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$3,500,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,744 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 105 White Oak Shade Rd

General

  • Sold For: $3,500,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24157134
  • Added to Site: 97 day(s) ago

Interior

  • Number of Rooms: 14
  • Rooms/Areas: Laundry Room, Mud Room
  • Interior Features: Auto Garage Door Opener, Cable - Available, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Range, Oven/Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Electric Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Remodeled, Beams, Fireplace, Full Bath, Walk-In Closet, Wide Board Floor, Upper
  • Bedroom 1: Bedroom - Remodeled, Wide Board Floor, Upper
  • Bedroom 2: Bedroom - Remodeled, Beams, Wide Board Floor, Upper
  • Bedroom 3: Bedroom - Remodeled, Wide Board Floor, On 3rd Floor, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, Beams, Fireplace, French Doors, Wide Board Floor, Main
  • Family Room: Family Room - Remodeled, Beams, French Doors, Wide Board Floor, Main
  • Kitchen: Kitchen - Beams, Built-Ins, Half Bath, Island, Wide Board Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, Beams, Built-In Hutch, Dining Area, French Doors, Wi, Main
  • Dining Room: Dining Room - Remodeled, Beams, Built-Ins, Fireplace, French Doors, Wide Board Floor, Main
  • Office: Office - Skylight, 9 ft+ Ceilings, Other
  • Den: Den - Remodeled, Beams, Built-Ins, Dry Bar, Wide Board Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Remodeled, Built-Ins, Wide Board Floor, On 3rd Floor, Upper
  • Rec Room: Remodeled, Built-Ins, Wide Board Floor, On 3rd Floor, Upper
  • Laundry: Main Level

Additional Information

  • Pool: Yes
  • Pool Description: Heated, In Ground Pool

Exterior

  • Exterior Features: Porch-Wrap Around, Wrap Around Deck, French Doors, Patio, Grill, Shed, Porch, Garden Area, Stone Wall, Underground Sprinkler
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking: Detached Garage, Driveway

Location

  • County: Fairfield
  • Driving Directions: Main St to White Oak Shade

School Information

  • Elementary School: South
  • Middle School: Saxe Middle
  • High School: New Canaan

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, 50 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Antique
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Unfinished, Sump Pump, Storage, Interior Access, Concrete Floor
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,744
  • Above Ground: 3,744 Sq. Ft.
  • Year Built: 1850

Lot Features

  • Lot Size (Acres): 1.26
  • Driveway/Sidewalk: Asphalt, Crushed Stone
  • Zoning: 1AC
  • Lot Description: Fence - Partial, Lightly Wooded, Level Lot, Professionally Landscaped, Rolling

Financial Considerations

  • Assessment Amount: $1,099,560
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 189542

Meet the selling agent

Meet the selling agent
— 105 White Oak Shade Rd —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 105 White Oak Shade Rd

School District:New Canaan School District
NameGradesDistance
Saxe Middle School
468 South Avenue, New Canaan, CT 06840
5-80.3 mi
South School
8 Farm Road, New Canaan, CT 06840
K-40.5 mi
New Canaan High School
11 Farm Road, New Canaan, CT 06840
9-120.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 105 White Oak Shade Rd

Date
Details
Price
Change
Source
4/30/2026
Sold
$3,500,000
16.86%
MLS
3/05/2026
Listed
$2,995,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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105 White Oak Shade Road, New Canaan, CT 06840 (MLS# 24157134) is a Single Family property that was sold at $3,500,000 on April 30, 2026. This property was sold by Cindy Raney & Team from our Westport Office.Want to learn more about 105 White Oak Shade Road? Do you have questions about finding other Single Family real estate for sale in New Canaan? You can browse all New Canaan real estate or contact a Coldwell Banker agent to request more information.