Fairfield, CT / 5 DAYS ON MARKET

195 Old South RoadFairfield, CT 06890

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*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received.

Asking price$4,950,000Active

Our Take

195 Old South Road is an 1829 Federal/Greek Revival residence on 1.25 acres in Southport Village, with mature plantings and a large, level lawn. Inside, a curved staircase anchors the Front Hall, while the living, dining, kitchen, and family room/sunroom are connected for daily use and entertaining. Three wood-burning fireplaces are part of the interior. The home includes a primary suite, separate guest suite, and two additional bedrooms; a historic barn/garage accommodates two cars and has a full second floor.

Estimated buyer rebate

Buy with Cress and Save $61,875 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24206984
Bedrooms
4
BathroomsBaths
3 full / 2 half
Square feet
4,254
Year built
1829
Acres
1.25
Property taxes
$44,426

July 2026-June 2027

What stands out

  • 1829 Federal/Greek Revival residence
  • Curved staircase anchoring the Front Hall
  • Sun-filled living room with arched passage
  • Connected family room, dining room, and kitchen
  • Three wood-burning fireplaces
  • Primary suite with dressing room and private bath
  • Separate guest suite and two additional bedrooms
  • Historic barn/garage with full second floor
Read the full listing description

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.

Schools

Elementary
Per Board of Ed
Middle
Not provided
High
Fairfield Ludlowe

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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195 Old South Road, Fairfield, CT 06890

Price history

DateEventPrice
Originally listed$4,950,000

Intermediate price changes and previous listings may not be included.

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Closest recorded sales

*Estimate: $4,950,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $61,875. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered or actual compensation.

Listed by Higgins Group Real Estate · (203) 254-9000

Matt Lahey · (203) 767-4190

SmartMLS · Listing #24206984 · Active

Listing data checked: Oct 11, 2026, 6:02 AM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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