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)

$2,942,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $19,252/mo*
Refinance Your Home

$2,942,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $19,252/mo*
Refinance Your Home
5 Beds
3 Baths
3,028 sqft
(on 1.22 acres)

Home Value

Trulia Estimate
$2.94M
Since last month
Increased$92K (+3.2%)
Since last year
Increased$388K (+15.1%)
Since last sale
Increased$464K (+18.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +79% in the last 10 years
MonthEstimated value
2026
August 2026$2.96M
July 2026$2.87M
June 2026$2.78M
May 2026$2.69M
April 2026$2.64M
March 2026$2.65M
February 2026$2.65M
January 2026$2.6M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
29 Hillcrest Avenue, Darien, CT
0.33
Single-Family Home
$3,352,000
08/19/26
5
3.5
3,621
19 Chester Road, Darien, CT
0.46
Single-Family Home
$2,365,000
07/31/26
4
2.5
3,264
201 Middlesex Road, Darien, CT
0.45
Single-Family Home
$2,760,000
08/20/26
4
2.5
3,293
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
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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
3 Hickory Lane, Darien, CT 06820
0.13
$2,875,000
4
4
2,920
Recently Sold
1 Hickory Lane, Darien, CT 06820
0.16
$2,684,200
4
3.5
3,094
Off Market
39 Deepwood Road, Darien, CT 06820
0.19
$4,281,500
5
3.5
4,932
Off Market
76 Deepwood Road, Darien, CT 06820
0.20
$2,287,500
5
4
3,897
Recently Sold
300 Hollow Tree Ridge Road, Darien, CT 06820
0.21
$5,209,000
5
7
6,118
Off Market
4 Laurel Lane, Darien, CT 06820
0.26
$2,931,300
5
4
4,058
Off Market
261 Hollow Tree Ridge Road, Darien, CT 06820
0.26
$4,350,000
5
5.5
6,135
Recently Sold
15 Waterbury Lane, Darien, CT 06820
0.23
$4,400,000
5
5
6,052
Recently Sold
280 Hollow Tree Ridge Road, Darien, CT 06820
0.27
$4,324,100
5
5
5,579
Off Market
121 Middlesex Road, Darien, CT 06820
0.27
$2,354,600
4
2.5
3,074
Off Market
7 Lantern Lane, Darien, CT 06820
0.28
$2,510,200
4
3.5
3,742
Off Market

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

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Lot Size
1.22 acres
Living Area
3,028 sqft
Price/Sqft
$972
Parking
2 Car Garage
HOA
$33/Monthly

About this House

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 $2,942,300, with a rent estimate of $7,953/month.
Last check for updates: about 17 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

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)

Price and Tax history

DateEventPrice
Mar 1, 2025
Source: Halstead / Brown Harris Stevens #24064233
ListingRemoved
$9,000
Feb 3, 2025
Source: Zillow Rentals
ListingRemoved
$9,000
Feb 3, 2025
Source: Halstead / Brown Harris Stevens #24064233
Pending
$9,000
Jan 20, 2025
Source: Zillow Rentals
PriceChange
$9,000
Price decreased by 22%
Jan 9, 2025
Source: Zillow Rentals
Listed For Rent
$11,500

Market trends in Darien

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.98M
$246KMoM
Sale-to-List Price
108.9%
3.3%MoM
Price per sq ft
$800
$12MoM
Available listings
36
18MoM

Around this home

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

  • 82 % 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
    Flag
  • 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
    Flag
  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

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.

Frequently asked questions about 8 Windsor Road

  • What is 8 Windsor Road estimated to be worth?
    Trulia's estimated value for 8 Windsor Road in Darien, CT is $2,942,300.
  • What is the price history for 8 Windsor Road?
    8 Windsor Road in Darien, CT last sold for $2,500,000 in December 2024.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.98M. That is up $246K from the prior month.
  • Does 8 Windsor Road have air conditioning?
    Yes, 8 Windsor Road in Darien, CT has air conditioning.
  • Does 8 Windsor Road have laundry facilities?
    Yes, 8 Windsor Road in Darien, CT has in-unit laundry.

Explore by feature - Pet Friendly

6 pet-friendly rentals in Darien, CT

Explore by feature - Garage

12 rentals with a garage in Darien, CT

Explore by feature - Air Conditioning

15 rentals with air conditioning in Darien, CT

Explore by feature - Pool

7 rentals with a pool in Darien, CT

Explore by feature - Washer/dryer

17 rentals with a washer/dryer in Darien, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 8 Windsor Road

Skip to last item
Skip to first item

Homes for sale near 8 Windsor Road

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item