George Cress of Real Broker Email: george@cress.co (dot co) Call/Text: 212-203-5251
Westport, CT / SOLD
50 Sylvan RoadWestport, CT 06880
The buyer could have saved $46,875 in 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. Based on the recorded closed price; this is a hypothetical estimate, not a statement of actual commission or rebate paid.
Sale Price$3,750,000ClosedDecember 8, 2024
Open house
Our Take
50 Sylvan Road is a 1920 stone-and-brick property in Westport’s Old Hill Estate Area, set on three acres behind stonewalls and iron gates. The grounds include a heated gunite pool and tennis/sports court, while the main house and guest-house wing include six and three bedrooms, respectively. Interior features include custom millwork, nine fireplaces, high ceilings, beams, large windows, French doors, and a kitchen opening to a patio and courtyard. Two-plus offices, space above the three-car garage, and a pool cabana add further utility.
At a glance
Closed · MLS #170591446- Bedrooms
- 9
- BathroomsBaths
- 8 full / 1 half
- Square feet
- 10,959
- Year built
- 1920
- Acres
- 3
- Property taxes
- $52,197
July 2023-June 2024
What stands out
- 1920 stone-and-brick construction
- Three acres behind stonewalls and iron gates
- Heated gunite pool and tennis/sports court
- Main house with six bedrooms
- Guest-house wing with three bedrooms
- Kitchen opening to patio and courtyard
- Two-plus offices and space above three-car garage
- Pool cabana with kitchenette, changing rooms, bath, and laundry
Read the full listing description
Dramatic & inspiring, this 1920's stone & brick Family Compound in Westport's Premier Old Hill Estate Area neighborhood achieves the perfect balance of old world charm, intimacy, and opulence with distinctive custom millwork and modern expensive upgrades throughout. Tucked behind tall privacy stonewalls and iron gates on a beautifully manicured and professionally landscaped 3 acres w/heated gunite pool and tennis/sports court, 50 Sylvan Rd N is the epitome of fine living. Nearly 11,000sf which includes 6 bedrooms in the main house & 3 bdrms in the guest house wing over the pool cabana, you'll fall in love with the unrivaled personality & excitement at every turn: oversized public rooms with high ceilings; beams; 9 fireplaces; big windows & french doors; gourmet kitchen with cozy fireplace & French doors that open to the back patio and courtyard for al fresco dining; impressive master suite with soaring ceilings & sitting room w/fplc. Ideal for today's hybrid or work-from-home lifestyle, there are 2+ offices & 500sf+ above the 3-car garage. Other special features include pool cabana w/kitchenette, changing rooms, full bath & laundry; multiple patios for large scale entertaining; & tennis court/sports court with fun viewing party hut. Just minutes to shops, downtown, Westport's delicious restaurants, gorgeous beaches, train & highways.
Schools
- Elementary
- Kings Highway
- Middle
- Coleytown
- High
- Staples
Schools as reported by SmartMLS. Confirm attendance assignments with the district.
Price history
| Date | Event | Price |
|---|---|---|
| Closed price | $3,750,000 | |
| Original list price | $3,900,000 |
Intermediate price changes and previous listings may not be included.
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*Estimate: $3,750,000 closed price × assumed 2.5% buyer-agent commission × 50% rebate = $46,875. 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. This is a hypothetical estimate, not a rebate paid on this sale.
Listed by Higgins Group Bedford Square
Jaclyn Picarillo
SmartMLS · Listing #170591446 · Closed
Listing data checked: Sep 25, 2026, 5:37 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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