Date
Details
Price
Change
Source
2/02/2026
Listed
$7,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/26
$7,500 Just Listed
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1/26
Property 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 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.
Full Property Details
Full Property Details for 21 Olmstead Hill Rd
General
- Rent: $7,500
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24150831
- Updated: 2/4/2026
- Added to Site: 2 day(s) ago
Rental Information
- Rental Type: Yearly Unfurnished, Yearly Furnished, Flexible Terms
- Lease Terms: Per Month
Interior
- Number of Rooms: 8
- Rooms/Areas: Laundry Room
- Interior Features: Security System
- Fireplace: Yes
- Number of Fireplaces: 3
- Appliances: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom - Fireplace, Full Bath, Hardwood Floor, Upper
- Bedroom 1: Bedroom - Full Bath, Hardwood Floor, Other
- Bedroom 2: Bedroom - Hardwood Floor, Upper
- Bedroom 3: Bedroom - Wall/Wall Carpet, Upper
Other Rooms
- Living Room: Living Room - Fireplace, Hardwood Floor, Main
- Family Room: Family Room - Balcony/Deck, Sliders, Hardwood Floor, Main
- Eat In Kitchen: Eat-In Kitchen - Granite Counters, Dining Area, Island, Hardwood Floor, Main
- Dining Room: Dining Room - Balcony/Deck, Fireplace, Sliders, Hardwood Floor, Main
- Laundry: Upper Level
Exterior
- Color: Gray
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking: Under House Garage
Location
- County: Fairfield
- Driving 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.
School Information
- Elementary School: Miller-Driscoll
- Middle School: Middlebrook
- Intermediate School: Cider Mill
- High School: Wilton
Community
- Pet Restrictions: One small non-shedding do
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Domestic
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Contemporary
- Construction Status: No/Resale
- Exterior Const.: Cedar, Wood
- Basement Desc.: Full, Unfinished
- Square Feet: 3,461
- Above Ground: 3,461 Sq. Ft.
- Year Built: 1973
Lot Features
- Lot Size (Acres): 4.02
- Zoning: R-2
- Lot Description: Secluded, Some Wetlands, Interior Lot, Level Lot, Cleared, Water View
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Pond, Brook
Financial Considerations
- Tenant Pays: All Utilities, Cable TV, Credit Check, Grounds Maintenance, Insurance, Liability Insurance
Disclosures and Reports
- Property ID: 1927089
Listed by Compass Connecticut, LLC, The Marion Filley Team, Marion Filley
Schools
Schools serving 21 Olmstead Hill Rd
School District:Wilton School District
| Name | Grades | Distance |
|---|---|---|
Cider Mill School 240 School Road, Wilton, CT 06897 | 3-5 | 1.3 mi |
Miller-Driscoll School 217 Wolfpit Road, Wilton, CT 06897 | PK-2 | 2.7 mi |
Middlebrook School, Wilton, CT 131 School Road, Wilton, CT 06897 | 6-8 | 1.1 mi |
Wilton High School 395 Danbury Road, Wilton, CT 06897 | 9-12 | 1.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 21 Olmstead Hill Rd
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- Single Family
- Active
- Updated 2 hours ago
- 5Beds
- 3Total Baths
- 4,201Sq. Ft.
- Single Family
- Active
- Updated 7 hours ago
- 3Beds
- 3Total Baths
- 1,682Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 4Total Baths
- 2,294Sq. Ft.
![[Address not provided], Westport, CT 06880 - Photo 1](https://m.cbhomes.com/p/229/24150839/5de3416e31014BF/s23cc.webp)
- Single Family
- Active
- Updated 2 hours ago
- 6Beds
- 6Total Baths
- 4,818Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 5Beds
- 4Total Baths
- 3,886Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,212Sq. Ft.
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- Single Family
- Closed
- 3Beds
- 3Total Baths
- 2,810Sq. Ft.
Listed by Cathy McGee
Sold by Compass Connecticut, LLC
Sold by Compass Connecticut, LLC
21 Olmstead Hill Road, Wilton, CT 06897 (MLS# 24150831) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 21 Olmstead Hill Road is currently listed for rent at $7,500 and was received on February 02, 2026. Want to learn more about 21 Olmstead Hill Road? Do you have questions about finding other real estate for sale or rent in Wilton? You can browse all Wilton rentals or contact a Coldwell Banker agent to request more information.