42-44 Whipstick Rd, Ridgefield, CT 06877

Off Market Oct 2022 for $2.6M

$3,253,976

Est. refi paymentEst. refi $16,239/mo

•

6,575

sq ft

42-44 Whipstick Rd, Ridgefield, CT 06877

About this home

One of Ridgefield's most iconic Estate properties, beautifully sited on 6 bucolic acres! Walking distance to Main Street it allows for a wonderful in-town lifestyle while the quintessential CT architecture is beautifully renovated & reflects an elegant, yet casual vibe. Formal spaces blend seamlessly into the heart of the home creating an amazing indoor/outdoor entertaining experience. Fabulous, renovated Chef's EIK features quartz countertops, prof appliances, handmade white subway tile backsplash & modern cabinetry. A spacious Great Room has a wood burning fireplace & Butler’s Pantry w/wet bar & a Sunroom a beautiful brick patio. Fab Mudroom + Powder Rm complete the main floor. Upstairs, the Primary Suite has WIC, gas fireplace, sitting area & beautiful bath w/oversized shower, jacuzzi tub & 2 marble-topped vanities. 2 add'l large BRs have WIC & share a Jack & Jill bath, while the other 3BR & bonus office/7th BR share a full bath. The legal Cottage guest house features 3BR, 2 full baths, updated Kitchen, Dining Rm, Family Rm w/FP, Games Rm + laundry/mudroom. The gunite pool & spa are perfectly sited central to all buildings. Originally a working dairy farm, the century old barn is currently used as entertaining space & 2nd barn is flex space w/room for 6 cars, gym, climbing space etc. Add'l outbuildings incl potting shed, chicken coop, small lofted play/pool house. Possibilities are endless! SW commute approx 1hr to NYC. Once in a lifetime opportunity!

Single-familyProperty Type

1780Year Built

5.82 acresLot Size

$495Est. Price/Sq.Ft.

7 car garageParking

Listed by Karla Murtaugh • Compass Connecticut, LLC

Bought with Karla Murtaugh • Compass Connecticut, LLC

Source:Smart MLS #170506766

Redfin Estimate

$3,253,976

$621K since sold in October 2022$34K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.9% higher than the average sale price ($2.65M) of 6 comparable homes.

SOLD AUG 20, 2026
$2,050,000
A
5 beds3.5 baths6,087 sq ft
261 Wilton Rd W, Ridgefield, CT 06877
SOLD AUG 28, 2026
$3,050,000
B
5 beds5 baths6,962 sq ft
41 Peaceable St, Ridgefield, CT 06877
SOLD AUG 18, 2026
$1,400,000
C
4 beds3.5 baths5,426 sq ft
41 Nutmeg Rdg, Ridgefield, CT 06877
SOLD APR 20, 2026
$4,800,000
D
5 beds5 baths7,776 sq ft
54 Main St, Ridgefield, CT 06877
SOLD JUN 23, 2026
$1,800,000
E
4 beds3.5 baths3,547 sq ft
371 Wilton Rd W, Ridgefield, CT 06877
SOLD JUL 29, 2026
$2,790,000
F
5 beds5.5 baths5,258 sq ft
20 Lounsbury Rd, Ridgefield, CT 06877

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Earn from this home

Sell

$1,113,113

Est. take-home

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Refinance

Est. cash available

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Market trends in 06877, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

104.8%

+0.4% MoM

Median sale price

$1.2M

$109K MoM

Avg. days on market

29d

0 days MoM

Recently sold homes

109

16 MoM

New listings for sale

NEW 20 HRS AGO
$1,275,000
4 beds2.5 baths4,006 sq ft
152 George Washington Hwy, Ridgefield, CT 06877
COMING SOON
$750,000
3 beds2.5 baths2,184 sq ft
32 Lincoln Ln, Ridgefield, CT 06877
COMING SOON
$1,300,000
4 beds2.5 baths2,913 sq ft
96 Indian Cave Rd, Ridgefield, CT 06877
COMING SOON
$1,285,000
4 beds4.5 baths3,086 sq ft
314 Barrack Hill Rd, Ridgefield, CT 06877
COMING SOON
$859,000
3 beds2 baths2,014 sq ft
212 Old Sib Rd, Ridgefield, CT 06877
$1,575,000
4 beds3.5 baths2,774 sq ft
105 Sleepy Hollow Rd, Ridgefield, CT 06877
$2,700,000
6 beds6 baths6,671 sq ft
269 West Ln, Ridgefield, CT 06877
$1,399,000
4 beds3.5 baths3,072 sq ft
38 Hickory Ln, Ridgefield, CT 06877
$1,289,000
3 beds2.5 baths2,904 sq ft
104 Stonecrest Rd, Ridgefield, CT 06877
$975,000
4 beds2.5 baths2,458 sq ft
20 Pocconock Trl, Ridgefield, CT 06877
See all

Provided by Redfin

Sale history for 42-44 Whipstick Rd

Date

Event

Price

Smart MLS #170506766

Oct 31, 2022

Sold

$2,632,500

$400/sq ft

Sep 27, 2022

Pending

—

Sep 16, 2022

Contingent

—

Jul 8, 2022

Listed

$2,750,000

$418/sq ft

Smart MLS #170483870

Jul 7, 2022

Listing Removed

—

Apr 29, 2022

Listed

$2,850,000

$433/sq ft

Apr 26, 2022

Coming Soon

Smart MLS #99141428

Oct 19, 2016

Listing Removed

—

Apr 20, 2016

Listed

$2,195,000

$334/sq ft

Smart MLS #99090484

Apr 20, 2016

Listing Removed

—

Apr 30, 2015

Listed

$2,295,000

$349/sq ft

Smart MLS #98462728

Jun 24, 2010

Listing Removed

—

May 12, 2010

Listed

$2,499,000

$380/sq ft

Public Records

Jan 15, 2009

Sold

$2,080,875

$316/sq ft

Smart MLS #98397690

Oct 13, 2008

Listed

$2,499,000

$380/sq ft

Smart MLS #98373454

Oct 4, 2008

Listing Removed

—

Apr 7, 2008

Listed

$2,699,000

$410/sq ft

Smart MLS #98352473

Apr 4, 2008

Listing Removed

—

Oct 4, 2007

Listed

$2,699,000

$410/sq ft

Smart MLS #98332824

Nov 10, 2007

Listing Removed

—

May 14, 2007

Listed

$1,850,000

$281/sq ft

Smart MLS #98312219

Oct 1, 2007

Listing Removed

—

Dec 12, 2006

Listed

$2,890,000

$440/sq ft

Smart MLS #98318437

Aug 4, 2007

Listing Removed

—

Feb 5, 2007

Listed

$1,799,000

$274/sq ft

Smart MLS #98286604

Dec 2, 2006

Listing Removed

—

Jun 2, 2006

Listed

$2,999,999

$456/sq ft

Smart MLS #98273794

Jun 1, 2006

Listing Removed

—

Mar 9, 2006

Listed

$3,250,000

$494/sq ft

Smart MLS #93131533

Nov 10, 1993

Listed

$950,000

$144/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$29,660 (+0.8%)

$329,230 + $714,020

$1,043,250

2021

$29,430 (+0.3%)

$329,230 + $714,020

$1,043,250

2020

$29,336

$329,230 + $714,020

$1,043,250

2019

$29,336 (+1.2%)

$329,230 + $714,020

$1,043,250

2018

$28,981 (−4.7%)

$329,230 + $714,020

$1,043,250

2017

$30,395 (+1.9%)

$436,620 + $680,450

$1,117,070

2016

$29,815 (+2.6%)

$436,620 + $680,450

$1,117,070

2014

$29,055 (+2.5%)

$436,620 + $680,450

$1,117,070

2011

$28,351

$436,620 + $680,450

$1,117,070

Tax history for 42-44 Whipstick Rd

Year

Property tax

Land + Additions

Assessment*

2022

$29,660 (+0.8%)

$329,230 + $714,020

$1,043,250

2021

$29,430 (+0.3%)

$329,230 + $714,020

$1,043,250

2020

$29,336

$329,230 + $714,020

$1,043,250

2019

$29,336 (+1.2%)

$329,230 + $714,020

$1,043,250

2018

$28,981 (−4.7%)

$329,230 + $714,020

$1,043,250

2017

$30,395 (+1.9%)

$436,620 + $680,450

$1,117,070

2016

$29,815 (+2.6%)

$436,620 + $680,450

$1,117,070

2014

$29,055 (+2.5%)

$436,620 + $680,450

$1,117,070

2011

$28,351

$436,620 + $680,450

$1,117,070

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

Public record

Public record
Permits

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

5.82 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

280972

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Apr 21, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage, Paved
Garages Number: 7

Interior

Interior Information
Total Rooms: 11
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Security System
In-Law Apartment: Yes
In-Law Access: Detached
Fireplaces Total: 4
Cooling System: Central Air, Zoned
Appliances Included: Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Mud Room
Room Count: 12
Basement Description: Full, Unfinished
Has Attic
Attic Description: Walk-up, Partially Finished, Storage Space

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Shake, Clapboard, Cedar
Exterior Features: Barn, Deck, French Doors, Guest House, Patio, Porch, Shed, Underground Sprinkler

Lot Information
Lot Description: Dry, Cleared, Level Lot, Treed, Fence - Stone

Pool Information
Swimming Pool
Pool Description: Pool House, In Ground Pool, Spa, Heated, Gunite

Building Information
Foundation Type: Concrete, Stone
Construction Description: Frame
Color: White

Property Information
Property Type: Single Family For Sale
Driveway Type: Private, Asphalt

Financial

Assessments Information
Assessed Value: $1,043,250

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Domestic
Heat Type: Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Generator, Programmable Thermostat

Location

School Information
Middle Jr High School: East Ridge
High School: Ridgefield
Elementary School: Branchville

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Shopping/Mall
Directions: Main Street to Wilton Road East, Left on Whipstick Road to #42 (cottage) and #44 (main house)
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 5.82 acres
Style: Other
Year Built: —
Year Renovated: —
County: Fairfield County
APN: 280972

Home facts updated by county records on Apr 21, 2023

Other

Documents & Disclosures
Supplement Count Public: 7

Around this home

Schools

Branchville Elementary School

Public PreK-5 • Assigned • 2.2mi

8/10

East Ridge Middle School

Public 6-8 • Assigned • 0.7mi

9/10

Ridgefield High School

Public 9-12 • Assigned • 4.8mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Historical weather

Ridgefield, CT • 06877

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$3.09M – $3.74M

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Home values near 42-44 Whipstick Rd

Data from public records.

Address	Redfin Estimate
31 Whipstick Road, Ridgefield, CT 4 Beds \| 3 Baths \| 2800 Sq. Ft.	$1,273,516
63 Whipstick Road, Ridgefield, CT 4 Beds \| 2.5 Baths \| 2541 Sq. Ft.	$1,163,798

Address	Redfin Estimate
43 Whipstick Road, Ridgefield, CT 5 Beds \| 5 Baths \| 6099 Sq. Ft.	$2,144,432
81 Whipstick Road, Ridgefield, CT 4 Beds \| 2.5 Baths \| 1582 Sq. Ft.	$966,384

Address	Redfin Estimate
65 Whipstick Road, Ridgefield, CT 4 Beds \| 2.5 Baths \| 2563 Sq. Ft.	$1,293,782
66 Whipstick Road, Ridgefield, CT 5 Beds \| 3.5 Baths \| 4216 Sq. Ft.	$1,654,896

Property information provided by Smart MLS when last listed in 2022. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06877, CT

Sale history for 42-44 Whipstick Rd

Tax history for 42-44 Whipstick Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06877

Home values near 42-44 Whipstick Rd

More real estate resources