5,109

Winchester, CT Homes

Section Image
  • 99 Hubbard St, Winsted, CT 06098
    99 Hubbard St, Winsted, CT 06098
    /2

    $49,000

    • Land
    • 0.37 Acre
    • $132,432 per Acre

    99 Hubbard St, Winsted, CT 06098

    99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

    David Sartirana Northwest CT Realty

    99 Hubbard St, Winsted, CT 06098
  • 233 Grantville Rd, Winsted, CT 06098

    $250,000 Sold Aug 22, 2025

    • 1,168 Sq Ft
    • $214/SF
    • 2 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1920

    233 Grantville Rd, Winsted, CT 06098

    Welcome to 233 Grantville Rd-a delightful 1,168 sq ft cottage-style home nestled on a quiet, level country lot in Winchester. Inside, you'll find a cozy kitchen, a comfortable living room, a modest bedroom, a small office, and a spacious bonus room that can serve as a second bedroom, family room, or flexible living space to suit your needs.The property also features an attached two-story

    David Sartirana Northwest CT Realty

    233 Grantville Rd, Winsted, CT 06098
  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $515,000

    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

    David Sartirana Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • 50 Lakeview Rd, Winsted, CT 06098

    $425,000 Sold Aug 13, 2025

    • 2,086 Sq Ft
    • $204/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    50 Lakeview Rd, Winsted, CT 06098

    Located just a short stroll from Holland Beach and only a 3-minute drive to the public boat launch, this charming Colonial offers the perfect blend of comfort, convenience, and year-round recreation. Nestled on a level corner lot in a well-established neighborhood, this home invites you to enjoy all the amenities of Connecticut's second-largest lake - from kayaking and boating to lakeside walks

    Paula Nelson William Raveis Real Estate

    50 Lakeview Rd, Winsted, CT 06098
  • 77 Deer Hill Rd, Colebrook, CT 06021
    77 Deer Hill Rd, Colebrook, CT 06021
    77 Deer Hill Rd, Colebrook, CT 06021
    /26

    $1,200,000

    • 5 Beds
    • 2.5 Baths
    • 3,307 Sq Ft

    77 Deer Hill Rd, Colebrook, CT 06021

    Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

    MICHAEL CONLOGUE William Pitt Sotheby's Int'l

    77 Deer Hill Rd, Colebrook, CT 06021
  • 711 W Wakefield Blvd, Winchester Center, CT 06098

    $281,000 Sold Aug 13, 2025

    • Land
    • 0.61 Acre
    • $460,656 per Acre
    • 371 Days On Market

    711 W Wakefield Blvd, Winchester Center, CT 06098

    Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.

    Peter Kores The Washington Agency

    711 W Wakefield Blvd, Winchester Center, CT 06098
  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /40

    $2,199,000

    • 9 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    431 W Wakefield Blvd, Winsted, CT 06098

    LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
  • 97 Taylor Rd, Barkhamsted, CT 06063

    $583,000 Sold Aug 08, 2025

    • 3,100 Sq Ft
    • $188/SF
    • 43 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1990

    97 Taylor Rd, Barkhamsted, CT 06063

    Welcome to this beautifully updated country retreat home, nestled in a peaceful setting, just minutes from everyday amenities. Enjoy serene summer evenings on the inviting covered front porch, where the sounds of nature & a nearby river within walking distance create the perfect ambiance. Ideal for entertaining, the outdoor space features a spacious deck, bluestone patio & hot tub. Inside, the

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    97 Taylor Rd, Barkhamsted, CT 06063
  • 843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
    843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
    843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
    /5

    $158,000

    • Land
    • 1.18 Acres
    • $133,898 per Acre

    843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

    1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL

    David D'Amore Northwest CT Realty

    843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
  • 141 Maloney Ct, Winsted, CT 06098

    $320,000 Sold Aug 06, 2025

    • 1,752 Sq Ft
    • $183/SF
    • 24 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1963

    141 Maloney Ct, Winsted, CT 06098

    A charming ranch-style home, located in a desirable area, offers the convenience of single-level living. It features 4 bedrooms and 3 bathrooms, making it perfect for families or anyone in need of extra space. Upon entering the main floor, you'll find a spacious living room filled with natural light, which creates a warm and inviting atmosphere. The kitchen provides ample counter space and opens

    Marcy D'Angelo Coldwell Banker Realty

    141 Maloney Ct, Winsted, CT 06098
  • 393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    /5

    $295,000

    • Land
    • 51 Acres
    • $5,784 per Acre

    393 Winchester Rd, Winsted, CT 06098

    WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

    Tom McGowan Elyse Harney Real Estate

    393 Winchester Rd, Winsted, CT 06098
  • 144 Marshall St, Winsted, CT 06098

    $540,000 Sold Aug 06, 2025

    • 1,744 Sq Ft
    • $310/SF
    • 51 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    144 Marshall St, Winsted, CT 06098

    Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-level living. Step inside to find hardwood floors throughout and three cozy fireplaces that bring warmth and character to

    Monica Palmerie RE/MAX RISE

    144 Marshall St, Winsted, CT 06098
  • 52 White St, Winsted, CT 06098
    52 White St, Winsted, CT 06098
    /2

    $29,000

    • Land
    • 1.88 Acres
    • $15,426 per Acre

    52 White St, Winsted, CT 06098

    Discover the possibilities with this 1.8-acre parcel located on a peaceful in-town street. The property offers a convenient location close to town amenities while maintaining a quiet, private setting. Public water and sewer are available in the street, though not currently connected to the property. While the land is developable, the seller will retain easements for drainage and access to

    David Sartirana Northwest CT Realty

    52 White St, Winsted, CT 06098
  • 266 Perch Rock Trail, Winsted, CT 06098

    $800,000 Sold Aug 04, 2025

    • 1,488 Sq Ft
    • $538/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1928

    266 Perch Rock Trail, Winsted, CT 06098

    Wake up to sparkling water views and savor the serenity of lakefront living in this storybook Cape Cod-style retreat on Highland Lake's desirable east side. Tucked away on a peaceful private lane, this year-round haven offers 3 bedrooms & 2 full baths, perfectly blending classic charm with modern comfort. Step into the spacious kitchen, where sun-drenched mornings begin at the breakfast nook and

    Laurie Murray KW Legacy Partners

    266 Perch Rock Trail, Winsted, CT 06098
  • 32 Norfolk Rd, Winchester, CT 06098
    32 Norfolk Rd, Winchester, CT 06098
    /2

    $299,900

    • Land
    • 63 Acres
    • $4,760 per Acre

    32 Norfolk Rd, Winchester, CT 06098

    63-Acre Rural Retreat Abutting Algonquin State Forest - A Nature Lover's Dream! Discover the perfect blend of seclusion and accessibility with this 63-acre wooded paradise, directly abutting Algonquin State Forest. Located on a state highway and directly across from a scenic dry dam, this unique parcel provides endless possibilities-whether you're looking to build your dream home, start a

    David D'Amore Northwest CT Realty

    32 Norfolk Rd, Winchester, CT 06098
  • 17 Woodland Ave, Winsted, CT 06098

    $410,000 Sold Jul 31, 2025

    • 2,105 Sq Ft
    • $195/SF
    • 39 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1938

    17 Woodland Ave, Winsted, CT 06098

    Beautiful 3 bedroom updated colonial walking distance to Highland lake beach.Large eat in kitchen with granite counter tops,center island,bar area ,spacious sitting area with antique cooking stove that burns wood creates good heat.Living room with hardwood floors,fireplace and built ins.Nice patio off kitchen,yard is landscaped with fountains.2 car garage.This home is in great condition and wont

    Vincent DeVico Showcase Realty, Inc.

    17 Woodland Ave, Winsted, CT 06098
  • 503 N Main St, Winsted, CT 06098
    503 N Main St, Winsted, CT 06098
    /2

    $69,000

    • Land
    • 2 Acres
    • $34,500 per Acre

    503 N Main St, Winsted, CT 06098

    Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

    Charles Albertario William Raveis Real Estate

    503 N Main St, Winsted, CT 06098
  • 102 Hollow Hill Rd, Winsted, CT 06098

    $639,000 Sold Jul 31, 2025

    • 2,692 Sq Ft
    • $237/SF
    • 49 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    102 Hollow Hill Rd, Winsted, CT 06098

    Highest & Best Due by 6/17/2025 at 5PM. First time to the market this turnkey 2,692 sq ft Grand Ranch is nestled in on 2.78 bucolic acres surrounded by nature & mature trees. Lovingly maintained, this home provides the perfect set up for stress free living & entertaining boasting a large eat in kitchen with center island, dining area, SS appliances, dual wall ovens and propane cooktop, French

    Dawn Rousseau Showcase Realty, Inc.

    102 Hollow Hill Rd, Winsted, CT 06098
  • 48 Bridge St, Winsted, CT 06098
    48 Bridge St, Winsted, CT 06098
    /2

    $23,900

    • Land
    • 0.15 Acre
    • $159,333 per Acre

    48 Bridge St, Winsted, CT 06098

    Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

    David Sartirana Northwest CT Realty

    48 Bridge St, Winsted, CT 06098
  • 139 Bunnell St, Colebrook, CT 06021

    $799,900 Sold Jul 28, 2025

    • 3,427 Sq Ft
    • $233/SF
    • 66 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1792

    139 Bunnell St, Colebrook, CT 06021

    Wonderful Old Colonial Farmhouse on 30+ Scenic Acres! Charming and full of character, this beautiful old farmhouse offers a rare blend of original features and modern updates. The heart of the home is an updated kitchen that blends seamlessly with the historic charm. Enjoy cozy evenings by the brick fireplaces in both the family room, bedroom and the living room, each adding warmth and timeless

    Mitzi Muller William Raveis Real Estate

    139 Bunnell St, Colebrook, CT 06021
  • 19 Hill St, Winsted, CT 06098
    19 Hill St, Winsted, CT 06098
    /2

    $23,900

    • Land
    • 0.22 Acre
    • $108,636 per Acre

    19 Hill St, Winsted, CT 06098

    Located on a lightly traveled side street, this .22-acre lot offers a peaceful getaway with easy access to downtown. The property features a flat area at the street before gently sloping upward, creating a unique setting for potential future use. City water and sewer are available in the street, but buyers should conduct their own due diligence regarding buildability. Whether you're looking for a

    David Sartirana Northwest CT Realty

    19 Hill St, Winsted, CT 06098
  • 126 Williams Ave, Winsted, CT 06098

    $292,000 Sold Jul 25, 2025

    • 2,225 Sq Ft
    • $131/SF
    • 42 Days On Market
    • 6 Beds
    • 2 Baths
    • Built 1890

    126 Williams Ave, Winsted, CT 06098

    Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income. The property has been completely overhauled in the past few years with almost everything updated. It is located in a great neighborhood in walking distance to all the schools in town. Close to playgrounds and the library. The recently painted exterior of this classic home

    Michelle Grant Coldwell Banker Premier Real Estate

    126 Williams Ave, Winsted, CT 06098
  • 00 Ramsgate Ln, Barkhamsted, CT 06063
    00 Ramsgate Ln, Barkhamsted, CT 06063
    /2

    $299,900

    • Land
    • 30 Acres
    • $9,997 per Acre

    00 Ramsgate Ln, Barkhamsted, CT 06063

    30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    00 Ramsgate Ln, Barkhamsted, CT 06063
  • 200 Perch Rock Trail, Winsted, CT 06098

    $1,200,000 Sold Jul 23, 2025

    • 2,407 Sq Ft
    • $499/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1948

    200 Perch Rock Trail, Winsted, CT 06098

    Exceptional Waterfront Living on Highland Lake - Your Dream Home Awaits! Seize this rare opportunity to own a stunning YEAR-ROUND WATERFRONT property on the highly sought-after EAST SIDE of Highland Lake! This turnkey gem is move-in ready and packed with modern features, offering the ultimate retreat for those seeking the serenity and excitement of lake life. Step into an open-concept kitchen and

    Annie Simard LPT Realty

    200 Perch Rock Trail, Winsted, CT 06098
  • 105,107 E Mountain Rd, Winchester, CT 06098
    105,107 E Mountain Rd, Winchester, CT 06098
    /2

    $59,900

    • Land
    • 0.41 Acre
    • $146,098 per Acre

    105,107 E Mountain Rd, Winchester, CT 06098

    105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON

    David D'Amore Northwest CT Realty

    105,107 E Mountain Rd, Winchester, CT 06098
  • 112 Shore Dr, Winsted, CT 06098

    $862,500 Sold Jul 23, 2025

    • 2,113 Sq Ft
    • $408/SF
    • 61 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1955

    112 Shore Dr, Winsted, CT 06098

    Live like you're on vacation every day! This beautifully updated lakefront home sits directly on the water in Highland Lake's first Bay, offering a level backyard & a private dock just steps from your door. With 50+ feet of direct waterfront and a fenced, low-maintenance yard, this charming year-round home is the perfect blend of comfort, style, & lakefront living. The interior boasts an open

    Nancy Reardon Berkshire Hathaway NE Prop.

    112 Shore Dr, Winsted, CT 06098

Showing Results 121 - 160, Page 4 of 18

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