Kathy Schmitt Team
  • About
    1. Meet The Team
    2. Meet Kathy
    3. Client Reviews
  • Sellers
    1. Seller Experience
    2. Why Sell With Us
    3. Sell My Home
    4. Home Valuation
    5. Recently Sold
  • Buyers
    1. The Buyer Experience
    2. Featured Listings
    3. Property Search
  • Communities
  • Blog
  • Contact
  • MORE
    1. My Homes
    2. My Tours
    3. My Favorites
    4. My Searches
  • Sign In
  • Register
Filters Reset
Save Search (2)
Save your search to get Alerts
81 Properties

81 Properties Available

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
Map
Grid
205 Old New Hartford Road, Winchester, CT 06098
1/7 7

$499,900

Coming Soon

Multi-Family

6 Beds 5 Baths 2,864 SqFt

205 Old New Hartford Road, Winchester, CT 06098

Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled ...

Listed by TK Krumm of Berkshire Hathaway NE Prop.

68 Wetmore Avenue, Winchester, CT 06098
1/28 28

$349,999

New

Multi-Family

6 Beds 3 Baths 2,555 SqFt

68 Wetmore Avenue, Winchester, CT 06098

Extremely well-cared-for two-family home located on a desirable street! This property offers plenty of off-street parkin...

Listed by Alex King of Lock and Key Realty, Inc

30 Upland Road, Winchester, CT 06098
1/25 25

$220,000

New

Single Family Home

4 Beds 2 Baths 1,844 SqFt

30 Upland Road, Winchester, CT 06098

Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood wh...

Listed by Jeffrey Liskin of Northwest CT Realty

936 Main Street #14, Winchester, CT 06098
1/9 9

$1,500

New

Single Family Home

2 Beds 2 Baths 1,000 SqFt

936 Main Street #14, Winchester, CT 06098

Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance ...

Listed by Michael Block of Building Blocks LLC

736 West Wakefield Boulevard, Winchester, CT 06098
1/24 24

$544,000

Active

Single Family Home

1 Bed 2 Baths 1,308 SqFt

736 West Wakefield Boulevard, Winchester, CT 06098

Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland ...

Listed by Ed Richman of Lakefront Living Realty, LLC

9 Loomis Street, Winchester, CT 06098
1/19 19

$469,900

Active

Single Family Home

3 Beds 2 Baths 1,768 SqFt

9 Loomis Street, Winchester, CT 06098

Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Be...

Listed by Marshall Cohen of Cohen Agency

63 Meadow Street, Winchester, CT 06098
1/38 38

$345,000

Under Contract

Multi-Family

5 Beds 3 Baths 2,602 SqFt

63 Meadow Street, Winchester, CT 06098

Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location com...

Listed by Lauren Hill of Mark Tavares Realty, LLC

147 E. Wakefield Boulevard, Winchester, CT 06098
1/29 29

$299,900

Active

Single Family Home

2 Beds 1 Bath 702 SqFt

147 E. Wakefield Boulevard, Winchester, CT 06098

Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of...

Listed by Kristin Leblanc of Mary LeBlanc Realty

69 Prospect Street, Winchester, CT 06098
1/32 32

$274,900

Under Contract

Multi-Family

7 Beds 3 Baths 2,204 SqFt

69 Prospect Street, Winchester, CT 06098

Opportunity awaits with this versatile 3-family property located at 69 Prospect Street in Winchester, perfect for both i...

Listed by Adam Cannon of Coldwell Banker Realty

624 Wynne Road, Winchester, CT 06098
1/23 23

$199,900

Active

Single Family Home

2 Beds 1 Bath 672 SqFt

624 Wynne Road, Winchester, CT 06098

Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from be...

Listed by AJ Davis of Better Homes and Gardens Real Estate Executive Real Estate

34 Hannifin Road, Winchester, CT 06098
1/16 16

$85,000

Active

Single Family Home

3 Beds 1 Bath 1,435 SqFt

34 Hannifin Road, Winchester, CT 06098

Set on 1.8 private acres amid the scenic rolling hills of Winsted, this circa-1850 home offers a rare opportunity to res...

Listed by Michael Barnes of Coldwell Banker Realty

111 Torringford Street #33, Winchester, CT 06098
1/24 24

$189,900

Under Contract

Condo

2 Beds 2 Baths 1,102 SqFt

111 Torringford Street #33, Winchester, CT 06098

Tucked within the desirable Green Ridge community, this inviting townhouse-style condo offers comfortable living with th...

Listed by Ryan Horvay of Smith & DeGroat Real Estate

184 Smith Hill Road, Winchester, CT 06098
1/37 37

$765,000

Under Contract

Single Family Home

3 Beds 3 Baths 4,387 SqFt

184 Smith Hill Road, Winchester, CT 06098

Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). N...

Listed by Mary New of Berkshire Hathaway NE Prop.

660 East Wakefield Boulevard, Winchester, CT 06098
1/28 28

$749,999

Active

Single Family Home

2 Beds 2 Baths 1,320 SqFt

660 East Wakefield Boulevard, Winchester, CT 06098

Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the wa...

Listed by Matthew Smith of Smith & DeGroat Real Estate

104 Maloney Court, Winchester, CT 06098
1/26 26

$289,000

Active

Single Family Home

3 Beds 1 Bath 1,008 SqFt

104 Maloney Court, Winchester, CT 06098

Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full...

Listed by Lisa Garten Johnson of Turning Point Realty, LLC

258 Perch Rock Trail, Winchester, CT 06098
1/39 39

$795,000

Under Contract

Single Family Home

4 Beds 2 Baths 1,373 SqFt

258 Perch Rock Trail, Winchester, CT 06098

Turn-key direct waterfront gem on Highland Lake! Perfectly positioned on the desirable east side of the lake, this beaut...

Listed by Nancy Reardon of Berkshire Hathaway NE Prop.

111 Torringford Street #7, Winchester, CT 06098
1/40 40

$179,900

Under Contract

Condo

2 Beds 2 Baths 1,156 SqFt

111 Torringford Street #7, Winchester, CT 06098

SELLER REQUESTS ALL OFFERS BY SATURDAY, MAY 9TH @ 5:00 Have I got a home for you! Unpack and relax in this rarely availa...

Listed by Janice Madore of Country Manor Realty

469 Platt Hill Road, Winchester, CT 06098
1/40 40

$895,000

Active

Single Family Home

4 Beds 2 Baths 3,088 SqFt

469 Platt Hill Road, Winchester, CT 06098

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're...

Listed by Marshall Cohen of Cohen Agency

424 East Wakefield Boulevard, Winchester, CT 06098
1/40 40

$1,595,000

Under Contract

Single Family Home

5 Beds 2 Baths 3,693 SqFt

424 East Wakefield Boulevard, Winchester, CT 06098

Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality ...

Listed by Karen Newton of William Pitt Sotheby's Int'l

674 East Wakefield Boulevard, Winchester, CT 06098
1/31 31

$990,000

Under Contract

Single Family Home

3 Beds 3 Baths 2,097 SqFt

674 East Wakefield Boulevard, Winchester, CT 06098

Experience the best of year-round waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath ho...

Listed by Matthew Smith of Smith & DeGroat Real Estate

748 Lake Drive, Winchester, CT 06098
1/40 40

$1,249,900

Under Contract

Single Family Home

5 Beds 4 Baths 3,584 SqFt

748 Lake Drive, Winchester, CT 06098

Rare opportunities like this do not come around often on Highland Lake! Located on the east side of 3rd bay, this unique...

Listed by Ryan Horvay of Smith & DeGroat Real Estate

217 Walnut Street, Winchester, CT 06098
1/34 34

$399,000

Under Contract

Multi-Family

5 Beds 4 Baths 2,779 SqFt

217 Walnut Street, Winchester, CT 06098

In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, viny...

Listed by David D'Amore of Northwest CT Realty

267 Rockwell Street #1st fl, Winchester, CT 06098
1/10 10

$1,300

Active

Multi-Family

1 Bed 1 Bath 600 SqFt

267 Rockwell Street #1st fl, Winchester, CT 06098

Ground level 1 bedroom 1 bath unit. Walking distance to Highland Lake. Laundry hookups in the unit. No Pets No Smoking, ...

Listed by Diane Carroll of The Washington Agency

149 East Mountain Avenue, Winchester, CT 06098
1/38 38

$274,900

Under Contract

Single Family Home

2 Beds 1 Bath 993 SqFt

149 East Mountain Avenue, Winchester, CT 06098

Welcome to this beautifully updated single-level home offering the ease of one-floor living. This charming property feat...

Listed by Kevin Eagan of Berkshire Hathaway NE Prop.

  • 1
  • 2
  • 3
  • 4

explore listings

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
Kathy Schmitt TeamWilliam Raevies

Realtor

Kathy Schmitt

License ID: RES.0767186

+1(203) 349-9422 kathy.schmitt@raveis.com

      About
      1. Meet The Team
      2. Meet Kathy
      3. Client Reviews
      Sellers
      1. Seller Experience
      2. Why Sell With Us
      3. Sell My Home
      4. Home Valuation
      5. Recently Sold
      Buyers
      1. The Buyer Experience
      2. Featured Listings
      3. Property Search
      Communities
      Blog
      Contact

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved. Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

QUICK SEARCH
  • Homes For Sale in Weston, CT
  • Homes For Sale in New Fairfield, CT
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
Kathy Schmitt TeamWilliam Raevies

Realtor

Kathy Schmitt

License ID: RES.0767186

+1(203) 349-9422 kathy.schmitt@raveis.com

      About
      1. Meet The Team
      2. Meet Kathy
      3. Client Reviews
      Sellers
      1. Seller Experience
      2. Why Sell With Us
      3. Sell My Home
      4. Home Valuation
      5. Recently Sold
      Buyers
      1. The Buyer Experience
      2. Featured Listings
      3. Property Search
      Communities
      Blog
      Contact

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved. Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility