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195 Old South Road

Fairfield, Connecticut 06890

ACTIVE - NEW$4,950,000
Beds
4
Baths
3 | 1
SqFt
4,254
Acres
1.25
Year Built
1829
Matt Caiola

Matt Caiola

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Waterfront2-Car Garage4 Fireplaces

About This Home

Set on 1.25 acres in the heart of historic Southport Village, 195 Old South Road offers something increasingly rare: the character and presence of an 1829 Federal/Greek Revival residence with an unusually expansive yard. Private and surrounded by mature plantings, the 4,254-square-foot home offers four bedrooms, three full and two half baths across three floors. A gracious Front Hall, anchored by a sweeping curved staircase, opens easily to the home's principal rooms. The sun-filled, 30-foot Living Room features 9-foot ceilings and connects to the Dining Room through a passage framed by arched openings and a built-in wet bar. An expansive Family Room/Sunroom is accessible from the Living Room, Dining Room and Kitchen, creating an easy flow for everyday living and entertaining. Three wood-burning fireplaces add warmth and character. The generous Primary Suite features a gas fireplace, dressing room and private bath. A separate Guest Suite, two additional bedrooms and unfinished upper-level space offer flexibility. A substantial historic barn/garage accommodates two cars, with potential for three, and offers a full second floor. A large, level lawn provides remarkable privacy in close proximity to Southport Harbor, Southport Beach and Metro-North. A rare combination of acreage, architectural character and Village location. 195 Old South Road can be enjoyed immediately while offering its next owners the freedom to make the home distinctly their own over time.

Key Facts

City/Town
Fairfield
Neighborhood
Southport
Property / Style
Single Family · Colonial,Antique
Year Built
1829
Days on Market
0 days
Beds
4
Baths
3 full · 1 half
Living Area
4,254 sq ft
Lot Size
1.25 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$44,426 / Annually

Market Snapshot

The Fairfield Market

Single Family · trailing 12 months

View area

Median Days on Market

27

112 active listings

Median $ / Sq Ft

$506

112 active listings

Sale-to-List Ratio

102.5%

581 sales

How this home compares

List Price

$4.95M

vs $1.20M median

4.1× the median

Price / Sq Ft

$1,164

vs $506 median

2.3× the median

Days on Market

0 days

vs 27 days median

27 days fresher than median

Based on 112 active and 581 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of October 7, 2026.

Location

195 Old South Road, Fairfield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$32,447

per month

  • Principal & Interest$27,095
  • Property Taxes$3,702
  • Insurance$1,650
  • HOA$0

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

Location

City/Town
Fairfield
Neighborhood
Southport
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial,Antique
Year Built
1829
New Construction
No/Resale
Living Area
4,254 sq ft

Schools

Elementary
Per Board of Ed
High
Fairfield Ludlowe

Interior

Heating
Radiator
Heat Fuel
Oil
Cooling
Wall Unit
Fireplaces
4
Laundry
Main Level
Laundry Location
Off of Kitchen
Appliances
Gas RangeRefrigeratorWasherElectric Dryer
Basement
FullUnfinishedSump PumpHatchway AccessInterior AccessConcrete FloorFull With Hatchway
In-Law Apartment
No
Interior Features
Auto Garage Door Opener

Exterior & Lot

Lot Size
1.25 acres
Zoning
R3
Garage / Parking
2 garage spaces6 total parking spacesBarnDetached GarageOff Street ParkingDrivewayPrivateCrushed StoneGravel
Waterfront
Direct waterfront
Waterfront Details
Walk to WaterBeach RightsWater CommunityHarbor
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Construction
Shingle
Color
White
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
SidewalkPorchBarnGuttersCovered Deck
Lot Description
Fence - WoodFence - PartialFence - Chain LinkTreedDryLevel LotClearedHistoric District

Listing & Financials

Property Taxes
$44,426 / Annually
Days on Market
0
MLS #
24206984
MLS Status
Active

Similar Properties

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Listed By

Matt Lahey

(203) 767-4190

Higgins Group Real Estate

(203) 254-9000

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/7/2026. 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 10/7/2026 at 12:00 AM UTC.