sherman Hill Rd, Woodbury, CT 06798

Home values near 66 Rucuum Road Ext

Data from public records.

Address	Redfin Estimate
36 Rucuum Road Extension, Woodbury, CT 3 Beds \| 2.5 Baths \| 2040 Sq. Ft.	$585,143
46 Rucuum Road Extension, Woodbury, CT 4 Beds \| 2.5 Baths \| 3495 Sq. Ft.	$702,657

Address	Redfin Estimate
64 Rucuum Road Extension, Woodbury, CT 3 Beds \| 3.5 Baths \| 2760 Sq. Ft.	$822,479
24 Rucuum Road Extension, Woodbury, CT 4 Beds \| 2.5 Baths \| 2696 Sq. Ft.	$650,215

Address	Redfin Estimate
84 Rucuum Road Extension, Woodbury, CT 3 Beds \| 2.5 Baths \| 2156 Sq. Ft.	$615,668
56 Rucuum Road Extension, Woodbury, CT 4 Beds \| 2.5 Baths \| 3513 Sq. Ft.	$856,063

Property information provided by Smart MLS when last listed in 2014. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Litchfield County	Agents near me	Westport, CT homes for sale	Litchfield County Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Litchfield County Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

Naugatuck homes for sale
Bristol homes for sale
Waterbury homes for sale

Westchester County homes for sale
Dutchess County homes for sale
Suffolk County homes for sale