258 Hollow Tree Ridge Rd, Darien, CT 06820

Off Market Dec 2020 for $1.5M

$2,865,539

Est. refi paymentEst. refi $9,349/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

$978Est. 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

$2,865,539

$1.4M since sold in December 2020$107K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.8% higher than the average sale price ($2.33M) of 6 comparable homes.

SOLD JUL 31, 2026
$2,365,000
A
4 beds2.5 baths3,264 sq ft
19 Chester Rd, Darien, CT 06820
SOLD JUL 1, 2026
$2,875,000
B
4 beds4 baths2,920 sq ft
3 Hickory Ln, Darien, CT 06820
SOLD JUN 24, 2026
$2,976,000
C
4 beds4.5 baths2,928 sq ft
16 Libby Ln, Darien, CT 06820
SOLD MAY 19, 2026
$2,400,000
D
4 beds2.5 baths2,850 sq ft
86 Middlesex Rd, Darien, CT 06820
SOLD JUL 30, 2026
$1,565,000
E
4 beds2.5 baths2,460 sq ft
17 Briar Brae Rd, Darien, CT 06820
SOLD JUN 30, 2026
$1,825,000
F
4 beds2.5 baths2,067 sq ft
182 Hollow Tree Ridge Rd, Darien, CT 06820

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Earn from this home

Sell

$1,632,972

Est. take-home

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Refinance

Est. cash available

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Rent

$5,952/mo

Redfin rental estimate

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Market trends in 06820, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

112.0%

+1.8% MoM

Median sale price

$3.0M

$202K MoM

Avg. days on market

12d

1 days MoM

Recently sold homes

30 MoM

New listings for sale

OPEN SUN, 1PM TO 3PM
$1,495,000
4 beds2 baths3,182 sq ft
1646 Boston Post Rd, Darien, CT 06820
COMING SOON
$1,999,000
4 beds2.5 baths3,065 sq ft
2 Stony Brook Rd S, Darien, CT 06820
$1,750,000
4 beds2.5 baths2,427 sq ft
2 Fairfield Ave, Darien, CT 06820
COMING SOON
$7,500,000
5 beds7 baths10,213 sq ft
460 Middlesex Rd, Darien, CT 06820
$1,299,000
3 beds2 baths3,094 sq ft
53 Maple St, Darien, CT 06820
$3,950,000
5 beds5.5 baths5,500 sq ft
700 Hollow Tree Ridge Rd, 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

Oct 1, 2019

Delisted

—

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
Places
Transit

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

$2.72M – $3.30M

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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.	$3,849,289
266 Hollow Tree Ridge Rd, Darien, CT 3 Beds \| 2.5 Baths \| 2068 Sq. Ft.	$2,180,214

Address	Redfin Estimate
269 Hollow Tree Ridge Rd, Darien, CT 4 Beds \| 4.5 Baths \| 5385 Sq. Ft.	$4,386,598
280 Hollow Tree Ridge Rd, Darien, CT 5 Beds \| 5 Baths \| 5579 Sq. Ft.	$4,560,006

Address	Redfin Estimate
244 Hollow Tree Ridge Rd, Darien, CT 4 Beds \| 4.5 Baths \| 4279 Sq. Ft.	$3,536,589
275 Hollow Tree Ridge Rd, Darien, CT 5 Beds \| 4.5 Baths \| 5673 Sq. Ft.	—

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

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