27 Windy Rdg
Trumbull, CT 06611
Trumbull Center
5 Beds
2 Baths
2,566 sqft (on 0.31 acres)
5 Beds
2 Baths
2,566 sqft
(on 0.31 acres)
Local Information
- Map ViewExplore the area around 27 Windy Rdg.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
WE ARE CALLING FOR FINAL & BEST MONDAY EVENING BY 5 PM Please use standard 3 page contract, to submit all offers.
Welcome to 27 Windy Ridge located in the Trumbull Center section of town. This beautiful cape has a spectacular leveled backyard that is fully fenced in with a fire pit and shed that has running electricity. This shed adds to the aesthetic of the backyard. The two full bathrooms have been completely renovated. One in 2018 & one in 2019 consecutively. This home boasts over 2500 square feet of space on the first and second floors. Hardwood lines the first level with a gas fireplace in the living room. The kitchen has beautiful granite countertops with an island. The open sunroom is right off of the kitchen which leads out to your own private deck. One of the bedrooms on the main level has a bay window. Three bedrooms on the main level. There is a sitting area off of one of the bedrooms on the second level with access to the bathroom area that also has a door for the private use of shower and toilet. The basement has been freshly painted and newly carpeted. This property is not to be missed. Exclusions: Lockers and metal cabinets in garage, red cabinets & shelves in laundry area, potted plants in yard and on deck, wall dcor unit in main bathroom.
Welcome to 27 Windy Ridge located in the Trumbull Center section of town. This beautiful cape has a spectacular leveled backyard that is fully fenced in with a fire pit and shed that has running electricity. This shed adds to the aesthetic of the backyard. The two full bathrooms have been completely renovated. One in 2018 & one in 2019 consecutively. This home boasts over 2500 square feet of space on the first and second floors. Hardwood lines the first level with a gas fireplace in the living room. The kitchen has beautiful granite countertops with an island. The open sunroom is right off of the kitchen which leads out to your own private deck. One of the bedrooms on the main level has a bay window. Three bedrooms on the main level. There is a sitting area off of one of the bedrooms on the second level with access to the bathroom area that also has a door for the private use of shower and toilet. The basement has been freshly painted and newly carpeted. This property is not to be missed. Exclusions: Lockers and metal cabinets in garage, red cabinets & shelves in laundry area, potted plants in yard and on deck, wall dcor unit in main bathroom.
27 Windy Rdg, Trumbull, CT 06611 is a 5 bedroom, 2 bathroom, 2,566 sqft single-family home in Trumbull Center, built in 1952. It last sold for $530,000 on Jul 16, 2021. It is currently off market. The Trulia Estimate is $787,900, with a rent estimate of $4,771/month.
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 Windy Rdg
|
|---|
Interior Details BasementNumber of Rooms: 9 |
Heating & Cooling Heating: Other, OilAir ConditioningHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Fireplace & Spa Fireplace |
|
|---|
Exterior Home Features Roof: AsphaltDeckExterior: Wood |
Parking & Garage GarageParking: Garage Attached |
|
|---|
Year Built Year Built: 1952 |
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod |
|
|---|
Units in Building: 1 |
|
|---|
Lot Area: 0.31 acres |
Price History for 27 Windy Rdg
| Date | Price | Event | Source |
|---|---|---|---|
| 07/16/2021 | $530,000 | Sold | Smart MLS #170399504 |
| 05/25/2021 | $489,000 | Pending | RE/MAX International #170399504 |
| 05/25/2021 | $489,000 | Contingent | Smart MLS #170399504 |
| 05/20/2021 | $489,000 | Listed For Sale | Smart MLS #170399504 |
| 07/06/2005 | $483,500 | Sold | Smart MLS #98218963 |
| 10/30/2001 | $377,500 | Sold | Smart MLS #98110082 |
| 05/27/1998 | $237,500 | Sold | N/A |
| 05/31/1989 | $230,000 | Sold | N/A |
Market trends in Trumbull
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
74
8MoM
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,870 |
| Assessment | $321,510 |
Home facts updated by county records
Comparable Sales for 27 Windy Rdg
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.04 | Single-Family Home | $831,000 | 03/23/26 | 3 | 2.5 | 2,259 | |
0.07 | Single-Family Home | $685,000 | 09/17/25 | 3 | 2 | 1,658 | |
0.39 | Single-Family Home | $610,000 | 12/05/25 | 4 | 2.5 | 2,540 | |
0.40 | Single-Family Home | $675,000 | 07/31/25 | 3 | 2 | 2,524 | |
0.23 | Single-Family Home | $610,000 | 06/15/26 | 4 | 2.5 | 2,716 | |
0.12 | Single-Family Home | $950,000 | 01/06/26 | 4 | 4 | 3,862 | |
0.24 | Single-Family Home | $720,000 | 06/04/26 | 3 | 2 | 1,440 | |
0.49 | Single-Family Home | $650,000 | 09/05/25 | 4 | 3 | 2,143 | |
0.54 | Single-Family Home | $565,000 | 07/30/25 | 3 | 2 | 1,912 | |
0.19 | Single-Family Home | $600,000 | 05/08/26 | 3 | 2 | 1,479 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDMAR 23, 2026BHGRE Gaetano Marra Homes
OFF MARKETRE/MAX Right Choice
SOLDJAN 6, 2026BHGRE Gaetano Marra Homes
OFF MARKETKeller Williams Realty
OFF MARKETCarbutti & Co., Realtors
OFF MARKETDouglas Elliman of Connecticut
SOLDMAY 8, 2026Berkshire Hathaway NE Prop.
SOLDJUN 15, 2026RE/MAX Right Choice
SOLDJUN 4, 2026Berkshire Hathaway NE Prop.
Assigned Schools
These are the assigned schools for 27 Windy Rdg.
- Madison Middle School
- 6-8
- Public
- 857 Students
8/10GreatSchools RatingParent Rating AverageWorst school ever go to Hillcrest. I don't care if madison is closer, I'm telling you, for your mental health go to Hillcrest....Parent Review4y ago - Trumbull High School
- 9-12
- Public
- 2152 Students
10/10GreatSchools RatingParent Rating Averageterrible school always looking to get the kids who have a reputation into trouble, i’ve been searched over 7 times at this school and none of the time was there ever any contraband on me. From dean down to the police stationed there it is terrible and needs a lot of work, they discriminate against people based on their reputation and are more worried about how they look compared to how the kids are prepared for the next step.Student Review2y ago - Frenchtown Elementary
- K-5
- Public
- 516 Students
9/10GreatSchools RatingParent Rating AverageI had heard great things about this school when we were looking for a rental house. Now that my child is in this school, it is the worst school ever. The principal is horrible and could care less about what my child is going through. She has threatened us because of him missing some days. This school has given him a lot of stress and has hurt him emotionally. If I could get him out I would but I have no other option right now. Good thing it is only one year. Stay away from here.Parent Review2y ago 
Check out schools near 27 Windy Rdg.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Trumbull Center
At least 2 Trulia users voted on each feature.
100 % Say there's wildlife
100 % Say it's dog friendly
100 % Say they plan to stay for at least 5 years
100 % Say there's holiday spirit
100 % Say yards are well-kept
100 % Say parking is easy
75 % Say it's quiet
67 % Say kids play outside
67 % Say people would walk alone at night
67 % Say car is needed
60 % Say neighbors are friendly
50 % Say there are sidewalks
50 % Say streets are well-lit
50 % Say it's walkable to grocery stores
50 % Say there are community events
33 % Say it's walkable to restaurants
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
NEW - 1 DAY AGOPET FRIENDLYTotal price$1,935 - $3,390/mo1-3 bd1-2 baThe Royce at Trumbull | 100 Avalon Gates #1211,
Trumbull, CT 06611
PET FRIENDLYTotal price$2,536 - $3,800/mo1-2 bd1-3 baWoodside Trumbull | 100 Woodside Ct #2205,
Trumbull, CT 06611
PET FRIENDLY$2,345 - $3,200/moFees may apply1-2 bd1-2 baThe Residences at Main | 5085 Main St #10,
Trumbull, CT 06611
PET FRIENDLYTotal price$1,835 - $2,035/moStudio-1 bd1-2 baBrookside Gardens | 150 Anton St #130-C3,
Bridgeport, CT 06606
PET FRIENDLYINCOME RESTRICTED
PET FRIENDLY
PET FRIENDLY
PET FRIENDLY$2,469 - $3,229/moFees may apply1-2 bd1-2 baTen Trumbull | 100 Oakview Dr #f9b251641,
Trumbull, CT 06611
PET FRIENDLY
See more homes for rent inTrumbull
Explore by feature - Air Conditioning
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYTotal price$1,935 - $3,390/mo1-3 bd1-2 baThe Royce at Trumbull | 100 Avalon Gates #1211,
Trumbull, CT 06611 - SPECIAL OFFERPET FRIENDLYTotal price$2,536 - $3,800/mo1-2 bd1-3 baWoodside Trumbull | 100 Woodside Ct #2205,
Trumbull, CT 06611 - PET FRIENDLY$2,469 - $3,229/moFees may apply1-2 bd1-2 baTen Trumbull | 100 Oakview Dr #f9b251641,
Trumbull, CT 06611 
NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLY
PET FRIENDLY
Explore by feature - Pool
- SPECIAL OFFERPET FRIENDLY$2,345 - $3,200/moFees may apply1-2 bd1-2 baThe Residences at Main | 5085 Main St #10,
Trumbull, CT 06611 - NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYTotal price$1,935 - $3,390/mo1-3 bd1-2 baThe Royce at Trumbull | 100 Avalon Gates #1211,
Trumbull, CT 06611 - SPECIAL OFFERPET FRIENDLYTotal price$2,536 - $3,800/mo1-2 bd1-3 baWoodside Trumbull | 100 Woodside Ct #2205,
Trumbull, CT 06611 - PET FRIENDLY$2,469 - $3,229/moFees may apply1-2 bd1-2 baTen Trumbull | 100 Oakview Dr #f9b251641,
Trumbull, CT 06611 - APPLY INSTANTLY
Explore by feature - Washer/dryer
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYTotal price$1,935 - $3,390/mo1-3 bd1-2 baThe Royce at Trumbull | 100 Avalon Gates #1211,
Trumbull, CT 06611 - SPECIAL OFFERPET FRIENDLYTotal price$2,536 - $3,800/mo1-2 bd1-3 baWoodside Trumbull | 100 Woodside Ct #2205,
Trumbull, CT 06611 - PET FRIENDLY$2,469 - $3,229/moFees may apply1-2 bd1-2 baTen Trumbull | 100 Oakview Dr #f9b251641,
Trumbull, CT 06611 - NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLY
NEW - 2 DAYS AGOAPPLY INSTANTLY
APPLY INSTANTLY- APPLY INSTANTLY
- PET FRIENDLY
Homes for sale near 27 Windy Rdg
OPEN SUN, 12-2PM0.33 ACRESPreston Gray Real Estate
NEW - 2 DAYS AGO0.66 ACRESEquity Realty Group, LLC
0.53 ACRESCarbutti & Co., Realtors
See more homes for sale inTrumbull
Off Market Homes Near 27 Windy Rdg
SOLDJUL 2, 2026Roundtree Realty LLC
SOLDJUL 2, 2026Preston Gray Real Estate
SOLDJUL 2, 2026RE/MAX Right Choice
SOLDJUL 1, 2026William Raveis Real Estate
SOLDJUL 1, 2026Luxe Realty LLC
SOLDJUL 1, 2026Davis Owen Real Estate
SOLDJUL 1, 2026William Raveis Real Estate
SOLDJUL 1, 2026Century 21 AllPoints Realty
SOLDJUL 1, 2026Coldwell Banker Realty
SOLDJUL 1, 2026RE/MAX Right Choice- See more homes for sale inTrumbull