53 Windsor Rd, Fairfield, CT 06824
OFF MARKET

53 Windsor Rd
Fairfield, CT 06824

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

$852,000

Trulia Estimate
as of Jun 4, 2026

$852,000

Trulia Estimate
as of Jun 4, 2026
3 Beds
2 Baths
1,903 sqft
(on 0.33 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 53 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
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 History for 53 Windsor Rd

DatePriceEventSource
05/31/2017$406,000Sold
Smart MLS #99179473
04/20/2017$406,000PendingAgent Provided
03/30/2017$406,000Listed For SaleAgent Provided
06/15/2007$447,500Sold
Smart MLS #98309512
08/20/2004$460,000Sold
Smart MLS #98200832
06/27/2002$329,000Sold
N/A
12/23/1999$202,500Sold
N/A
08/16/1996$150,000Sold
N/A

Market trends in Fairfield

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$958K
$96.16KMoM
Sale-to-List Price
102.1%
1.3%MoM
Price per sq ft
$473
$29MoM
Available listings
131
12MoM
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Property Tax and Assessment

Year2025
Tax$11,584
Assessment$408,030
Home facts updated by county records

Comparable Sales for 53 Windsor Rd

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
100 Mayfair Road, Fairfield, CT
0.07
Single-Family Home
$800,000
07/29/25
4
3
2,394
42 Green Knolls Lane, Fairfield, CT
0.21
Single-Family Home
$820,000
11/19/25
2
2
1,568

Nearby homes

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Assigned Schools

These are the assigned schools for 53 Windsor Rd.
View nearby schools on GreatSchools
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 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

  • 78 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 67 % 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

  • 49 % Say there are community events

  • 47 % 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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53 Windsor Rd, Fairfield, CT 06824 is a 3 bedroom, 2 bathroom, 1,903 sqft single-family home built in 1962. This property is not currently available for sale. 53 Windsor Rd was last sold on May 31, 2017 for $406,000. The current Trulia Estimate for 53 Windsor Rd is $852,000.