RENTED FEB 25, 2026

21 Olmstead Hill Rd Wilton, CT 06897

Wilton Area

Estimated Value: $1,509,000 - $1,906,000

4 Beds
3.5 Baths
3,461 Sq Ft
$478/Sq Ft Est. Value

Sale Details

Date Sold: October 27, 2020

Last sale price $910,000 $263 Per Sq Ft

Est. 82% increase in value since last sale

Current estimated payment $10,555 / mo

Highlights

  • Waterfront
  • 4.02 Acre Lot
  • 3 Fireplaces
  • Miller-Driscoll School Rated A
  • Contemporary Architecture
  • Home Security System

About This Home

As of February 2026

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.

Last Agent to Rent the Property

Marion Filley

Compass Connecticut, LLC Brokerage Phone: (203) 515-1387 License #RES.0224030 Listed on: 02/02/2026

Compass Connecticut, LLC

Last Renter's Agent

Unrepresent Buyer/Tenant

Unrepresented Buyer

Home Details

Home Type

  • Single Family

Year Built

  • Built in 1973

Lot Details

  • 4.02 Acre Lot
  • Waterfront
  • Property is zoned R-2

Parking

  • 2 Car Garage

Home Design

  • Contemporary Architecture
  • Wood Siding
  • Cedar Siding

Interior Spaces

  • 3,461 Sq Ft Home
  • 3 Fireplaces
  • Unfinished Basement
  • Basement Fills Entire Space Under The House

Kitchen

  • Built-In Oven
  • Electric Cooktop
  • Microwave
  • Dishwasher

Bedrooms and Bathrooms

  • 4 Bedrooms

Laundry

  • Laundry Room
  • Laundry on upper level
  • Dryer
  • Washer

Home Security

  • Home Security System
  • Smart Lights or Controls
  • Smart Thermostat

Eco-Friendly Details

  • Energy-Efficient Lighting

Schools

  • Miller-Driscoll Elementary School
  • Middlebrook School
  • Cider Mill Middle School
  • Wilton High School

Utilities

  • Central Air
  • Heating System Uses Oil
  • Private Company Owned Well
  • Fuel Tank Located in Basement

Listing and Financial Details

  • Assessor Parcel Number 1927089

Home Details

Home Type

Single Family

Year Built

Built in 1973

Lot Details

4.02 Acres

Rental Info

  • Pets Allowed Info: One small non-shedding do
  • Lease Price Description: Per Month
  • Pets Allowed: Restrictions
  • Rental Duration: Yearly Unfurnished, Yearly Furnished, Flexible Terms Unfurnished, Flexible Terms Furnished
  • Smoking Allowed: No

Listing Details

  • Neighborhood: N/A
  • Property Type: Residential Rental
  • Style: Contemporary
  • Sq Ft Est Heated Above Grade: 3461
  • Total Sq Ft: 3461
  • Year Built: 1973
  • New Construction: No/Resale
  • Nearby Amenities: Health Club, Library, Medical Facilities, Paddle Tennis, Park, Tennis Courts
  • Remarks Public Addendum: Rental includes a gas grill, smoker, Solo Stove fire pit, outdoor furniture, and a canoe for the pond.
  • Property Sub Type: Single Family Rental
  • Direct Waterfront: Yes
  • 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.
  • In Law Apartment: No
  • Street Type: Road
  • Tenant Responsibility: All Utilities Cable TV Credit Check Grounds Maintenance Insurance Liability Insurance
  • Office Attribution Contact: (203) 293-9715
  • Reserve Prospect: No
  • Special Features: None

Interior Features

  • Total Bedrooms: 4
  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Fireplaces: 3
  • Basement Description: Full, Unfinished
  • Interior Amenities: Security System
  • Appliances: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Additional Rooms: Laundry Room
  • Laundry Room Info: Upper Level
  • Attic: No
  • Home Automation: Lighting, Security System, Thermostat(s)

Exterior Features

  • Exterior Siding: Cedar, Wood
  • Waterfront Description: Pond Brook
  • Swimming Pool: No

Garage/Parking

  • Garages Number: 2
  • Garage And Parking: Under House Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Domestic
  • Water Source: Private Well
  • Sewer: Septic

Schools

  • Intermediate School: Cider Mill

Lot Info

  • Acres: 4.02
  • Lot Description: Secluded Some Wetlands Interior Lot Level Lot Cleared Water View
  • Zoning: R-2
  • Parcel #: 1927089

MLS Schools

  • Elementary School: Miller-Driscoll
  • Middle Jr High School: Middlebrook
  • High School: Wilton

Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Listed on
Sep 3, 2020
Closed on
Oct 22, 2020
Sold by
Bought by
Seller's Agent
Carissa McMahon
Coldwell Banker Realty
Buyer's Agent
Carissa McMahon
Coldwell Banker Realty
List Price
$870,000
Sold Price
$910,000
Premium/Discount to List
$40,000
4.6%
Current Estimated Value
$1,653,976

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$743,976
Avg. Annual Appreciation
10.99%
Original Mortgage
$636,000
Interest Rate
0.028%
Mortgage Type
Purchase Money Mortgage

Purchase Details

Closed on
Oct 26, 1988
Sold by
Bought by
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
$910,000 None Available
$485,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Open $636,000
Previous Owner $350,000
Previous Owner $185,000
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft Prior Sale
02/25/2026 02/25/26 Rented $7,500 0.0% --
02/10/2026 02/10/26 Under Contract -- -- --
02/02/2026 02/02/26 For Rent $7,500 0.0% --
10/27/2020 10/27/20 Sold $910,000 +4.6% $263 / Sq Ft View Prior Sale
10/02/2020 10/02/20 Pending -- -- --
09/03/2020 09/03/20 For Sale $870,000 -- $251 / Sq Ft
Source: SmartMLS

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $18,832 $771,470 $396,130 $375,340
2024 $18,469 $771,470 $396,130 $375,340
2023 $16,848 $575,820 $378,560 $197,260
2022 $16,255 $575,820 $378,560 $197,260
2021 $16,048 $575,820 $378,560 $197,260
2020 $15,812 $575,820 $378,560 $197,260
2019 $16,434 $575,820 $378,560 $197,260
2018 $16,702 $592,480 $395,640 $196,840
2017 $16,453 $592,480 $395,640 $196,840
2016 $16,198 $592,480 $395,640 $196,840
2015 $15,896 $592,480 $395,640 $196,840
2014 $15,707 $592,480 $395,640 $196,840
Source: Public Records

Agents Affiliated with this Home

  • Marion Filley

    Landlord's Agent in 2026

    Marion Filley

    Compass Connecticut, LLC

    (203) 515-1387

    100 Total Sales

    Marion Filley
    Section Image

  • U

    Tenant's Agent in 2026

    Unrepresent Buyer/Tenant

    Unrepresented Buyer

  • Carissa McMahon

    Seller's Agent in 2020

    Carissa McMahon

    Coldwell Banker Realty

    (203) 442-4159

    28 Total Sales

    Carissa McMahon
    Section Image

  • D

    Seller Co-Listing Agent in 2020

    Douglas Jones

    Coldwell Banker Realty

See All Agents

Map

Source: SmartMLS

MLS Number: 24150831

SmartMLS

APN: WILT-000090-000011

Connecticut Fairfield County Wilton 06897

21 Olmstead Hill Rd, Wilton, CT

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