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209 Main Street

Deep River, Connecticut 06417

ACTIVE$1,199,999
Beds
9
Baths
9
SqFt
4,982
Acres
0.45
Year Built
1845
Matt Caiola

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,740

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Diane Devries

(860) 204-7645

William Pitt Sotheby's Int'l

(203) 245-6700

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.