256 Winthrop Rd
Deep River, CT 06417
3 Beds
2 Baths
1,898 sqft (on 75.50 acres)
3 Beds
2 Baths
1,898 sqft
(on 75.50 acres)
Local Information
- Map ViewExplore the area around 256 Winthrop Rd.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1860
Lot Size
75.5 acres
Living Area
1,898 sqft
Price/Sqft
$620
About this House
This single-family home is located at 256 Winthrop Rd, Deep River, CT. 256 Winthrop Rd is in Deep River, CT and in ZIP code 06417. This property has 3 bedrooms, 2 bathrooms and approximately 1,898 sqft of floor space. This property has a lot size of 75.50 acres and was built in 1860.
256 Winthrop Rd, Deep River, CT 06417 is a 3 bedroom, 2 bathroom, 1,898 sqft single-family home built in 1860. It last sold for $580,000 on May 14, 2014. It is currently off market. The Trulia Estimate is $1,176,100, with a rent estimate of $3,029/month.
Home Details for 256 Winthrop Rd
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Interior Details BasementAtticNumber of Rooms: 7 |
Heating & Cooling Heating: GasHeating Fuel: Gas |
Levels, Entrance, & Accessibility Stories: 2 |
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Exterior Home Features Roof: AsphaltExterior: WoodPatio |
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Year Built Year Built: 1860 |
Property Type / Style Property Type: Single Family HomeArchitecture: Old Style |
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Units in Building: 1 |
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Lot Area: 75.50 acres |
Price History for 256 Winthrop Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 05/14/2014 | $580,000 | Sold | Smart MLS #M9124757 |
Market trends in Deep River
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
21
7MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $17,498 |
| Assessment | $547,150 |
Home facts updated by county records
Comparable Sales for 256 Winthrop Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.73 | Single-Family Home | $450,000 | 01/15/26 | 3 | 2 | 1,958 | |
0.78 | Single-Family Home | $600,000 | 12/22/25 | 3 | 2 | 1,414 | |
0.72 | Single-Family Home | $605,000 | 04/29/26 | 4 | 3 | 2,969 | |
0.96 | Single-Family Home | $450,000 | 05/22/26 | 3 | 2 | 1,789 | |
0.61 | Single-Family Home | $825,000 | 11/18/25 | 4 | 3.5 | 3,697 | |
0.88 | Single-Family Home | $700,000 | 10/29/25 | 4 | 2.5 | 2,828 | |
1.00 | Single-Family Home | $730,000 | 07/29/26 | 3 | 2.5 | 2,848 | |
1.28 | Single-Family Home | $441,000 | 05/21/26 | 3 | 1.5 | 2,283 | |
1.23 | Single-Family Home | $414,900 | 12/23/25 | 3 | 1.5 | 1,432 | |
1.20 | Single-Family Home | $385,000 | 11/04/25 | 3 | 2.5 | 2,179 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETWilliam Raveis Real Estate
OFF MARKETWilliam Raveis Real Estate
SOLDNOV 18, 2025William Pitt Sotheby's Int'l
SOLDAPR 29, 2026Compass Connecticut, LLC
SOLDJAN 15, 2026William Raveis Real Estate
OFF MARKETRe/Max Valley Shore
SOLDOCT 29, 2025William Raveis Real Estate
Assigned Schools
These are the assigned schools for 256 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 256 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 256 Winthrop Rd
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Off Market Homes Near 256 Winthrop Rd
SOLDAUG 7, 2026William Raveis Real Estate
SOLDAUG 3, 2026William Pitt Sotheby's Int'l
SOLDAUG 3, 2026William Pitt Sotheby's Int'l
SOLDJUL 31, 2026William Raveis Real Estate
SOLDJUL 31, 2026William Pitt Sotheby's Int'l
SOLDJUL 30, 2026William Pitt Sotheby's Int'l
SOLDJUL 29, 2026William Raveis Real Estate
SOLDJUL 24, 2026William Pitt Sotheby's Int'l
SOLDJUL 24, 2026William Pitt Sotheby's Int'l- SOLDJUL 24, 2026Compass Connecticut, LLC
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Frequently asked questions about 256 Winthrop Rd
- What is 256 Winthrop Rd estimated to be worth?Trulia's estimated value for 256 Winthrop Rd in Deep River, CT is $1,176,100.
- What is the price history for 256 Winthrop Rd?256 Winthrop Rd in Deep River, CT last sold for $580,000 in May 2014.
- 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.
- How big is the lot at 256 Winthrop Rd?The lot at 256 Winthrop Rd in Deep River, CT is about 75.5 acres.