New Canaan, CT / 366 DAYS ON MARKET

44 Benedict Hill RoadNew Canaan, CT 06840

Asking price$2,750,000Active

Our Take

44 Benedict Hill Road is a five-bedroom, three-full-bath, one-half-bath mid-century modern residence on 4.6 acres in New Canaan. Designed in 1961 by architect James Evans, it has a hyperbolic paraboloid roof, an open main level, and floor-to-ceiling windows alongside wooded views. The main level includes a primary suite, living room, dining room, office/study, powder room, and wraparound deck. A finished walk-out lower level adds four bedrooms, two full bathrooms, laundry, and storage.

44 Benedict Hill Road — photo 1
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Estimated buyer rebate

Buy with Cress and Save $34,375 on brokerage fees*

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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.

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At a glance

Active · MLS #24126532
Bedrooms
5
BathroomsBaths
3 full / 1 half
Square feet
3,200
Year built
1960
Acres
4.6
Property taxes
$14,520

July 2026-June 2027

What stands out

  • Hyperbolic paraboloid roof by James Evans
  • Floor-to-ceiling windows on the open main level
  • Serene wooded views throughout the home
  • See-through fireplace in the dining room
  • Sliding doors connect to the wraparound deck
  • Walk-out lower level with four bedrooms
  • Two full bathrooms on the lower level
Read the full listing description

Welcome to the iconic Evans House - a striking work of mid-century modern architecture. Designed in 1961 by renowned architect James Evans, this one-of-a-kind residence showcases a striking hyperbolic paraboloid roof that allows for a completely open main level filled with soaring floor-to-ceiling windows. Every room is immersed in natural light and surrounded by serene wooded views, offering unmatched privacy and a sense of retreat. The main level features an effortless open flow with a primary suite, living room, dining room with a see-through fireplace, office/study, powder room, and expansive sliding doors that connect seamlessly to the wraparound deck. The fully finished, walk-out lower level offers four additional bedrooms, two full bathrooms, a dedicated laundry room, and storage. This rare architectural gem is not just a home, but an experience in design, nature, and modern living.

Schools

Elementary
East
Middle
Saxe Middle
High
New Canaan

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

A closer look at the location

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44 Benedict Hill Road, New Canaan, CT 06840

Price history

DateEventPrice
Originally listed$2,750,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $2,750,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $34,375. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Harbor Bridge Realty · (203) 667-3443

John-Michael Rachinsky-Wood

SmartMLS · Listing #24126532 · Active

Listing data checked: Sep 17, 2026, 7:06 PM 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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