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$1,575,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,774 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago
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Privacy, craftsmanship, and a nearly new home come together at 105 Sleepy Hollow Road. Constructed in 2021, this distinctive Ridgefield residence offers generous proportions and a polished interior filled with sunlight. The main level was created with connection in mind, bringing the kitchen, gathering areas, and dining spaces together naturally. A substantial center island anchors the kitchen, complemented by extensive prep space and a separate butler's pantry. Nearby, a gas fireplace adds warmth and character. The second floor includes four bedrooms, highlighted by an impressive owner's suite with two walk-in closets and a beautifully finished bathroom with dual sinks, a freestanding soaking tub, and large glass-enclosed shower. Two additional full bathrooms serve the remaining bedrooms. Below, a large unfinished walk-out basement with high ceilings provides exciting possibilities for future finished space, whether envisioned as a gym, media room, recreation area, or additional living space. The property offers multiple outdoor areas, including a deck, patio, and hot tub, all surrounded by established landscaping and a peaceful natural backdrop. A whole-house generator, 2-car garage, mudroom, separate laundry room, and walk-up attic add everyday practicality. Close to Ridgefield's town center and commuter routes, this special property pairs a newer build with space, seclusion, and convenience.

Full Property Details for 105 Sleepy Hollow Rd

General

  • Price: $1,575,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24203399
  • Updated: 9/6/2026
  • Added to Site: 6 day(s) ago

Interior

  • Number of Rooms: 8
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Full Bath: Stall Shower, Tile Floor, Upper

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Full Bath, Walk-In Closet, Hardwood Floor, 18.3 x 13.4, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 10.9 x 10.8, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, 13.9 x 13.2, Upper
  • Bedroom 3: Bedroom - Built-Ins, Hardwood Floor, 14.6 x 11.3, Upper

Other Rooms

  • Family Room: Family Room - Built-Ins, Gas Log Fireplace, Sliders, Hardwood Floor, 18.1 x 16.3, Main
  • Kitchen: Kitchen - Quartz Counters, Dry Bar, Island, Hardwood Floor, 19.3 x 12.5, Main
  • Dining Room: Dining Room - Hardwood Floor, 12.1 x 12.1, Main

Exterior

  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Driving Directions: GPS Friendly

School Information

  • Elementary School: Scotland
  • Middle School: Scotts Ridge
  • High School: Ridgefield

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Propane
  • Heating Fuel: Propane
  • Water Heater: Propane, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,774
  • Above Ground: 2,774 Sq. Ft.
  • Year Built: 2021

Lot Features

  • Lot Size (Acres): 1.2
  • Zoning: RAA
  • Lot Description: Lightly Wooded, Professionally Landscaped

Green Features

  • Energy Features: Generator

Financial Considerations

  • Assessment Amount: $700,840
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 273420

Listed by Property Twins Real Estate, Derek Heering and Property Twins Real Estate, Stephanie Heering

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Listing agents

— 105 Sleepy Hollow Rd —

  • Derek Heering

    Property Twins Real Estate

  • Stephanie Heering

    Property Twins Real Estate

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 Sleepy Hollow Rd

School District:Ridgefield School District
NameGradesDistance
Scotland Elementary School, Ridgefield, CT
111 Barlow Mountain Road, Ridgefield, CT 06877
K-51.6 mi
Scotts Ridge Middle School
750 North Salem Road, Ridgefield, CT 06877
6-81.1 mi
Ridgefield High School
700 North Salem Road, Ridgefield, CT 06877
9-121.1 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 Sleepy Hollow Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/04/2026
Listed
$1,575,000
570.21%
MLS
2/05/2021
Sold
$235,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 105 Sleepy Hollow Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$19,196
4%
$700,840
—
2023
$18,467
2%
$700,840
—
2023
$18,089
6%
$700,840
17%
2022
$17,052
—
$599,780
333%
2021
$17,052
338%
$138,600
—
2020
$3,897
—
$138,600
—
2019
$3,897
1%
$138,600
—
2018
$3,850
2%
$138,600
—
2017
$3,771
2%
$138,600
—
2016
$3,699
-26%
$138,600
-27%
2015
$4,971
25%
$191,100
25%
2014
$3,991
-18%
$153,440
-20%
2011
$4,855
—
$191,310
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 105 Sleepy Hollow Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Property Twins Real Estate, Derek Heering and Property Twins Real Estate, Stephanie Heering

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105 Sleepy Hollow Road, Ridgefield, CT 06877 (MLS# 24203399) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 105 Sleepy Hollow Road is currently listed for $1,575,000 and was received on September 02, 2026. Want to learn more about 105 Sleepy Hollow Road? Do you have questions about finding other Single Family real estate for sale in Ridgefield? You can browse all Ridgefield real estate or contact a Coldwell Banker agent to request more information.

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