Off market dec 2021 for $3.3M

$4,653,416

Est. refi paymentEst. refi $22,561/mo

•

6,392

sq ft

275 Middlesex Rd, Darien, CT 06820

About this home

Quality never goes out of style. Designed by highly regarded local architect Renato Gasparian, built with the utmost quality and craftsmanship. Middlesex is a sophisticated, beautifully curated home that’s also extremely comfortable and inviting. Cedar shingles, 5” hardwood floors, hand-crafted millwork, premium stone and tiles, custom cabinetry, and top-of-the-line appliances are just a few of the classic finishes. Meticulous attention was paid to each layer of this home - from the custom-tailored built-ins to the designer lighting, integrated smart home tech and security systems, landscape design, bespoke window treatments, and the perfect home office. Every detail enhances the convenience, sophistication, and warmth of the original design. Each room is perfectly appointed to support the ever-changing landscape of today’s home/work life. Add to that an unmatched dedication to home care, and the result is a pristine, timeless space. Located in the heart of Darien, beyond the gated drive every amenity is mere minutes away. Over 6,100 sq feet in total, including a 1,100 sqft pro Gym on the lower level. Plenty of room for a pool. 20K generator, 6-Zone HVAC & tankless hot water. A gorgeous, flat acre lot with elegant, mature landscaping fully fenced including the gated driveway. 3-car garage. Space for an in-law/au pair. To say this home is “better than new” would truly be an understatement. Full specs, video tour, floor plans @ 275middlesex.com

Single-familyProperty Type

2013Year Built

1 acresLot Size

$728Est. Price/Sq.Ft.

3 car garageParking

Listed by Carrie Perkins • RE/MAX Heritage

Listed by Virginia Klein • RE/MAX Heritage

Bought with Stephanie O'Grady • Houlihan Lawrence

Source:Smart MLS #170428748

Redfin Estimate

$4,653,416

$1.3M since sold in December 2021$106K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17.2% higher than the average sale price ($3.97M) of 6 comparable homes.

SOLD JUN 17, 2026
$3,775,000
A
5 beds6.5 baths7,200 sq ft
43 Stony Brook Rd, Darien, CT 06820
SOLD AUG 7, 2026
$3,250,000
B
5 beds5.5 baths5,226 sq ft
14 Revere Rd, 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 JUN 29, 2026
$4,597,500
D
5 beds6.5 baths6,308 sq ft
21 Fox Hill Ln, Darien, CT 06820
SOLD JUL 29, 2026
$4,000,000
E
5 beds4.5 baths5,166 sq ft
16 Overbrook Ln, Darien, CT 06820
SOLD APR 28, 2026
$4,400,000
F
5 beds5 baths6,052 sq ft
15 Waterbury Ln, Darien, CT 06820

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Earn from this home

Sell

$1,974,225

Est. take-home

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Refinance

Est. cash available

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Rent

$7,474/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

106.9%

2.0% MoM

Median sale price

$2.9M

$131K MoM

Avg. days on market

17d

4 days MoM

Recently sold homes

21 MoM

New listings for sale

NEW 10 HRS AGO
$5,025,000
6 beds3 baths4,477 sq ft
6 Berry Ln, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$4,725,000
6 beds6 baths6,459 sq ft
12 Seagate Rd, Darien, CT 06820
COMING SOON
$4,995,000
6 beds5 baths6,040 sq ft
8 Bouton Ln, Darien, CT 06820
$1,850,000
4 beds3 baths3,414 sq ft
101 Hoyt St, Darien, CT 06820
$1,649,000
3 beds3 baths2,007 sq ft
27 Lakeside Ave, Darien, CT 06820
$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
$1,795,000
4 beds2 baths2,091 sq ft
150 Holmes Ave, Darien, CT 06820
See all

Provided by Redfin

Sale history for 275 Middlesex Rd

Date

Event

Price

Public Records

Dec 6, 2021

Sold

$3,325,000

$520/sq ft

Smart MLS #170428748

Dec 2, 2021

Listing Removed

—

Dec 2, 2021

Sold

$3,325,000

$520/sq ft

Sep 25, 2021

Listed

$3,475,000

$544/sq ft

Sep 20, 2021

Coming Soon

$3,475,000

$544/sq ft

Smart MLS #99046244

Mar 14, 2014

Sold

$2,695,000

$422/sq ft

Nov 8, 2013

Listed

$2,695,000

$422/sq ft

Outstanding new construction on a private one-acre lot near town. Meticulously built colonial by renowned local builder features five bedrooms, seven baths, a three-car garage, a beautiful two-story main foyer, and a dramatic two-story side entrance. Spacious open floor plan w/ an expansive family room showcasing a masonry fireplace and crafted beams. Paneled computer/reading nook connects family room and living room. Easy flow for entertaining with custom gourmet kitchen and a large center island adjacent to wet bar and walk-in pantry. French doors open to an expansive flagstone patio with extensive private backyard views. Walk in closets in all bedrooms and vaulted Master bedroom suite. Extensive trim work and exquisite detail throughout.

Smart MLS #99023863

Aug 15, 2013

Listing Removed

—

Apr 18, 2013

Listed

$2,595,000

$406/sq ft

Smart MLS #98544119

Jan 16, 2013

Sold

$890,000

$139/sq ft

Jun 25, 2012

Listed

$899,000

$141/sq ft

Public Records

Jul 30, 2003

Sold

$770,000

$120/sq ft

Smart MLS #98156209

Mar 12, 2003

Listed

$789,000

$123/sq ft

Public Records

Sep 21, 1992

Sold

$250,000

$39/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$30,907 (+2.2%)

$507,500 + $1,247,610

$1,755,110

2022

$30,241 (+2.9%)

$507,500 + $1,247,610

$1,755,110

2021

$29,382 (+3.1%)

$507,500 + $1,237,250

$1,744,750

2020

$28,492 (−0.8%)

$507,500 + $1,237,250

$1,744,750

2019

$28,736 (−2.6%)

$507,500 + $1,237,250

$1,744,750

2018

$29,514 (−0.5%)

$560,000 + $1,275,470

$1,835,470

2017

$29,661 (+2.5%)

$560,000 + $1,275,470

$1,835,470

2016

$28,945 (+7.5%)

$560,000 + $1,275,470

$1,835,470

2014

$26,919

$560,000 + $1,233,400

$1,793,400

Tax history for 275 Middlesex Rd

Year

Property tax

Land + Additions

Assessment*

2023

$30,907 (+2.2%)

$507,500 + $1,247,610

$1,755,110

2022

$30,241 (+2.9%)

$507,500 + $1,247,610

$1,755,110

2021

$29,382 (+3.1%)

$507,500 + $1,237,250

$1,744,750

2020

$28,492 (−0.8%)

$507,500 + $1,237,250

$1,744,750

2019

$28,736 (−2.6%)

$507,500 + $1,237,250

$1,744,750

2018

$29,514 (−0.5%)

$560,000 + $1,275,470

$1,835,470

2017

$29,661 (+2.5%)

$560,000 + $1,275,470

$1,835,470

2016

$28,945 (+7.5%)

$560,000 + $1,275,470

$1,835,470

2014

$26,919

$560,000 + $1,233,400

$1,793,400

*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

1 Acre

Year renovated

—

Sq. Ft.

5,326

Year built

2013

Style

Single Family Residential

County

Fairfield County

APN

103876

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, Paved, Security
Garages Number: 3

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 12
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Humidifier, Open Floor Plan, Security System
Security System
Fireplaces Total: 1
Cooling System: Central Air, Zoned
Appliances Included: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 2

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer, Laundry Room
Room Count: 15
Basement Description: Full, Partially Finished, Heated, Cooled, Interior Access, Sump Pump
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Fiberglass Shingle
Exterior Siding: Shake, Cedar
Exterior Features: French Doors, Gutters, Lighting, Patio, Porch

Lot Information
Lot Description: Some Wetlands, Level Lot, Treed

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

Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 5326
Driveway Type: Private, Paved

Financial

Assessments Information
Assessed Value: $1,744,750

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Tankless Hotwater
Heat Type: Hot Air, Hydro Air, Zoned
Heat Fuel Type: Propane
Fuel Tank Location: In Ground
Energy Features: Extra Insulation, Generator, Humidistat, Thermopane Windows

Location

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

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Paddle Tennis, Park, Private Rec Facilities, Public Rec Facilities, Shopping/Mall, Stables/Riding, Tennis Courts
Directions: Leroy Avenue to Middlesex. Across from Community Center.
County: Fairfield

Public facts

Beds: 5
Baths: 6.0
Sq. Ft.: 5,326
Stories: 2.0
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 2013
Year Renovated: —
County: Fairfield County
APN: 103876

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 5

Around this home

Schools

Ox Ridge Elementary School

Public PreK-5 • Assigned • 1.6mi

10/10

Middlesex Middle School

Public 6-8 • Assigned • 0.6mi

10/10

Darien High School

Public 9-12 • Assigned • 0.4mi

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, 16 days in 30 years

6/10 Wind Factor

73% 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

$4.42M – $5.35M

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Home values near 275 Middlesex Rd

Data from public records.

Address	Redfin Estimate
265 Middlesex Road, Darien, CT 3 Beds \| 2.5 Baths \| 2002 Sq. Ft.	$1,789,632
259 Middlesex Road, Darien, CT 6 Beds \| 8 Baths \| 8552 Sq. Ft.	$7,986,315

Address	Redfin Estimate
253 Middlesex Road, Darien, CT 5 Beds \| 5.5 Baths \| 9033 Sq. Ft.	$5,269,999
305 Middlesex Road, Darien, CT 4 Beds \| 3.5 Baths \| 4697 Sq. Ft.	$3,285,427

Address	Redfin Estimate
245 Middlesex Road, Darien, CT 5 Beds \| 5 Baths \| 6647 Sq. Ft.	$4,728,787
288 Middlesex Road, Darien, CT 4 Beds \| 3.5 Baths \| 4960 Sq. Ft.	$4,919,372

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

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