105 Sleepy Hollow Road

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Attic Stairway
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Active
$1,475,000
4 beds2,774 sqft
105 Sleepy Hollow Rd, Ridgefield, CT 06877
Est: $9,222/moGet pre-approved
Single FamilyProperty Type
1.2 acresLot Size
2021Year Built
$532/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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.
16 days on Market
  • Listed by: Derek A Heering 203.832.7677 derek@propertytwinsteam.com • Property Twins Real Estate
  • Listed by: Stephanie Heering 203.832.7677 stephanie@propertytwinsteam.com • Property Twins Real Estate
Last updated: 09/20/2026 11:40 PM • Source: SMARTMLS, MLS#: 24203399

Location

Listing Courtesy of Property Twins Real Estate, Derek A Heering; Property Twins Real Estate, Stephanie Heering
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$9,222 per month

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Property Taxes

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Property Information for 105 Sleepy Hollow Road

Property Details
  • Taxes: $19,196 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Full, Full With Walk-Out
  • Direct Waterfront: No
  • Expected Active Date: 09-04-2026
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
  • Expected On Market Date: 09-04-2026
Building Information
  • Year Built: 2021
  • Lot Size: 1.20 AC / 52,272 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Scotland
  • High School: Ridgefield
  • Latitude: 41.31245
  • Longitude: -73.540338
  • Middle Jr High School: Scotts Ridge
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $19,196
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Length: 12.1
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 12.1
Room 2
  • Room Entry Order: 2
  • Room Features: Quartz Counters,Dry Bar,Island,Hardwood Floor
  • Room Length: 19.3
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 12.5
Room 3
  • Room Entry Order: 3
  • Room Features: Built-Ins,Gas Log Fireplace,Sliders,Hardwood Floor
  • Room Length: 18.1
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 16.3
Room 4
  • Room Entry Order: 4
  • Room Features: Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 18.3
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 13.4
Room 5
  • Listing Key: 5A5E126CF25CAA54E0631A01100A1069
  • Room Entry Order: 5
  • Room Features: Built-Ins,Hardwood Floor
  • Room Length: 14.6
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.3
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 13.9
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.2
Room 7
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 10.9
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.8
Room 8
  • Room Entry Order: 8
  • Room Features: Stall Shower,Tile Floor
  • Room Level: Upper
  • Room Type: Full Bath
Room 9
  • Listing Key: 5A5E126CF25CAA54E0631A01100A1069
  • Room Entry Order: 9
  • Room Features: Tub w/Shower,Tile Floor
  • Room Level: Upper
  • Room Type: Full Bath
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2021
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 2774
Lot Information
  • Lot Description: Lightly Wooded, Professionally Landscaped
  • Parcel Number: 273420
  • Sq Ft Est Heated Above Grade: 2774.0
  • Sq Ft Total: 2774.0
  • Zoning: RAA
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Propane
  • Hot Water Description: Propane, Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 105 Sleepy Hollow Road

DateEvent & SourcePriceAppreciation
Feb 5, 2021

Closed (Public Record)

Public Record #1450936595

$235,000

-3.3% / yr

May 18, 2006

Closed (Public Record)

Public Record #197356358

$382,500—
DateEvent & SourcePrice
02/05/2021

Closed (Public Record)

Public Record #1450936595

$235,000

-3.3% / yr

05/18/2006

Closed (Public Record)

Public Record #197356358

$382,500

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

Public Records for 105 Sleepy Hollow Road

Taxable ValueLand$189,000Additions$511,840Total$700,840
Tax Record2025$19,196 ($1,600 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt2,774 SqFtAbove Grade Finished SqFt2,774 SqFtStories2Lot Size52,272 SqFtStyleSingle Family ResidenceYear Built2021Year Renovated2021ZoningRAACountyWESTERN CONNECTICUTAPNRIDG M:B10 B:0022

Schools near 105 Sleepy Hollow Road

This home is within Ridgefield School District.
Rating
School
Type
Grades
Distance
Scotland Elementary School
Public - PK to 5
Scotts Ridge Middle School
Public - 6 to 8
Ridgefield High School
Public - 9 to 12
District Program Res
Public - 3 to 5
Rating
School
Distance
Scotland Elementary School
PublicPK to 5

Scotts Ridge Middle School
Public6 to 8

Ridgefield High School
Public9 to 12

District Program Res
Public3 to 5

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.

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More information about 105 Sleepy Hollow Road, Ridgefield, CT 06877

105 Sleepy Hollow Road is a single family home for sale in Ridgefield, CT 06877. This property was listed for sale on September 2, 2026 by Property Twins Real Estate, it's currently listed at $1,475,000. It has been on the market for a total of 16 days and was last sold on February 5, 2021. This listing's school district is Ridgefield School District. Nearby schools include Scotland Elementary School, Scotts Ridge Middle School and Ridgefield High School. 105 Sleepy Hollow Road is a 4-bed, 4-bath, 2,774 sqft single family home built in 2021.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Property Twins Real Estate, Derek A Heering; Property Twins Real Estate, Stephanie Heering

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.