185 Windsor Road
Fairfield, CT 06824
4 Beds
3.5 Baths
2,959 sqft
4 Beds
3.5 Baths
2,959 sqft
Local Information
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Description
Tucked away on a quiet cul-de-sac in the desirable University area of Fairfield, this move-in-ready Colonial combines thoughtful updates, flexible living space, and an impressive, detached studio. Offering nearly 3,000 square feet of finished living space across three levels, this 4-bedroom, 3.5-bath home features a remodeled eat-in kitchen with new appliances, quartz countertops, farmhouse sink, and wood-burning fireplace with custom mantle. Sliding French doors open to a large deck overlooking the private, fenced yard. The light-filled family room showcases vaulted ceilings and floor-to-ceiling built-ins, while the spacious dining room opens to both the kitchen and family room - perfect for hosting gatherings. A custom mudroom with built-ins provides excellent storage. The flexible layout includes an en-suite bedroom on the main level ideal for guests or in-laws, plus an additional bedroom and updated full bath. Upstairs, the primary suite features a wall of built-ins and a beautifully updated bath, as well as a 4th bedroom and laundry room. The lower level offers additional living space for a recreation room and gym plus a half bath, ample storage, and direct backyard access. A standout feature is the detached studio, currently used as a home office, with vaulted ceilings, natural wood interior, double French doors, and its own heating and cooling system. Ideally located just minutes from downtown, Metro-North train, beaches and parks, this is Fairfield living at its best! *New driveway just installed!
Home Highlights
Parking
No Info
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$429
Listed
67 days ago
Home Details for 185 Windsor Road
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Interior Details Basement: Full,Heated,Storage Space,Interior Entry,Partially FinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Dining Room, Family Room, Kitchen, Other, Rec Play Room, Studio Apt |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2959 Square Feet |
Appliances & Utilities Appliances: Electric Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Gas Water Heater, Water HeaterDishwasherDryerLaundry: Upper Level,Mud RoomRefrigeratorWasher |
Heating & Cooling Heating: Hot Water,Zoned,Natural GasHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Hot Water |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Windows, Doors, Floors & Walls Door: French Doors |
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Exterior Home Features Roof: AsphaltPatio / Porch: DeckFencing: Wood, FullOther Structures: Shed(s)Exterior: Rain Gutters, Garden, LightingFoundation: MasonryGardenNo Private Pool |
Parking & Garage No Garage |
Frontage Waterfront: Beach AccessNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 2151 Square FeetFinished Area (below surface): 808 Square Feet |
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Days on Market: 67 |
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Year Built Year Built: 1959 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 125965 |
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Price List Price: $1,269,000Price Per Sqft: $429 |
Status Change & Dates Off Market Date: Fri May 08 2026Possession Timing: Negotiable |
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MLS Status: Under Contract |
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Direction & Address City: FairfieldCommunity: University |
School Information Elementary School: Osborn HillJr High / Middle School: Fairfield WoodsHigh School: Fairfield Ludlowe |
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Listing Agent Listing ID: 24162856 |
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Building Area Building Area: 2959 Square Feet |
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No HOA |
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Lot Area: 10018.8 sqft |
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BasementMls Number: 24162856Zillow Contingency Status: Under ContractAttic: Pull Down StairsAttribution Contact: (203) 521-1119Above Grade Unfinished Area: 2151Activation Date: Thu Apr 02 2026 |
Last check for updates: about 9 hours ago
Listing courtesy of Carrie Sakey, (203) 521-1119
Coldwell Banker Realty, (203) 521-1119
Source: Smart MLS, MLS#24162856
Also Listed on Smart MLS.
Market trends in Fairfield
Last updated April 2026
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
Price History for 185 Windsor Road
| Date | Price | Event | Source |
|---|---|---|---|
| 05/09/2026 | $1,269,000 | Pending | Smart MLS #24162856 |
| 04/15/2026 | $1,269,000 | PriceChange | Smart MLS #24162856 |
| 04/02/2026 | $1,295,000 | Listed For Sale | Smart MLS #24162856 |
| 04/05/2021 | $721,550 | Sold | N/A |
| 02/27/2021 | $750,000 | Pending | N/A |
| 02/13/2021 | $750,000 | PendingToActive | N/A |
| 02/13/2021 | $750,000 | Pending | N/A |
| 01/29/2021 | $750,000 | Listed For Sale | N/A |
| 08/10/2007 | $439,900 | Sold | Smart MLS #98326105 |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,528 |
| Assessment | $406,070 |
Home facts updated by county records
Comparable Sales for 185 Windsor Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $800,000 | 07/29/25 | 4 | 3 | 2,394 | |
0.21 | Single-Family Home | $1,225,000 | 08/01/25 | 5 | 3.5 | 2,930 | |
0.05 | Single-Family Home | $800,000 | 09/03/25 | 3 | 2 | 1,655 | |
0.44 | Single-Family Home | $850,000 | 09/22/25 | 4 | 2.5 | 2,860 | |
0.17 | Single-Family Home | $1,160,000 | 04/02/26 | 4 | 3 | 2,012 | |
0.20 | Single-Family Home | $829,500 | 04/28/26 | 3 | 2.5 | 1,988 | |
0.23 | Single-Family Home | $1,590,000 | 04/08/26 | 4 | 3.5 | 3,636 | |
0.25 | Single-Family Home | $1,640,000 | 04/24/26 | 4 | 3 | 3,778 | |
0.07 | Single-Family Home | $985,000 | 05/29/26 | 3 | 1.5 | 1,430 | |
0.40 | Single-Family Home | $1,275,000 | 03/09/26 | 4 | 4 | 2,670 |
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Assigned Schools
These are the assigned schools for 185 Windsor Road.
- Fairfield Woods Middle School
- 6-8
- Public
- 743 Students
8/10GreatSchools RatingParent Rating AverageI LOVE THE PASSION IN THIS SCHOOL. All the teachers and principals are welcoming and they put there hard work in to us and care about what we doOther Review15y ago - Osborn Hill School
- K-5
- Public
- 441 Students
9/10GreatSchools RatingParent Rating AverageBoth of my boys attend OHS and it’s an amazing school! Wonderful teachers and staff and Mr. Hudspeth is wonderful! He is clearly dedicated to staff and students and leads by example each day. On numerous occasions he has gone out of his way to help our family, as well as many others I know. OHS is the best of the best and we are fortunate to to live around the corner. It’s the main reason we chose our home so that we could walk each dayParent Review5y ago - Fairfield Ludlowe High School
- 9-12
- Public
- 1498 Students
9/10GreatSchools RatingParent Rating AverageThey never taught me on how to find a college for students who have autism or a disability. 3. They never taught me on how every college has different academics, Services, sports, clubs, and activities. The auditorium is way too small. You can’t fit everyone in there. Parking was just hell. There wasn’t enough spots for all students and as well they just let people who live close enough to walk drive to school and then people who don’t live close enough to walk won’t get a spot. There’s no baseball field on campus. More facilities on campus will decrease global warming as they don’t have to hire bus transportation and staying on campus burns less fossil fuels. Football season and all other fall sports start too early in the summer time and because of that sometimes people aren’t able to play since they’ll be away. No breakfast is sold at period 2 at all. Sometimes people don’t eat breakfast at all since high school starts at 7:30 pm. Don’t have enough food selections at lunchtime. Senior lounge has doesn’t have enough seats for people to sit next to friends and because of that a lot of the times I sat isolated on the benches in the senior lounge. It doesn’t feel like a new school year, it’s hard to separate others if they’re being too nonsense, not getting along with one another, causing too much trouble, and sometimes one homeroom can become more crowded than another if one student transfers to a different school or if one student transfers to FLHS because you’re locked in the same homeroom all four years of high school.Other Review5y ago 
Check out schools near 185 Windsor Road.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Carrie Sakey, Coldwell Banker Realty, (203) 521-1119
Agent Phone: (203) 521-1119
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.
185 Windsor Road, Fairfield, CT 06824 is a 4 bedroom, 4 bathroom, 2,959 sqft single-family home built in 1959. This property is currently available for sale and was listed by Smart MLS on Mar 28, 2026. The MLS # for this home is MLS# 24162856.