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

39 Windsor Rd
Fairfield, CT 06824

  • 3 Beds
  • 2 Baths
  • 3,310 sqft (on 0.36 acres)

$1,064,200

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,017/mo*
Refinance Your Home

$1,064,200

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,017/mo*
Refinance Your Home
3 Beds
2 Baths
3,310 sqft
(on 0.36 acres)

Home Value

Trulia Estimate
$1.06M
Since last month
Decreased$2K (-0.2%)
Since last year
Increased$65K (+6.5%)
Since last sale
Increased$268K (+33.6%)
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 +89% in the last 10 years
MonthEstimated value
2026
August 2026$1.06M
July 2026$1.07M
June 2026$1.09M
May 2026$1.09M
April 2026$1.09M
March 2026$1.08M
February 2026$1.02M
January 2026$1M
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
158 Mayfair Road, Fairfield, CT
0.07
Single-Family Home
$829,500
04/28/26
3
2.5
1,988
14 Windsor Place, Fairfield, CT
0.10
Single-Family Home
$800,000
09/03/25
3
2
1,655
79 Mayfair Road, Fairfield, CT
0.08
Single-Family Home
$900,000
12/10/25
3
2.5
1,635
115 Mayfair Road, Fairfield, CT
0.02
Single-Family Home
$1,160,000
04/02/26
4
3
2,012
42 Green Knolls Lane, Fairfield, CT
0.19
Single-Family Home
$820,000
11/19/25
2
2
1,568
70 Allen Road, Fairfield, CT
0.15
Single-Family Home
$985,000
05/29/26
3
1.5
1,430
52 Robin Lane, Fairfield, CT
0.31
Single-Family Home
$755,000
07/21/26
4
2
1,735
245 Reid Street, Fairfield, CT
0.18
Single-Family Home
$685,000
04/01/26
3
2
1,421
498 Judd St, Fairfield, CT
0.19
Single-Family Home
$610,000
09/09/25
3
2.5
1,986
203 Burroughs Road, Fairfield, CT
0.42
Single-Family Home
$800,000
07/08/26
3
2.5
2,290

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
0.02
$1,160,000
4
3
2,012
Recently Sold
100 Mayfair Road, Fairfield, CT 06824
0.06
$851,600
4
3
2,394
Off Market
14 Windsor Place, Fairfield, CT 06824
0.10
$848,300
3
2
1,655
Off Market
79 Mayfair Road, Fairfield, CT 06824
0.08
$900,000
3
2.5
1,635
Recently Sold
158 Mayfair Road, Fairfield, CT 06824
0.07
$829,500
3
2.5
1,988
Recently Sold
11 Tuckahoe Lane, Fairfield, CT 06824
0.12
$1,590,000
4
3.5
3,636
Recently Sold
170 Windsor Road, Fairfield, CT 06824
0.11
$1,991,100
5
4.5
4,975
Off Market
217 Greenbriar Road, Fairfield, CT 06824
0.12
$1,126,400
4
2.5
2,800
Off Market
233 Mayfair Road, Fairfield, CT 06430
0.10
$1,176,500
4
2.5
2,900
Off Market
233 Mayfair Road, Fairfield, CT 06824
0.11
$1,446,800
4
2.5
3,547
Off Market
15 Olivia Place, Fairfield, CT 04937
0.14
$1,121,500
4
2.5
2,750
Off Market
180 Lower Farm Road, Fairfield, CT 06824
0.13
$2,024,900
5
4
3,900
Off Market

Local Information

  • Map ViewExplore the area around 39 Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Lot Size
0.36 acres
Living Area
3,310 sqft
Price/Sqft
$322
Parking
Garage

About this House

Move-in ready! Pristine. This home is so welcoming from the minute you walk through the door. The open-concept floor plan is perfect for entertaining. Beautifully finished hardwood floors throughout. The kitchen is very spacious with tons of (granite) counter space, stainless steel appliances, lots of cabinets for storage. Special touches make this home so special like the dining room chandelier and matching chandelier in the hallway. There are two fireplaces (living room and lower level). The font of the house has stone detailing. The private master suite is very spacious with a stunning walk-in closet, the one you've always dreamed of complete with an organization system! The sizable master bath in pristine condition. This house had a 2 car garage and a large gym or bonus space beyond the garage. This space can work well as a home office, craft space, man-cave, or whatever additional space you may need. The lower level is finished beautifully complete with a wood-burning fireplace. Plenty of space. Works as a separate family room, rec. room or play space.  There is a separate additional room in the basement currently set up with an extra bed. The backyard is level and quite large. Fantastic neighborhood for walking!
39 Windsor Rd, Fairfield, CT 06824 is a 3 bedroom, 2 bathroom, 3,310 sqft single-family home built in 1956. It last sold for $796,500 on Aug 26, 2022. It is currently off market. The Trulia Estimate is $1,064,200, with a rent estimate of $5,321/month.

Home Details for 39 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1956Year Updated: 1956
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.36 acres

Price and Tax history

DateEventPrice
Aug 26, 2022
Source: Smart MLS #170492594
Sold
$796,500
Jul 19, 2022
Source: Smart MLS #170492594
Contingent
$799,000
May 20, 2022
Source: Smart MLS #170492594
Listed For Sale
$799,000
May 5, 2020
Source: Smart MLS #170278829
Sold
$586,000
Apr 3, 2020
Source: Agent Provided
Pending
$599,000

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 39 Windsor Rd

  • What is 39 Windsor Rd estimated to be worth?
    Trulia's estimated value for 39 Windsor Rd in Fairfield, CT is $1,064,200.
  • What is the price history for 39 Windsor Rd?
    39 Windsor Rd in Fairfield, CT last sold for $796,500 in August 2022.
  • 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 39 Windsor Rd have air conditioning?
    Yes, 39 Windsor Rd in Fairfield, CT has air conditioning.
  • Does 39 Windsor Rd have laundry facilities?
    Yes, 39 Windsor Rd in Fairfield, CT has in-unit laundry.

Explore by feature - Pet Friendly

25 pet-friendly rentals in Fairfield, CT

Explore by feature - Garage

42 rentals with a garage in Fairfield, CT

Explore by feature - Air Conditioning

88 rentals with air conditioning in Fairfield, CT

Explore by feature - Pool

11 rentals with a pool in Fairfield, CT

Explore by feature - Washer/dryer

111 rentals with a washer/dryer in Fairfield, CT

Explore by feature - Outdoor Space

26 rentals with an outdoor space in Fairfield, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 39 Windsor Rd

Skip to last item
Skip to first item

Homes for sale near 39 Windsor Rd

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