8 Windsor Road, Darien, CT 06820
OFF MARKET

8 Windsor Road
Darien, CT 06820

  • 5 Beds
  • 3 Baths
  • 3,028 sqft (on 1.22 acres)

$2,782,200

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $17,930/mo*
Refinance Your Home

$2,782,200

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $17,930/mo*
Refinance Your Home
5 Beds
3 Baths
3,028 sqft
(on 1.22 acres)

Local Information

  • Map ViewExplore the area around 8 Windsor Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Hidden away in a most convenient location, sits this beautiful home on a professionally landscaped 1.22 acres. Sun shines into this beautiful 1950's home throughout the day. As you enter the welcoming foyer, the formal LR and DR flow seamlessly into the eat-in kitchen, den with fireplace and 3 season sunroom, all which open to the expansive deck and private, peaceful back yard. 4 generously sized BRs, a second-floor family room and 3 full baths complete this wonderful home. The 1950's workmanship, encompassing fine period detail and moldings, makes this home especially unique and eye catching!
8 Windsor Road, Darien, CT 06820 is a 5 bedroom, 3 bathroom, 3,028 sqft single-family home built in 1956. It last sold for $2,500,000 on Dec 12, 2024 (4% below the $2,600,000 asking price). More recently, it was listed as a rental in January 2025 with an asking price of $11,500 per month. That rental listing was removed on February 3, 2025. It is currently off market. The Trulia Estimate is $2,782,200, with a rent estimate of $8,210/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
$33/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 8 Windsor Road

Interior Features

Interior Details
Basement: Full,Unfinished,Storage Space,Interior Entry,Walk-Out Access,ConcreteNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Sun Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 3028 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,OilHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Window: Storm Window(s)Door: Storm Door(s)

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Patio, Porch, DeckOther Structures: Shed(s)Exterior: Breezeway, Rain Gutters, Lighting, Garden, Stone WallFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
Waterfront: Water CommunityNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3028 Square Feet

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle Siding, ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105595

Price & Status

Price
List Price: $2,600,000
Status Change & Dates
Off Market Date: Mon Oct 21 2024Possession Timing: Negotiable

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesJr High / Middle School: MiddlesexHigh School: Darien

Building

Building Area
Building Area: 3028 Square Feet

Community

Community Features: Health Club, Library, Medical Facilities, Paddle Tennis, Park, Near Public Transport, Tennis Court(s)

HOA

HOA Fee Includes: Snow RemovalHas an HOAHOA Fee: $400/Annually

Lot Information

Lot Area: 1.22 Acres

Energy

Energy Efficiency Features: Thermostat, Doors, Windows

Miscellaneous

BasementMls Number: 24048348Attic: Storage, Floored, Walk-upAbove Grade Unfinished Area: 3028

Additional Information

Health ClubLibraryMedical FacilitiesPaddle TennisParkNear Public TransportTennis Court(s)
Last check for updates: about 4 hours ago
Listed by Debbie Lawrence, (203) 536-7408
Brown Harris Stevens, (203) 655-1418
Bought with: Serena A Richards, (203) 273-2073, Brown Harris Stevens, (203) 655-1418
Source: Smart MLS, MLS#24048348

Price History for 8 Windsor Road

DatePriceEventSource
03/01/2025$9,000ListingRemovedHalstead / Brown Harris Stevens #24064233
02/03/2025$9,000ListingRemovedZillow Rentals
02/03/2025$9,000PendingHalstead / Brown Harris Stevens #24064233
01/20/2025$9,000PriceChange
Zillow Rentals
01/09/2025$11,500Listed For RentZillow Rentals
01/02/2025$11,500ListingRemovedSmart MLS #24064233
12/19/2024$11,500Listed For RentSmart MLS #24064233
12/12/2024$2,500,000Sold
Smart MLS #24048348
10/20/2024$2,600,000PendingHalstead / Brown Harris Stevens #24048348
10/19/2024$2,600,000PendingToActiveSmart MLS #24048348
10/17/2024$2,600,000PendingSmart MLS #24048348
09/27/2024$2,600,000Listed For SaleSmart MLS #24048348
07/31/1995$700,000Sold
N/A

Market trends in Darien

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
1MoM
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Property Tax and Assessment

Year2025
Tax$20,779
Assessment$1,342,320
Home facts updated by county records

Comparable Sales for 8 Windsor Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
76 Deepwood Road, Darien, CT
0.20
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
3 Hickory Lane, Darien, CT
0.13
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
39 Deepwood Road, Darien, CT
0.19
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
16 Libby Lane, Darien, CT
0.52
Single-Family Home
$2,976,000
06/24/26
4
4.5
2,928
86 Middlesex Road, Darien, CT
0.38
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
326 Hollow Tree Ridge Road, Darien, CT
0.25
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
15 Waterbury Lane, Darien, CT
0.23
Single-Family Home
$4,400,000
04/28/26
5
5
6,052
26 Holly Lane, Darien, CT
0.58
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
3 Revere Road, Darien, CT
0.49
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
39 Briar Brae Road, Darien, CT
0.61
Single-Family Home
$2,358,000
08/01/25
4
3
3,242

Nearby homes

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Assigned Schools

These are the assigned schools for 8 Windsor Road.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Darien

At least 147 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say parking is easy

  • 87 % Say car is needed

  • 84 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 80 % Say kids play outside

  • 73 % Say there's wildlife

  • 71 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are community events

  • 58 % Say there are sidewalks

  • 55 % Say it's walkable to restaurants

  • 48 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Kimrichardnyc
    "Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
    0
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  • Trulia User
    "This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
    0
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
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  • Jessica_hatch7
    "NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
    3
    Flag
  • Peter S.
    "Holidays and school events. Dining and activities such as sports, the arts and many many social events"
    0
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  • Mzengo8
    "My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
    0
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  • Bill T.
    "Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
    3
    Flag
  • Tad
    "My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
    1
    Flag
  • Allison w.
    "They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
    0
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  • Chad W.
    "Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
    0
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  • Jessica_hatch7
    "The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
    2
    Flag
  • Victoria_belluscio
    "Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
    0
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  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
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  • Bill T.
    "Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
    1
    Flag
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
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Apartments for Rent

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Homes for sale near 8 Windsor Road

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Off Market Homes Near 8 Windsor Road

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.