209 Main Street
Deep River, CT 06417
Deep River Center
9 Beds
9 Baths
4,982 sqft (on 0.45 acres)
9 Beds
9 Baths
4,982 sqft
(on 0.45 acres)
Local Information
- Map ViewExplore the area around 209 Main Street.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and carefully selected reproduction details creating warmth and authenticity. Multiple living and dining spaces unfold effortlessly, anchored by six fireplaces, including an impressive 12' natural stone Rumford. With seven spacious bedrooms-each with its own private bath-the home is uniquely suited for multi-generational living, hosting, or continued hospitality use. The third-floor suite offers a private retreat with a wood-burning fireplace, perfect for extended family or guests. A new kitchen addition further enhances flexibility, easily accommodating in-law living or private guest quarters. Curated perennial gardens, a white oak pergola, and a beautifully crafted stone terrace create a setting designed for gathering and relaxation. Enjoy evenings by the fire pit, surrounded by timeless landscape design. This property offers style, comfort and charm all amidst the local shops, restaurants, marinas, and nearby shoreline destinations-all within two hours of both NY and Boston. Previously, an Award-Winning Bed & Breakfast, and currently featuring two Airbnb guest suites with private access. The property remains ideally configured for a return to hospitality or continued income-producing use. This is a rare opportunity to own a thoughtfully expanded and highly functional Antique and Reproduction Colonial-where historic inspiration meets modern livability.
Home Highlights
Parking
Open Parking
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
$241
Listed
42 days ago
Home Details for 209 Main Street
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Interior Details Basement: Full,Storage Space,Interior Entry,ConcreteNumber of Rooms: 16Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Other |
Beds & Baths Number of Bedrooms: 9Number of Bathrooms: 9Number of Bathrooms (full): 9 |
Dimensions and Layout Living Area: 4982 Square Feet |
Appliances & Utilities Appliances: Electric Cooktop, Gas Range, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Hot Water,Natural Gas,OilHas CoolingAir Conditioning: Ductless,Window Unit(s)Has HeatingHeating Fuel: Hot Water |
Fireplace & Spa Number of Fireplaces: 6Has a Fireplace |
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Exterior Home Features Roof: AsphaltPatio / Porch: Wrap Around, Porch, PatioOther Structures: Shed(s)Exterior: Sidewalk, Rain Gutters, GardenFoundation: Concrete Perimeter, StoneGardenNo Private Pool |
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 10Parking: Driveway |
Frontage Not on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 4982 Square Feet |
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Days on Market: 42 |
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Year Built Year Built: 1845 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Antique |
Building Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 962263 |
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Price List Price: $1,199,999Price Per Sqft: $241 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: Deep River |
School Information Elementary School: Deep RiverJr High / Middle School: Per Board of Ed, Regional District 4High School: Per Board of Ed |
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Listing Agent Listing ID: 24179935 |
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Building Area Building Area: 4982 Square Feet |
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Community Features: Near Public Transport, Golf, Library, Park |
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No HOA |
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Lot Area: 0.45 acres |
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BasementMls Number: 24179935Attic: Finished, Walk-upAttribution Contact: (860) 204-7645Above Grade Unfinished Area: 4982 |
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Near Public TransportGolfLibraryPark |
Last check for updates: about 1 hour ago
Listing courtesy of Diane Devries, (860) 204-7645
William Pitt Sotheby's Int'l, (860) 204-7645
Source: Smart MLS, MLS#24179935
Also Listed on Smart MLS.
Market trends in Deep River
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
21
7MoM
Price History for 209 Main Street
| Date | Price | Event | Source |
|---|---|---|---|
| 06/01/2026 | $1,199,999 | Listed For Sale | Smart MLS #24179935 |
| 06/01/2026 | $1,199,999 | ListingRemoved | Smart MLS #24136051 |
| 10/30/2025 | $1,199,999 | Listed For Sale | Smart MLS #24136051 |
| 07/21/2022 | ListingRemoved | Smart MLS #170421090 | |
| 07/21/2021 | $950,000 | Listed For Sale | Smart MLS #170421090 |
| 07/21/2021 | ListingRemoved | Smart MLS #170318466 | |
| 07/23/2020 | $950,000 | Listed For Sale | Agent Provided |
| 01/25/2016 | $798,000 | ListingRemoved | Agent Provided |
| 07/23/2015 | $798,000 | Listed For Sale | Agent Provided |
| 01/01/2013 | $899,000 | ListingRemoved | Agent Provided |
| 08/20/2012 | $899,000 | Listed For Sale | Agent Provided |
| 07/23/2002 | $545,700 | Sold | Smart MLS #M9067245 |
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Comparable Sales for 209 Main Street
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.17 | Single-Family Home | $454,000 | 12/02/25 | 5 | 4 | 2,935 | |
0.17 | Single-Family Home | $426,000 | 04/16/26 | 3 | 1.5 | 2,012 | |
0.61 | Single-Family Home | $460,000 | 08/29/25 | 4 | 3 | 2,232 | |
0.17 | Single-Family Home | $407,000 | 11/24/25 | 2 | 1.5 | 1,440 | |
0.45 | Single-Family Home | $421,000 | 12/19/25 | 4 | 1.5 | 1,878 | |
0.60 | Single-Family Home | $393,000 | 03/17/26 | 4 | 1.5 | 1,688 | |
0.40 | Single-Family Home | $393,000 | 11/21/25 | 3 | 2 | 1,352 | |
0.63 | Single-Family Home | $495,000 | 03/03/26 | 3 | 2.5 | 2,018 | |
0.93 | Single-Family Home | $727,900 | 07/17/25 | 7 | 2 | 3,157 | |
0.79 | Single-Family Home | $563,500 | 06/15/26 | 4 | 1.5 | 1,241 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETWilliam Pitt Sotheby's Int'l
OFF MARKETWilliam Raveis Real Estate
OFF MARKETWilliam Pitt Sotheby's Int'l
FOR SALE0.4 ACRESColdwell Banker Realty
SOLDAPR 16, 2026Re/Max Valley Shore
SOLDNOV 24, 2025Coldwell Banker Realty
OFF MARKETBerkshire Hathaway NE Prop.
Assigned Schools
These are the assigned schools for 209 Main Street.
- 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 209 Main Street.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Deep River Center
At least 10 Trulia users voted on each feature.
100 % Say it's dog friendly
94 % Say there's wildlife
94 % Say car is needed
86 % Say it's walkable to grocery stores
85 % Say yards are well-kept
84 % Say it's walkable to restaurants
82 % Say streets are well-lit
80 % Say parking is easy
76 % Say kids play outside
75 % Say people would walk alone at night
75 % Say there's holiday spirit
73 % Say there are sidewalks
72 % Say neighbors are friendly
60 % Say they plan to stay for at least 5 years
42 % Say there are community events
36 % Say it's quiet
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Diane Devries, William Pitt Sotheby's Int'l, (860) 204-7645
Agent Phone: (860) 204-7645
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.
209 Main Street, Deep River, CT 06417 is a 9 bedroom, 9 bathroom, 4,982 sqft single-family home built in 1845. 209 Main Street is located in Deep River Center, Deep River. This property is currently available for sale and was listed by Smart MLS on Jun 1, 2026. The MLS # for this home is MLS# 24179935.