44 Winslow Road, Trumbull, CT 06611
OFF MARKET

$702,700

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,719 sqft (on 0.32 acres)

44 Winslow Road, Trumbull, CT 06611

Refinance Your Home
Currently Off Market - Sold Dec 11, 2023 for $585,000

Home Value

Trulia Estimate
$703K
Since last month
Decreased$4K (-0.5%)
Since last year
Increased$28K (+4.1%)
Since last sale
Increased$119K (+20.3%)
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 +77% in the last 10 years
MonthEstimated value
2026
August 2026$704K
August 2026$703K
July 2026$707K
June 2026$718K
May 2026$718K
April 2026$712K
March 2026$712K
February 2026$691K
January 2026$690K
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
121 Campbell Road, Trumbull, CT
0.22
Single-Family Home
$660,000
04/22/26
3
2.5
2,325
4161 Madison Avenue, Trumbull, CT
0.19
Single-Family Home
$750,000
06/01/26
4
3.5
2,805
18 Ridgebury Drive, Trumbull, CT
0.21
Single-Family Home
$437,000
08/28/26
3
2.5
2,012
121 Richfield Road, Bridgeport, CT
0.19
Single-Family Home
$495,000
01/29/26
3
2
2,213
18 Maple Street, Trumbull, CT
0.35
Single-Family Home
$700,000
06/04/26
4
3
2,230
12 Chatfield Drive, Trumbull, CT
0.37
Single-Family Home
$612,000
09/01/26
3
2
1,828
56 Waller Road, Trumbull, CT
0.41
Single-Family Home
$595,000
11/07/25
4
2.5
2,580
42 Hickory Street, Trumbull, CT
0.38
Single-Family Home
$540,000
09/19/25
3
2
2,244

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
56 Winslow Road, Trumbull, CT 06611
0.05
$696,900
3
3
2,688
Off Market
26 Gaylord Road, Trumbull, CT 06611
0.08
$604,100
5
2
1,477
Off Market
29 Winslow Road, Trumbull, CT 06611
0.07
$761,600
4
2
2,240
Off Market
7 Leighton Road, Trumbull, CT 06611
0.07
$799,300
3
2.5
2,324
Off Market
8 Shelbourne Road, Trumbull, CT 06611
0.09
$643,100
4
2
1,732
Off Market
26 Bonheur Road, Trumbull, CT 06611
0.08
$871,600
4
3.5
3,061
Off Market
5 Lawn Circle, Trumbull, CT 06611
0.14
$650,800
3
2
2,300
Off Market
310 Plattsville Road, Trumbull, CT 06611
0.13
$899,900
4
4
3,260
For Sale
280 Plattsville Road, Trumbull, CT 06611
0.15
$599,100
3
1.5
1,348
Off Market
18 Ridgebury Drive, Trumbull, CT 06611
0.21
$437,000
3
2.5
2,012
Recently Sold
142 Richfield Road, Trumbull, CT 06611
0.17
$663,700
3
2.5
1,969
Off Market

Local Information

  • Map ViewExplore the area around 44 Winslow Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1952
0.32 acre lot
2,719 sqft
$258/sqft
2 Car Garage

About this House

This custom colonial/contemporary masterpiece offers 3 bedrooms and 3 bathrooms, including a spacious primary suite. The two other generously sized bedrooms provide ample space for relaxation and personalization, ensuring that everyone feels right at home. Prepare to be inspired in the eat in kitchen, with sleek granite countertops that elegantly complement the stainless-steel appliances and functional cabinetry. Gather around the cozy gas fireplace in the family room and stay comfortable year-round with the convenience of central air. Lounge by in-ground pool, inviting you to relax and unwind. For those seeking a shaded sanctuary, the screened-in porch offers a serene space to enjoy the outdoors without the hassle of insects. This home comes complete with dedicated office space, providing the perfect environment for remote work. Ideally situated near Sacred Heart University, and a host of amenities, everything you desire is just a stone's throw away. Don't miss your chance to own this remarkable custom colonial/contemporary home that redefines suburban living –H schedule a tour today and make this dream home your reality.( House-Deck-Pool Is As Is ) House Pool-Deck Is Being Sold AS-IS ( Call agent if any questions please ) Significant price improvement, submit all offers !!
44 Winslow Road, Trumbull, CT 06611 is a 3 bedroom, 3 bathroom, 2,719 sqft single-family home built in 1952. It last sold for $585,000 on Dec 11, 2023 (6% below the $620,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $702,700, with a rent estimate of $5,021/month.
Last check for updates: 1 day ago
Listed by Mary Keklik, (203) 581-1467
Coldwell Banker Realty, (203) 254-7100
Bought with: Aziz Seyal, (203) 209-9396, William Raveis Real Estate, (203) 255-6841
Source: Smart MLS, MLS#170591974

Home Details for 44 Winslow Road

Interior Features

Interior Details
Basement: Full,Unfinished,Interior Entry,Storage Space,Sump PumpNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Other
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2719 Square Feet
Appliances & Utilities
Appliances: Gas Range, Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Gas Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Gas on Gas,Forced Air,Hot Water,Zoned,Natural GasHas CoolingAir Conditioning: Central Air,Window Unit(s),ZonedHas HeatingHeating Fuel: Gas On Gas
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, Patio, Porch, ScreenedFencing: Partial, WoodExterior: SidewalkFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Garage Door Opener,Private,Asphalt
Pool
Pool: In Ground, VinylPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2719 Square Feet

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Contemporary
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 391758

Price & Status

Price
List Price: $620,000
Status Change & Dates
Off Market Date: Mon Nov 27 2023Possession Timing: Negotiable / Call Agent

Active Status

MLS Status: Closed

Location

Direction & Address
City: TrumbullCommunity: St. Theresa's
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Trumbull

Building

Building Area
Building Area: 2719 Square Feet

Community

Community Features: Medical Facilities, Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 0.32 acres

Miscellaneous

BasementMls Number: 170591974Above Grade Unfinished Area: 2719

Additional Information

Medical FacilitiesShopping/Mall

Price and Tax history

DateEventPrice
Dec 11, 2023
Source: Smart MLS #170591974
Sold
$585,000
Nov 27, 2023
Source: Smart MLS #170591974
Pending
$620,000
Oct 16, 2023
Source: Smart MLS #170591974
PriceChange
$620,000
Price decreased by 2%
Oct 4, 2023
Source: Smart MLS #170591974
PriceChange
$630,000
Price decreased by 2%
Sep 20, 2023
Source: Smart MLS #170591974
PriceChange
$640,000
Price decreased by 3%

Market trends in Trumbull

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$665K
$11.67KMoM
Sale-to-List Price
103.7%
Price per sq ft
$320
$12MoM
Available listings
83
5MoM

Around this home

What Locals Say about Trumbull

At least 235 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 86 % Say parking is easy

  • 85 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 77 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 66 % Say kids play outside

  • 66 % Say it's quiet

  • 65 % Say people would walk alone at night

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

  • 54 % Say neighbors are friendly

  • 37 % Say streets are well-lit

  • 33 % Say there are sidewalks

  • 32 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Excellent schools, kid friendly town, swimming pools, plenty of parks and trails, quiet and clean area. "
    0
    Flag
  • Emily.stumph
    "The parks are great but there is no safe way to bike between them, you need a car to enjoy Trumbull’s nature "
    0
    Flag
  • Mjconstructionpro
    "Yes I do see people walking with their dogs, I love my neighbors. People are so nice… Trumbull is the town for me "
    0
    Flag
  • E Rocco
    "not bad. trumbull is nice and close to the merit. i grew up here and wouldn’t change a thing! its a safe and friendly town"
    0
    Flag
  • Xgv8mhqqpg
    "My commute is short with easy access to highway systems. Very little traffic lights and I am only limited by stop signs. Cars are on the road are friendly. "
    0
    Flag
  • Trulia User
    "The area is quiet and family oriented. Neighbors look out for neighbors to keep the peace and order. Nice park with playground area and sports events next to a nice library "
    0
    Flag
  • RMV
    "There are many young families and parks all over town. I live around the corner from the entrance of a walking trail that leads into a park that’s great for a hike or recreation. There are not many restaurants on my side of town except a wine bar, but Starbucks and Dunkin Donuts are walking distance."
    11
    Flag
  • Nicole D.
    "dog friendly area. plenty of state parks and trails for the dogs. just watch out for wildlife with the smaller dogs."
    1
    Flag
  • Jnapoli2521
    "I live in Trumbull Town Commons and some dog owners do not pick up after their dog despite the signs "
    2
    Flag
  • Msvindland
    "Town movies, town pools and block parties. They have a wonderful walking trail that my dog and I use frequently and a wonderful dog park. They have the Trumbull mall which is very well maintained and the movie theater that has security"
    5
    Flag
  • Rebeccalore
    "There are a lot of dogs in the neighborhood and they are well cared for. There is also a good dog park near by. "
    1
    Flag
  • Ashley U.
    "My neighborhood is almost perfect. The only problem is that everything is spaced out. The mall is in one direction, the movie theater in another and the small shops and such are all about. It’s quite boring here if you ask me. "
    9
    Flag
  • KMM
    "I’ve grown up/lived here for 25 years. Amazing town to grow up in! School system is great too. People are friendly and it feels like home."
    2
    Flag
  • Bruce S.
    "We have lived here for more than 50 years. I would never want to move. Beautiful year round, near nice beaches, excellent schools, safe neighborhoods and reasonably affordable. "
    6
    Flag
  • Heather Uva
    "Trumbull is very blue collar down to earth people.. we are friendly, nonjudgemental, who work hard, and love our children. It is a pleasure to live here. Trumbull is close to major highway also for quick ride to the major cities around her."
    2
    Flag
  • Olgui L.
    "Great school system. Very safe town. I have lived here for 42 years, have never had any bad experiences. "
    2
    Flag
  • KB
    "It’s a great residential neighborhood, however there aren’t a ton of options for restaurants in the city itself, however it is really close to surrounding towns with plenty of life."
    0
    Flag
  • Mike s.
    "You can get a fair amount of property that you can expand upon. Even though it’s a double yellow I feel safe when my little ones are playing. "
    1
    Flag
  • Adeliofpimenta
    "I love living here because of the neiborhoods are very nice , and quiet my kids can save ride a bike , and enjoy the weather outside with the beautiful parks around ! "
    0
    Flag
  • Mike s.
    "The school system is trumbull is amazing. Both of our boys are thriving thanks to TECEC. There are also some private school options which we have taken advantage of and have not been disappointed. "
    0
    Flag
  • Lsosa2007
    "This neighborhood is unique because of all the nice people that make it a neighborhood. All the fun things that happen in my neighborhood bring us together."
    1
    Flag
  • Tobiascarling
    "I’ve lived here for eight years and cherish the warm, friendly neighborhood. People are constantly out walking or running, kids playing, and neighbors are chatty."
    0
    Flag
  • Loveeherrr
    "It’s a gated community, everyone is friendly . There’s a gym, pool area, cookout area, guest lounge. You need a key to get in and there’s security that do hourly walks through the neighborhood to keep an eye for anything "
    0
    Flag
  • Tobiascarling
    "We have a very friendly neighborhood, full of families and empty nesters. I love being close to the Merritt, playgrounds, the Trumbull mall, and the grocery store."
    0
    Flag

LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 44 Winslow Road

  • What is 44 Winslow Road estimated to be worth?
    Trulia's estimated value for 44 Winslow Road in Trumbull, CT is $702,700.
  • What is the price history for 44 Winslow Road?
    44 Winslow Road in Trumbull, CT last sold for $585,000 in December 2023.
  • Is Trumbull a buyer's or seller's market?
    Trumbull is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Trumbull?
    The median sale price in Trumbull is $665K. That is up $11.67K from the prior month.
  • Does 44 Winslow Road have air conditioning?
    Yes, 44 Winslow Road in Trumbull, CT has air conditioning.
  • Does 44 Winslow Road have a pool?
    Yes, 44 Winslow Road in Trumbull, CT has a pool.

Explore by feature - Pet Friendly

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