50 Overlook Road

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Active
$339,900
3 beds1,488 sqft
50 Overlook Rd, Winchester, CT 06098
Est: $2,172/moGet pre-approved
Single FamilyProperty Type
0.97 acresLot Size
1949Year Built
$228/sq ftPrice per sq ft
8 carsParking Spaces

Description

Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious...Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious features include three heating sources: an oil-fired boiler, pellet stove in the living room and a magnificent soapstone wood stove in the lower level. The home also offers plenty of insulation, thermopane windows and a roof installed in 2021. Outside, you'll find excellent garage and storage space, including a large barn/garage with room for vehicles and a workshop, plus an additional detached garage. Set on nearly an acre with convenient access to Highland Lake and town amenities, this well-cared-for home is ready for its next chapter. This one is worth seeing!
1 day on Market
  • Listed by: David Sartirana 860.806.0225 dsart3@hotmail.com • Northwest CT Realty
  • Listed by: Amy Sartirana 860.379.7245 amysart4@hotmail.com • Northwest CT Realty
Last updated: 09/26/2026 03:05 PM • Source: SMARTMLS, MLS#: 24210012

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Listing Courtesy of Northwest CT Realty, David Sartirana; Northwest CT Realty, Amy Sartirana
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$2,172 per month

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$1,815

Property Taxes

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Property Information for 50 Overlook Road

Property Details
  • Taxes: $4,284 / year
  • MLS Type: Residential
  • County: Litchfield County
  • Basement Description: Full, Concrete Floor, Full With Hatchway
  • Direct Waterfront: No
  • Garages Number: 3
  • Neighborhood: Winsted
  • Style: Colonial
  • Garage Parking Info: Barn, Detached Garage, Off Street Parking
  • Swimming Pool: No
Building Information
  • Year Built: 1949
  • Lot Size: 0.97 AC / 42,253 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: 50 Overlook Rd
  • Elementary School: Per Board of Ed
  • High School: Gilbert
  • Latitude: 41.921067
  • Longitude: -73.092134
  • Neighborhood Amenities: Golf Course, Lake, Library, Medical Facilities, Park, Public Transportation
  • State: Connecticut
Parking
  • Parking Total Spaces: 8
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2026-June 2027
  • Property Tax: $4,284
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Washer, Dryer
  • Attic Description: Storage Space, Access Via Hatch
  • Cooling System: None
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Interior Features: Cable - Available
  • Laundry Room Info: Lower Level
  • Rooms Total: 7
Room 1
  • Room Entry Order: 1
  • Room Features: Pellet Stove,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 12.0
Room 2
  • Room Entry Order: 2
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 11.0
Room 3
  • Room Entry Order: 3
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 13.0
Room 4
  • Room Entry Order: 4
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 5
  • Listing Key: 5C645123D2132FB8E063E201100A2125
  • Room Entry Order: 5
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 6
  • Room Entry Order: 6
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 7
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 7.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Block, Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1949
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1488
Lot Information
  • Lot Description: Corner Lot, Lightly Wooded, Level Lot
  • Parcel Number: 924483
  • Sq Ft Est Heated Above Grade: 1488.0
  • Sq Ft Total: 1488.0
  • Zoning: TSF
Utilities
  • Energy Features: Generator Ready, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Public Records for 50 Overlook Road

Taxable ValueLand$37,170Additions$105,630Total$142,800
Tax Record2025$4,165 ($347 / month)
Home Facts
Beds3Baths1Total Finished SqFt1,488 SqFtAbove Grade Finished SqFt1,488 SqFtUnfinished Basement SqFt744 SqFtStories2Lot Size42,253 SqFtStyleSingle Family ResidenceYear Built1949Year Renovated1949ZoningHLDCountyNORTHWEST HILLSAPNWSTR M:027 B:153A L:198199

Schools near 50 Overlook Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Pearson Middle School
Public - 2 to 6
Mary P. Hinsdale School
Public - PK to 2
Able School
Public - 1 to 4
St Anthony School
Private - PK to 8
Rating
School
Distance
Pearson Middle School
Public2 to 6

Mary P. Hinsdale School
PublicPK to 2

Able School
Public1 to 4

St Anthony School
PrivatePK to 8

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.

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More information about 50 Overlook Road, Winchester, CT 06098

50 Overlook Road is a single family home for sale in Winchester, CT 06098. This property was listed for sale on September 25, 2026 by Northwest CT Realty, it's currently listed at $339,900. This listing's school district is Winchester School District. Nearby schools include Pearson Middle School, Mary P. Hinsdale School and Able School. 50 Overlook Road is a 3-bed, 1-bath, 1,488 sqft single family home built in 1949.

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 Northwest CT Realty, David Sartirana; Northwest CT Realty, Amy Sartirana

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.