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.
Sold for $3,750,000
$3,750,000
50 Sylvan Road North, Westport, CT 06880
9beds
10,959sqft
Single Family Residence
Built in 1920
3 Acres Lot
$1,400,200 Zestimate®
$342/sqft
$6,416 Estimated rent
Home value
$1,400,200
$1.33M - $1.47M
$6,416/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Jaclyn Picarillo 203-981-5012,
Higgins Group Bedford Square 203-226-0300
Bought with:
Jessica Brookbanks, RES.0795389
Coldwell Banker Realty
Source: Smart MLS,MLS#: 170591446
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 9
- Full bathrooms: 8
- 1/2 bathrooms: 1
Rooms
- Room types: Bonus Room, Breezeway, Sitting Room, Staff Quarters
Primary bedroom
- Features: High Ceilings, Fireplace, Full Bath, Walk-In Closet(s), Wall/Wall Carpet, Hardwood Floor
- Level: Upper
Bedroom
- Features: Built-in Features, Fireplace, Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Built-in Features, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Fireplace, Full Bath, Wall/Wall Carpet
- Level: Main
Bedroom
- Features: High Ceilings, Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Dining room
- Features: Beamed Ceilings, Fireplace, French Doors
- Level: Main
Family room
- Features: High Ceilings, Slate Floor
- Level: Main
Kitchen
- Features: Dining Area, Double-Sink, Fireplace, French Doors, Kitchen Island, Pantry
- Level: Main
Living room
- Features: High Ceilings, Fireplace, Half Bath, Hardwood Floor
- Level: Main
Office
- Features: High Ceilings, Bookcases, Built-in Features, Fireplace, French Doors, Hardwood Floor
- Level: Main
Other
- Features: Dining Area, French Doors, Slate Floor
- Level: Main
Study
- Features: High Ceilings, French Doors, Hardwood Floor
- Level: Main
Heating
- Steam, Zoned, Oil, Propane
Cooling
- Central Air, Zoned
Appliances
- Included: Gas Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level
Features
- Open Floorplan, Entrance Foyer, In-Law Floorplan
- Doors: French Doors
- Basement: Full,Unfinished,Hatchway Access,Interior Entry,Concrete
- Attic: Storage,Floored,Walk-up
- Number of fireplaces: 9
Interior area
- Total structure area: 10,959
- Total interior livable area: 10,959 sqft
- Finished area above ground: 10,959
Property
Parking
- Total spaces: 3
- Parking features: Detached
- Garage spaces: 3
Features
- Patio & porch: Terrace, Patio
- Exterior features: Lighting, Garden, Stone Wall
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground
- Fencing: Stone
- Waterfront features: Beach Access, Water Community
Lot
- Size: 3 Acres
- Features: Dry, Level, Cleared
Details
- Additional structures: Cabana, Guest House, Gazebo
- Parcel number: 412929
- Zoning: AA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Tudor
- Property subtype: Single Family Residence
Materials
- Brick, Stone
- Foundation: Concrete Perimeter, Masonry
- Roof: Tile
Condition
- New construction: No
- Year built: 1920
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Golf, Health Club, Library, Park, Private School(s), Pool, Shopping/Mall
- Security: Security System
- Subdivision: Old Hill
HOA
- Has HOA: No
Location
- Region: Westport
Financial & listing details
- Price per square foot: $342/sqft
- Tax assessed value: $2,844,500
- Annual tax amount: $52,197
- Date on market: 12/18/2024
Price history
| Date | Event | Price |
|---|---|---|
| 7/30/2026 | Listing removed | $1,475,000$135/sqft |
Source:  Smart MLS #24151295 Report a problem | ||
| 1/29/2026 | Listed for sale | $1,475,000-60.7%$135/sqft |
Source: Smart MLS #24151295 Report a problem | ||
| 12/9/2024 | Sold | $3,750,000-3.8%$342/sqft |
Source: Smart MLS #170591446 Report a problem | ||
| 8/15/2023 | Price change | $3,900,000-10.9%$356/sqft |
Source: Smart MLS #170591446 Report a problem | ||
| 2/1/2023 | Listed for sale | $4,375,000-4.9%$399/sqft |
Source: Smart MLS #170547881 Report a problem | ||
| 5/1/2022 | Listing removed | -- |
Source: Smart MLS #170396466 Report a problem | ||
| 1/14/2022 | Price change | $4,600,000-6.1%$420/sqft |
Source: Smart MLS #170396466 Report a problem | ||
| 8/19/2021 | Price change | $4,900,000-10.9%$447/sqft |
Source: Smart MLS #170396466 Report a problem | ||
| 5/5/2021 | Listed for sale | $5,500,000+193.3%$502/sqft |
Source: Smart MLS #170396466 Report a problem | ||
| 3/20/2020 | Listing removed | $13,000$1/sqft |
Source: Higgins Group Real Estate #170267257 Report a problem | ||
| 1/31/2020 | Listed for rent | $13,000$1/sqft |
Source: Higgins Group Real Estate #170267257 Report a problem | ||
| 6/20/2012 | Sold | $1,875,000-16.7%$171/sqft |
Source: Public Record Report a problem | ||
| 8/28/1997 | Sold | $2,250,000$205/sqft |
Source: Smart MLS #97024710 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $53,647 +1.3% | $2,844,500 |
| 2024 | $52,965 +1.5% | $2,844,500 |
| 2023 | $52,197 +1.6% | $2,844,500 |
| 2022 | $51,400 +0% | $2,844,500 +0% |
| 2021 | $51,395 +4.7% | $2,844,200 -3.2% |
| 2020 | $49,087 -0.9% | $2,937,600 |
| 2019 | $49,528 | $2,937,600 |
| 2018 | $49,528 | $2,937,600 |
| 2017 | $49,528 | $2,937,600 |
| 2016 | $49,528 | $2,937,600 |
Find assessor info on the county website
Neighborhood: Old Hill
Nearby homes
- $3,557,5008 bd5 ba4.5k sqft56 Sylvan Rd N, Westport, CT 06880Off Market
- $--5 bd5 ba3.3k sqft40 Sylvan Rd N, Westport, CT 06880Off Market
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- $2,205,0005 bd5 ba3.4k sqft7 Indian Point Ln, Westport, CT 06880Sold
- $1,989,0004 bd3 ba3k sqft58 Sylvan Rd N, Westport, CT 06880Off Market
Nearby schools
GreatSchools rating
- 9/10King's Highway Elementary SchoolGrades: K-5Distance: 0.6 mi
- 9/10Coleytown Middle SchoolGrades: 6-8Distance: 3.2 mi
- 10/10Staples High SchoolGrades: 9-12Distance: 2.9 mi
Schools provided by the listing agent
- Elementary: Kings Highway
- Middle: Coleytown
- High: Staples
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Westport
- 06880
- Old Hill
- 50 Sylvan Road North
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