38 Rolling Hill Rd

Ridgefield, CT 06877

$1,360,000
Last Sold Price
4
Beds
5,450 Sq. Ft.
$250 / Sq. Ft.
5,450
Sq. Ft.
$250
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 10/29/25
Closed 10/29/25

Description

If you're looking for upscale living wrapped in small-town charm, look no further than 38 Rolling Hill Rd. This home blends modern amenities & extraordinary craftsmanship in an unmatched setting along Aldrich Park. The 2-story foyer is flanked by the living room and the dining room, with a powder room and office nearby. The dramatic 2-story family room fills the home with light and views of the backyard. The chef's kitchen is the heart of the home and nothing short of spectacular. With custom inset...If you're looking for upscale living wrapped in small-town charm, look no further than 38 Rolling Hill Rd. This home blends modern amenities & extraordinary craftsmanship in an unmatched setting along Aldrich Park. The 2-story foyer is flanked by the living room and the dining room, with a powder room and office nearby. The dramatic 2-story family room fills the home with light and views of the backyard. The chef's kitchen is the heart of the home and nothing short of spectacular. With custom inset cabinetry, leathered marble countertops, an island, AGA 5-burner range w/ French antiqued mirror backsplash, AGA fridge, breakfast nook and mudroom, every detail has been thoughtfully designed and make this kitchen as functional as it is beautiful. Upstairs, the primary bedroom features 2 walk-in closets and a luxurious bath; 3 additional bedrooms share the hall bath. The 560 sq ft 4th bedroom can double as a bonus room, gym or playroom. The walk-out LL has been fully transformed to an in-law apartment with a kitchen, family room, bedroom, full bath & laundry. Stone walls line the driveway and hydrangeas & magnolia trees create a lovely backdrop. The backyard retreat features a fire pit area & zip line among the trees. This home is close to Martin Park, Ridgefield's vibrant downtown, Ridgefield Playhouse, Aldrich Art Museum & more. With stunning renovations, sophisticated design & a setting that combines privacy, community & culture, this home offers the best of Ridgefield living.
  1. Listed by Sarah Pritchard Provenzano • William Raveis Real Estate
    P: (203)-255-6841 C: (203)-414-5571 Sarah@PritchardHomesTeam.com

Property Details for 38 Rolling Hill Road

Basement Description
Full, Fully Finished, Interior Access, Liveable Space, Full With Walk-Out
Direct Waterfront
No
Garages Number
2
Neighborhood
Village Center
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
No
LISTING CLOSED: 10/29/2025 12:00 AM

Property Details for 38 Rolling Hill Road

StatusClosed
MLS #24121630
Days on Market18
Taxes$19,911 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1995
Lot Size2.04 AC / 88,862 SF
CountyFairfield County
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Location

Listing Courtesy of William Raveis Real Estate, Sarah Pritchard Provenzano

Sold By William Pitt Sotheby's Int'l, Kristi Vaughan

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Building Information for 38 Rolling Hill Road

Stories-Year Built1995Building Size-Lot Size2.04 AC / 88,862 SF

Payment Calculator

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$8,436 per month

30 year fixed, 6.36% Interest

Principal and Interest

$6,777

Property Taxes

$1,659

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 38 Rolling Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 7 to Haviland Road to Still Road to Nursery Road to Rolling Hill Road; house at end of cul-de-sac
  • Elementary School: Farmingville
  • High School: Ridgefield
  • Latitude: 41.306264
  • Longitude: -73.468764
  • Middle Jr High School: East Ridge
  • Neighborhood Amenities: Lake, Library, Paddle Tennis, Park, Public Rec Facilities, Shopping/Mall, Stables/Riding
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $19,911
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Deck, Gutters, Garden Area, Lighting, Stone Wall, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Unfinished, Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener
  • Laundry Room Info: Lower Level, Upper Level
  • Laundry Room Location: 2nd floor hallway & lower level
  • Rooms Additional: Foyer, Laundry Room, Mud Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.0
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 3
  • Room Entry Order: 11
  • Room Features: Hardwood Floor
  • Room Length: 28.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 20.0
Room 4
  • Room Entry Order: 12
  • Room Features: Tub w/Shower,Tile Floor
  • Room Length: 9.0
  • Room Level: Upper
  • Room Type: Full Bath
  • Room Width: 10.0
Room 5
  • Listing Key: 3D32B8BCB6C2B576E063E201100A5A5A
  • Room Entry Order: 13
  • Room Length: 27.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 34.0
Room 6
  • Room Entry Order: 14
  • Room Features: Dining Area
  • Room Length: 11.0
  • Room Level: Lower
  • Room Type: Kitchen
  • Room Width: 25.0
Room 7
  • Room Entry Order: 15
  • Room Length: 16.0
  • Room Level: Lower
  • Room Type: Other
  • Room Width: 13.0
Room 8
  • Room Entry Order: 16
  • Room Length: 8.0
  • Room Level: Lower
  • Room Type: Full Bath
  • Room Width: 8.0
Room 9
  • Listing Key: 3D32B8BCB6C2B576E063E201100A5A5A
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.0
Room 10
  • Room Entry Order: 3
  • Room Features: Vaulted Ceiling,Sliders,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 16.0
Room 11
  • Room Entry Order: 4
  • Room Features: Hardwood Floor
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 13.0
Room 12
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 6.0
  • Room Level: Main
  • Room Type: Half Bath
  • Room Width: 8.0
Room 13
  • Room Entry Order: 6
  • Room Features: Dining Area,Island,Sliders,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 22.0
Room 14
  • Room Entry Order: 7
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 14.0
Room 15
  • Room Entry Order: 8
  • Room Features: Stall Shower,Whirlpool Tub
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Primary Bath
  • Room Width: 14.0
Room 16
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Property
Property and Assessments
  • Color: Brick & yellow
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Brick
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1995
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level
  • In Law Apartment: Yes
  • Sq Ft Est Heated Below Grade: 1704
  • Living Area SQFT Per Public Records: 3746
Lot Information
  • Lot Description: On Cul-De-Sac
  • Parcel Number: 281464
  • Sq Ft Est Heated Above Grade: 3746.0
  • Sq Ft Total: 5450.0
  • Zoning: RAA
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Other
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 38 Rolling Hill Road

DateEvent & SourcePriceAppreciation
Oct 29, 2025

Closed (Public Record)

Public Record #1920103849

$1,360,000

+14.6% / yr

Jun 14, 2021

Closed (Public Record)

Public Record #1464425958

$750,000

-2.2% / yr

Jun 27, 2005

Closed (Public Record)

Public Record #162975344

$1,070,000

+6.5% / yr

DateEvent & SourcePrice
10/29/2025

Closed (Public Record)

Public Record #1920103849

$1,360,000

+14.6% / yr

06/14/2021

Closed (Public Record)

Public Record #1464425958

$750,000

-2.2% / yr

06/27/2005

Closed (Public Record)

Public Record #162975344

$1,070,000

+6.5% / yr

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

Public Records for 38 Rolling Hill Road

Taxable ValueLand$236,460Additions$490,490Total$726,950
Tax Record2024$19,911 ($1,659 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt3,746 SqFtAbove Grade Finished SqFt3,746 SqFtUnfinished Basement SqFt604 SqFtStories2Lot Size88,862 SqFtStyleSingle Family ResidenceYear Built1995Year Renovated2000ZoningRAACountyWESTERN CONNECTICUTAPNRIDG M:G11 B:0094Fireplace TypeHas Fireplace

Schools near 38 Rolling Hill Road

This home is within Ridgefield School District.
Rating
School
Type
Grades
Distance
Farmingville Elementary School
Public - PK to 5
East Ridge Middle School
Public - 6 to 8
Ridgefield High School
Public - 9 to 12
District Program Erms
Public - PK to 1
Rating
School
Distance
Farmingville Elementary School
PublicPK to 5

East Ridge Middle School
Public6 to 8

Ridgefield High School
Public9 to 12

District Program Erms
PublicPK to 1

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.

Ridgefield
Ridgefield
Verdant surroundings and a storybook downtown. A beautiful, forested enclave nestled along the border of Westchester County, Ridgefield is home to 25,000 residents who enjoy a charming Main Street town center and a peaceful way of life centered on community and creativity. Here, you'll find...
Ridgefield Guide

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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 William Raveis Real Estate, Sarah Pritchard Provenzano

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.