585 Winthrop Rd
Deep River, CT 06417
3 Beds
3.5 Baths
2,112 sqft (on 3.18 acres)
3 Beds
3.5 Baths
2,112 sqft
(on 3.18 acres)
Local Information
- Map ViewExplore the area around 585 Winthrop Rd.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1997
Lot Size
3.18 acres
Living Area
2,112 sqft
Price/Sqft
$324
Parking
Garage
About this House
Beautiful serene country living yet minutes to civilization! Tucked away in the heart of historic WINTHROP, this modern ranch has everything you could possible want in a home! Close to CEDAR LAKE & CHATFIELD HOLLOW STATE PARK, this location has many fun activities in DEEP RIVER & ESSEX. Experience dramatic sunsets and spectacular views over TOWER HILL LAKE. Popular "open plan" concept is ideal for entertaining large gatherings be it holiday's or other special events. Love to cook? This kitchen is for you An abundance of custom cabinetry,attractive granite counters and island is great for guests to gather around. Vaulted ceilings give the great room a spacious feel offering spectacular views and sunsets with TOWER HILL LAKE in the background.Custom bar area with wine rack & built ins make happy hour a snap! A beautiful brick fireplace heats up the room nicely during chilly early Spring.The master bedroom is strategically placed on the opposite side of the main bedrooms giving the owners privacy and overlooks the natural surroundings.The other 2 bedrooms share a full bathroom . First floor laundry in located in the mud room area. Go Green! Energy efficient solar panels help reduce electric costs and saves the environment. These panels are owned NOT leased. Take a stroll down to the waterfront with 50' lake access enjoy watching the BLUE HERONS, EAGLES and other local waterfowl. This is an amazing and truly one of kind home 40 Minutes to HARTFORD- NEW HAVEN make commuting easy.
585 Winthrop Rd, Deep River, CT 06417 is a 3 bedroom, 4 bathroom, 2,112 sqft single-family home built in 1997. It last sold for $415,000 on Jul 31, 2018. It is currently off market. The Trulia Estimate is $683,900, with a rent estimate of $3,766/month.
Home Details for 585 Winthrop Rd
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Interior Details BasementAtticNumber of Rooms: 5Types of Rooms: Dining Room, Laundry Room |
Heating & Cooling Heating: Other, Stove, CoalAir ConditioningCooling System: CentralHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 1Floors: Tile, Carpet, Hardwood |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
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Exterior Home Features Roof: OtherDeckExterior: Vinyl |
Parking & Garage GarageParking Spaces: 2Parking: Garage Detached |
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Year Built Year Built: 1997 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
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Units in Building: 1 |
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Lot Area: 3.18 acres |
Price History for 585 Winthrop Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 07/31/2018 | $415,000 | Sold | Smart MLS #170075391 |
| 06/11/2018 | $425,000 | Pending | Agent Provided |
| 04/23/2018 | $425,000 | Listed For Sale | Agent Provided |
| 06/30/2014 | $410,000 | Sold | Smart MLS #M9146459 |
| 05/16/2014 | $449,000 | Pending | Agent Provided |
| 04/11/2014 | $449,000 | PriceChange | Agent Provided |
| 04/02/2014 | $465,000 | Listed For Sale | Agent Provided |
| 07/29/2005 | $439,000 | Sold | N/A |
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 | $9,131 |
| Assessment | $285,530 |
Home facts updated by county records
Comparable Sales for 585 Winthrop Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.31 | Single-Family Home | $480,000 | 09/16/25 | 3 | 2.5 | 2,550 | |
0.65 | Single-Family Home | $660,000 | 10/21/25 | 3 | 2.5 | 2,386 | |
0.67 | Single-Family Home | $750,000 | 07/13/26 | 3 | 3 | 2,231 | |
0.76 | Single-Family Home | $610,000 | 05/12/26 | 3 | 2.5 | 1,887 | |
0.95 | Single-Family Home | $450,000 | 05/22/26 | 3 | 2 | 1,789 | |
1.13 | Single-Family Home | $605,000 | 04/29/26 | 4 | 3 | 2,969 | |
1.30 | Single-Family Home | $600,000 | 04/08/26 | 3 | 2.5 | 1,728 | |
1.14 | Single-Family Home | $825,000 | 11/18/25 | 4 | 3.5 | 3,697 | |
0.21 | Single-Family Home | $300,000 | 04/30/26 | 2 | 1 | 650 | |
1.22 | Single-Family Home | $700,000 | 10/29/25 | 4 | 2.5 | 2,828 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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SOLDJUL 13, 2026William Pitt Sotheby's Int'l
Assigned Schools
These are the assigned schools for 585 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 585 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 585 Winthrop Rd
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Off Market Homes Near 585 Winthrop Rd
SOLDJUL 31, 2026William Raveis Real Estate
SOLDJUL 31, 2026William Pitt Sotheby's Int'l
SOLDJUL 31, 2026Real Broker CT, LLC
SOLDJUL 29, 2026William Raveis Real Estate
SOLDJUL 24, 2026Berkshire Hathaway NE Prop.
SOLDJUL 24, 2026William Raveis Real Estate
SOLDJUL 24, 2026William Pitt Sotheby's Int'l- SOLDJUL 24, 2026Compass Connecticut, LLC
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Frequently asked questions about 585 Winthrop Rd
- What is 585 Winthrop Rd estimated to be worth?Trulia's estimated value for 585 Winthrop Rd in Deep River, CT is $683,900.
- What is the price history for 585 Winthrop Rd?585 Winthrop Rd in Deep River, CT last sold for $415,000 in July 2018.
- 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.
- Does 585 Winthrop Rd have air conditioning?Yes, 585 Winthrop Rd in Deep River, CT has air conditioning.
- Does 585 Winthrop Rd have laundry facilities?Yes, 585 Winthrop Rd in Deep River, CT has in-unit laundry.