39 Winthrop Road
Deep River, CT 06417
3 Beds
3.5 Baths
3,478 sqft (on 12.45 acres)
3 Beds
3.5 Baths
3,478 sqft
(on 12.45 acres)
Local Information
- Map ViewExplore the area around 39 Winthrop Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1985
Lot Size
12.45 acres
Living Area
3,478 sqft
Price/Sqft
$695
Parking
Garage
About this House
A Rare Find! An amazing home in a special setting! Totally redone and updated 3,500 sqft. home, set upon a hill overlooking 3 ponds, 2 covered bridges, and a waterwheel. The main house has an open floor plan, huge eat-in kitchen, 5 fireplaces, generous Primary Suite with custom bath, spacious walk-in closet, and "Silo" sitting area or home office. The lower level has been finished with a Gym, or Cardio Room, Sauna & Full bath which could easily become additional bedrooms or other living area. An abundance of outdoor entertainment is available with a large Stone & Brick patio with a built-in fireplace, and a heated in-ground pool with Gazebo and Cabana. Additional features include Central air, Central Vac, Irrigation System, and a whole house generator system. 2 beautiful garages. One 3,000 sqft. 5 car garage with spacious shop area and a 1,000 sqft. apartment above. One 1,400 sqft. 4 car garage with 700 sqft. apartment above. Each apartment can be guest accommodations, an in law apartment or provide rental income. All privately set on over 12 acres.
39 Winthrop Road, Deep River, CT 06417 is a 3 bedroom, 4 bathroom, 3,478 sqft single-family home built in 1985. It last sold for $2,200,000 on Feb 14, 2025 (12% below the $2,495,000 asking price). It is currently off market. The Trulia Estimate is $2,416,000, with a rent estimate of $5,302/month.
Home Details for 39 Winthrop Road
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Interior Details Basement: Full,FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Other, Rec Play Room, Sun Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 3478 Square Feet |
Appliances & Utilities Appliances: Oven/Range, Refrigerator, Washer, Dryer, Wine Cooler, Water HeaterDryerLaundry: Upper LevelRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 5Has a Fireplace |
Windows, Doors, Floors & Walls Window: Thermopane Windows |
View Has a ViewView: Water |
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Exterior Home Features Roof: Asphalt FiberglassPatio / Porch: Enclosed, Porch, PatioOther Structures: Gazebo, CabanaFoundation: Concrete PerimeterHas a Private Pool |
Parking & Garage Number of Garage Spaces: 9Number of Covered Spaces: 9No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 9Parking: Barn,Detached,Paved,Driveway |
Pool Pool: Heated, In GroundPool |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 3478 Square Feet |
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Year Built Year Built: 1985 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 2644594 |
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Price List Price: $2,495,000 |
Status Change & Dates Off Market Date: Fri Feb 14 2025Possession Timing: . |
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MLS Status: Closed |
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Direction & Address City: Deep RiverCommunity: Winthrop |
School Information Elementary School: Deep RiverHigh School: Per Board of Ed |
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Buyer Agent Buyer Company Name: The One Team At William Raveis Real Estate |
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Building Area Building Area: 3478 Square Feet |
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No HOA |
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Lot Area: 12.45 Acres |
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Energy Efficiency Features: Windows |
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BasementMls Number: 24037674Attic: NoneWater ViewWater View: WaterAbove Grade Unfinished Area: 3478 |
Last check for updates: about 3 hours ago
Listed by Craig Milton, (860) 391-3811
Re/Max Valley Shore, (860) 388-1228
Bought with: Amber Bova, (860) 801-3474, William Raveis Real Estate, (203) 453-0391
Source: Smart MLS, MLS#24037674
Price History for 39 Winthrop Road
| Date | Price | Event | Source |
|---|---|---|---|
| 02/14/2025 | $2,200,000 | Sold | Smart MLS #24037674 |
| 10/07/2024 | $2,495,000 | PriceChange | Smart MLS #24037674 |
| 09/13/2024 | $2,950,000 | PriceChange | Smart MLS #24037674 |
| 08/19/2024 | $3,200,000 | Listed For Sale | Smart MLS #24037674 |
Market trends in Deep River
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
7MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $30,033 |
| Assessment | $939,120 |
Home facts updated by county records
Comparable Sales for 39 Winthrop Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.45 | Single-Family Home | $450,000 | 01/15/26 | 3 | 2 | 1,958 | |
0.52 | Single-Family Home | $441,000 | 05/21/26 | 3 | 1.5 | 2,283 | |
0.92 | Single-Family Home | $640,000 | 12/19/25 | 4 | 2.5 | 2,550 | |
0.49 | Single-Family Home | $419,588 | 02/03/26 | 2 | 1 | 1,100 | |
1.24 | Single-Family Home | $825,000 | 11/18/25 | 4 | 3.5 | 3,697 | |
1.14 | Single-Family Home | $775,000 | 04/15/26 | 3 | 4 | 2,611 | |
1.22 | Single-Family Home | $650,000 | 11/10/25 | 3 | 2.5 | 2,816 | |
1.49 | Single-Family Home | $847,000 | 06/25/26 | 3 | 3.5 | 3,476 | |
1.16 | Single-Family Home | $600,000 | 05/28/26 | 4 | 3 | 2,062 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDJAN 15, 2026William Raveis Real Estate
SOLDMAY 21, 2026Coldwell Banker Realty
OFF MARKETWilliam Raveis Real Estate
OFF MARKETColdwell Banker Realty
OFF MARKETWilliam Raveis Real Estate
OFF MARKETWilliam Raveis Real Estate
SOLDDEC 19, 2025Re/Max Valley Shore
FOR SALE4.4 ACRESWilliam Raveis Real Estate
Assigned Schools
These are the assigned schools for 39 Winthrop Road.
- 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 39 Winthrop Road.
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 39 Winthrop Road
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Off Market Homes Near 39 Winthrop Road
SOLDAUG 7, 2026William Raveis Real Estate
SOLDJUL 11, 2026William Pitt Sotheby's Int'l
SOLDJUN 4, 2026William Raveis Real Estate
SOLDMAY 15, 2026
SOLDAPR 7, 2026William Pitt Sotheby's Int'l- SOLDMAR 6, 2026
SOLDJAN 27, 2026William Pitt Sotheby's Int'l
SOLDDEC 12, 2025William Raveis Real Estate- See more homes for sale inDeep River
Frequently asked questions about 39 Winthrop Road
- What is 39 Winthrop Road estimated to be worth?Trulia's estimated value for 39 Winthrop Road in Deep River, CT is $2,416,000.
- What is the price history for 39 Winthrop Road?39 Winthrop Road in Deep River, CT last sold for $2,200,000 in February 2025.
- 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 39 Winthrop Road have air conditioning?Yes, 39 Winthrop Road in Deep River, CT has air conditioning.
- Does 39 Winthrop Road have a pool?Yes, 39 Winthrop Road in Deep River, CT has a pool.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.