469 Brookside Rd

New Canaan, CT 06840

$3,800,000
Price
6
Beds
5,275 Sq. Ft.
$720 / Sq. Ft.
5,275
Sq. Ft.
$720
per Sq. Ft.
Listed By CompassUnder Contract
Listed By CompassUnder Contract
a view of house with a yard
a front view of a house with a garden
a view of entryway and hall with wooden floor
a living room with fireplace furniture and a large window
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a dining room with furniture and window
a dining room with furniture a chandelier and wooden floor
a view of a dining room with furniture and chandelier
a living room with furniture and a fireplace
a living room with furniture a flat screen tv and a fireplace
a living room with furniture and a potted plant
a kitchen with stainless steel appliances kitchen island granite countertop a sink a stove and a refrigerator
a large kitchen with kitchen island a sink a counter space appliances and a window
a view of a dining room with furniture window and outside view
a view of a dining room with furniture window and outside view
a living room with furniture a fireplace and a table
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a spacious bathroom with a tub sink and mirror
a spacious bedroom with a bed and a large window
a living room with furniture and a window
a bathroom with a sink a toilet and a mirror
a view of a house with backyard and garden
a bedroom with a bed a couch and a chandelier
a kitchen with a sink cabinets and window
a front view of a house with a garden
a living room with furniture and a flat screen tv
a backyard of a house with a yard and outdoor seating
a swimming pool with outdoor seating and yard
an aerial view of a house with a yard and garden
a view of a park with a slide
a backyard of a house with lots of green space
a front view of a house with a garden
a view of a back yard and patio
a view of a swimming pool with a patio
a front view of a house with a garden and sitting area
a view of a yard and front view of a house
a view of a house with a yard

Description

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,...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 Agents

  1. Christine Saxe

    Christine Saxe

    Listing Agent

    Compass

    CallTextEmail
  2. Amanda Bryan

    Amanda Bryan

    Alternative Listing Agent

    Compass

    amandabryan@compass.com

    P: (203)-246-1064

    CallTextEmail

Property Details for 469 Brookside Road

Basement Description
Partial
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Antique
Garage Parking Info
Barn, Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 10/31/2025 09:52 PM

Property Details for 469 Brookside Road

StatusUnder Contract
MLS #24131109
Days on Market25
Taxes$32,766 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1820
Lot Size3.43 AC / 149,410 SF
CountyFairfield County

Location

Add your commute

Virtual Tour

Building Information for 469 Brookside Road

Stories-Year Built1820Building Size-Lot Size3.43 AC / 149,410 SF

Payment Calculator

$21,508 per month

30 year fixed, 6.28% Interest

Principal and Interest

$18,777

Property Taxes

$2,731

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 469 Brookside Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 1 or White Oak Shade Road to Brookside
  • Elementary School: South
  • High School: New Canaan
  • Intermediate School: Per Board of Ed
  • Latitude: 41.116195
  • Longitude: -73.47423
  • Neighborhood Amenities: Golf Course, Library, Park, Private School(s), Public Pool, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $32,766
Interior and Exterior Features
Exterior Features
  • Exterior Features: Terrace, Barn, Lighting, Guest House, Hot Tub, Shed, Tennis Court, Fruit Trees, Underground Sprinkler
  • Pool Description: Gunite, Pool House, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Walk-up
  • Cooling System: Central Air
  • Heat Type: Baseboard, Hot Water, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 4
  • Interior Features: Auto Garage Door Opener, Cable - Available, Sauna, Security System
  • Laundry Room Info: Upper Level
  • Laundry Room Location: Second Floor
  • Rooms Additional: Foyer, Laundry Room, Mud Room, Steam/Sauna
  • Rooms Total: 13
Room 1
  • Room Entry Order: 1
  • Room Features: Remodeled,Bay/Bow Window,Built-Ins,Fireplace,Hardwood Floor
  • Room Length: 19.8
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 30.7
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Length: 19.3
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.8
Room 3
  • Room Entry Order: 11
  • Room Features: Bay/Bow Window,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.3
Room 4
  • Room Entry Order: 12
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 14.1
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 18.6
Room 5
  • Listing Key: 4041B4447B947FE7E0631A01100AEDB2
  • Room Entry Order: 13
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 10.8
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.1
Room 6
  • Room Entry Order: 14
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 9.5
Room 7
  • Room Entry Order: 15
  • Room Features: Skylight
  • Room Length: 7.8
  • Room Level: Upper
  • Room Type: Other
  • Room Width: 8.1
Room 8
  • Room Entry Order: 16
  • Room Features: Skylight,9 ft+ Ceilings,Full Bath,Hardwood Floor
  • Room Level: Other
  • Room Type: Studio Apt
Room 9
  • Listing Key: 4041B4447B947FE7E0631A01100AEDB2
  • Room Entry Order: 17
  • Room Features: Full Bath,Tile Floor
  • Room Level: Other
  • Room Type: Other
Room 10
  • Room Entry Order: 2
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 17.11
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 14.8
Room 11
  • Room Entry Order: 3
  • Room Features: Book Shelves,Wet Bar,Fireplace,French Doors,Patio/Terrace,Stone Floor
  • Room Length: 17.6
  • Room Level: Main
  • Room Type: Library
  • Room Width: 22.3
Room 12
  • Room Entry Order: 4
  • Room Features: Book Shelves,Wet Bar,Hardwood Floor
  • Room Length: 10.8
  • Room Level: Main
  • Room Type: Office
  • Room Width: 10.9
Room 13
  • Room Entry Order: 5
  • Room Features: Remodeled,Breakfast Nook,Dining Area,Wet Bar,Island,Hardwood Floor
  • Room Length: 17.3
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 16.5
Room 14
  • Room Entry Order: 6
  • Room Features: Built-Ins,Fireplace,Hardwood Floor
  • Room Length: 17.3
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 18.2
Room 15
  • Room Entry Order: 7
  • Room Features: Remodeled,Bay/Bow Window,Built-Ins,Patio/Terrace,Hardwood Floor
  • Room Length: 23.2
  • Room Level: Main
  • Room Type: Other
  • Room Width: 16.3
Room 16
  • Room Entry Order: 8
  • Room Features: Wet Bar,French Doors,Full Bath,Hot Tub,Steam/Sauna,Patio/Terrace
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Other
  • Room Width: 9.5
Room 17
  • Room Entry Order: 9
  • Room Features: Full Bath,Whirlpool Tub,Walk-In Closet,Hardwood Floor
  • Room Length: 17.11
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 18.6
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exclusions: Flat screen TV's
  • Exterior Siding: Clapboard
  • Foundation Type: Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1820
  • Year Built Source: Approximate
  • Bank Owned Property: No
  • In Law Access: Detached, Separate Entry
  • In Law Apartment: Possible
  • Sq Ft Description: Approximate
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Level Lot, Professionally Landscaped, Rolling, Open Lot
  • Parcel Number: 185775
  • Sq Ft Est Heated Above Grade: 5275.0
  • Sq Ft Total: 5275.0
  • Zoning: 1AC
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: Unknown
  • Radon Mitigation Water: Unknown
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 469 Brookside Road

DateEvent & SourcePriceAppreciation
Jul 2, 2021

Closed (Public Record)

Public Record #1467841027

$2,675,000

+0.1% / yr

Nov 25, 2002

Closed (Public Record)

Public Record #107833547

$2,645,000—
DateEvent & SourcePrice
07/02/2021

Closed (Public Record)

Public Record #1467841027

$2,675,000

+0.1% / yr

11/25/2002

Closed (Public Record)

Public Record #107833547

$2,645,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 469 Brookside Road

Taxable ValueLand$826,000Additions$1,137,220Total$1,963,220
Tax Record2024$32,766 ($2,730 / month)
Home Facts
Beds0Lot Size149,411 SqFtStyleSingle Family ResidenceZoning1ACCountyFAIRFIELDAPNNCAN M:0036 B:053 L:000K6

Schools near 469 Brookside Road

This home is within New Canaan School District.
Rating
School
Type
Grades
Distance
South School
Public - K to 4
Saxe Middle School
Public - 5 to 8
New Canaan High School
Public - 9 to 12
Rating
School
Distance
South School
PublicK to 4

Saxe Middle School
Public5 to 8

New Canaan High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.