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236 & 250 Main Street

Ridgefield, Connecticut 06877

ACTIVE$7,995,000
Beds
8
Baths
7 | 2
SqFt
8,934
Acres
3.16
Year Built
1826
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Guest HousePool4-Car Garage7 FireplacesVirtual Tour

About This Home

Unprecedented opportunity to purchase two landmark, historic residences, situated side by side on Ridgefield's beloved Main St., which have been developed into an unparalleled lifestyle compound. This once in a lifetime sale includes the treasured Hawley House at 236 Main St. - Ridgefield's oldest home, on its original lot (5) which was built by the proprietors in 1713 for the Rev. Thomas Hawley, first pastor & town clerk. It also includes 250 Main St. - the iconic & brightly colored neighboring Gothic Revival Victorian, built Ca. 1826 by Hawley descendants. Working with Peter Coffin of DCA Architects & the Historic District Commission, the home underwent a meticulous full restoration & renovation, thoughtfully balancing historic preservation with modern luxury updates. Over $10M has been spent in top of the line improvements & designer appointments inside & out. Together, both homes span a pastoral 3.16 acres, juxtaposing sidewalks to vibrant downtown Ridgefield with rear privacy including 2 magnificent barns. 236 Main's "Red Barn," Ca. 1900 & renovated in 2012 features: 2,015 sf, indoor basketball court, home office/conference rm, arts & crafts studio, 1 full/2 half bths & 2 car garage. 250 Main's Pool/Carriage house includes: 3,684 sf, 1-2 BRs, 2 full/1 half bths, 2 fplcs, 2 car garage (2 Tesla chargers), gym with sauna, game room/bar, poker room, arcade, 30+ seat movie theater, plus kitchen/great room open to the heated, gunite, saltwater pool, spa & outdoor resort oasis.

Key Facts

City/Town
Ridgefield
Neighborhood
Village Center
Property / Style
Single Family · Antique,Victorian
Year Built
1826
Days on Market
133 days
Beds
8
Baths
7 full · 2 half
Living Area
8,934 sq ft
Lot Size
3.16 acres
Garage / Parking
4 garage
Property Taxes
$81,088 / Annually

Market Snapshot

The Ridgefield Market

Single Family · trailing 12 months

View area

Median Days on Market

55

53 active listings

Median $ / Sq Ft

$437

53 active listings

Sale-to-List Ratio

101.8%

232 sales

How this home compares

List Price

$8.00M

vs $1.28M median

6.2× the median

Price / Sq Ft

$895

vs $437 median

2.0× the median

Days on Market

133 days

vs 55 days median

78 days longer than median

Based on 53 active and 232 closed sales (trailing 12 mo) of single family in Ridgefield. Source: SmartMLS · As of September 10, 2026.

Location

236 & 250 Main Street, Ridgefield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$50,736

per month

  • Principal & Interest$41,314
  • Property Taxes$6,757
  • Insurance$2,665
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Ridgefield
Neighborhood
Village Center
County
Fairfield

Residence

Property Type
Single Family
Style
Antique,Victorian
Year Built
1826
New Construction
No/Resale
Living Area
8,934 sq ft
Below Grade
929 sq ft

Schools

Elementary
Veterans Park
High
Ridgefield

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
7
Laundry
Lower Level
Appliances
Gas RangeMicrowaveRange HoodRefrigeratorIcemakerDishwasherWasherDryerWine Chiller
Basement
FullPartially Finished
In-Law Apartment
PossibleDetached
Interior Features
Audio SystemSecurity System
Additional Rooms
GymLaundry RoomSteam/SaunaSitting RoomWorkshop

Exterior & Lot

Lot Size
3.16 acres
Zoning
RA
Garage / Parking
4 garage spacesBarnDetached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Pool
GuniteHeatedPool HouseSalt WaterIn Ground Pool
Construction
ClapboardWood
Roof
Asphalt ShingleWood Shingle
Foundation
ConcreteStone
Exterior Features
SidewalkPorchBarnGarden AreaLightingGuest HouseFrench DoorsPatio
Lot Description
Level LotProfessionally LandscapedHistoric District

Listing & Financials

Property Taxes
$81,088 / Annually
Days on Market
133
MLS #
24170626
MLS Status
Active

Similar Properties

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

Listed By

Laura Ancona

(203) 733-7053

William Pitt Sotheby's Int'l

(203) 438-9531

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/10/2026. 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 9/10/2026 at 6:30 AM UTC.