27 Winthrop Pl, Monroe, CT 06468
OFF MARKET

27 Winthrop Pl
Monroe, CT 06468

  • 3 Beds
  • 1 Bath
  • 1,870 sqft (on 1.03 acres)

$608,600

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $3,984/mo*
Refinance Your Home

$608,600

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $3,984/mo*
Refinance Your Home
3 Beds
1 Bath
1,870 sqft
(on 1.03 acres)

Local Information

  • Map ViewExplore the area around 27 Winthrop Pl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Your Monroe Home Sweet Home With So Many Thoughtful Updates and Move In Ready Condition Awaits! Beautifully Appointed, Meticulously Maintained and Renovated Ranch in Desirable Central Town Location and Quiet Neighborhood on Picturesque 1 Acre Property! Large Living Room with Fireplace Opens to Gorgeous Newer Kitchen with Granite, Island, Tile Backsplash and Stainless Appliances and Dining Area. HUGE Family Room with Vaulted Beamed Ceiling off Back of Home w/Built Ins, 2nd Fireplace and Slider to Expansive Trex Deck and Wonderful Private Yard Perfect for Entertaining! 3 Bedrooms, Updated Full Bath with New Vanity, Partially Finished Lower Level w/Large Walk In Closet with Storage Adds 330 Sq Feet! Just Some of the Wonderful Updates Include New Walkway, Entry Steps and Handrails, Exterior Painted Spring 2019, New Hot Water Heater, Gutters and Trim, Driveway Recently Repaved, Newer Garage Door and Opener, Ductless Split Central Air System, Natural Gas and So Much More! Come Preview this Beauty and Get into a Fantastic Town at an Incredible Price! Award Winning Schools and Amazing Amenities, this Home is Close to Library, Shopping, Lake, and Parks! Don't Delay!
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
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27 Winthrop Pl

Interior Features

Heating & Cooling
Heating: Other, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 7
Appliances & Utilities
MicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not Wood, Stone, Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1962
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1.03 acres

Price History for 27 Winthrop Pl

DatePriceEventSource
09/10/2019$330,000Sold
Smart MLS #170209999
07/10/2019$325,000PendingAgent Provided
06/25/2019$325,000Listed For SaleAgent Provided

Market trends in Monroe

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
63
23MoM
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Property Tax and Assessment

Year2025
Tax$8,619
Assessment$300,640
Home facts updated by county records

Comparable Sales for 27 Winthrop Pl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
40 Winthrop Place, Monroe, CT
0.06
Single-Family Home
$610,000
02/17/26
3
3
2,219
115 Williamsburg Drive, Monroe, CT
0.16
Single-Family Home
$580,000
06/26/26
3
2.5
1,632
132 Old Tannery Road, Monroe, CT
0.57
Single-Family Home
$450,200
12/10/25
3
1
1,200
136 Wheeler Road, Monroe, CT
0.23
Single-Family Home
$555,000
09/12/25
3
2.5
2,752
134 Walnut Street, Monroe, CT
0.45
Single-Family Home
$555,000
08/22/25
3
2
1,994
115 Wheeler Road, Monroe, CT
0.32
Single-Family Home
$575,000
04/16/26
3
2
1,298
27 Osborn Lane, Monroe, CT
0.44
Single-Family Home
$574,000
12/30/25
3
2
2,018
142 Old Tannery Rd, Monroe, CT
0.62
Single-Family Home
$410,000
12/16/25
3
2
1,420
22 Plumer Ln, Monroe, CT
0.61
Single-Family Home
$995,000
10/31/25
3
2
2,400
215 Wheeler Road, Monroe, CT
0.23
Single-Family Home
$775,000
04/30/26
4
3
3,595

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Winthrop Pl.
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 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

Sourced by Trulia users. 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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7 rentals with air conditioning in Monroe, CT

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Homes for sale near 27 Winthrop Pl

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Off Market Homes Near 27 Winthrop Pl

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27 Winthrop Pl, Monroe, CT 06468 is a 3 bedroom, 1 bathroom, 1,870 sqft single-family home built in 1962. This property is not currently available for sale. 27 Winthrop Pl was last sold on Sep 10, 2019 for $330,000. The current Trulia Estimate for 27 Winthrop Pl is $608,600.