21 Olmstead Hill Rd

3,461 Sq. Ft.
$26 / Sq. Ft.
3,461
Sq. Ft.
$26
per Sq. Ft.

Description

Tucked away on one of Wilton's most picturesque streets, this private retreat feels like a getaway every single day. Set back from the road, the property welcomes you with an expansive, level lawn that gently rolls down to a serene private pond with its own dock-ideal for year-round fun. Imagine fishing on a quiet morning, paddling across the water on a sunny afternoon, or lacing up your skates for some winter magic. Inside, sunlight pours into every corner, highlighting spacious rooms that seamlessly...Tucked away on one of Wilton's most picturesque streets, this private retreat feels like a getaway every single day. Set back from the road, the property welcomes you with an expansive, level lawn that gently rolls down to a serene private pond with its own dock-ideal for year-round fun. Imagine fishing on a quiet morning, paddling across the water on a sunny afternoon, or lacing up your skates for some winter magic. Inside, sunlight pours into every corner, highlighting spacious rooms that seamlessly connect indoor and outdoor living. The main floor features a bright, inviting eat-in kitchen with a center island and dining area, perfect for both casual meals and festive gatherings. The living room has walls of glass framing stunning views and a cozy double-sided fireplace shared with the dining room. Just steps away, the family room offers the perfect spot to unwind. And when the weather calls, step out onto the wrap-around deck, where there's plenty of room to host lively get-togethers or simply soak in the peace and quiet. Upstairs, the primary suite is a true haven, complete with an updated bath, a fireplace for cozy evenings, and tranquil views. Two additional generously sized bedrooms and a convenient laundry room complete the second floor. For added flexibility, a spacious bedroom and/or office with a brand-new bath sits above the garage, offering a private space for guests, work, or creative pursuits. It's more than a home-it's a sanctuary.

Listing Agent

  1. Marion Filley

    Marion Filley

    Listing Agent

    Compass

    marion.filley@compass.com

    P: (203)-515-1387

Property Details for 21 Olmstead Hill Road

Basement Description
Full, Unfinished
Direct Waterfront
Yes
Garages Number
2
Neighborhood
N/A
Style
Contemporary
Garage Parking Info
Under House Garage
Swimming Pool
No
LISTING UPDATED: 02/02/2026 10:54 PM

Property Details for 21 Olmstead Hill Road

StatusActive
MLS #24150831
Days on MarketListed Today
Rental Incentives-
Available Date03/01/2026
Lease Term-
Furnished-
Compass TypeRental
MLS TypeResidential Rental / Single Family Rental
Year Built1973
Lot Size4.02 AC / 175,111 SF
CountyFairfield County

Location

Add your commute

Building Information for 21 Olmstead Hill Road

Building/Complex21 Olmstead Hill RdFloor-Stories-Pet Policy-Pet Policy DetailsRestrictionsYear Built1973Building Size-Lot Size4.02 AC / 175,111 SF

Property Information for 21 Olmstead Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Ridgefield Road to Nod Hill to Olmstead Hill. See the group of mailboxes (#15 & 19) on the right. At the end of the driveway.
  • Elementary School: Miller-Driscoll
  • High School: Wilton
  • Intermediate School: Cider Mill
  • Latitude: 41.211839
  • Longitude: -73.455625
  • Middle Jr High School: Middlebrook
  • Neighborhood Amenities: Health Club, Library, Medical Facilities, Paddle Tennis, Park, Tennis Courts
  • Pets Allowed Info: One small non-shedding do
  • Pets Allowed: Restrictions
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Pond, Brook
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: No
  • Fireplaces Total: 3
  • Home Automation: Lighting, Security System, Thermostat(s)
  • Interior Features: Security System
  • Laundry Room Info: Upper Level
  • Rooms Additional: Laundry Room
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Balcony/Deck,Fireplace,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Granite Counters,Dining Area,Island,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 4
  • Room Entry Order: 4
  • Room Features: Balcony/Deck,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 5
  • Listing Key: 491815D0C25E33CAE063E201100A9DEC
  • Room Entry Order: 5
  • Room Features: Fireplace,Full Bath,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Other
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: Gray
  • Exterior Siding: Cedar, Wood
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Smoking Allowed: No
  • Year Built: 1973
  • Year Built Source: Public Records
  • In Law Apartment: No
  • Living Area SQFT Per Public Records: 3461
Lot Information
  • Lot Description: Secluded, Some Wetlands, Interior Lot, Level Lot, Cleared, Water View
  • Parcel Number: 1927089
  • Sq Ft Est Heated Above Grade: 3461.0
  • Sq Ft Total: 3461.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner
Rental
Rental
  • Rental Duration: Yearly Unfurnished, Yearly Furnished, Flexible Terms Unfurnished, Flexible Terms Furnished

Schools near 21 Olmstead Hill Road

This home is within Wilton School District.
Rating
School
Type
Grades
Distance
Public - PK to 2
Public - 3 to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Miller-Driscoll School
PublicPK to 2

Cider Mill School
Public3 to 5

Middlebrook School
Public6 to 8

Wilton High School
Public9 to 12

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.

21 Olmstead Hill Road is available for rent in Wilton, CT 06897. This listing's school district is Wilton School District. Nearby schools include Miller-Driscoll School, Cider Mill School and Middlebrook School. 21 Olmstead Hill Road is a 4-bed, 4-bath, 3,461 sqft a property built in 1973.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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.