5 Bailey Rd
Chester, CT 06412
3 Beds
1 Bath
990 sqft (on 0.32 acres)
3 Beds
1 Bath
990 sqft
(on 0.32 acres)
Local Information
© Google
-- mins to
Description
This single-family home is located at 5 Bailey Rd, Chester, CT. 5 Bailey Rd is in Chester, CT and in ZIP code 06412. This property has 3 bedrooms, 1 bathroom and approximately 990 sqft of floor space. This property has a lot size of 0.32 acres and was built in 1959.
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
No Info
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 5 Bailey Rd
|
|---|
Interior Details BasementNumber of Rooms: 5 |
Heating & Cooling Heating: Other, OilHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 1 |
Fireplace & Spa Hot Tub or Spa |
|
|---|
Exterior Home Features Roof: AsphaltDeckExterior: Other, Wood |
|
|---|
Year Built Year Built: 1959Year Updated: 1982 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
|
|---|
Lot Area: 0.32 acres |
Price History for 5 Bailey Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 12/21/1987 | $142,000 | Sold | N/A |
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $4,250 |
| Assessment | $156,940 |
Home facts updated by county records
Comparable Sales for 5 Bailey Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.31 | Single-Family Home | $220,000 | 04/21/26 | 3 | 1 | 748 | |
0.25 | Single-Family Home | $875,000 | 07/25/25 | 4 | 3 | 3,206 | |
1.57 | Single-Family Home | $436,000 | 07/31/25 | 3 | 2 | 1,270 | |
2.24 | Single-Family Home | $319,900 | 01/20/26 | 3 | 1 | 912 | |
1.23 | Single-Family Home | $525,000 | 07/25/25 | 3 | 2.5 | 2,272 | |
2.26 | Single-Family Home | $273,000 | 10/07/25 | 3 | 1 | 1,048 | |
2.22 | Single-Family Home | $220,000 | 02/03/26 | 2 | 1 | 1,200 | |
1.52 | Single-Family Home | $715,000 | 03/06/26 | 3 | 2.5 | 2,139 | |
1.54 | Single-Family Home | $610,000 | 12/01/25 | 3 | 2.5 | 2,324 | |
1.44 | Single-Family Home | $580,000 | 12/10/25 | 2 | 3 | 3,091 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETWilliam Raveis Real Estate
OFF MARKETWilliam Raveis Real Estate
SOLDAPR 21, 2026Exceptional Real Estate LLC
OFF MARKETWilliam Raveis Real Estate
OFF MARKETRe/Max Valley Shore
OFF MARKETOur Home Realty Advisors
OFF MARKETWilliam Raveis Real Estate
Assigned Schools
These are the assigned schools for 5 Bailey Rd.
- John Winthrop Middle School
- 7-8
- Public
- 238 Students
4/10GreatSchools RatingParent Rating AverageI think bullying was the worst problem that happened during my time at JWMS. The adult authorities at the school had a difficult time understanding situations and that often made it worse. I'm also not stating that it was just the kids at the school who would bully but it was also teachers. I remember my 8th grade science teacher would verbally bully girls and pick on them, and it was always girls he was picking on. I was one of them. It didn't help that I had a counselor who couldn't care less if one of there students just jumped off a bridge. They could care less of there students well being, and the same goes with the principles. I honestly would recommend going to a different school, I mean unless you want your child to become depressed.Other Review8y ago - Valley Regional High School
- 9-12
- Public
- 489 Students
7/10GreatSchools RatingParent Rating AverageI enjoyed going to Valley. It is different as a parent I see things differently. However compared to other schools I would say Valley is above the rest.Parent Review7y ago - Chester Elementary School
- PK-6
- Public
- 222 Students
7/10GreatSchools RatingParent Rating AverageCES has a lot of potential with the proper leadership, which it lacks.Other Review6y ago 
Check out schools near 5 Bailey Rd.
What Locals Say about Chester
At least 14 Trulia users voted on each feature.
95 % Say car is needed
94 % Say it's dog friendly
93 % Say there's holiday spirit
93 % Say yards are well-kept
84 % Say people would walk alone at night
79 % Say parking is easy
78 % Say they plan to stay for at least 5 years
74 % Say it's walkable to restaurants
74 % Say there's wildlife
69 % Say it's quiet
63 % Say neighbors are friendly
59 % Say there are sidewalks
52 % Say kids play outside
44 % Say streets are well-lit
37 % Say there are community events
18 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
Homes for sale near 5 Bailey Rd
2.3 ACRESWilliam Pitt Sotheby's Int'l
FORECLOSURE0.33 ACRESRealhome Services & Solutions
NEW - 1 DAY AGO1.38 ACRESWilliam Pitt Sotheby's Int'l
See more homes for sale inChester
Off Market Homes Near 5 Bailey Rd
SOLDMAY 21, 2026Coldwell Banker Realty
SOLDMAY 15, 2026Sailpoint Property Group
SOLDAPR 30, 2026Compass Connecticut, LLC
SOLDAPR 30, 2026Eagle Eye Realty PLLC
SOLDAPR 28, 2026Williams Realty Services- SOLDAPR 21, 2026Exceptional Real Estate LLC
SOLDAPR 16, 2026Re/Max Valley Shore
SOLDMAR 31, 2026Coldwell Banker Realty- SOLDMAR 26, 2026
SOLDMAR 25, 2026William Pitt Sotheby's Int'l- See more homes for sale inChester
Homes for rent near 5 Bailey Rd
22.45 ACRES
See more homes for rent inChester
5 Bailey Rd, Chester, CT 06412 is a 3 bedroom, 1 bathroom, 990 sqft single-family home built in 1959. This property is not currently available for sale. 5 Bailey Rd was last sold on Dec 21, 1987 for $142,000. The current Trulia Estimate for 5 Bailey Rd is $337,000.