258 Hollow Tree Ridge Rd, Darien, CT 06820

Off market dec 2020 for $1.5M

$2,640,776

Est. refi paymentEst. refi $10,253/mo

•

2,930

sq ft

258 Hollow Tree Ridge Rd, Darien, CT 06820

About this home

The Zachariah Dibble House, c. 1735, sits behind a stone wall on 1.53 glorious acres with brick paths, exquisite boxwood hedges, mature specimen trees & terraced gardens. This Pre-Revolutionary War gem will transported you back in time. The home retained much of its original character throughout its many facelifts as it kept pace with the modern world. The hearth has remained the center of the home, complete with beehive and hanging tea kettles. Random width planked floors & whimsical custom features not found in today’s architecture add to the rustic charm. A breezeway leads to a 1BR guest cottage w/covered patio overlooking the stunning sprawling lawn & pool. Rich in history, this home has been a cherished gathering place for generations.

Single-familyProperty Type

1734Year Built

1.53 acresLot Size

$901Est. Price/Sq.Ft.

2 car garageParking

Listed by Eileen Hanford • Brown Harris Stevens

Bought with Sara Littlefield • Coldwell Banker Realty

Source:Smart MLS #170044242

Redfin Estimate

$2,640,776

$1.1M since sold in December 2020$49K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.6% higher than the average sale price ($2.52M) of 6 comparable homes.

SOLD SEP 2, 2026
$2,870,000
A
4 beds3.5 baths2,750 sq ft
12 Libby Ln, Darien, CT 06820
SOLD JUL 31, 2026
$2,365,000
B
4 beds2.5 baths3,264 sq ft
19 Chester Rd, Darien, CT 06820
SOLD AUG 26, 2026
$2,052,000
C
3 beds2.5 baths3,151 sq ft
12 Laurel Ln, Darien, CT 06820
SOLD SEP 23, 2026
$1,750,000
D
4 beds2.5 baths2,427 sq ft
2 Fairfield Ave, Darien, CT 06820
SOLD AUG 20, 2026
$2,760,000
E
4 beds2.5 baths3,293 sq ft
201 Middlesex Rd, Darien, CT 06820
SOLD AUG 19, 2026
$3,352,000
F
5 beds3.5 baths3,621 sq ft
29 Hillcrest Ave, Darien, CT 06820

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

Earn from this home

Sell

$1,423,111

Est. take-home

List your home with Redfin and save $26,408

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$6,023/mo

Redfin rental estimate

List your home for rent

Market trends in 06820, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

109.1%

1.1% MoM

Median sale price

$3.0M

$24K MoM

Avg. days on market

13d

0 days MoM

Recently sold homes

110

7 MoM

New listings for sale

NEW 6 HRS AGO
$1,850,000
4 beds3 baths3,414 sq ft
101 Hoyt St, Darien, CT 06820
OPEN TODAY, 1PM TO 3PM
$1,649,000
3 beds3 baths2,007 sq ft
27 Lakeside Ave, Darien, CT 06820
COMING SOON
$4,725,000
6 beds6 baths6,459 sq ft
12 Seagate Rd, Darien, CT 06820
OPEN TODAY, 1PM TO 3PM
$2,699,000
5 beds4.5 baths4,084 sq ft
53 Country Club Rd, Darien, CT 06820
$7,995,000
5 beds6.5 baths5,172 sq ft
3 Coves End Rd, Darien, CT 06820
$1,895,000
4 beds2.5 baths2,456 sq ft
9 Wilson Ridge Rd E, Darien, CT 06820
$3,795,000
4 beds4 baths4,361 sq ft
5 Cross Rd, Darien, CT 06820
OPEN SUN, 12PM TO 3PM
$1,795,000
4 beds2 baths2,091 sq ft
150 Holmes Ave, Darien, CT 06820
FOR SALE BY OWNER
$2,200,000
5 beds4 baths4,600 sq ft
13 Silver Lakes Dr, Darien, CT 06820
See all

Provided by Redfin

Sale history for 258 Hollow Tree Ridge Rd

Date

Event

Price

Smart MLS #170044242

Dec 18, 2020

Sold

$1,500,000

$512/sq ft

Nov 13, 2020

Contingent

—

Mar 11, 2020

Price Changed

$1,650,000

$563/sq ft

Jan 3, 2019

Price Changed

$1,695,000

$578/sq ft

Apr 23, 2018

Price Changed

$1,995,000

$681/sq ft

Jan 17, 2018

Listed

$2,125,000

$725/sq ft

GMLS #105167

Jan 4, 2019

Listed

$1,695,000

$578/sq ft

Smart MLS #99180634

Jan 16, 2018

Listing Removed

—

Apr 10, 2017

Listed

$2,195,000

$749/sq ft

Smart MLS #99116822

Dec 21, 2015

Listing Removed

—

Sep 13, 2015

Listed

$2,490,000

$850/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$17,026 (+2.2%)

$689,640 + $277,200

$966,840

2022

$16,659 (+2.3%)

$689,640 + $277,200

$966,840

2021

$16,282 (+3.1%)

$689,640 + $277,200

$966,840

2020

$15,788 (−0.9%)

$689,640 + $277,200

$966,840

2019

$15,924 (−0.2%)

$689,640 + $277,200

$966,840

2018

$15,955 (−0.2%)

$649,040 + $343,210

$992,250

2017

$15,979 (+2.5%)

$649,040 + $339,780

$988,820

2016

$15,594 (+5.1%)

$649,040 + $339,780

$988,820

2014

$14,842

$649,040 + $339,780

$988,820

Tax history for 258 Hollow Tree Ridge Rd

Year

Property tax

Land + Additions

Assessment*

2023

$17,026 (+2.2%)

$689,640 + $277,200

$966,840

2022

$16,659 (+2.3%)

$689,640 + $277,200

$966,840

2021

$16,282 (+3.1%)

$689,640 + $277,200

$966,840

2020

$15,788 (−0.9%)

$689,640 + $277,200

$966,840

2019

$15,924 (−0.2%)

$689,640 + $277,200

$966,840

2018

$15,955 (−0.2%)

$649,040 + $343,210

$992,250

2017

$15,979 (+2.5%)

$649,040 + $339,780

$988,820

2016

$15,594 (+5.1%)

$649,040 + $339,780

$988,820

2014

$14,842

$649,040 + $339,780

$988,820

*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

66,646

Year renovated

—

Sq. Ft.

2,930

Year built

1734

Style

Single Family Residential

County

Fairfield County

APN

103812

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

—

Garage

Yes

Features

Views, Green, Pool

Last updated by owner on Jan 12, 2021.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 2

Interior

Interior Information
Total Rooms: 10
Laundry Room Location: first floor
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Dishwasher, Dryer, Oven/Range, Refrigerator, Washer

Bathroom Information
# of Baths (Full): 3

Bedroom Information
Beds Total: 4

Room Information
Room Count: 9
Basement Description: Partial
Has Attic
Attic Description: Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Shingle
Exterior Features: Guest House

Lot Information
Lot Description: Level Lot

Pool Information
Swimming Pool
Pool Description: Heated, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Concrete
Color: Brown

Property Information
Waterfront Description: Water Community
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2972

Financial

Assessments Information
Assessed Value: $966,840

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Heat Type: Baseboard, Radiator
Heat Fuel Type: Oil

Location

School Information
Middle Jr High School: Middlesex
High School: Darien
Elementary School: Ox Ridge

Location Information
State: Connecticut
Directions: Middlesex to Hollow Tree Ridge Rd. House is on the east side of the street
County: Fairfield

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,930
Stories: 2.0
Parking Spaces: 2
Basement: Yes
Accessible: Yes
Lot Size: 1.53 acres
Style: Single Family Residential
Year Built: 1734
Year Renovated: —
County: Fairfield County
APN: 103812
HOA Dues: —
Garage: Yes
Features: Views, Green, Pool

Home facts updated by owner on Jan 12, 2021

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Ox Ridge Elementary School

Public PreK-5 • Assigned • 1.8mi

10/10

Middlesex Middle School

Public 6-8 • Assigned • 0.3mi

10/10

Darien High School

Public 9-12 • Assigned • 0.6mi

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

5/10 Heat Factor

7 days above 99° expected this year, 15 days in 30 years

6/10 Wind Factor

71% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Darien, CT • 06820

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 8.8 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.51M – $3.04M

Reach more buyers when you sell with Redfin. Save up to $26,408 in fees. 3 minutes to get started.

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

Nearby similar homes

OPEN SUN, 12PM TO 3PM

$1,795,000

4 beds2 baths2,091 sq ft

150 Holmes Ave, Darien, CT 06820

$3,850,000

4 beds3.5 baths6,021 sq ft

15 Wildcat Rd, Darien, CT 06820

$699,000

3 beds2 baths1,917 sq ft

80 Leonard St, Stamford, CT 06905

Mike Parelli Real Estate LLC

NEW CONSTRUCTION

$3,249,000

5 beds4.5 baths6,406 sq ft

20 Locust Hill Rd, Darien, CT 06820

$749,000

4 beds4.5 baths4,058 sq ft

638 Hope St #4, Stamford, CT 06907

$674,000

3 beds2 baths1,248 sq ft

218 Knickerbocker Ave, Stamford, CT 06907

New listings for sale in 06820

NEW 6 HRS AGO

$1,850,000

4 beds3 baths3,414 sq ft

101 Hoyt St, Darien, CT 06820

OPEN TODAY, 1PM TO 3PM

$1,649,000

3 beds3 baths2,007 sq ft

27 Lakeside Ave, Darien, CT 06820

COMING SOON

$4,725,000

6 beds6 baths6,459 sq ft

12 Seagate Rd, Darien, CT 06820

OPEN TODAY, 1PM TO 3PM

$2,699,000

5 beds4.5 baths4,084 sq ft

53 Country Club Rd, Darien, CT 06820

$7,995,000

5 beds6.5 baths5,172 sq ft

3 Coves End Rd, Darien, CT 06820

$1,895,000

4 beds2.5 baths2,456 sq ft

9 Wilson Ridge Rd E, Darien, CT 06820

$3,795,000

4 beds4 baths4,361 sq ft

5 Cross Rd, Darien, CT 06820

OPEN SUN, 12PM TO 3PM

$1,795,000

4 beds2 baths2,091 sq ft

150 Holmes Ave, Darien, CT 06820

FOR SALE BY OWNER

$2,200,000

5 beds4 baths4,600 sq ft

13 Silver Lakes Dr, Darien, CT 06820

Home values near 258 Hollow Tree Ridge Rd

Data from public records.

Address	Redfin Estimate
290 Hollow Tree Ridge Rd, Darien, CT 7 Beds \| 5 Baths \| 5866 Sq. Ft.	$4,333,447
266 Hollow Tree Ridge Rd, Darien, CT 3 Beds \| 2.5 Baths \| 2068 Sq. Ft.	$2,131,421

Address	Redfin Estimate
269 Hollow Tree Ridge Rd, Darien, CT 4 Beds \| 4.5 Baths \| 5385 Sq. Ft.	$3,882,570
280 Hollow Tree Ridge Rd, Darien, CT 5 Beds \| 5 Baths \| 5579 Sq. Ft.	$4,262,441

Address	Redfin Estimate
244 Hollow Tree Ridge Rd, Darien, CT 4 Beds \| 4.5 Baths \| 4279 Sq. Ft.	$3,407,702
275 Hollow Tree Ridge Rd, Darien, CT 5 Beds \| 4.5 Baths \| 5673 Sq. Ft.	$2,941,630

Property information provided by Smart MLS when last listed in 2018. This data may not show owner updates. Learn more.

More real estate resources

Zip Codes
Neighborhoods
Cities
Minor Civil Divisions
Popular Searches

06820 homes for sale
06854 homes for sale
06902 homes for sale
06905 homes for sale
06907 homes for sale

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.

West Norwalk homes for sale
Rowayton homes for sale
South Norwalk homes for sale
Glenbrook homes for sale
Long Island homes for sale

Wilton homes for sale
Weston homes for sale
Monroe homes for sale
Fairfield homes for sale
New Canaan homes for sale

Houses for rent in Darien	Agents near me	Westport, CT homes for sale	Darien 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	Darien Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

Greenwich homes for sale
Stamford homes for sale
Yonkers homes for sale