209 Main Street
Deep River, Connecticut 06417
- Beds
- 9
- Baths
- 9
- SqFt
- 4,982
- Acres
- 0.45
- Year Built
- 1845
- Property Type
- Single Family

Matt Caiola
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About This Home
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.
Key Facts
- City/Town
- Deep River
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1845
- Days on Market
- 56 days
- Beds
- 9
- Baths
- 9 full
- Living Area
- 4,982 sq ft
- Lot Size
- 0.45 acres
- Garage / Parking
- 10 total
- Property Taxes
- $14,667 / Annually
Market Snapshot
The Deep River Market
Single Family · trailing 12 months
Active Listings
10
12 under contract
Median List Price
$887,000
10 active listings
Median Closed Price
$457,000
42 sales
Median Days on Market
33
10 active listings
Median $ / Sq Ft
$317
10 active listings
Sale-to-List Ratio
100.0%
42 sales
How this home compares
List Price
$1.20M
vs $887,000 median
35.3% above median
Price / Sq Ft
$241
vs $317 median
24.0% below median
Days on Market
56 days
vs 33 days median
23 days longer than median
Based on 10 active and 42 closed sales (trailing 12 mo) of single family in Deep River. Source: SmartMLS · As of July 28, 2026.
Location
209 Main Street, Deep River, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$6,118
- Property Taxes$1,222
- Insurance$400
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Deep River
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1845
- New Construction
- No/Resale
- Living Area
- 4,982 sq ft
Schools
- Elementary
- Deep River
- Middle
- Regional District 4
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural GasOil
- Cooling
- Split SystemWindow Unit
- Fireplaces
- 6
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Electric CooktopGas RangeWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullStorageInterior AccessConcrete FloorFull With Hatchway
- In-Law Apartment
- YesFirst FloorSeparate Entry
Exterior & Lot
- Lot Size
- 0.45 acres
- Zoning
- VCD
- Garage / Parking
- 10 total parking spacesDrivewayCrushed Stone
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Clapboard
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- Porch-Wrap AroundSidewalkShedPorchWrap Around DeckGuttersGarden AreaPatio
- Lot Description
- Level LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $14,667 / Annually
- Days on Market
- 56
- MLS #
- 24179935
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 5:25 AM UTC.