4 Windsor Rd, Monroe, CT 06468
OFF MARKET

4 Windsor Rd
Monroe, CT 06468

  • 4 Beds
  • 2 Baths
  • 1,520 sqft (on 1 acre)

$623,900

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $4,102/mo*
Refinance Your Home

$623,900

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $4,102/mo*
Refinance Your Home
4 Beds
2 Baths
1,520 sqft
(on 1 acre)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Beautiful 4 bedroom family home on the market for the first time. Lovingly cared for this open bright floor plan has lots of space. There are hardwood floors throughout...new runner in hallway and many upgrades. The eat in kitchen has beautiful cherry cabinets, doors are solid pine and both full baths have been remodeled. The exterior of the home has new double pane windows and new siding. Automatic door opener and steel garage doors have been added and the drive paved. The level acre is bordered by trickling stream and stone walls. Walk to historic town center and to business area. Great house in great location.
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
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 4 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1964
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 4 Windsor Rd

DatePriceEventSource
06/30/2014$325,000Sold
Smart MLS #99065064
05/20/2014$339,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$8,866
Assessment$309,260
Home facts updated by county records

Comparable Sales for 4 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
30 Longview Road, Monroe, CT
0.39
Single-Family Home
$625,000
09/17/25
4
1.5
2,123
63 Far Horizon Drive, Monroe, CT
0.42
Single-Family Home
$530,000
12/05/25
3
1.5
2,204
17 Admiral Dr, Monroe, CT
0.11
Single-Family Home
$1,250,000
09/08/25
4
3
3,482
72 Twin Brook Terrace, Monroe, CT
0.43
Single-Family Home
$565,000
08/14/25
3
2
1,500
104 Maplewood Drive, Monroe, CT
0.65
Single-Family Home
$575,000
06/04/25
4
2
1,520
331 Elm Street, Monroe, CT
0.59
Single-Family Home
$550,000
08/19/25
4
2
2,368
129 Fan Hill Road, Monroe, CT
0.72
Single-Family Home
$492,500
11/26/25
3
1.5
1,674
6 Crossbow Lane, Monroe, CT
0.41
Single-Family Home
$725,000
01/09/26
4
3
3,082
48 Crestwood Road, Monroe, CT
0.66
Single-Family Home
$500,000
06/30/25
4
2.5
2,268
4 Sweetbrier Lane, Monroe, CT
0.42
Single-Family Home
$950,000
06/17/25
4
3.5
3,255

Assigned Schools

These are the assigned schools for 4 Windsor Rd.
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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 Monroe

At least 69 Trulia users voted on each feature.

  • 97 % Say car is needed

  • 92 % Say there's holiday spirit

  • 90 % Say parking is easy

  • 88 % Say yards are well-kept

  • 82 % Say it's dog friendly

  • 79 % Say there's wildlife

  • 76 % Say it's quiet

  • 71 % Say people would walk alone at night

  • 63 % Say they plan to stay for at least 5 years

  • 60 % Say neighbors are friendly

  • 60 % Say kids play outside

  • 30 % Say there are community events

  • 17 % Say streets are well-lit

  • 14 % Say it's walkable to grocery stores

Learn more about our methodology.
  • Timnorton7
    "Drive to NYC awful hour and a half to get into work. 1-4 hours to get home. Would have to drive to Fairfield or Bridgeport train station 30 minutes and hour 20 to grand central and 30 minutes downtown to commute by train."
    0
    Flag
  • Nicole Velez
    "Great parks! Library host various events. Various committees have different events and festivals. I wish there were more connecting sidewalks. "
    1
    Flag
  • Danielle B.
    "Easy commute with multiple alternative routes with similar ETAs. Two out of three routes don't require any highway driving. "
    0
    Flag
  • Wulfranoflores
    "is a great town for living here has a good shools great nearborhod is a good place for famly events you can walk or run for yours daily exersise and is very safe "
    2
    Flag
  • Kyle C.
    "Families with kids are common, parks, close knit community. Many town activities. Lots of great food nearby (Home Plate Deli, Gaetano’s, Soup Thyme)"
    0
    Flag
  • Larisabarrera
    "Very convenient to grocery stores , Home Depot, all the necessities close by , we love the area to live "
    0
    Flag
  • Johnny M.
    "Music in Wolfe park on Friday nights and dogs,walkers and families riding bikes together on the trails. "
    1
    Flag
  • Jeneen R.
    "Plenty of people have dogs in our neighborhood and I always see them out walking when the weather is nice."
    0
    Flag
  • Kevin N.
    "Dogs owners would love and hate Monroe. Monroe there is no sidewalks so walking on the main road in most cases, just wouldn’t be an option. Also, most of the traffic is on the main road so on your side street, you will have plenty of room and non action from cars to walk your dog"
    2
    Flag
  • Kwilliams1473
    "The schools are great, there is no “bad” part of town, there is an adorable farmers market in the summer, it’s very quaint feeling but not far away from many convinces "
    1
    Flag
  • jcbermud
    "Easy... With 25 down the road I can get to 95 or the Merritt very easily. We need a Trader Joe's though please! "
    1
    Flag
  • Johnny M.
    "Quiet, safe, friendly, beautiful, active, trump haters, good schools, music in the park, pickle ball courts, good wings and pizza restaurants. "
    6
    Flag
  • Lalemanfamily
    "I enjoy the small town character of Monroe, while having access to bigger city amenities within a 45-90 minute drive! "
    1
    Flag
  • Cherry4507
    "You definitely need a car because there isn’t any bus lines or trains that you can take to get where I gotta go "
    0
    Flag
  • Johnny M.
    "Safety, good schools, friendly people, brewery, nice Congregational church, free concerts in the park Friday nights"
    2
    Flag
  • Nls10356
    "It is very private,but people look out for one another. It is always very clean and beautiful. It is dog friendly. It is a convenient location "
    0
    Flag
  • Ray K.
    "Great family neighborhood with no HOA fees. Walk the gold course, fish in the river, or walk over to Stone Barn Sandtrap Grill and Bar for dinner or drinks and dancing. Walk home or ride golf cart. "
    0
    Flag
  • Leah
    "This quiet, upscale neighborhood is perfect for retirees, young couples, singles, or families. It is the safest area I have ever lived in. The schools are great, and you will be close to all the advantages of fairfield county without the extreme expense or frantic lifestyle. Enjoy the woods, the parks, the quiet neighborhoods, or the great local restaurants and shops. There are conveniently located grocery stores and service shops, that are not too crowded or large. I have enjoyed living here for many years, and it's by far my favorite area in the northeast. "
    0
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  • uptwolate
    "Redcoat (Red Coat) Lane and the surrounding area is filled with friendly, caring people at all stages of their lives including retirees and families with children of all ages. Monroe's schools are excellent and this area is within about a mile from Fawn Hollow Elementary School and Jockey Hollow Middle School. Masuk High School is only about two miles away. The Monroe Police Department is top notch and the Volunteer Fire Departments are well-trained and situated in several areas around the town for speedy access in case of need. The highway department keeps the local roads in great shape during winter storms and has been resurfacing and repaving many stretches of the worst roads during the summer. Although the immediate area has plenty of quiet roads for walking and running during periods of better weather, we also have a rails to trails area and several parks within a couple of miles that are very popular but would need to be driven to for easier access. There are also local shopping opportunities that are only a mile or two away either on Monroe Turnpike (Rte. 111) or Main Street (Rte. 25), which includes a multitude of gift shops, convenience stores, paint and hardware stores, book and card shops and even two competing grocery stores on Monroe Tpke and a Natural Foods store on Main Street. There are many drug stores, cleaners, barbers, hairstylists and restaurants galore from McD's to sports bars, Mexican, Oriental, Italian and American cuisine, including a new diner on Main Street, several Dunkin Donuts and, yes, we have a Starbucks!!! What more could you want? There are walk-in clinics and many doctors in town as well as a muriad of specialists just south of Monroe but still on Monroe Tpke. as you drive into Trumbull, where there is also a Home Depot and just a few miles further, the Trumbull Mall. There are churches of every denomination in town whose activities make for happy strawberry festivals in the spring and apple festivals at harvest time. Join us!!"
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4 Windsor Rd, Monroe, CT 06468 is a 4 bedroom, 2 bathroom, 1,520 sqft single-family home built in 1964. This property is not currently available for sale. 4 Windsor Rd was last sold on Jun 30, 2014 for $325,000. The current Trulia Estimate for 4 Windsor Rd is $623,900.