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$1,850,000
9 Beds ⋅ 6 Baths ⋅ 24159989 MLS
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

431 W Wakefield Blvd, Winchester
$1,600,000
5 Beds ⋅ 2 Baths ⋅ 24171266 MLS
Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer appliances and farm sink, open floorplan greatroom with fireplace. Separate oversized two car detached garage with second floor and HVAC units for heating/cooling.

424 E Wakefield Blvd, Winchester
$1,475,000
3 Beds ⋅ 4 Baths ⋅ 24166368 MLS
A true vacation retreat on the shore of Highland Lake! Rare offering in exceptional condition ready for summer enjoyment. Central AC/heat with an open floorplan offering spacious family and entertaining opportunity. Folding glass doors to large lakefront deck with panoramic views of the water. Original house completely renovated inside and out in 2016, with recent stone patio and fire pit added and lakefront hot tub. Boathouse with full size refrigerator, granite countertop and ample storage at the shore front as well as sandy inlet for swimming and launching. Finished lower level for guests with bath walks out to the lake. Attic level with additional finished private office / rec room. Tucked off a private drive with expansive paved parking / boat storage area, this is the epitome of lake house living.

129 E Lake St, Winchester
$1,250,000
5 Beds ⋅ 4 Baths ⋅ 24171778 MLS
Rare opportunities like this do not come around often on Highland Lake! Located on the east side of 3rd bay, this unique waterfront property offers beautiful views and magnificent sunsets. This unique waterfront layout offers endless opportunities; from a family compound, multi generational living, guest space or a private lake retreat! Enjoy outdoor living on the massive deck, custom dock, and your very own private boat launch! Property consists of 2 parcels of land allowing for plenty of off street parking. Multi-car carport and one car garage offers even more parking and storage space. Whether you are looking for a weekend escape, year round lake living, or a place to share with generations to come, this is a rare chance to own one of Highland lakes most versatile waterfronts.

748 Lake Dr, Winchester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 24176238 MLS
WATERFRONT AND PRIVACY-WIN, WIN! PACK YOUR CLOTHES AND TOOTHBRUSH, THIS GEM IS TURN KEY AND WAITING FOR YOU! FULLY REMODELED INSIDE AND OUT! Nestled along the shores of HIGHLAND LAKE, this stunning waterfront retreat offers the perfect blend of year-round living and vacation-style comfort. Featuring 4 bedrooms and 3 bathrooms, this spacious home is designed to capture breathtaking lake views while providing plenty of room for entertaining and relaxing. The main living is an OPEN FLOOR PLAN with a cozy fireplace, expansive windows that show-off the gorgeous water views, and seamless access to oversized lakeside decks with retractable awnings-ideal for morning coffee, summer gatherings, or sunset cocktails overlooking the water. A large family room with wet bar and sliders to the deck creates the ultimate entertaining space. The spacious lower level is currently being used for extra sleeping space, but could be a great game room or home theatre. This home comes with TWO DOCKS! Whether you're searching for a full-time residence or the ultimate lake getaway, this Highland Lake lake house delivers exceptional waterfront living in the heart of Northwest Connecticut. Your opportunity to live the dream, lake life!

878 W Wakefield Blvd, Winchester
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 24168140 MLS
Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy effortless indoor-outdoor living with a walkout lower level leading to a covered patio, hot tub and your own private dock-already in place and ready for summer fun. The two-car attached garage, basement storage and workshop, location off main road and numerous upgrades add convenience and value. Whether you're watching the sunrise or sunset, relaxing by the water, or entertaining friends and family, this home offers year-round vacation vibes and in immaculate condition. A rare opportunity on one of Connecticut's most desirable lakes-don't miss it!

722 Lake Dr, Winchester
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 24170488 MLS
Experience the best of year-round waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home with stunning panoramic views and direct water access. Ideally located in the sought-after 3rd Bay, this property features a private dock-perfect for boating, swimming, kayaking, and enjoying everything lake life has to offer. Inside, an open and inviting layout connects the living room, dining area, and updated kitchen, ideal for entertaining. Expansive windows flood the home with natural light and frame breathtaking lake views throughout. The primary bedroom offers generous closet space, while additional bedrooms provide flexibility for guests, family, or a home office. Outdoor living is equally impressive, with a lakeside deck, screened porch, and low-maintenance landscaped yard-perfect for relaxing or hosting. A spacious paver driveway allows for ample parking, and a detached storage shed provides room for all your lake gear. Enjoy four-season recreation just minutes away, including skiing and snowboarding at Ski Sundown and Butternut, along with nearby dining, shopping, and outdoor activities. Whether you're looking for a full-time residence or a weekend retreat, this move-in-ready home offers the perfect blend of comfort, lifestyle, and location.

674 E Wakefield Blvd, Winchester
$960,000
2 Beds ⋅ 2 Baths ⋅ 24194765 MLS
Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with multiple sliders leading to a large wraparound waterfront deck, creating a seamless connection between indoor and outdoor living. The beautiful oak kitchen is highlighted by quartz countertops, newer stainless steel appliances, and an open layout that flows effortlessly into the main living areas, making it ideal for entertaining. Upstairs, the primary bedroom boasts soaring 12-foot cathedral ceilings and an abundance of windows overlooking the lake, providing a spectacular place to wake up each morning. Outside, the waterfront has been thoughtfully improved with an updated seawall that includes an aluminum dock, making it easy to enjoy boating, swimming, fishing. Highland Lake is a pristine 444-acre lake renowned for its clean water. Conveniently located just 45 minutes from Hartford and Bradley International Airport, and within easy reach of the Berkshires, Infinity Music Hall, the Warner Theatre, New York City, and Boston, this property offers the perfect blend of year-round living and a weekend retreat. A rare opportunity to create a lifetime of memories.

204 E Wakefield Blvd, Winchester
$925,000
4 Beds ⋅ 2 Baths ⋅ 24171657 MLS
Turn-key direct waterfront gem on Highland Lake! Perfectly positioned on the desirable east side of the lake, this beautifully maintained Cape offers abundant sunshine, gorgeous sunsets, & stunning water views. The updated kitchen features a breakfast bar, generous cabinet space, & opens to the dining room & inviting great room with hardwood floors & a gas fireplace. Enjoy lake views from the enclosed sunroom with sliders to the spacious deck, overlooking the level yard & private dock. The first floor offers a possible bedroom or office, full bath, and laundry. Upstairs are four additional bedrooms, including a beautiful lake facing primary bedroom with a large bay window, & breathtaking views. A full bath is conveniently located in the hall serving the upper level. Additional highlights include central air, whole-house generator, town water and sewer, newer roof, a full basement for storage & a putting green! Live like you are on vacation every day-swimming, boating, relaxing, and making memories with family and friends. This fabulous location offers quick access to Routes 8 & 44, with nearby attractions including Ski Sundown, Warner Theatre, wineries, breweries, hiking, and biking trails. Approx. 40 minutes to Hartford and Bradley International Airport, with convenient access toward New Haven and New York. Don't miss this rare opportunity to own your own slice of paradise on Highland Lake!

258 Perch Rock Trl, Winchester
$825,000
3 Baths ⋅ 24137086 MLS
Exceptional Investment Opportunity, Business & Building for Sale! Discover this rare gem located at 354 Main Street, Winsted, CT, a one of a kind commercial property offering both business and real estate ownership. This historic movie theatre is among the few in the nation that allow guests to enjoy food and alcoholic beverages while watching on the big screen. The property features two full size theatres with seating for up to 200 guests, a separate restaurant, and a lounge bar spread across the first and second floors, creating multiple income streams under one roof. Recent capital improvements include a $200,000 Fire Sprinkler System and a brand new $30,000 Digital Marquee, ensuring modern safety and visibility. With Town Center (TC) Zoning, this space offers endless possibilities, continue operating the successful theatre business, or transform it into a music venue, event space, brewery, or mixed-use entertainment hub. Whether you're an investor seeking a turnkey opportunity or a visionary entrepreneur ready to bring new life to a local landmark, this property is your ticket to success.

354 Main St, Winchester
$765,000
3 Beds ⋅ 3 Baths ⋅ 24173895 MLS
Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining room opens to large back deck overlooking fenced in private backyard-Massive sunken fireplaced living room -1st floor office-Private fireplaced Family room-huge master suite with fireplaced sitting room,walk-in closet & thermo-spa master bath. Large upper level bonus room with cozy private office-CAIR& whole house generator system are pluses-Beautiful professionally landscaped private level yard add lasting ambiance to this special home

184 Smith Hill Rd, Winchester
$750,000
2 Beds ⋅ 2 Baths ⋅ 24174215 MLS
Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and lakeside living, including use of a semi-private boat launch that makes getting out on the water effortless. Positioned on the east shore, the property captures magnificent sunset views across the lake, where evening skies melt into the water like brushed copper and glass. Whether you're dreaming of a cozy seasonal getaway, a year-round lake home, or a stunning custom renovation, this property offers the perfect canvas to create the waterfront home of your dreams. Opportunities like this on Highland Lake don't come around often.

660 E Wakefield Blvd, Winchester
$721,000
2 Beds ⋅ 1 Baths ⋅ 24192463 MLS
Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home. Outdoor amenities include a spacious waterfront patio, outdoor shower, and walk-in staircase for easy water access, making it ideal for swimming, boating, and relaxing lakeside. Adjacent to a state park, the property enjoys a picturesque setting with added privacy and natural surroundings. Move right in and enjoy as-is or update to suit your personal style. An additional parcel across the street is included, providing extra space and excellent long-term potential. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this waterfront property offers an exceptional combination of location, views, and lifestyle.

812 W Wakefield Blvd, Winchester
$691,000
5 Beds ⋅ 2 Baths ⋅ 24160676 MLS
Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor activities, lakeside relaxation, or simply soaking in the sun. Don't miss out on this incredible opportunity - properties like this don't come around often!

156 Shore Dr, Winchester
$670,000
4 Beds ⋅ 4 Baths ⋅ 24159801 MLS
PRICE REDUCTION !! Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent major upgrades ensure worry free enjoyment, including a high-efficiency HVAC (2024), new roof (2022), new siding, exterior doors, added insulation, two remodeled baths, full interior paint, and newer carpet throughout. Extensive landscaping has been completed, including new front railings, leveling and removal of several large trees. Previously a successful Airbnb, this property offers abundant parking, a two-car garage, and dual laundry facilities. Embrace all seasons on Highland Lake - from summer boating and fishing, lake is stocked with trout and bass for fishing enthusiasts, to winter ice skating/fishing. Your lakeside dream awaits!

121 W Wakefield Blvd, Winchester
$660,000
3 Beds ⋅ 3 Baths ⋅ 24186150 MLS
Custom built log Home!This home sits on a 3 acre, private landscaped lot with mountains laurel and a park nearby. This sprawling home with a covered front porch(28x 8)is perfect for relaxing and features over 1100 sq of decking which wraps around the house for entertaining. The Home features a stunning living room with interior balcony, chandeliers, field stone wood fireplace, cathedral ceiling, and sliders to a deck.The kitchen has a breakfast bar, stainless steel appliances and a pizza oven. It's opened to a dining room with a scenic view. The 1st floor primary bedroom suite has a cathedral ceiling, wood floors,2 walk in closets, one is cedar lined, the bath features a whirlpool tub and full shower, marble sink, tile floor and vaulted ceiling.Open the sliders from the bedroom to enjoy views from a 4 season sunroom.There is a 2nd bedroom on the main level and a 2nd full bath. Upstairs there is bedroom ,a 1/2 bath ,plus a Den (used as a bedroom).The lower level features a family room and a fieldstone wood fireplace .The full basement has a laundry room,utility room, storage, and a workshop.The oversized 2 car garage has a wood stove, and a 1000 gallon oil tank. All windows are energy efficient with krypton argon gas. The solar panels are lease at $68 a month.The large shed has electric and concrete floor .It's a short drive to great fishing, hiking ,swimming,skiing, town,shopping, restaurants, theaters, entertainment, festivals and vineyards. Enjoy Litchfield County.

426 Platt Hill Rd, Winchester
$650,000
3 Beds ⋅ 3 Baths ⋅ 24167312 MLS
Experience the beauty and privacy of this pristine log home set on 16.53 picturesque acres. A long, level gravel driveway welcomes you to the expansive 43' x 8' covered front porch, the perfect place to enjoy breathtaking winter sunrises overlooking your own blueberry bushes. Surrounded by abundant wildlife, this property offers a true country retreat. Inside, you'll find soaring ceilings, a stunning stone fireplace ideal for holiday gatherings, and a spacious first-floor primary suite. The second floor features two large bedrooms with high ceilings, a loft, and a full bath. The eat-in kitchen opens to a mudroom with additional pantry and closet storage. The walkout lower level offers even more potential living space. Utility features include two oil tanks, a wood furnace capable of heating the entire home, a new high-end pellet stove insert, and a generator hookup at the rear of the home. Three outbuildings provide ample room for all of your equipment, recreational vehicles, and storage needs.

162 Spencer Hill Rd, Winchester
$575,000
24080217 MLS
Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property. Ancient stone walls stand as a testament to the land's rich history, while open fields and wooded glades create a landscape teeming with natural beauty. Whether you envision a private retreat, a working farm, or a conservation haven, this bucolic sanctuary provides endless possibilities. A rare opportunity to own a piece of Connecticut's pastoral heritage-come explore the possibilities!

Old Robertsville Road, Winchester
$550,000
3 Beds ⋅ 3 Baths ⋅ 24179574 MLS
Set on 6 beautiful acres of open meadows with extensive road frontage and picturesque views, this exceptional Cape offers privacy, efficiency, and convenience...... Thoughtfully updated throughout, the home features 3 spacious bedrooms, 2.5 baths, a dedicated office, and a functional floor plan designed for comfortable living. Energy-conscious buyers will appreciate the solar system with backup battery storage, providing efficiency and peace of mind. Additional features include a newer roof, full basement, attached 2-car garage, and a welcoming breezeway connecting the home and garage. Enjoy the serenity of country living while remaining just minutes from shopping, dining, schools, and major commuting routes. Located on the outskirts of town, this property offers the best of both worlds-close to everything, yet surrounded by the beauty and tranquility of nature. One of the finest properties currently available, this move-in-ready home is a rare opportunity to own a truly special piece of real estate.

257 Wallens Hill Rd, Winchester
$525,000
1 Beds ⋅ 2 Baths ⋅ 24098872 MLS
Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family room with a stone fireplace, and an efficient kitchen with storage. The lower walk-out level can be accessed by the spiral staircase, and includes a 1/2 bath with potential for additional sleeping and a closet. Off the lower level is a patio overlooking the private beach and dock. There is also an outdoor shower! The expansive deck off the main level, truly gives one a treehouse vibe, with the stunning vista of Third Bay. It is a wonderful, outdoor space for relaxing or entertaining. From the deck one can wind their way down the stone stairway lined with rhododendrons, and when in blossom a tranquil, private oasis is yours to enjoy. Unlike many lakeside homes this three season cottage has privacy areas both shaded and sunny. The cottage is connected to a town sewer system and has a shared private well. Highland Lake has two public beaches, a privately owned marina and a public boat launch. Over the years downtown known as Winsted, has been experiencing a renaissance, with new restaurants, a brewery, grocery stores, and unique shops along Main Street. Don't miss this quintessential Lakefront retreat! A parcel of .72 acres across the road, known as #735 is included with the sale.

736 W Wakefield Blvd, Winchester
$485,000
7 Beds ⋅ 5 Baths ⋅ 24168665 MLS
Owner Occupants take notice: Rare three family home with market rents (one three-bedroom unit vacant) building is in exceptional condition!! A new roof will be installed in May before closing. One unit, a three-bedroom with a kitchen, living room, dining room, and two full bathrooms, this unit is rented @ $2136. per month ($2221.00 for the June 30, 2026-May 31, 2027 lease).) A one-year lease for the one bed unit expires on 5-31-26. This unit, an efficiency one-bedroom with a living room, kitchen, and full bath, unit is rented for $1160 per month. Total income now/$ 3381! Potential income for INVESTORS $5831! All tenants are current. 2 months' security deposits held in savings. The vacant unit is a three-bedroom unit with a kitchen, living room, dining room, and two full baths, and it will be vacant as of April 30 2026. Landlord owns most appliances. Natural gas heating units and electric water heaters have all been updated (servicing scheduled. May 26). Separate utilities for everyone. Very well cared for. Rents are at market rate. Plenty of off street parking. Each tenant has secure basement storage. Landlord electric panel, resulting in a $9-10$ per month bill for common area lighting. Fire marshal inspected and approved in 2025. No open violations.

51 Hinsdale Ave, Winchester
$483,000
8 Beds ⋅ 4 Baths ⋅ 24178174 MLS
A positive income even if you live in one of the units. Two 2 family homes(4 units total) on one parcel. Good parking. Large lot. Residential setting. Second floor of back house has a private deck, back yard and woods, yet is convenient to downtown. Highest and best offers must be submitted by 6/12/26 at 12pm.

71-73 Wheeler St, Winchester
$475,000
3 Beds ⋅ 2 Baths ⋅ 24164624 MLS
This one-of-a-kind custom Ranch is tucked well back from the road for exceptional privacy and was thoughtfully designed for its present owner. The stunning kitchen is truly the heart of the home, featuring a dramatic floor-to-ceiling stone fireplace, an expansive island with breakfast bar, an endless array of cabinets, and a built-in range with gas cooktop. The dining area flows seamlessly from the kitchen, perfect for everyday living and entertaining. Step down into the spacious yet inviting sunken living room, where a cathedral ceiling and an abundance of oversized windows frame serene, panoramic views of the surrounding natural landscape. The primary suite offers a charming bow window and a full bath complete with a relaxing whirlpool tub. A massive unfinished basement provides endless possibilities for future expansion or customization. Energy saving 2x6 construction. Outdoors, enjoy your own private retreat-complete with a deck overlooking a large patio and hot tub, all set within a secluded backyard. Don't miss this rare, distinctive Ranch home!

123 Old North Rd, Winchester
$475,000
4 Beds ⋅ 3 Baths ⋅ 24159478 MLS
Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home offers both privacy and convenience. The main level features a very large eat-in kitchen, a family room with vaulted ceilings and a fireplace, formal living and dining rooms, and a private office suite-ideal for working from home or running a small business. The second floor includes four generously sized bedrooms and two full baths, while the third floor offers additional flexible space currently used as a library, perfect for a study, hobby room, or potential additional living area. Located just minutes from everyday amenities, shopping, and dining, the property also provides easy access to the many outdoor and recreational opportunities that make Winchester and the surrounding Litchfield County area so desirable. Conveniently situated roughly halfway between New York City and Boston.

5 Stadler Hts, Winchester
$433,000
4 Beds ⋅ 3 Baths ⋅ 24167287 MLS
Tucked away in a peaceful country setting just minutes from Winchester Center, this well-maintained 4-bedroom Colonial offers space, comfort, and timeless charm. Proudly owned by just one owner, this home reflects true pride of ownership throughout, with thoughtfully updated mechanicals and the added peace of mind of a whole-house generator. The inviting main level features a spacious family room with a cozy fireplace and slider leading to the outdoors-perfect for relaxing or entertaining. A warm and welcoming den showcases natural wood paneling and hardwood flooring, while the formal dining room is accented by classic pegged wood floors, adding character and elegance. The large eat-in kitchen offers ample space for gatherings and includes a convenient pantry. Upstairs, you'll find a generous primary suite complete with a private full bath, along with three additional bedrooms and another full bath, providing plenty of room for family and guests. Set on 2.76 lightly wooded acres, this property offers both privacy and a beautiful natural backdrop, making it the perfect place to call home. FINAL AND BEST IS DUE ON SUNDAY AT 3:00 PM

118 South Rd, Winchester
$430,000
1 Baths ⋅ 24112471 MLS
Open 10:30-12:30 Sunday 11/9/25. Motivated Seller! Seller financing available. A wonderful opportunity to own a mixed use property in the town center of Winsted. Currently used as a cleaner and tailoring shop on the first floor with an apartment on the second floor. Opportunity exists for the new owner to take over a turn key business with a strong existing client base and several commercial clients. The second floor offers the opportunity for a live in space, rental residential space with 3 bedrooms, a kitchen, living room and bathroom or the opportunity for office space. This building is located on a main road with great road frontage and a brand new freshly paved parking lot and some new siding on the building. The location offers an opportunity for a new owner to take over the existing business or completely start a new one in this prime location. Book your showing today.

57 Main St, Winchester
$420,000
5 Beds ⋅ 3 Baths ⋅ 24182777 MLS
Welcome to 26 Elm Street, a newly renovated and legally converted three-family property in the heart of Winsted. This is a rare opportunity for investors or owner-occupants seeking a move-in-ready, income-producing asset with strong upside potential. Two of the units have been completely renovated, featuring updated interiors that appeal to today's tenants, while the exterior has also been recently improved, enhancing curb appeal and reducing near-term maintenance costs. The third unit provides additional income potential, making this a well-balanced investment with multiple revenue streams. The property has been legally converted to a 3-family, offering peace of mind and compliance for financing and long-term ownership. Prime Location & Rental Appeal Situated on Elm Street in Winsted, the property benefits from a convenient location close to downtown amenities, shopping, and dining. Easy access to commuter routes and nearby employment hubs helps drive consistent tenant demand. The area's small-town charm combined with accessibility makes it attractive for a wide range of renters. Strong Income Potential with two newly renovated units ready to command market rents and a third unit adding additional cash flow, this property is positioned for immediate income generation. Whether you're looking to expand your portfolio or live in one unit while renting the others, 26 Elm Street offers flexibility and solid returns.

26 Elm St, Winchester
$420,000
5 Beds ⋅ 4 Baths ⋅ 24168016 MLS
In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a 2-bedroom apartment, the other a 3-bedroom apartment. Both units include 1.5 baths, updated kitchens with appliances, and tastefully renovated bathrooms. Gleaming hardwood floors run throughout, adding warmth and timeless character. Enjoy the charm of a classic wrap-around covered porch-perfect for relaxing or entertaining. The property also includes a detached 2-car garage and an additional shed for storage. Centrally located close to shopping, dining, schools, and major routes, this home is ideal as a strong rental investment or an in-law setup. Meticulously cared for and in extraordinary condition-this is a must-see property!

217 Walnut St, Winchester
$410,000
3 Beds ⋅ 2 Baths ⋅ 24157783 MLS
Welcome to this spacious and well-maintained 2,196 sq. ft. one-owner home offering comfortable living in a convenient in-town location. This 3-bedroom, 2-bath residence features an open floor plan on the main living level, highlighted by a large formal living room with fireplace, dining room, expansive family room, and an updated kitchen-perfect for both everyday living and entertaining. Beautiful hardwood floors run throughout much of the home, adding warmth and character. The property sits on a generous level lot totaling approximately .70 acres, which includes an additional .04-acre garden lot. Updated windows throughout the home provide efficiency and natural light. Step outside to enjoy the covered patio overlooking the level and private rear yard-an ideal space for relaxing or hosting gatherings. Additional features include an attached two-car garage and a standby generator for added peace of mind. Conveniently located close to Routes 8 and 44 and just minutes from downtown shopping, dining, and everyday conveniences.

35 Glendale Ave, Winchester
$400,000
3 Beds ⋅ 2 Baths ⋅ 24190790 MLS
Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area, and a dedicated dining space with large sliding glass doors overlooking the backyard. The main floor includes a bedroom and full bathroom, providing flexibility for a variety of uses such as a guest room, home office, or convenient one-level living arrangement. The finished lower level with a walk-out entrance and full basement adds valuable additional space with endless possibilities for a recreation room, home gym, playroom, workshop, or additional storage. Enjoy the comfort of central air conditioning, along with a relaxing porch, outdoor shed, and a private backyard with plenty of space to relax, garden, or entertain. Located near Highland Lake, this property provides convenient access to outdoor recreation throughout the seasons. With thoughtful renovations, spacious rooms, and a great indoor-outdoor connection, this home is ready for its next owner. Schedule your private showing today and see everything this beautifully updated Winsted property has to provide.

195 Reaching Hill Rd, Winchester

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