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Valued by Redfin at $497,000 and Realtor at $516,000 - this house is a gem! Welcome to 205 Perch Rock Trail, a spacious 4-bedroom, 2.5-bath home in the highly desirable Highland Lake area of Winsted. Offering an incredible combination of space, location, and value, this property is a rare opportunity for a buyer looking to create something special. The home needs renovations and is being sold As Is, but the potential is substantial.The home offers approximately 2,369 square feet of living space, including a finished lower level with a kitchenette and full bath - ideal for an in-law setup, guest suite, home office, recreation space, or extended-family living. Enjoy lake views, nearby water access, a private backyard, two fireplaces, a balcony, generous storage, and an under-house garage. Public water and public sewer. With 4 bedrooms, multiple living areas, and flexible lower-level space, the possibilities here are exceptional. Whether you are looking for a year-round residence, weekend lake retreat, renovation opportunity, or investment property, 205 Perch Rock Trail offers tremendous upside. Bring your vision and make this Highland Lake gem your own!

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24210637 MLS

Valued by Redfin at $497,000 and Realtor at $516,000 - this house is a gem! Welcome to 205 Perch Rock Trail, a spacious 4-bedroom, 2.5-bath home in the highly desirable Highland Lake area of Winsted. Offering an incredible combination of space, location, and value, this property is a rare opportunity for a buyer looking to create something special. The home needs renovations and is being sold As Is, but the potential is substantial.The home offers approximately 2,369 square feet of living space, including a finished lower level with a kitchenette and full bath - ideal for an in-law setup, guest suite, home office, recreation space, or extended-family living. Enjoy lake views, nearby water access, a private backyard, two fireplaces, a balcony, generous storage, and an under-house garage. Public water and public sewer. With 4 bedrooms, multiple living areas, and flexible lower-level space, the possibilities here are exceptional. Whether you are looking for a year-round residence, weekend lake retreat, renovation opportunity, or investment property, 205 Perch Rock Trail offers tremendous upside. Bring your vision and make this Highland Lake gem your own!

205 Perch Rock Trl, Winchester

$239,900

3 bedroom home offering comfortable living with the convenience of gas heat as well as a wood stove and main level laundry. The layout provides plenty of space for everyday living, relaxing, and entertaining. Enjoy Highland Lake with Resha Beach just a half mile away, perfect for summer days by the water. A short drive takes you to the nearby boat launch, making it easy to enjoy boating, fishing, and all that the area's lakes have to offer.

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24210294 MLS

3 bedroom home offering comfortable living with the convenience of gas heat as well as a wood stove and main level laundry. The layout provides plenty of space for everyday living, relaxing, and entertaining. Enjoy Highland Lake with Resha Beach just a half mile away, perfect for summer days by the water. A short drive takes you to the nearby boat launch, making it easy to enjoy boating, fishing, and all that the area's lakes have to offer.

35 Prospect St, Winchester

$289,900

Welcome to this charming 4-bedroom, 1.5 bath home in Winsted, where classic character meets comfortable everyday living. Built in 1927, this well-maintained home features beautiful hardwood floors, original woodwork, detailed trim, and spacious rooms filled with natural light. The main level offers generous living and dining spaces while the bright kitchen features ample cabinetry, stainless steel appliances, and plenty of counter space. A convenient half bath completes the main level. Upstairs, you'll find four well sized bedrooms, a full bath, and additional built-in storage, along with preserved woodwork and charm throughout. This property offers a private yard with mature trees and established landscaping, providing a nice outdoor space to enjoy. A wonderful opportunity to own a character-filled home with space, charm, and comfort in the heart of Winsted!

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210073 MLS

Welcome to this charming 4-bedroom, 1.5 bath home in Winsted, where classic character meets comfortable everyday living. Built in 1927, this well-maintained home features beautiful hardwood floors, original woodwork, detailed trim, and spacious rooms filled with natural light. The main level offers generous living and dining spaces while the bright kitchen features ample cabinetry, stainless steel appliances, and plenty of counter space. A convenient half bath completes the main level. Upstairs, you'll find four well sized bedrooms, a full bath, and additional built-in storage, along with preserved woodwork and charm throughout. This property offers a private yard with mature trees and established landscaping, providing a nice outdoor space to enjoy. A wonderful opportunity to own a character-filled home with space, charm, and comfort in the heart of Winsted!

173 Gilbert Ave, Winchester

$339,900

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!

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24210012 MLS

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!

50 Overlook Rd, Winchester

$215,000

A Stylish two-bedroom one and half bath condo featuring numerous updates that makes this an inviting comfortable home. The remodeled kitchen offers a fresh, modern space for cooking, newer flooring adds style though out the main living area. Additional updates are the three energy saving split units for A/C and heating plus an additional source of heat is the pellet stove. Two new sliders open out to private deck, wonderful for enjoying a beverage or just the outdoors. A well maintained move in ready condo offering comfortable low-maintenance living with many of the update already completed. There is always something for you to do in the area, entertainment, restaurants and an easy distance to RT 8.

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209492 MLS ⋅ Riverwalk BLDG.

A Stylish two-bedroom one and half bath condo featuring numerous updates that makes this an inviting comfortable home. The remodeled kitchen offers a fresh, modern space for cooking, newer flooring adds style though out the main living area. Additional updates are the three energy saving split units for A/C and heating plus an additional source of heat is the pellet stove. Two new sliders open out to private deck, wonderful for enjoying a beverage or just the outdoors. A well maintained move in ready condo offering comfortable low-maintenance living with many of the update already completed. There is always something for you to do in the area, entertainment, restaurants and an easy distance to RT 8.

111 Riverton Road Unit 79, Winchester

$374,900

Opportunity and flexibility come together at 95 Williams Street in Winsted. Offering approximately 2,887 square feet of living space, this spacious multi-family property is currently configured as two generously sized units with plenty of room both inside and out. Set on a uniquely large .49-acre corner lot, the property offers an impressive amount of outdoor space and privacy-something rarely found with a multi-family home. The left-side unit features four bedrooms and two full baths, while the right-side unit offers three bedrooms and one full bath-providing a total of seven bedrooms and three full baths. Each unit also benefits from additional attic and basement storage, a feature that is always appreciated in a multi-family home. According to the property card, the home is classified as a three-family property. The two units on the left side were previously combined, creating the larger four-bedroom residence that exists today. A future owner may have the opportunity to separate the space again and restore the property to a three-unit configuration, subject to any required municipal approvals. Whether you're looking for an investment property, an owner-occupied multi-family with rental income, or a property with the potential for a future three-unit configuration, 95 Williams Street offers an unusual combination of space, versatility, privacy and possibilities that are increasingly hard to find. Property being sold AS IS, WHERE IS.

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24207726 MLS

Opportunity and flexibility come together at 95 Williams Street in Winsted. Offering approximately 2,887 square feet of living space, this spacious multi-family property is currently configured as two generously sized units with plenty of room both inside and out. Set on a uniquely large .49-acre corner lot, the property offers an impressive amount of outdoor space and privacy-something rarely found with a multi-family home. The left-side unit features four bedrooms and two full baths, while the right-side unit offers three bedrooms and one full bath-providing a total of seven bedrooms and three full baths. Each unit also benefits from additional attic and basement storage, a feature that is always appreciated in a multi-family home. According to the property card, the home is classified as a three-family property. The two units on the left side were previously combined, creating the larger four-bedroom residence that exists today. A future owner may have the opportunity to separate the space again and restore the property to a three-unit configuration, subject to any required municipal approvals. Whether you're looking for an investment property, an owner-occupied multi-family with rental income, or a property with the potential for a future three-unit configuration, 95 Williams Street offers an unusual combination of space, versatility, privacy and possibilities that are increasingly hard to find. Property being sold AS IS, WHERE IS.

95 Williams Ave, Winchester

$260,000

This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204964 MLS

This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

118 Meadow St, Winchester

$359,900

Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. Both units have been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms. This level offers a fresh, move-in-ready appeal that renters or owners will love.

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206509 MLS

Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. Both units have been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms. This level offers a fresh, move-in-ready appeal that renters or owners will love.

77 Hubbard St, Winchester

$289,000

Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the oversized screened porch, where you can unwind with family or friends while taking in the beautiful perennial plantings and natural surroundings. This charming cottage features two bedrooms, a loft, one full bath, an open-concept kitchen, dining area, and living room. For your comfort, oil heat and a mini-split unit provide heat and air conditioning. Additionally, there's a rear deck area perfect for outdoor dining & grilling. An extra outdoor shower is available to refresh after spending time on the lake.

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24202928 MLS

Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the oversized screened porch, where you can unwind with family or friends while taking in the beautiful perennial plantings and natural surroundings. This charming cottage features two bedrooms, a loft, one full bath, an open-concept kitchen, dining area, and living room. For your comfort, oil heat and a mini-split unit provide heat and air conditioning. Additionally, there's a rear deck area perfect for outdoor dining & grilling. An extra outdoor shower is available to refresh after spending time on the lake.

347 W Wakefield Blvd, Winchester

$304,900

Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features wide-plank wood flooring, a small dining area, and a walk-out porch leading to a Trex deck-perfect for enjoying the outdoors and water views. A small first-floor bedroom offers flexibility for guests, an office, or additional living space. Upstairs, the primary bedroom is generously sized to easily accommodate a king-size bed and features wood flooring and propane-fired baseboard heat. The second bedroom also offers wood flooring, a large closet, ceiling fan, two large windows, and propane-fired baseboard heat. The full bathroom includes a newer vanity, stall shower, and laminate tile flooring. Additional features include forced-air propane heating on the main level, window air-conditioning units, a carpeted stairway, and two off-street parking spaces. A boat launch on Highland Lake provides an exceptional opportunity to enjoy boating and waterfront recreation.Book a showing today. This property will not last!

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201785 MLS

Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features wide-plank wood flooring, a small dining area, and a walk-out porch leading to a Trex deck-perfect for enjoying the outdoors and water views. A small first-floor bedroom offers flexibility for guests, an office, or additional living space. Upstairs, the primary bedroom is generously sized to easily accommodate a king-size bed and features wood flooring and propane-fired baseboard heat. The second bedroom also offers wood flooring, a large closet, ceiling fan, two large windows, and propane-fired baseboard heat. The full bathroom includes a newer vanity, stall shower, and laminate tile flooring. Additional features include forced-air propane heating on the main level, window air-conditioning units, a carpeted stairway, and two off-street parking spaces. A boat launch on Highland Lake provides an exceptional opportunity to enjoy boating and waterfront recreation.Book a showing today. This property will not last!

325 E Wakefield Blvd, Winchester

$325,000

Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors seeking steady cash flow.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199882 MLS

Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors seeking steady cash flow.

48 Center St, Winchester

$319,900

New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage with area for a work space. Garage door opener, Paved driveway. Room dimensions are approximate.

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24200816 MLS

New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage with area for a work space. Garage door opener, Paved driveway. Room dimensions are approximate.

14 Bank St, Winchester

$389,900

Welcome home to this well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. The newly renovated eat-in kitchen features updated cabinetry, countertops, and finishes, creating a great space for everyday living and gathering. The spacious living room and dining area offer plenty of room to make the home your own, while four bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the large yard, charming enclosed front porch, and back deck with a Sunsetter awning for comfortable outdoor living. A generator adds peace of mind. Conveniently located close to town, shopping, and everyday amenities, this move-in-ready home offers a great combination of updates, space, and the opportunity to add your own personal touch and make it truly yours.

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24196702 MLS

Welcome home to this well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. The newly renovated eat-in kitchen features updated cabinetry, countertops, and finishes, creating a great space for everyday living and gathering. The spacious living room and dining area offer plenty of room to make the home your own, while four bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the large yard, charming enclosed front porch, and back deck with a Sunsetter awning for comfortable outdoor living. A generator adds peace of mind. Conveniently located close to town, shopping, and everyday amenities, this move-in-ready home offers a great combination of updates, space, and the opportunity to add your own personal touch and make it truly yours.

122 Standard Ave, Winchester

$395,000

Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level commercial space is ready for its next chapter. Previously operating as a successful cafe, it includes a commercial kitchen setup with hood ventilation, refrigerator, restroom, and a spacious open layout that can easily accommodate a restaurant, coffee shop, boutique, salon, professional office, or countless other business concepts. Upstairs, you'll find a beautifully renovated three-bedroom apartment designed for modern comfort. Completely rebuilt down to the studs, the residence showcases a stylish new kitchen, updated windows, a newer roof, a private deck perfect for relaxing, and an energy-efficient on-demand hot water system. Separate gas and electric meters provide flexibility and convenience for owner-occupants or tenants alike. Just moments from Highland Lake, Route 44, shopping, dining, and all of Winsted's downtown attractions, this property offers incredible versatility. Live where you work, lease one or both units, or expand your investment portfolio with a property that offers excellent income-producing potential in a highly desirable location.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190347 MLS

Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level commercial space is ready for its next chapter. Previously operating as a successful cafe, it includes a commercial kitchen setup with hood ventilation, refrigerator, restroom, and a spacious open layout that can easily accommodate a restaurant, coffee shop, boutique, salon, professional office, or countless other business concepts. Upstairs, you'll find a beautifully renovated three-bedroom apartment designed for modern comfort. Completely rebuilt down to the studs, the residence showcases a stylish new kitchen, updated windows, a newer roof, a private deck perfect for relaxing, and an energy-efficient on-demand hot water system. Separate gas and electric meters provide flexibility and convenience for owner-occupants or tenants alike. Just moments from Highland Lake, Route 44, shopping, dining, and all of Winsted's downtown attractions, this property offers incredible versatility. Live where you work, lease one or both units, or expand your investment portfolio with a property that offers excellent income-producing potential in a highly desirable location.

720 Main St, Winchester

$365,000

Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for added flexibility. The updated kitchen features quartz counter tops, stainless steel appliances, and ample cabinetry, with warm pine ceilings adding character throughout. Additional features include two full baths, first-floor laundry, newer windows, public water and sewer, natural gas, on-demand hot water, and a wood stove. Outside, enjoy a peaceful backyard garden and convenient rear access from Ontario Street. Located within one mile of local schools and a half mile of town, the home offers easy access to everyday amenities while maintaining a peaceful lake setting.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184417 MLS

Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for added flexibility. The updated kitchen features quartz counter tops, stainless steel appliances, and ample cabinetry, with warm pine ceilings adding character throughout. Additional features include two full baths, first-floor laundry, newer windows, public water and sewer, natural gas, on-demand hot water, and a wood stove. Outside, enjoy a peaceful backyard garden and convenient rear access from Ontario Street. Located within one mile of local schools and a half mile of town, the home offers easy access to everyday amenities while maintaining a peaceful lake setting.

132 E Lake St, Winchester

$239,000

Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space. The possibilities are endless. The barn has the capability for multiple uses as well such as a workshop, studio, office, storage or to just park vehicles.

7 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24169258 MLS

Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space. The possibilities are endless. The barn has the capability for multiple uses as well such as a workshop, studio, office, storage or to just park vehicles.

Winchester