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72 Properties

72 Properties Available In 06098

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804 West Wakefield Boulevard, Winchester, CT 06098
1/37 37

$799,900

Open Sat 1PM-3PM

Single Family Home

2 Beds 1 Bath 1,044 SqFt

804 West Wakefield Boulevard, Winchester, CT 06098

Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-roun...

Listed by Pamela Dostilio of Coldwell Banker Realty

139 North Main Street #LL, Winchester, CT 06098
1/4 4

$1,095

New

Multi-Family

1 Bed 1 Bath 500 SqFt

139 North Main Street #LL, Winchester, CT 06098

Cozy one-bedroom apartment with a practical layout. Features a living room, kitchen, bedroom, and in-unit washer and dry...

Listed by Amanda Balaski of Northwest CT Realty

14 Bank Street, Winchester, CT 06098
1/23 23

$339,900

New

Single Family Home

2 Beds 1 Bath 1,034 SqFt

14 Bank Street, Winchester, CT 06098

New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitc...

Listed by David White of OwnerEntry.com

205 Wallens Street, Winchester, CT 06098
1/40 40

$600,000

New

Single Family Home

4 Beds 3 Baths 3,486 SqFt

205 Wallens Street, Winchester, CT 06098

Welcome to this beautifully crafted 3,486 sq. ft. Colonial, offering exceptional quality, thoughtful design, and plenty ...

Listed by Kelly Sullivan of Sullivan Real Estate Inc

50 High Street, Winchester, CT 06098
1/38 38

$324,900

New

Multi-Family

4 Beds 2 Baths 3,044 SqFt

50 High Street, Winchester, CT 06098

Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walki...

Listed by David Sartirana of Northwest CT Realty

99-101 Elm Street, Winchester, CT 06098
1/4 4

$1,495

New

Multi-Family

2 Beds 1 Bath 856 SqFt

99-101 Elm Street, Winchester, CT 06098

Two bedroom, first floor apartment with laundry hook-up in the unit. Washer/dryer can be added for an additional $100 pe...

Listed by Amanda Balaski of Northwest CT Realty

104 Elm Street, Winchester, CT 06098
1/17 17

$1,400

Active

Multi-Family

2 Beds 2 Baths 1,100 SqFt

104 Elm Street, Winchester, CT 06098

Spacious two-bedroom, 1.5-bath apartment conveniently located close to downtown. The kitchen features a convenient pantr...

Listed by Jeffrey Liskin of Northwest CT Realty

600 East Wakefield Boulevard, Winchester, CT 06098
1/38 38

$649,900

Active

Single Family Home

2 Beds 1 Bath 1,361 SqFt

600 East Wakefield Boulevard, Winchester, CT 06098

Set along the highly desirable east side of Highland Lake, 600 East Wakefield Boulevard offers a unique opportunity to c...

Listed by Stacy Anselmo of Coldwell Banker Realty

59 Cook Street #7, Winchester, CT 06098
1/28 28

$1,950

Active

Condo

2 Beds 2 Baths 1,289 SqFt

59 Cook Street #7, Winchester, CT 06098

Rarely available 2-story townhouse condo for rent! Start your mornings with coffee on the rear deck with a lake view in ...

Listed by Debra Jablonski of Berkshire Hathaway NE Prop.

122 Standard Avenue, Winchester, CT 06098
1/16 16

$399,900

Active

Single Family Home

4 Beds 2 Baths 1,944 SqFt

122 Standard Avenue, Winchester, CT 06098

Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated...

Listed by Amanda Balaski of Northwest CT Realty

936 Main Street #LOT 12, Winchester, CT 06098
1/8 8

$1,500

Active

Single Family Home

2 Beds 2 Baths 950 SqFt

936 Main Street #LOT 12, Winchester, CT 06098

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

Listed by Michael Block of Building Blocks LLC

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

$1,500

Active

Single Family Home

2 Beds 2 Baths 950 SqFt

936 Main Street #LOT 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

111 Rockwell Street #1, Winchester, CT 06098
1/17 17

$1,225

Under Contract

Multi-Family

2 Beds 1 Bath 756 SqFt

111 Rockwell Street #1, Winchester, CT 06098

Rustic charm meets modern convenience in this beautifully updated first floor 2 bedroom, 1 bath apartment located in a w...

Listed by Mike Gregor of Cohen Agency SiM, LLC

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

$959,900

Under Contract

Single Family Home

2 Beds 2 Baths 1,472 SqFt

204 East Wakefield Boulevard, Winchester, CT 06098

Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality constructi...

Listed by David Sartirana of Northwest CT Realty

64 Wheeler Street, Winchester, CT 06098
1/14 14

$299,000

Under Contract

Multi-Family

4 Beds 2 Baths 2,270 SqFt

64 Wheeler Street, Winchester, CT 06098

Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of ch...

Listed by David Sartirana of Northwest CT Realty

729 West Wakefield Boulevard, Winchester, CT 06098

$320,000

Under Contract

Single Family Home

2 Beds 1 Bath 1,128 SqFt

729 West Wakefield Boulevard, Winchester, CT 06098

Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where e...

Listed by Annie Simard of LPT Realty

812 West Wakefield Boulevard, Winchester, CT 06098
1/39 39

$749,900

Under Contract

Single Family Home

2 Beds 1 Bath 760 SqFt

812 West Wakefield Boulevard, Winchester, CT 06098

Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-mai...

Listed by Ryan Horvay of Smith & DeGroat Real Estate

46 Cherry Street, Winchester, CT 06098
1/23 23

$199,900

Active

Single Family Home

4 Beds 2 Baths 1,376 SqFt

46 Cherry Street, Winchester, CT 06098

A wonderful opportunity to own a spacious antique Colonial with endless potential! This 4-bedroom, 2-full-bath home feat...

Listed by Debra Jablonski of Berkshire Hathaway NE Prop.

119 West Wakefield Boulevard, Winchester, CT 06098
1/36 36

$849,900

Active

Multi-Family

4 Beds 2 Baths 1,781 SqFt

119 West Wakefield Boulevard, Winchester, CT 06098

Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This excep...

Listed by Mela Veltri Case of KW Legacy Partners

195 Reaching Hill Road, Winchester, CT 06098
1/36 36

$353,500

Under Contract

Single Family Home

3 Beds 2 Baths 1,324 SqFt

195 Reaching Hill Road, Winchester, CT 06098

Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, ...

Listed by Nicolle Estrella of eXp Realty

720 Main Street, Winchester, CT 06098
1/24 24

$395,000

Active

Multi-Family

3 Beds 2 Baths 1,909 SqFt

720 Main Street, Winchester, CT 06098

Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of d...

Listed by Arlene Gonzalez of The Gonzalez Property Group

112 Rockwell Street #2, Winchester, CT 06098

$1,550

Under Contract

Multi-Family

4 Beds 2 Baths 900 SqFt

112 Rockwell Street #2, Winchester, CT 06098

Large four bedroom apartment with one full bath and one half bath. Large kitchen, light filled living room. Washer/dryer...

Listed by Amanda Balaski of Northwest CT Realty

70 Walnut Street, Winchester, CT 06098
1/28 28

$349,900

Under Contract

Single Family Home

4 Beds 2 Baths 2,722 SqFt

70 Walnut Street, Winchester, CT 06098

Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bed...

Listed by David Sartirana of Northwest CT Realty

120 East Lake Street, Winchester, CT 06098
1/30 30

$325,000

Under Contract

Multi-Family

4 Beds 2 Baths 2,103 SqFt

120 East Lake Street, Winchester, CT 06098

Excellent opportunity for both owner-occupants and investors! This well-maintained two-family home features two spacious...

Listed by David Sartirana of Northwest CT Realty

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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

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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