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. Central air vents throughout except in dining room, living room, library and spa. All measurements are approximate
Sold for $3,850,000 on 12/16/25
$3,850,000
469 Brookside Road, New Canaan, CT 06840
6beds
5,275sqft
Single Family Residence
Built in 1820
3.43 Acres Lot
$3,852,300 Zestimate®
$730/sqft
$18,713 Estimated rent
Home value
$3,852,300
$3.51M - $4.24M
$18,713/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: December 16, 2025 at 01:15pm
Listed by:
TEAM SAXE + BRYAN OF COMPASS,
Christine D. Saxe (203)273-1548,
Compass Connecticut, LLC 203-442-6626,
Co-Listing Agent: Amanda Bryan 203-246-1064,
Compass Connecticut, LLC
Bought with:
Christine D. Saxe, RES.0768323
Compass Connecticut, LLC
Source: Smart MLS,MLS#: 24131109
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 5
Primary bedroom
- Features: Full Bath, Whirlpool Tub, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 318.25 Square Feet
- Dimensions: 18.6 x 17.11
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 247.04 Square Feet
- Dimensions: 12.8 x 19.3
Bedroom
- Features: Bay/Bow Window, Hardwood Floor
- Level: Upper
- Area: 171.6 Square Feet
- Dimensions: 14.3 x 12
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
- Area: 262.26 Square Feet
- Dimensions: 18.6 x 14.1
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
- Area: 163.08 Square Feet
- Dimensions: 15.1 x 10.8
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
- Area: 180.5 Square Feet
- Dimensions: 9.5 x 19
Dining room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 253.23 Square Feet
- Dimensions: 14.8 x 17.11
Family room
- Features: Built-in Features, Fireplace, Hardwood Floor
- Level: Main
- Area: 314.86 Square Feet
- Dimensions: 18.2 x 17.3
Kitchen
- Features: Remodeled, Breakfast Nook, Dining Area, Wet Bar, Kitchen Island, Hardwood Floor
- Level: Main
- Area: 285.45 Square Feet
- Dimensions: 16.5 x 17.3
Library
- Features: Bookcases, Wet Bar, Fireplace, French Doors, Patio/Terrace, Stone Floor
- Level: Main
- Area: 392.48 Square Feet
- Dimensions: 22.3 x 17.6
Living room
- Features: Remodeled, Bay/Bow Window, Built-in Features, Fireplace, Hardwood Floor
- Level: Main
- Area: 607.86 Square Feet
- Dimensions: 30.7 x 19.8
Office
- Features: Bookcases, Wet Bar, Hardwood Floor
- Level: Main
- Area: 117.72 Square Feet
- Dimensions: 10.9 x 10.8
Other
- Features: Remodeled, Bay/Bow Window, Built-in Features, Patio/Terrace, Hardwood Floor
- Level: Main
- Area: 378.16 Square Feet
- Dimensions: 16.3 x 23.2
Other
- Features: Wet Bar, French Doors, Full Bath, Hot Tub, Steam/Sauna, Patio/Terrace
- Level: Main
- Area: 95 Square Feet
- Dimensions: 9.5 x 10
Other
- Features: Skylight
- Level: Upper
- Area: 63.18 Square Feet
- Dimensions: 8.1 x 7.8
Other
- Features: Full Bath, Tile Floor
- Level: Other
Other
- Features: Skylight, High Ceilings, Full Bath, Hardwood Floor
- Level: Other
Heating
- Baseboard, Hot Water, Zoned, Oil
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Upper Level, Mud Room
Features
- Sauna, Entrance Foyer
- Basement: Partial
- Attic: Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 5,275
- Total interior livable area: 5,275 sqft
- Finished area above ground: 5,275
Property
Parking
- Total spaces: 2
- Parking features: Barn, Detached, Garage Door Opener
- Garage spaces: 2
Features
- Patio & porch: Terrace
- Exterior features: Lighting, Tennis Court(s), Fruit Trees, Underground Sprinkler
- Has private pool: Yes
- Pool features: Gunite, In Ground
- Spa features: Heated
Lot
- Size: 3.43 Acres
- Features: Level, Landscaped, Rolling Slope, Open Lot
Details
- Additional structures: Barn(s), Guest House, Shed(s), Pool House
- Parcel number: 185775
- Zoning: 1AC
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Antique
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1820
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Golf, Library, Park, Private School(s), Pool, Shopping/Mall
Location
- Region: New Canaan
Price history
| Date | Event | Price |
|---|---|---|
| 12/16/2025 | Sold | $3,850,000+1.3%$730/sqft |
Source:  Smart MLS #24131109 | ||
| 10/31/2025 | Pending sale | $3,800,000$720/sqft |
Source: Smart MLS #24131109 | ||
| 10/6/2025 | Listed for sale | $3,800,000+42.1%$720/sqft |
Source: Smart MLS #24131109 | ||
| 7/2/2021 | Sold | $2,675,000+7542.9%$507/sqft |
Source: Smart MLS #170385217 | ||
| 7/24/2020 | Sold | $35,000-98.7%$7/sqft |
Source: BHHS NE Properties sold #170298911_06840 | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $32,766 +3.4% | $1,963,220 |
| 2024 | $31,686 +10.3% | $1,963,220 +29.5% |
| 2023 | $28,722 +3.1% | $1,516,480 |
Find assessor info on the county website
Neighborhood: 06840
Nearby schools
GreatSchools rating
- 9/10Saxe Middle SchoolGrades: 5-8Distance: 1.3 mi
- 10/10New Canaan High SchoolGrades: 9-12Distance: 1.2 mi
- 9/10South SchoolGrades: K-4Distance: 1.3 mi
Schools provided by the listing agent
- Elementary: South
- High: New Canaan
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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$3,852,300
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