185 Windsor Road, Fairfield, CT 06824
SOLD
JUN 18, 2026

$1,216,800

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,959 sqft

185 Windsor Road, Fairfield, CT 06824

Est. Refi. Payment $8,103/mo*
Refinance Your Home
Currently Off Market - Sold Jun 18, 2026 for $1,200,000 (5% below list price)

Home Value

Trulia Estimate
$1.22M
Since last month
Increased$10K (+0.9%)
Since last year
Increased$216K (+21.6%)
Since last sale
Increased$18K (+1.5%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$1.22M
August 2026$1.22M
July 2026$1.21M
June 2026$1.2M
May 2026$1.25M
April 2026$1.25M
March 2026$1.09M
February 2026$997K
January 2026$988K
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
692 Stillson Road, Fairfield, CT
0.27
Single-Family Home
$1,599,000
07/13/26
4
2.5
2,962
115 Mayfair Road, Fairfield, CT
0.17
Single-Family Home
$1,160,000
04/02/26
4
3
2,012
11 Tuckahoe Lane, Fairfield, CT
0.23
Single-Family Home
$1,590,000
04/08/26
4
3.5
3,636
73 Oxbow Road, Fairfield, CT
0.27
Single-Family Home
$970,000
08/07/26
4
3
2,343
10 Pansy Road, Fairfield, CT
0.25
Single-Family Home
$1,640,000
04/24/26
4
3
3,778
2032 North Benson Road, Fairfield, CT
0.14
Single-Family Home
$1,156,000
07/01/26
4
2
1,725
12 Sugar Plum Lane, Fairfield, CT
0.40
Single-Family Home
$1,275,000
03/09/26
4
4
2,670
196 Robin Lane, Fairfield, CT
0.24
Single-Family Home
$1,850,000
03/31/26
4
3.5
4,124

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
207 Windsor Road, Fairfield, CT 06824
0.01
$1,511,100
4
3
3,510
Off Market
14 Windsor Place, Fairfield, CT 06824
0.05
$861,100
3
2
1,655
Off Market
170 Windsor Road, Fairfield, CT 06824
0.04
$1,981,600
5
4.5
4,975
Off Market
14 Greenbriar Circle, Fairfield, CT 06824
0.06
$800,400
3
2
1,874
Off Market
217 Greenbriar Road, Fairfield, CT 06824
0.06
$1,128,400
4
2.5
2,800
Off Market
78 Greenbrier Road, Fairfield, CT 06824
0.06
$546,500
3
1
1,000
Off Market
75 Centerbrook Road, Fairfield, CT 06824
0.06
$760,000
3
1.5
1,249
Recently Sold
70 Allen Road, Fairfield, CT 06824
0.07
$985,000
3
1.5
1,430
Recently Sold
23 Greenbriar Circle, Fairfield, CT 06824
0.09
$781,900
3
1.5
1,459
Off Market
280 Tuckahoe Lane, Fairfield, CT 06824
0.10
$2,199,999
6
6
4,709
For Sale
401 Reid Street, Fairfield, CT 06430
0.14
$916,900
3
2.5
2,063
Off Market

Local Information

  • Map ViewExplore the area around 185 Windsor Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1959
2,959 sqft
$406/sqft

About this House

Tucked away on a quiet cul-de-sac in the desirable University area of Fairfield, this move-in-ready Colonial combines thoughtful updates, flexible living space, and an impressive, detached studio. Offering nearly 3,000 square feet of finished living space across three levels, this 4-bedroom, 3.5-bath home features a remodeled eat-in kitchen with new appliances, quartz countertops, farmhouse sink, and wood-burning fireplace with custom mantle. Sliding French doors open to a large deck overlooking the private, fenced yard. The light-filled family room showcases vaulted ceilings and floor-to-ceiling built-ins, while the spacious dining room opens to both the kitchen and family room - perfect for hosting gatherings. A custom mudroom with built-ins provides excellent storage. The flexible layout includes an en-suite bedroom on the main level ideal for guests or in-laws, plus an additional bedroom and updated full bath. Upstairs, the primary suite features a wall of built-ins and a beautifully updated bath, as well as a 4th bedroom and laundry room. The lower level offers additional living space for a recreation room and gym plus a half bath, ample storage, and direct backyard access. A standout feature is the detached studio, currently used as a home office, with vaulted ceilings, natural wood interior, double French doors, and its own heating and cooling system. Ideally located just minutes from downtown, Metro-North train, beaches and parks, this is Fairfield living at its best! *New driveway just installed!
185 Windsor Road, Fairfield, CT 06824 is a 4 bedroom, 4 bathroom, 2,959 sqft single-family home built in 1959. It last sold for $1,200,000 on Jun 18, 2026 (5% below the $1,269,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,216,800, with a rent estimate of $7,470/month.
Last check for updates: about 6 hours ago
Listed by Carrie Sakey, (203) 521-1119
Coldwell Banker Realty, (203) 254-7100
Bought with: Allison Rogers, (203) 715-0028, William Raveis Real Estate, (203) 869-9263
Source: Smart MLS, MLS#24162856

Home Details for 185 Windsor Road

Interior Features

Interior Details
Basement: Full,Heated,Storage Space,Interior Entry,Partially FinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Dining Room, Family Room, Kitchen, Other, Rec Play Room, Studio Apt
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2959 Square Feet
Appliances & Utilities
Appliances: Electric Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Gas Water Heater, Water HeaterDishwasherDryerLaundry: Upper Level,Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Zoned,Natural GasHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckFencing: Wood, FullOther Structures: Shed(s)Exterior: Rain Gutters, Garden, LightingFoundation: MasonryGardenNo Private Pool
Parking & Garage
No Garage
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2151 Square FeetFinished Area (below surface): 808 Square Feet

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 125965

Price & Status

Price
List Price: $1,269,000Price Per Sqft: $406/sqft
Status Change & Dates
Off Market Date: Fri May 08 2026Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: FairfieldCommunity: University
School Information
Elementary School: Osborn HillJr High / Middle School: Fairfield WoodsHigh School: Fairfield Ludlowe

Building

Building Area
Building Area: 2959 Square Feet

HOA

No HOA

Lot Information

Lot Area: 10018.8 sqft

Miscellaneous

BasementMls Number: 24162856Attic: Pull Down StairsAttribution Contact: (203) 521-1119Above Grade Unfinished Area: 2151Activation Date: Thu Apr 02 2026

Price and Tax history

DateEventPrice
Jun 18, 2026
Source: Smart MLS #24162856
Sold
$1,200,000
May 9, 2026
Source: Smart MLS #24162856
Pending
$1,269,000
Apr 15, 2026
Source: Smart MLS #24162856
PriceChange
$1,269,000
Price decreased by 2%
Apr 2, 2026
Source: Smart MLS #24162856
Listed For Sale
$1,295,000
Apr 5, 2021
Source: N/A
Sold
$721,550

Market trends in Fairfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$957K
$29.79KMoM
Sale-to-List Price
103.7%
0.4%MoM
Price per sq ft
$477
$5MoM
Available listings
162
16MoM

Around this home

What Locals Say about Fairfield

At least 343 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 87 % Say car is needed

  • 85 % Say parking is easy

  • 82 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 66 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say there's wildlife

  • 61 % Say neighbors are friendly

  • 61 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 57 % Say it's walkable to restaurants

  • 50 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • teddyabby
    "It’s safe and pretty and everyone looks out for one another. There is a bunch of cute parks and a nice walkable downtown."
    0
    Flag
  • Bnsdkbr225
    "Friendly and beautiful. Close to Lake Mohegan and parks. Lake rights to Lake Hill’s association . "
    0
    Flag
  • Kevin.cohen318
    "Great place to raise a family, incredibly safe and has all the amenities you could want on a year round basis."
    0
    Flag
  • Alexande.pappas
    "Yes walking miking kids walking to school we have public beaches lake’s plenty of restaurants churches"
    0
    Flag
  • Samuel Rivera
    "Great town for families with kids. Fairfield offers great schools, good supermarkets, tons of restaurants and entertainment "
    0
    Flag
  • Timothy Moss
    "Very family friendly. Great place to live for people of any age. I’ve lived here for 10 years now….."
    0
    Flag
  • Kevin.cohen318
    "5 minutes to either I-95, the Merritt Parkway or metro north, train to NYC is just over an hour each way. Great town that’s close to everything but not too close to anything."
    1
    Flag
  • Trulia User
    "My neighbor is safe and friendly and very clean as well. I've lived in this neighborhood over 18 years and absolutely love it. Thank you "
    3
    Flag
  • Trulia User
    "A very well maintained area . Homes streets ,business ,beaches schools ,library’s ( 3 ) . So much to offer !"
    0
    Flag
  • Sauerh
    "My neighborhood is family-oriented with distinct yet harmonious homes with well- kept yards. We are a short trip from Bridgeport, Norwalk, and Stamford with excellent connections via Metro North and I-95."
    5
    Flag
  • Isabellecj
    "Great neighborhood , good schools, close to town and railway station and beach . Very safe and quiet , properties well maintained and kids friendly . Love my neighborhood!"
    3
    Flag
  • Collin M.
    "Tons of events. Parties. Free concerts etc. there is so much fun things to do and see here. Beaches are amazing!"
    0
    Flag
  • Ab h
    "Walk to absolutely everything from hop on the train to yankee stadium or going to your dentist. Beautiful beaches and parks at your fingertips and children’s activities galore."
    0
    Flag
  • Juan G.
    "Quiet, clean and a good place to raise your kids. The school system it’s awesome and you know your kids are in good hands. "
    1
    Flag
  • Imeiers
    "We have neighbourhood block parties, the best trick or treating in town and a wonderful community spirit. Easily one of the best neighbourhoods in Fairfield. "
    5
    Flag
  • Troy P.
    "I work in Fairfield and it’s a wonderful town. The drive from New Haven is pretty easy with 2 route options either 95 or the merit parkway. "
    0
    Flag
  • Juan G.
    "Best in Connecticut, I have lived here for 6 years and my kids love it. If you want a place to raise your kids this it is the place "
    0
    Flag
  • Sar K.
    "Block parties, neighborhood watch, strong neighbor community, varying ages, active community, holiday celebrations: memorial parade, pancake breakfast, Christmas tree lighting, movies at the beach, music on the green, amazing local restaurants, 4th of July fireworks and much more"
    3
    Flag
  • DE
    "Very safe and relatively diverse. Great schools and decent restaurants. The beach is close by and some good golf courses."
    1
    Flag
  • Raquel.noi
    "Would love it, plenty of space for the dogs to run. Walking trails, beautiful neighborhoods to got for a walk. You will love it here!!"
    0
    Flag
  • Raquel
    "Great place, great community environment! It is such nice to go for walks and feel safe. We love that we found our home here!"
    0
    Flag
  • Raquel
    "Great family environment, lots of parks. Neighbors are friendly and welcoming. A lot of activities for kids. "
    0
    Flag
  • Lisalberts
    "It’s friendly and easy to walk or ride bikes around. The schools are wonderful. A real community feel."
    0
    Flag
  • Alek M.
    "Great town to raise a family, good schools and safe neighborhoods for your kids. Friendly people and clean area all around."
    1
    Flag
  • Fortress.management
    "Excellent schools, great town amenities makes it a great area to raise a family. Commuting to NYC is a little over an hour. Vibrant restaurant scene."
    0
    Flag
  • John S. W. J.
    "A great family oriented town. We love the parks the beaches and the community atmosphere. We couldn’t imagine living anywhere else"
    0
    Flag
  • Blythe A. B.
    "Driving to the train station is easy but parking passes are hard to come by unless you find street parking. waiting list is 18 months. "
    0
    Flag
  • Blythe A. B.
    "Everyone walks their dogs. sidewalks are well maintained. there are plenty of parks as well, both dog parks and free space parks. it is well kept by all dog owners, and it’s expected that you pick up after them!"
    0
    Flag
  • Bellaamore99
    "Close to parks, Wholefoods , Homedepo, shopping and metronorth train. Great neighbores . And feel very safe. "
    5
    Flag
  • Mjcejbart
    "Dog walking Mecca at lake Mohegan. All dogs welcome. Very dog friendly. Nice lake and trails to enjoy with or without a dog. "
    0
    Flag
  • Cheetah4455
    "Christmas walk around in Toilsome Hill. Meet the neighbors and everyone brings a different plate of food"
    1
    Flag
  • al .P
    "Lots of dogs on leaches . Not having your dog on a leach is not a good idea . You know your dog but the other does not know your dog "
    1
    Flag
  • Nour Y.
    "One dog can annoy a lot of families since homes are close to each other so multiple dogs barking is even worse"
    5
    Flag
  • Bassickrachel
    "I do see dogs frequently. People seem friendly, neighbors are quiet. I love airfield for the commute and small Town atmosphere."
    1
    Flag
  • Bassickrachel
    "Excellent I am 5 minutes from I-95 and Fairfield Metro Train Station. It is close to grocery stores and it is quite with friendly people."
    0
    Flag
  • Dennis
    "Many dogs that are very pleasant. Owners stop and chat while dogs play. Great way to meet your neighbors."
    0
    Flag
  • Larry
    "Moved here from Dallas and absolutely love it. I commute to downtown New Haven by car and it’s about 30-35 minutes."
    0
    Flag

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Frequently asked questions about 185 Windsor Road

  • What is 185 Windsor Road estimated to be worth?
    Trulia's estimated value for 185 Windsor Road in Fairfield, CT is $1,216,800.
  • What is the price history for 185 Windsor Road?
    185 Windsor Road in Fairfield, CT last sold for $1,200,000 in June 2026.
  • Is Fairfield a buyer's or seller's market?
    Fairfield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Fairfield?
    The median sale price in Fairfield is $957K. That is down $29.79K from the prior month.
  • Does 185 Windsor Road have air conditioning?
    Yes, 185 Windsor Road in Fairfield, CT has air conditioning.
  • Does 185 Windsor Road have laundry facilities?
    Yes, 185 Windsor Road in Fairfield, CT has in-unit laundry.

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