53 Windsor Rd, Fairfield, CT 06824
Property image
Property image
OFF MARKET

$827,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,903 sqft (on 0.33 acres)

53 Windsor Rd, Fairfield, CT 06824

Est. Refi. Payment $5,503/mo*
Refinance Your Home
Currently Off Market - Sold May 31, 2017 for $406,000

Home Value

Trulia Estimate
$828K
Since last month
Decreased$2K (-0.2%)
Since last year
Increased$87K (+11.8%)
Since last sale
Increased$421K (+103.7%)
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 +119% in the last 10 years
MonthEstimated value
2026
August 2026$827K
July 2026$829K
June 2026$849K
May 2026$852K
April 2026$834K
March 2026$822K
February 2026$783K
January 2026$768K
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
14 Windsor Place, Fairfield, CT
0.09
Single-Family Home
$800,000
09/03/25
3
2
1,655
85 Tuckahoe Ln, Fairfield, CT
0.08
Single-Family Home
$496,000
10/06/25
3
2
1,130
158 Mayfair Road, Fairfield, CT
0.08
Single-Family Home
$829,500
04/28/26
3
2.5
1,988
79 Mayfair Road, Fairfield, CT
0.09
Single-Family Home
$900,000
12/10/25
3
2.5
1,635
245 Reid Street, Fairfield, CT
0.18
Single-Family Home
$685,000
04/01/26
3
2
1,421
498 Judd St, Fairfield, CT
0.20
Single-Family Home
$610,000
09/09/25
3
2.5
1,986
115 Mayfair Road, Fairfield, CT
0.03
Single-Family Home
$1,160,000
04/02/26
4
3
2,012
70 Allen Road, Fairfield, CT
0.14
Single-Family Home
$985,000
05/29/26
3
1.5
1,430
52 Robin Lane, Fairfield, CT
0.30
Single-Family Home
$755,000
07/21/26
4
2
1,735
42 Green Knolls Lane, Fairfield, CT
0.21
Single-Family Home
$820,000
11/19/25
2
2
1,568

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
115 Mayfair Road, Fairfield, CT 06824
0.03
$1,160,000
4
3
2,012
Recently Sold
100 Mayfair Road, Fairfield, CT 06824
0.07
$862,100
4
3
2,394
Off Market
14 Windsor Place, Fairfield, CT 06824
0.09
$861,100
3
2
1,655
Off Market
79 Mayfair Road, Fairfield, CT 06824
0.09
$900,000
3
2.5
1,635
Recently Sold
158 Mayfair Road, Fairfield, CT 06824
0.08
$829,500
3
2.5
1,988
Recently Sold
11 Tuckahoe Lane, Fairfield, CT 06824
0.13
$1,590,000
4
3.5
3,636
Recently Sold
170 Windsor Road, Fairfield, CT 06824
0.10
$1,971,400
5
4.5
4,975
Off Market
217 Greenbriar Road, Fairfield, CT 06824
0.11
$1,124,700
4
2.5
2,800
Off Market
233 Mayfair Road, Fairfield, CT 06430
0.10
$1,176,800
4
2.5
2,900
Off Market
233 Mayfair Road, Fairfield, CT 06824
0.11
$1,466,200
4
2.5
3,547
Off Market
15 Olivia Place, Fairfield, CT 04937
0.15
$1,098,500
4
2.5
2,750
Off Market
180 Lower Farm Road, Fairfield, CT 06824
0.14
$2,029,400
5
4
3,900
Off Market

Local Information

  • Map ViewExplore the area around 53 Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Lot Size
0.33 acres
Living Area
1,903 sqft
Price/Sqft
$435
Parking
Garage

About this House

Picture perfect university area home, lovingly customized by space planner, every inch has been maximized to its fullest potential. Move right in to this bright & sunny home w/ 2 bedrooms plus Murphy bed in living room, offering flexible opportunity for additional sleeping. Spacious foyer, gorgeous kitchen, dining room w/ sliders to deck to access to level yard, formal living room w/ fireplace and built-ins, updated full bath and access to garage complete the first floor. LL is finished and adds 698 SF w/ large playroom, office & walk-in closet. Walk 2 blocks to Osborne Hill school, minutes to Trader Joe's, Starbucks, fabulous dining & playgrounds, 1.7 miles to train,conv located to Merritt and I-95, quiet neighborhood.Amazing opportunity!
53 Windsor Rd, Fairfield, CT 06824 is a 3 bedroom, 2 bathroom, 1,903 sqft single-family home built in 1962. It last sold for $406,000 on May 31, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $827,500, with a rent estimate of $5,276/month.

Home Details for 53 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleExterior: OtherPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1962Year Updated: 2024
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
May 31, 2017
Source: Smart MLS #99179473
Sold
$406,000
Apr 20, 2017
Source: Agent Provided
Pending
$406,000
Mar 30, 2017
Source: Agent Provided
Listed For Sale
$406,000
Jun 15, 2007
Source: Smart MLS #98309512
Sold
$447,500
Aug 20, 2004
Source: Smart MLS #98200832
Sold
$460,000

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

LGBTQ Local Legal Protections

Frequently asked questions about 53 Windsor Rd

  • What is 53 Windsor Rd estimated to be worth?
    Trulia's estimated value for 53 Windsor Rd in Fairfield, CT is $827,500.
  • What is the price history for 53 Windsor Rd?
    53 Windsor Rd in Fairfield, CT last sold for $406,000 in May 2017.
  • 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.
  • How big is the lot at 53 Windsor Rd?
    The lot at 53 Windsor Rd in Fairfield, CT is about 0.33 acres (14,375 sq ft).
  • Does 53 Windsor Rd have a garage?
    Yes, 53 Windsor Rd in Fairfield, CT has a garage.

Explore by feature - Pet Friendly

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