495 Winthrop Rd
Deep River, CT 06417
5 Beds
2.5 Baths
2,288 sqft (on 16.69 acres)
5 Beds
2.5 Baths
2,288 sqft
(on 16.69 acres)
Local Information
- Map ViewExplore the area around 495 Winthrop Rd.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1962
Lot Size
16.69 acres
Living Area
2,288 sqft
Price/Sqft
$321
Parking
Garage
About this House
Very Private setting. Great price for a solid home on large acreage. Large eat in kitchen, fireplace in dining room kitchen area. 2nd fireplace in the living room. 4 bedrooms up. In law set up in lower level. House sits way back off Winthrop Rd (Rt 80) and offers seclusion yet you have deli shop right on 80. Only 1 other home sits back off this shared driveway. Property offers some cleared land with grass pastures. Balance is woodlands. Property could be purchased with MLS # G10065294. See listing # G10087487
495 Winthrop Rd, Deep River, CT 06417 is a 5 bedroom, 3 bathroom, 2,288 sqft single-family home built in 1962. It is currently off market. The Trulia Estimate is $734,700, with a rent estimate of $3,881/month.
Home Details for 495 Winthrop Rd
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Interior Details BasementAtticNumber of Rooms: 9Types of Rooms: Dining Room |
Heating & Cooling Heating: Baseboard, OilHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Carpet, Hardwood |
Appliances & Utilities DishwasherDryerRefrigeratorWasher |
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Exterior Home Features Roof: AsphaltExterior: Vinyl |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1962 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 2 |
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Lot Area: 16.69 acres |
Price History for 495 Winthrop Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 10/02/2015 | $339,900 | ListingRemoved | Agent Provided |
| 05/27/2015 | $339,900 | PriceChange | Agent Provided |
| 04/03/2015 | $364,900 | Listed For Sale | Agent Provided |
| 12/24/2014 | $465,000 | ListingRemoved | Agent Provided |
| 10/28/2014 | $465,000 | PriceChange | Agent Provided |
| 07/19/2014 | $525,000 | PriceChange | Agent Provided |
| 06/23/2014 | $545,000 | Listed For Sale | Agent Provided |
Market trends in Deep River
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
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Available listings
21
7MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $8,710 |
| Assessment | $272,370 |
Home facts updated by county records
Comparable Sales for 495 Winthrop Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.33 | Single-Family Home | $750,000 | 07/13/26 | 3 | 3 | 2,231 | |
0.45 | Single-Family Home | $610,000 | 05/12/26 | 3 | 2.5 | 1,887 | |
0.53 | Single-Family Home | $450,000 | 05/22/26 | 3 | 2 | 1,789 | |
0.80 | Single-Family Home | $700,000 | 10/29/25 | 4 | 2.5 | 2,828 | |
0.74 | Single-Family Home | $825,000 | 11/18/25 | 4 | 3.5 | 3,697 | |
0.72 | Single-Family Home | $480,000 | 09/16/25 | 3 | 2.5 | 2,550 | |
0.88 | Single-Family Home | $605,000 | 04/29/26 | 4 | 3 | 2,969 | |
1.00 | Single-Family Home | $600,000 | 04/08/26 | 3 | 2.5 | 1,728 | |
1.06 | Single-Family Home | $660,000 | 10/21/25 | 3 | 2.5 | 2,386 | |
0.81 | Single-Family Home | $414,900 | 12/23/25 | 3 | 1.5 | 1,432 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETKeller Williams Coastal
SOLDAPR 30, 2026Eagle Eye Realty PLLC
SOLDJUL 13, 2026William Pitt Sotheby's Int'l
OFF MARKETChiarito Real Estate LLC
OFF MARKETWilliam Raveis Real Estate
OFF MARKETPearce Real Estate
SOLDMAY 12, 2026Waterhouse Realty LLC
OFF MARKETBerkshire Hathaway NE Prop.
OFF MARKETColdwell Banker Realty
Assigned Schools
These are the assigned schools for 495 Winthrop Rd.
- John Winthrop Middle School
- 7-8
- Public
- 197 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
- 429 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 - Deep River Elementary School
- PK-6
- Public
- 189 Students
7/10GreatSchools RatingParent Rating AverageOutstanding teaching staff and principal! Very proactive in getting needed resources to each child with an awesome team approach. Focus on good citizenship. This school really fosters a great atmosphere for learning!Parent Review13y ago 
Check out schools near 495 Winthrop Rd.
What Locals Say about Deep River
At least 15 Trulia users voted on each feature.
100 % Say it's dog friendly
95 % Say car is needed
90 % Say there's wildlife
87 % Say yards are well-kept
83 % Say parking is easy
81 % Say there's holiday spirit
80 % Say kids play outside
76 % Say people would walk alone at night
76 % Say it's walkable to grocery stores
74 % Say it's walkable to restaurants
74 % Say streets are well-lit
70 % Say neighbors are friendly
57 % Say there are sidewalks
56 % Say they plan to stay for at least 5 years
53 % Say it's quiet
46 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 495 Winthrop Rd
NEW - 2 DAYS AGOAUCTION5 ACRES
OPEN SUN, 1-3PM3 ACRESBerkshire Hathaway NE Prop.
OPEN SAT, 12-2PM3 ACRESColdwell Banker Realty
4.4 ACRESWilliam Raveis Real Estate
See more homes for sale inDeep River
Off Market Homes Near 495 Winthrop Rd
SOLDJUL 31, 2026William Raveis Real Estate
SOLDJUL 31, 2026Real Broker CT, LLC
SOLDJUL 29, 2026William Raveis Real Estate
SOLDJUL 24, 2026William Raveis Real Estate
SOLDJUL 24, 2026William Pitt Sotheby's Int'l- SOLDJUL 24, 2026Compass Connecticut, LLC
- See more homes for sale inDeep River
Frequently asked questions about 495 Winthrop Rd
- What is 495 Winthrop Rd estimated to be worth?Trulia's estimated value for 495 Winthrop Rd in Deep River, CT is $734,700.
- Is Deep River a buyer's or seller's market?Deep River is currently a seller's market, based on recent for-sale activity.
- What do residents say about Deep River?Residents describe Deep River, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Deep River, CT.
- What are the closest schools to 495 Winthrop Rd?The closest schools to 495 Winthrop Rd in Deep River, CT are Deep River Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
- Does 495 Winthrop Rd have laundry facilities?Yes, 495 Winthrop Rd in Deep River, CT has in-unit laundry.
- How big is the lot at 495 Winthrop Rd?The lot at 495 Winthrop Rd in Deep River, CT is about 16.7 acres.