195 Old South Road
Fairfield, Connecticut 06890
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 4,254
- Acres
- 1.25
- Year Built
- 1829
- Neighborhood
- Southport
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
112
72 under contract
Median List Price
$1.20M
112 active listings
Median Closed Price
$1.17M
581 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per 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
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
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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 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.