66 Winterbrook Rd
Wolcott, CT 06716
5 Beds
5.5 Baths
5,684 sqft (on 1.25 acres)
5 Beds
5.5 Baths
5,684 sqft
(on 1.25 acres)
Local Information
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Description
Welcome to the house of your dreams, this oversized colonial boasts almost 6000 sq feet sitting on just about 1.25 acres in Wolcott's finest neighborhood. Enjoy top rated schools and all the local amenities. As you walk in you are greeted by high ceilings and a open renovated kitchen with all stainless steel appliances. Too many extras to list which include a steam room, fitness area, wine cellar, high efficiency fire place, hot tub etc. The roof is just about 6 years old, mechanics all newer and regularly serviced. The downstairs features an in-law suite which was recently renovated connecting to your own personal sports bar. Most of the items in the house are going to be sold and can be negotiated as a separate agreement. There is a few buttoning up items need to be done which can be negotiated, this is a finisher upper not a fixer upper. Come take a look and bring offers, this will not last long.
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
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 66 Winterbrook Rd
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Interior Details BasementNumber of Rooms: 9 |
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2 |
Appliances & Utilities DishwasherDisposalMicrowaveRefrigerator |
Fireplace & Spa FireplaceHot Tub or Spa |
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Year Built Year Built: 1992 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Exterior Home Features DeckExterior: OtherPatio |
Parking & Garage GarageParking Spaces: 3Parking: Garage Attached |
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Units in Building: 1 |
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Lot Area: 1.25 acres |
Price History for 66 Winterbrook Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 08/28/2019 | $370,000 | Sold | Smart MLS #170195306 |
| 06/26/2019 | $379,000 | PriceChange | Agent Provided |
| 06/06/2019 | $399,000 | PriceChange | Agent Provided |
| 06/04/2019 | $425,000 | PriceChange | Agent Provided |
| 05/30/2019 | $450,000 | PriceChange | Agent Provided |
| 05/29/2019 | $475,000 | PriceChange | Agent Provided |
| 05/15/2019 | $525,000 | Listed For Sale | Agent Provided |
| 01/20/2010 | $488,000 | Sold | Smart MLS #G538128 |
Market trends in Wolcott
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
52
14MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $14,439 |
| Assessment | $401,870 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$5,451/mo
Comparable Sales for 66 Winterbrook Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.11 | Single-Family Home | $550,000 | 07/18/25 | 3 | 3 | 2,804 | |
0.76 | Single-Family Home | $465,500 | 07/30/25 | 4 | 3 | 3,852 | |
0.37 | Single-Family Home | $550,000 | 03/20/26 | 3 | 3 | 2,415 | |
0.86 | Single-Family Home | $605,000 | 12/12/25 | 6 | 3.5 | 4,296 | |
0.27 | Single-Family Home | $345,000 | 06/11/26 | 3 | 2 | 1,736 | |
0.92 | Single-Family Home | $1,200,000 | 07/02/25 | 4 | 3.5 | 4,270 | |
0.86 | Single-Family Home | $510,000 | 04/28/26 | 3 | 2.5 | 2,616 | |
0.53 | Single-Family Home | $550,000 | 08/12/25 | 3 | 2.5 | 2,083 | |
0.77 | Single-Family Home | $399,900 | 01/09/26 | 3 | 2 | 1,340 | |
0.47 | Single-Family Home | $330,000 | 03/12/26 | 3 | 1.5 | 1,344 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETSerhant Connecticut, LLC
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Assigned Schools
These are the assigned schools for 66 Winterbrook Rd.
- Tyrrell Middle School
- 6-8
- Public
- 510 Students
6/10GreatSchools RatingParent Rating AverageI have never met a student who is happy at tms. As a former student, teachers always say they are there for you, but are not understanding of students and their conditions at all! Kids here are ruthless, and there is no control over the school.Other Review5y ago - Alcott School
- PK-5
- Public
- 298 Students
8/10GreatSchools RatingParent Rating AverageAlcott School is a terrific school. I recommend it highly. It was also recently named the Most Outstanding Elementary School in CT.Parent Review10y ago - Wolcott High School
- 9-12
- Public
- 649 Students
6/10GreatSchools RatingParent Rating AverageI moved here from New York during my junior year, and I can honestly say I do not like this school at all. Starting with safety it’s terrible. At my old school in Long Island, we had to scan our student IDs just to get in the building. Here? Anyone can walk right in with the crowd in the morning, no questions asked. We even had an incident where a student from another school came in and no one noticed until an actual student pointed it out. If you care about school security, this is not the place. Academics are just okay. If you’re expecting one of the top schools, this isn’t it. Coming from one of the best public schools in Long Island, I had high expectations and they weren’t met. If you're looking for a school where most students go off to top colleges or even just college in general, this probably won’t be a great fit. Some teachers are great and supportive, but like every school, some really aren’t.What really brings this school down is how overly strict they are with policies, especially lateness and attendance. You’re allowed only six excused latenesses a year. After that, even if you have a doctor’s note or verified reason, they give you detention. I personally got detention for being late because of migraines, even though I’m on medication and the school is aware. They just don’t care.Same goes for attendance, if you miss too many days (even with a valid excuse), they can make you retake the class. As a senior, it’s frustrating trying to meet unrealistic expectations while dealing with college applications and senioritis.Overall, I wouldn’t recommend this school. If I could switch, I would. There are way better options out there, don’t settle. You’d only be making things harder for yourself and your child.Student Review1y ago 
Check out schools near 66 Winterbrook Rd.
What Locals Say about Wolcott
At least 63 Trulia users voted on each feature.
92 % Say car is needed
91 % Say yards are well-kept
88 % Say parking is easy
85 % Say there's holiday spirit
81 % Say it's dog friendly
79 % Say there's wildlife
68 % Say it's quiet
68 % Say kids play outside
60 % Say they plan to stay for at least 5 years
55 % Say people would walk alone at night
54 % Say neighbors are friendly
29 % Say streets are well-lit
27 % Say it's walkable to grocery stores
24 % Say it's walkable to restaurants
22 % Say there are community events
14 % Say there are sidewalks
Sourced by Trulia users. Learn more about our methodology.
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Off Market Homes Near 66 Winterbrook Rd
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66 Winterbrook Rd, Wolcott, CT 06716 is a 5 bedroom, 6 bathroom, 5,684 sqft single-family home built in 1992. This property is not currently available for sale. 66 Winterbrook Rd was last sold on Aug 28, 2019 for $370,000. The current Trulia Estimate for 66 Winterbrook Rd is $847,600.