Off market apr 2021 for $2.4M

$3,599,646

Est. refi paymentEst. refi $15,366/mo

•

4,407

sq ft

27 Deepwood Rd, Darien, CT 06820

About this home

Welcome to 27 Deepwood Road. This updated, elegant home in a sought-after neighborhood is just what you have been waiting for. Situated on 1.03 acres this 5 bedroom, 4 full bath home has it all. A newly updated eat-in kitchen with center island, top of the line appliances including beverage drawers and 2 sinks. Entertaining is easy with excellent flow from kitchen to dining room and opening to a covered deck with room for couches, fire table and built-in TV. The family room is warm and inviting with a wood burning fireplace and wet bar. There is bonus/playroom on the 2nd floor that has lots of space for lounging and play. The main bedroom has been updated and features a stunning bathroom, gas fireplace and huge walk-in closet. The bedrooms are all spacious and include updated closet systems. The 5th bedroom can be used for office/au pair/guest area with full updated bathroom.

Single-familyProperty Type

1976Year Built

1.03 acresLot Size

$817Est. Price/Sq.Ft.

2 car garageParking

Listed by Heather Hilleman • Houlihan Lawrence

Bought with Shelley Sheridan • Houlihan Lawrence

Source:Smart MLS #170369028

Redfin Estimate

$3,599,646

$1.2M since sold in April 2021$77K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 24.4% higher than the average sale price ($2.89M) 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 SEP 1, 2026
$2,451,776
B
5 beds4.5 baths4,197 sq ft
43 Phillips Ln, Darien, CT 06820
SOLD SEP 10, 2026
$3,050,000
C
5 beds3.5 baths3,829 sq ft
28 Royle Rd, Darien, CT 06820
SOLD AUG 19, 2026
$3,352,000
D
5 beds3.5 baths3,621 sq ft
29 Hillcrest Ave, Darien, CT 06820
SOLD JUL 1, 2026
$2,875,000
E
4 beds4 baths2,920 sq ft
3 Hickory Ln, Darien, CT 06820
SOLD AUG 20, 2026
$2,760,000
F
4 beds2.5 baths3,293 sq ft
201 Middlesex Rd, Darien, CT 06820

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Earn from this home

Sell

$1,674,942

Est. take-home

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Refinance

Est. cash available

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Rent

$7,348/mo

Redfin rental estimate

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Market trends in 06820, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

109.0%

1.3% MoM

Median sale price

$3.0M

$23K MoM

Avg. days on market

13d

0 days MoM

Recently sold homes

112

9 MoM

New listings for sale

COMING SOON
$2,699,000
5 beds4.5 baths4,084 sq ft
53 Country Club Rd, Darien, CT 06820
COMING SOON
$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, 1PM TO 4PM
$1,795,000
4 beds2 baths2,091 sq ft
150 Holmes Ave, Darien, CT 06820
$3,600,000
5 beds4.5 baths4,423 sq ft
18 Bates Farm Ln, Darien, CT 06820
$2,200,000
5 beds4 baths3,033 sq ft
13 Silver Lakes Dr, Darien, CT 06820
$16,495,000
10 beds10.5 baths11,944 sq ft
155 Long Neck Point Rd, Darien, CT 06820
See all

Provided by Redfin

Sale history for 27 Deepwood Rd

Date

Event

Price

Smart MLS #170369028

Apr 29, 2021

Sold

$2,400,000

$545/sq ft

Feb 5, 2021

Contingent

—

Jan 28, 2021

Listed

$2,325,000

$528/sq ft

Smart MLS #99069854

Oct 2, 2014

Sold

$1,890,000

$429/sq ft

Jun 27, 2014

Listed

$1,895,000

$430/sq ft

WONDERFUL LOCATION...SCENIC STREET...A HOME OF DISTINCTIVE CLASSIC STYLE & CONVENIENT TO EVERTYTHING! Centrally located on a quiet street, this 4479 Sq.Ft. 5 bedroom, beautiful colonial has much to offer. Enter the gracious foyer sighting a perfectly sized living room with FP...open to dining room w/views of a beautifully private & landscaped rear yard. A remodeled modern kitchen, opens out to a large deck to relax and enjoy the outdoors. The family room with fireplace has wet bar & built-ins for library reading. 1st floor bedroom & bath is perfect for guests. Upstairs a master suite w/high ceiling, fireplace, 'his & her' baths, dressing & walk-in, plus 3 add'l rooms & a large vaulted play/media room w/full bath offering room to spread out.

Year

Property tax

Land + Additions

Assessment*

2023

$23,321 (+2.2%)

$661,080 + $663,250

$1,324,330

2022

$22,818 (+3.8%)

$661,080 + $663,250

$1,324,330

2021

$21,991 (+4.2%)

$661,080 + $644,770

$1,305,850

2020

$21,099 (+9.5%)

$661,080 + $630,980

$1,292,060

2019

$19,271 (−1.0%)

$658,420 + $511,630

$1,170,050

2018

$19,470 (−0.5%)

$662,270 + $548,520

$1,210,790

2017

$19,566 (+5.5%)

$662,270 + $548,520

$1,210,790

2016

$18,542 (+5.1%)

$662,270 + $513,520

$1,175,790

2014

$17,649

$662,270 + $513,520

$1,175,790

Tax history for 27 Deepwood Rd

Year

Property tax

Land + Additions

Assessment*

2023

$23,321 (+2.2%)

$661,080 + $663,250

$1,324,330

2022

$22,818 (+3.8%)

$661,080 + $663,250

$1,324,330

2021

$21,991 (+4.2%)

$661,080 + $644,770

$1,305,850

2020

$21,099 (+9.5%)

$661,080 + $630,980

$1,292,060

2019

$19,271 (−1.0%)

$658,420 + $511,630

$1,170,050

2018

$19,470 (−0.5%)

$662,270 + $548,520

$1,210,790

2017

$19,566 (+5.5%)

$662,270 + $548,520

$1,210,790

2016

$18,542 (+5.1%)

$662,270 + $513,520

$1,175,790

2014

$17,649

$662,270 + $513,520

$1,175,790

*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

4.5

Stories

Lot width

—

Lot depth

—

Lot size

1.03 Acres

Year renovated

—

Sq. Ft.

4,146

Year built

1976

Style

Single Family Residential

County

Fairfield County

APN

105575

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

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

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 11
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Cable - Available, Security System
Thermostat(s)
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Gas Range, Oven/Range, Microwave, Range Hood, Subzero, Dishwasher, Disposal, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 4

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer
Room Count: 10
Basement Description: Full, Crawl Space
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard, Wood
Exterior Features: Covered Deck, Deck, French Doors, Gutters

Lot Information
Lot Description: Some Wetlands, Level Lot, Fence - Partial, Professionally Landscaped

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

Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 4146
Driveway Type: Private, Circular, Paved

Financial

Assessments Information
Assessed Value: $1,292,060

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Oil, Other
Heat Type: Baseboard
Heat Fuel Type: Oil
Fuel Tank Location: In Garage
Energy Features: Generator Ready, Programmable Thermostat, Thermopane Windows

Location

School Information
Middle Jr High School: Middlesex
High School: Darien
Elementary School: Holmes

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Paddle Tennis, Park, Playground/Tot Lot, Public Transportation, Tennis Courts
Directions: Hollow Tree Ridge Road to Deepwood
County: Fairfield

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 4,146
Stories: 2.0
Lot Size: 1.03 acres
Style: Single Family Residential
Year Built: 1976
Year Renovated: —
County: Fairfield County
APN: 105575

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

Holmes Elementary School

Public PreK-5 • Assigned • 0.7mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 0.4mi

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

74% 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

$3.42M – $4.14M

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Home values near 27 Deepwood Rd

Data from public records.

Address	Redfin Estimate
49 Deepwood Rd, Darien, CT 4 Beds \| 4 Baths \| 5506 Sq. Ft.	$4,016,738
35 Deepwood Rd, Darien, CT 4 Beds \| 4 Baths \| 3715 Sq. Ft.	$3,040,977

Address	Redfin Estimate
11 Deepwood Rd, Darien, CT 5 Beds \| 4 Baths \| 4297 Sq. Ft.	$3,429,596
57 Deepwood Rd, Darien, CT 6 Beds \| 6.5 Baths \| 6198 Sq. Ft.	$4,573,518

Address	Redfin Estimate
41 Deepwood Rd, Darien, CT 3 Beds \| 3.5 Baths \| 2736 Sq. Ft.	$2,636,813
39 Deepwood Rd, Darien, CT 5 Beds \| 3.5 Baths \| 4932 Sq. Ft.	$4,647,668

Property information provided by Smart MLS when last listed in 2021. This data may not match . Learn more.

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