Totally transformed - English countryside meets classic CT! Prominently sited on ~1.3 private acres in the highly coveted South of the YMCA neighborhood, this stunning colonial estate offers an unparalleled lifestyle. Located just minutes from the heart of downtown New Canaan, Waveny Park, and top-rated schools, this extraordinary home is a rare gem. Thoughtfully transformed by its current owners, blending timeless charm with modern sophistication. This meticulously updated residence boasts 4+ spacious bedrooms, with 3.5 stunning baths, providing luxury and privacy. Every detail in this jewel box has been considered all the way down to the ultra high-end lighting, designer wallpaper, specialty paints, and SO much more. Bright and sun-drenched, the home's interiors exude warmth and character, creating a welcoming space for both relaxation and entertaining. This home is truly one-of-a-kind. Step outside and discover a true private oasis: lush manicured grounds, stunning flower beds and mature plantings. The sparkling pool, outdoor patio with fireplace & wraparound porch complete this outdoor paradise, offering the perfect setting for leisurely days or vibrant gatherings. This home is not just a property, but a lifestyle. It's the perfect combination of luxury, comfort, & convenience, and it's ready for you to move in & enjoy. Experience the best of New England living-bring your toothbrush & get ready to immerse yourself in the unparalleled beauty of this extraordinary property.
Under contract
$2,995,000
105 White Oak Shade Road, New Canaan, CT 06840
4beds
3,744sqft
Est.:
Single Family Residence
Built in 1850
1.26 Acres Lot
$-- Zestimate®
$800/sqft
$-- HOA
What's special
- 26 days |
- 3,666 |
- 400 |
Zillow last checked: 7 hours ago
Listing updated: March 10, 2026 at 01:58pm
Listed by:
Daniel R. McCamblau (917)848-1525,
Brown Harris Stevens 203-221-0666
Source: Smart MLS,MLS#: 24157134
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Rooms
- Room types: Laundry
Primary bedroom
- Features: Remodeled, Beamed Ceilings, Fireplace, Full Bath, Walk-In Closet(s), Wide Board Floor
- Level: Upper
Bedroom
- Features: Remodeled, Beamed Ceilings, Wide Board Floor
- Level: Upper
Bedroom
- Features: Remodeled, Wide Board Floor
- Level: Upper
Bedroom
- Features: Remodeled, Wide Board Floor
- Level: Third,Upper
Den
- Features: Remodeled, Beamed Ceilings, Built-in Features, Dry Bar, Wide Board Floor
- Level: Main
Dining room
- Features: Remodeled, Beamed Ceilings, Built-in Features, Fireplace, French Doors, Wide Board Floor
- Level: Main
Family room
- Features: Remodeled, Beamed Ceilings, French Doors, Wide Board Floor
- Level: Main
Kitchen
- Features: Beamed Ceilings, Built-in Features, Half Bath, Kitchen Island, Wide Board Floor
- Level: Main
Kitchen
- Features: Remodeled, Beamed Ceilings, Built-in Features, Dining Area, French Doors, Wide Board Floor
- Level: Main
Living room
- Features: Remodeled, Beamed Ceilings, Fireplace, French Doors, Wide Board Floor
- Level: Main
Office
- Features: Remodeled, Walk-In Closet(s), Wide Board Floor
- Level: Third,Upper
Office
- Features: Skylight, High Ceilings
- Level: Other
Rec play room
- Features: Remodeled, Built-in Features, Wide Board Floor
- Level: Third,Upper
Sun room
- Features: Remodeled, Slate Floor
- Level: Main
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Range, Oven/Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Main Level, Mud Room
Features
- Smart Thermostat
- Doors: French Doors
- Basement: Full,Unfinished,Sump Pump,Storage Space,Interior Entry,Concrete
- Attic: Heated,Storage,Floored
- Number of fireplaces: 3
Interior area
- Total structure area: 3,744
- Total interior livable area: 3,744 sqft
- Finished area above ground: 3,744
Property
Parking
- Total spaces: 8
- Parking features: Detached, Driveway, Garage Door Opener, Asphalt
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Wrap Around, Patio, Porch
- Exterior features: Outdoor Grill, Garden, Stone Wall, Underground Sprinkler
- Has private pool: Yes
- Pool features: Heated, In Ground
- Fencing: Partial
Lot
- Size: 1.26 Acres
- Features: Few Trees, Level, Landscaped, Rolling Slope
Details
- Additional structures: Shed(s)
- Parcel number: 189542
- Zoning: 1AC
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Antique
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter, Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1850
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Golf, Health Club, Library, Park, Playground, Private School(s), Near Public Transport, Shopping/Mall
- Security: Security System
HOA
- Has HOA: No
Location
- Region: New Canaan
Financial & listing details
- Price per square foot: $800/sqft
- Tax assessed value: $1,099,560
- Annual tax amount: $18,352
- Date on market: 3/3/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/10/2026 | Pending sale | $2,995,000$800/sqft |
Source:  Smart MLS #24157134 Report a problem | ||
| 3/3/2026 | Listed for sale | $2,995,000+8.5%$800/sqft |
Source:  Halstead / Brown Harris Stevens #24157134 Report a problem | ||
| 10/15/2025 | Sold | $2,760,000+10.6%$737/sqft |
Source: Smart MLS #24108491 Report a problem | ||
| 9/5/2025 | Pending sale | $2,495,000$666/sqft |
Source: Smart MLS #24108491 Report a problem | ||
| 9/2/2025 | Listed for sale | $2,495,000+100.4%$666/sqft |
Source: Smart MLS #24108491 Report a problem | ||
| 9/22/2003 | Sold | $1,245,000+81.8%$333/sqft |
Source: Public Record Report a problem | ||
| 7/7/1994 | Sold | $685,000+9.9%$183/sqft |
Source: Smart MLS #95056256 Report a problem | ||
| 12/5/1989 | Sold | $623,500$167/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $18,352 +3.4% | $1,099,560 |
| 2024 | $17,747 -8.1% | $1,099,560 +7.9% |
| 2023 | $19,304 +3.1% | $1,019,200 |
| 2022 | $18,723 +1.2% | $1,019,200 |
| 2021 | $18,509 | $1,019,200 |
| 2020 | $18,509 -0.4% | $1,019,200 |
| 2019 | $18,590 +8.3% | $1,019,200 +0.7% |
| 2018 | $17,163 +1.7% | $1,011,990 |
| 2017 | $16,870 +2.2% | $1,011,990 |
| 2016 | $16,506 +2% | $1,011,990 |
| 2015 | $16,182 +2.9% | $1,011,990 |
| 2014 | $15,726 -0.9% | $1,011,990 -6.9% |
| 2013 | $15,862 +3.6% | $1,087,200 |
| 2012 | $15,308 +1.7% | $1,087,200 |
| 2011 | $15,058 +2% | $1,087,200 |
| 2010 | $14,764 +1.7% | $1,087,200 |
| 2009 | $14,514 +0.2% | $1,087,200 +13.5% |
| 2008 | $14,483 +14.3% | $957,900 +9.9% |
| 2007 | $12,672 +3.5% | $871,500 0% |
| 2006 | $12,239 +4.9% | $871,700 |
| 2005 | $11,672 -3.8% | $871,700 -9.1% |
| 2004 | $12,135 +27.1% | $958,500 +40.4% |
| 2003 | $9,551 +16.4% | $682,710 +73.8% |
| 2001 | $8,204 +2% | $392,900 +0% |
| 2000 | $8,045 +5% | $392,840 |
| 1999 | $7,660 | $392,840 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$19,663/mo
Principal & interest
$15445
Property taxes
$4218
More affordability tools
Climate risks
Neighborhood: 06840
Nearby schools
GreatSchools rating
- 9/10Saxe Middle SchoolGrades: 5-8Distance: 0.3 mi
- 10/10New Canaan High SchoolGrades: 9-12Distance: 0.5 mi
- 9/10South SchoolGrades: K-4Distance: 0.5 mi
Schools provided by the listing agent
- Elementary: South
- Middle: Saxe Middle
- 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.
Local experts in 06840
- Connecticut
- Fairfield County
- New Canaan
- 06840
- 105 White Oak Shade Road
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