469 Brookside Rd New Canaan, CT 06840
Estimated payment $22,739/month
Highlights
- Guest House
- Steam Room
- Tennis Courts
- South Elementary School Rated A+
- Barn
- Pool House
About This Home
Dating back to the 1820's, "Shadowlyn" epitomizes the classic country compound combining beautiful vintage details with stylish, modern amenities. The bright and sunny main residence features six bedrooms, four full baths, four fireplaces and loads of comfortable living space accommodating a relaxing and easy lifestyle on over three acres with pool, charming pool house, garage/barn with apartment above and tennis court. The expansive kitchen has been thoughtfully reimagined and features a large island, extensive storage, vintage wet bar, expansive breakfast area adjacent to a cozy family room and oversized mudroom. The formal living and dining spaces boast high ceilings, tons of windows and intimate conversation alcoves, perfect for entertaining. The step down library is stunning and dramatic; wrapped in color, featuring French doors out to the terrace and private spa. The primary bedroom suite is well appointed with a walk in closet and a large, updated bath. All of these lovely spaces have direct access to sweeping vistas of this bucolic estate featuring a beautifully illuminated landscape in the evenings. Convenient to downtown New Canaan, Darien and Norwalk, Shadowlyn is accessible and exceptional. Schedule your private tour today.
Listing Agent
Compass Connecticut, LLC Brokerage Phone: (203) 273-1548 License #RES.0768323 Listed on: 10/06/2025
Co-Listing Agent
Compass Connecticut, LLC Brokerage Phone: (203) 273-1548 License #RES.0787038
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $32,766
Year Built
- Built in 1820
Lot Details
- 3.43 Acre Lot
- Sprinkler System
- Fruit Trees
- Property is zoned 1AC
Home Design
- Antique Architecture
- Stone Foundation
- Frame Construction
- Asphalt Shingled Roof
- Clap Board Siding
Interior Spaces
- 5,275 Sq Ft Home
- 4 Fireplaces
- Mud Room
- Entrance Foyer
- Steam Room
- Sauna
- Partial Basement
- Walkup Attic
- Home Security System
Kitchen
- Breakfast Area or Nook
- Built-In Oven
- Gas Cooktop
- Dishwasher
Bedrooms and Bathrooms
- 6 Bedrooms
- 5 Full Bathrooms
Laundry
- Laundry Room
- Laundry on upper level
- Dryer
- Washer
Parking
- 2 Car Garage
- Automatic Garage Door Opener
Pool
- Pool House
- In Ground Pool
- Spa
- Gunite Pool
Outdoor Features
- Tennis Courts
- Terrace
- Exterior Lighting
- Shed
Location
- Property is near shops
- Property is near a golf course
Schools
- South Elementary School
- New Canaan High School
Utilities
- Zoned Heating and Cooling System
- Baseboard Heating
- Hot Water Heating System
- Heating System Uses Oil
- Private Company Owned Well
- Hot Water Circulator
- Oil Water Heater
- Fuel Tank Located in Basement
- Cable TV Available
Additional Features
- Guest House
- Barn
Listing and Financial Details
- Exclusions: Flat screen TV's
- Assessor Parcel Number 185775
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $32,766 | $1,963,220 | $826,000 | $1,137,220 |
| 2024 | $31,686 | $1,963,220 | $826,000 | $1,137,220 |
| 2023 | $28,722 | $1,516,480 | $677,600 | $838,880 |
| 2022 | $27,858 | $1,516,480 | $677,600 | $838,880 |
| 2021 | $27,510 | $1,514,870 | $677,600 | $837,270 |
| 2020 | $27,510 | $1,514,870 | $677,600 | $837,270 |
| 2019 | $27,631 | $1,514,870 | $677,600 | $837,270 |
| 2018 | $28,536 | $1,682,520 | $590,450 | $1,092,070 |
| 2017 | $28,048 | $1,682,520 | $590,450 | $1,092,070 |
| 2016 | $27,442 | $1,682,520 | $590,450 | $1,092,070 |
| 2015 | $27,863 | $1,682,520 | $590,450 | $1,092,070 |
| 2014 | $26,146 | $1,682,520 | $590,450 | $1,092,070 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 10/31/2025 10/31/25 | Pending | -- | -- | -- | |
| 10/06/2025 10/06/25 | For Sale | $3,800,000 | +42.1% | $720 / Sq Ft | |
| 07/02/2021 07/02/21 | Sold | $2,675,000 | -4.3% | $507 / Sq Ft | View Prior Sale |
| 06/03/2021 06/03/21 | Pending | -- | -- | -- | |
| 04/08/2021 04/08/21 | For Sale | $2,795,000 | 0.0% | $530 / Sq Ft | |
| 07/24/2020 07/24/20 | Rented | $35,000 | 0.0% | -- | |
| 06/09/2020 06/09/20 | Under Contract | -- | -- | -- | |
| 06/03/2020 06/03/20 | Price Changed | $35,000 | -12.5% | $6 / Sq Ft | |
| 05/26/2020 05/26/20 | For Rent | $40,000 | -- | -- |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $2,675,000 | None Available | |
| Warranty Deed | $2,645,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $2,407,232 | Purchase Money Mortgage | |
| Previous Owner | $1,520,000 | No Value Available | |
| Previous Owner | $1,515,500 | No Value Available | |
| Previous Owner | $1,995,000 | Purchase Money Mortgage |
Source: SmartMLS
MLS Number: 24131109
APN: NCAN-000036-000053-K000006
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