Off Market Nov 2014 for $2.7M

$5,593,944

Est. refi paymentEst. refi $7,893/mo

•

7,244

sq ft

385 Middlesex Rd, Darien, CT 06820

About this home

Light abounds in this beautiful Georgian colonial on 2 private acres. This lovely home was extensively renovated by Fox Hill Builders in 2005.Customs features include a spacious central living area with state of the art eat-in kitchen overlooking a large sun room which flows seamlessly onto expansive stone terrace and pool. The elegant master suite has fireplace,balcony,built-ins, walk-in closet and lovely master bath. The other bedrooms are oversized and ensuite. Entertaining comes easily in this great family home. A beautifully landscaped yard has mature plantings, landscape lighting, 3 car garage and gracious circular drive. Other amenities include radiant floors,wet bar,wine cellar and sound system. Spotless and move-in condition!

Single-familyProperty Type

1962Year Built

2 acresLot Size

$772Est. Price/Sq.Ft.

3 car garageParking

Listed by Vicki Gatling • William Pitt Sotheby's Int'l

Bought with Cathy Thomas • Halstead Real Estate

Source:Smart MLS #99057657

Redfin Estimate

$5,593,944

$2.9M since sold in November 2014$424K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.3% higher than the average sale price ($4.65M) of 5 comparable homes.

SOLD JUN 29, 2026
$4,597,500
A
5 beds6.5 baths6,308 sq ft
21 Fox Hill Ln, Darien, CT 06820
SOLD JUN 22, 2026
$4,750,000
B
6 beds5 baths6,810 sq ft
8 Haskell Ln, Darien, CT 06820
SOLD AUG 6, 2026
$3,795,000
C
5 beds6.5 baths6,424 sq ft
39 Leeuwarden Rd, Darien, CT 06820
SOLD AUG 17, 2026
$4,475,000
D
5 beds4.5 baths5,506 sq ft
174 Leroy Ave, Darien, CT 06820
SOLD JUL 24, 2026
$5,625,000
E
5 beds6 baths9,039 sq ft
316 Mansfield Ave, Darien, CT 06820

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Earn from this home

Sell

$3,677,767

Est. take-home

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Refinance

Est. cash available

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Rent

$7,362/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

COMING SOON
$1,050,000
4 beds1.5 baths1,883 sq ft
29 Lynn Ct, Darien, CT 06820
OPEN SAT, 1PM TO 2:30PM
$949,000
2 beds1 bath910 sq ft
64 Noroton Ave, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$2,250,000
4 beds3.5 baths3,511 sq ft
1644 Boston Post Rd, Darien, CT 06820
$1,999,000
4 beds2.5 baths3,065 sq ft
2 Stony Brook Rd S, Darien, CT 06820
OPEN SUN, 1PM TO 3PM
$1,495,000
4 beds2 baths3,182 sq ft
1646 Boston Post Rd, 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 385 Middlesex Rd

Date

Event

Price

GMLS #90272

Nov 5, 2014

Sold

$2,700,000

$373/sq ft

May 13, 2014

Listed

$3,100,000

$428/sq ft

+23

Light abounds in this beautiful Georgian colonial on 2 private acres in central Darien. This lovely home was extensively renovated by Fox Hill Builders in 2005. Custom features include a spacious central living area with state of the art eat-in kitchen overlooking a large sunroom which flows seamlessly onto expansive stone terrace and pool. The elegant master suite has fireplace, balcony, built-ins, walk-in closet and lovely master bath. The other 5 bedrooms are oversized and en suite. Entertaining comes easily in this great family home. A beautiful landscaped yard with mature plantings, landscape lighting, 3 car garage and gracious circular drive. Other amenities include radiant floors, wet bar, wine cellar and sound system. Spotless and move in condition!

Smart MLS #99057657

Nov 5, 2014

Sold

$2,700,000

$373/sq ft

Mar 24, 2014

Listed

$3,100,000

$428/sq ft

Public Records

Jun 28, 2004

Sold

$2,362,500

$326/sq ft

Smart MLS #98186093

Jan 29, 2004

Listed

$2,390,000

$330/sq ft

Public Records

Mar 4, 2002

Sold

$1,900,000

$262/sq ft

GMLS #49269

Jan 22, 2002

Listed

$1,995,000

$275/sq ft

Smart MLS #98119622

Jan 13, 2002

Listed

$1,995,000

$275/sq ft

Smart MLS #98104589

Oct 20, 2001

Listing Removed

—

Jun 26, 2001

Listed

$2,300,000

$318/sq ft

Public Records

Jun 1, 2000

Sold

$1,500,000

$207/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$45,141 (+2.2%)

$728,000 + $1,835,400

$2,563,400

2022

$44,167 (+2.3%)

$728,000 + $1,835,400

$2,563,400

2021

$43,168 (+4.2%)

$728,000 + $1,835,400

$2,563,400

2020

$41,424 (−0.8%)

$728,000 + $1,808,660

$2,536,660

2019

$41,779 (+1.3%)

$728,000 + $1,808,660

$2,536,660

2018

$41,240 (−0.5%)

$840,000 + $1,724,660

$2,564,660

2017

$41,445 (+2.5%)

$840,000 + $1,724,660

$2,564,660

2016

$40,445 (+6.4%)

$840,000 + $1,724,660

$2,564,660

2014

$37,999

$840,000 + $1,691,550

$2,531,550

Tax history for 385 Middlesex Rd

Year

Property tax

Land + Additions

Assessment*

2023

$45,141 (+2.2%)

$728,000 + $1,835,400

$2,563,400

2022

$44,167 (+2.3%)

$728,000 + $1,835,400

$2,563,400

2021

$43,168 (+4.2%)

$728,000 + $1,835,400

$2,563,400

2020

$41,424 (−0.8%)

$728,000 + $1,808,660

$2,536,660

2019

$41,779 (+1.3%)

$728,000 + $1,808,660

$2,536,660

2018

$41,240 (−0.5%)

$840,000 + $1,724,660

$2,564,660

2017

$41,445 (+2.5%)

$840,000 + $1,724,660

$2,564,660

2016

$40,445 (+6.4%)

$840,000 + $1,724,660

$2,564,660

2014

$37,999

$840,000 + $1,691,550

$2,531,550

*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

2 Acres

Year renovated

2005

Sq. Ft.

8,405

Year built

1962

Style

Single Family Residential

County

Fairfield County

APN

103896

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: 3

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 12
Laundry Room Location: Basement
Interior Features: Audio System, Security System
Fireplaces Total: 3
Cooling System: Ceiling Fans, Central Air, Zoned
Appliances Included: Dishwasher, Disposal, Dryer, Icemaker, Microwave, Oven/Range, Refrigerator, Washer

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 3

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Bonus Room, Foyer, Laundry Room
Room Count: 14
Basement Description: Partially Finished, Storage, Sump Pump
Has Attic
Attic Description: Pull-Down Stairs, Storage Space

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Brick, Clapboard
Exterior Features: Balcony, Cabana, French Doors, Gutters, Lighting, Patio, Shed, Underground Sprinkler, Terrace

Lot Information
Lot Description: Level Lot, Some Wetlands, Treed, Fence - Partial, Fence - Stone

Pool Information
Swimming Pool
Pool Description: Concrete, Heated, In Ground Pool, Pool House, Safety Fence

Building Information
Foundation Type: Concrete, Block
Construction Description: Frame, Brick
Color: Beige

Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 8417

Financial

Assessments Information
Assessed Value: $2,516,010

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Heat Type: Hot Air, Radiant, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Storm Windows, Thermopane Windows

Location

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

Location Information
State: Connecticut
Directions: If I-95 take Exit 10 Noroton Ave to Middlesex Rd If Merritt Pwy take Exit 37 Mansfield Ave (124 South)to Middlesex
County: Fairfield

Public facts

Beds: 6
Baths: 5.0
Sq. Ft.: 8,405
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1962
Year Renovated: 2005
County: Fairfield County
APN: 103896

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Ox Ridge Elementary School

Public PreK-5 • Assigned • 1.0mi

10/10

Middlesex Middle School

Public 6-8 • Assigned • 1.2mi

10/10

Darien High School

Public 9-12 • Assigned • 0.3mi

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

69% 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

$5.32M – $6.43M

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Nearby similar homes

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New listings for sale in 06820

COMING SOON

$1,050,000

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OPEN SAT, 1PM TO 2:30PM

$949,000

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64 Noroton Ave, Darien, CT 06820

OPEN SAT, 1PM TO 3PM

$2,250,000

4 beds3.5 baths3,511 sq ft

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$1,999,000

4 beds2.5 baths3,065 sq ft

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OPEN SUN, 1PM TO 3PM

$1,495,000

4 beds2 baths3,182 sq ft

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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

Home values near 385 Middlesex Rd

Data from public records.

Address	Redfin Estimate
383 Middlesex Rd, Darien, CT 4 Beds \| 4.5 Baths \| 4508 Sq. Ft.	$3,714,148
393 Middlesex Rd, Darien, CT 7 Beds \| 4.5 Baths \| 4193 Sq. Ft.	$4,557,060

Address	Redfin Estimate
388 Middlesex Rd, Darien, CT 5 Beds \| 4.5 Baths \| 7703 Sq. Ft.	$5,036,694
373 Middlesex Rd, Darien, CT 4 Beds \| 2.5 Baths \| 3660 Sq. Ft.	$2,405,012

Address	Redfin Estimate
397 Middlesex Rd, Darien, CT 3 Beds \| 3.5 Baths \| 3250 Sq. Ft.	—
438 Middlesex Rd, Darien, CT 5 Beds \| 3.5 Baths \| 3451 Sq. Ft.	$3,084,935

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

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