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$7,500

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,461 Sq. Ft.
  • 2 Car Garage
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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 for 21 Olmstead Hill Rd

General

  • Rent: $7,500
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24150831
  • Added to Site: 51 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
Sold by Unrepresented Buyer, Unrepresent Buyer/Tenant

Listing agent

— 21 Olmstead Hill Rd —

  • Marion Filley

    Compass Connecticut, LLC

Agent Contact: (203) 515-1387 Office Contact: (203) 293-9715

Schools serving 21 Olmstead Hill Rd

School District:Wilton School District
NameGradesDistance
Cider Mill School
240 School Road, Wilton, CT 06897
3-51.3 mi
Miller-Driscoll School
217 Wolfpit Road, Wilton, CT 06897
PK-22.7 mi
Middlebrook School, Wilton, CT
131 School Road, Wilton, CT 06897
6-81.1 mi
Wilton High School
395 Danbury Road, Wilton, CT 06897
9-121.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price History for 21 Olmstead Hill Rd

Date
Details
Price
Change
Source
2/25/2026
Sold
$7,500
—
MLS
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.

Listed by Compass Connecticut, LLC, The Marion Filley Team, Marion Filley
Sold by Unrepresented Buyer, Unrepresent Buyer/Tenant

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21 Olmstead Hill Road, Wilton, CT 06897 (MLS# 24150831) is a Single Family property that was sold at $7,500 on February 25, 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.