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$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
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 24052635 MLS
Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious family room with granite fireplace with views in all directions. Sunroom with radiant heated stone flooring, extensive stone patios, pergola, gardens, terraces, sandy beach/swimming area. This is it!

538 Wheelers Pt, 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
$1,050,000
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
$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
$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
$690,000
5 Beds ⋅ 3 Baths ⋅ 24121140 MLS
This property is your personal sanctuary, complete with private trails for hiking your own land. Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with a hot tub - ideal for relaxing and entertaining! Start your day on the front porch with a cup of coffee in the morning listening to the birds chirp, and unwind in the evening in the hot tub on the back deck with a mocktail or glass of wine. The luxurious primary suite has a walk-in closet, an office nook, and a ensuite with double sinks, jetted soaking tub, and separate shower. The additional bedrooms offer great flex space for a home office, guests, studio, a gym, or playroom. The backyard has a custom built sweet staircase leading up to your private oasis in nature with trails to explore and room to get creative. There's space in the basement to bring your vision for a workshop, gym, home theater, or added living space, and a huge 3 car garage. Added features include fresh paint throughout, security system, new central AC, a standby generator, new refrigerator, new washer/dryer, new carpet, an updated water softener system, and energy-efficient solar panels. This is the escape you've been looking for. Explore all this home has to offer today and fall in love with this charming refu

151 Losaw 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
$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
$475,000
3 Beds ⋅ 2 Baths ⋅ 24134519 MLS
Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient laundry area. From the kitchen and sunroom, step out to a private rear deck perfect for relaxing or entertaining. Upstairs you'll find three comfortable bedrooms and a full bath. The lower level offers an additional 1,000 square feet of finished space - an ideal area for gatherings, hobbies, or a recreation room, along with a separate home office. Car enthusiasts and hobbyists will appreciate the impressive garage space, complete with its own heat and air conditioning. Recent updates within the past five years include the kitchen, garage A/C, and driveway, with additional improvements such as newer windows, baths, and hardwood floors. The roof on both the home and barn was replaced just two years ago. The barn provides great additional storage and versatility. A unique property combining space, function, and rural tranquility for the outdoor enthusiasts - come see all that 197 Spencer Hill Road has to offer!

197 Spencer Hill Rd, Winchester
$439,900
3 Beds ⋅ 2 Baths ⋅ 24125218 MLS
Perched directly across the street from Highland Lake's 3rd Bay, this charming 1,900 sq. ft. Cape offers sweeping lake views and the enjoyment of a permanent right-of-way to access the water. The home features 7 rooms, including 3 bedrooms and 1.5 baths, and has been thoughtfully maintained with important updates: new propane heating and hot water systems (2022), a new roof on both the house and garage (2023) along with a new skylight, and mini-splits for efficient cooling. A reverse osmosis system provides treated water for peace of mind. Inside, spacious living areas filled with natural light create the perfect setting for gatherings or quiet relaxation after a day on the lake. With its ideal location and solid upkeep, this home is move-in ready and waiting for its next owner to make it their own. There is a "right of way" for ingress and egress to the water.

819 E Wakefield Blvd, Winchester
$425,000
2 Beds ⋅ 1 Baths ⋅ 24121868 MLS
Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a low-maintenance opportunity to be ready QUICKLY for the next boating season! Highland Lake is a 445-acre reservoir in the Mountains, known for its recreational appeal. The lake is stocked annually, and it is designated a Trophy Trout and Bass Management Lake, making it an outstanding destination for anglers. Boating, swimming, and water skiing are among the many activities available, all within a community that values both recreation and tranquility. Don't miss the chance to own a piece of this serene, active, and beautiful lakeside community. Schedule a private tour today.

548 E Wakefield Blvd, 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
$389,900
8 Beds ⋅ 5 Baths ⋅ 24121899 MLS
Here is your perfect chance to build your investment portfolio! 2 houses and a vacant lot create the perfect investment opportunity! Comprised of a 4 unit apartment building and a single unit house with a 4 car garage under and an adjacent vacant lot. The vacant lot is perfect for additional parking and or play area! All tenants have been there long term and pay regularly. Buyer and buyer agent to do own due diligence.

27 Thibault Ave, Winchester
$370,000
3 Beds ⋅ 2 Baths ⋅ 24120271 MLS
Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area to make entertaining easy! The living room area is nestled at the end of the house with custom built in book shelves and a french door to close off if you want to enjoy some quiet time! Upstairs you will find the the primary bedroom with a large, walk in closet and two additional bedrooms and a full bath. Outside you can enjoy the view of the yard from a spacious deck. Don't worry about the dogs or littles, they have plenty of space to roam safely in the fenced in area.

166 Torringford St, Winchester
$368,500
3 Beds ⋅ 2 Baths ⋅ 24168531 MLS
This move-in-ready Colonial-style home blends classic charm with modern updates. Featuring a remodeled kitchen with a large center island, cherry cabinets, granite countertops, stainless steel appliances, and a wine fridge. The main level also offers a dining room with refinished hardwood floors, a living room, and a flexible family room. Upstairs includes three bedrooms and a full bath, with a spacious primary bedroom and a custom walk-in closet. Outside, enjoy a patio, pool, and fully fenced yard. Additional highlights include updated siding, roof, and driveway, a heated one-bay garage/workshop and plenty of parking with two driveways.

102 Wallens St, Winchester
$365,000
3 Beds ⋅ 2 Baths ⋅ 24162992 MLS
Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows have been installed. A more formal dining area flows from the kitchen, making entertaining convenient. The bedrooms, full bathroom and laundry nook are all found on the main floor. The tastefully finished basement with half bath leads directly to the one car garage. There is ample backyard space for playscapes and so much more! Don't wait! This home will not last long!

262 Holabird Ave, Winchester
$360,000
4 Beds ⋅ 2 Baths ⋅ 24138466 MLS
Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm, inviting space for cooking and gathering. Adjacent to the kitchen is a cozy breakfast nook with a bay window, opening seamlessly into the living room for easy everyday living. Across the hall, you'll find a generous family room and a separate dining room, offering plenty of room for entertaining and hosting holidays. A half bath completes the main level. Upstairs are four bedrooms, creating flexible options for family, guests, or office space. Outside, the property truly shines with a two-story garage/barn featuring a loft, perfect for storage, a workshop, or hobby space. Enjoy summer days in the above-ground pool. Appreciate new 5 year old roof. The 4-acre lot provides both open, usable yard space and lightly wooded areas, ideal for gardens, animals, recreation, or simply soaking in the peaceful surroundings. This charming property offers privacy, potential, and the opportunity to make it your own. Schedule your showing today!

187 Torringford St, Winchester
$350,000
3 Beds ⋅ 2 Baths ⋅ 24168127 MLS
Welcome to 9 Colony Dr, a charming 3-bedroom, 2 full bath Cape offering a versatile and comfortable layout suited for today's lifestyle. The main level features a bright living room, a convenient first-floor bedroom, a full bath, and a modern kitchen with dining area perfect for everyday living and entertaining. The upper level offers two modestly sized bedrooms along with an additional full bath, providing ample space for family or guests. The lower level adds approximately 400 square feet of finished living space ideal for a family room, home office, or flexible use to fit your needs, and includes a walkout to the rear fenced yard complete with a paver patio for outdoor enjoyment. Mechanically, the home is equipped with a natural gas boiler and hot water heater, offering efficiency and reliability. This well-rounded home is poised to attract strong interest and is truly destined to sell quickly. Easy access to Rte's 8 and 44 and a short drive to Farmington Valley.

9 Colony Dr, Winchester
$340,000
3 Beds ⋅ 2 Baths ⋅ 24164318 MLS
Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less than 5 years old) and new gas boiler and electric water heater. Located in the heart of the Litchfield Hills, you're just moments from Highland Lake, local parks, and the top-rated Gilbert School. Includes a shed for more storage. Agent/owner. Move-in ready and priced to sell-schedule your showing today! "Lower lot area is part of the property, which can be cleared and used as new owners envision.

1 Hamill Dr, Winchester
$335,000
3 Beds ⋅ 2 Baths ⋅ 24155057 MLS
Enjoy years of maintenance-free living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated on a quiet side street just minutes from the beach at Highland Lake and the shops, restaurants, and conveniences of downtown Winsted. Completely remodeled in 2017, this home offers a long list of updates at that time including a new roof, updated baths, remodeled kitchen, all new flooring, new deck, newer heating system, and freshly painted interior and exterior. The current owner has meticulously maintained the home, preserving its like-new condition. The lower level provides excellent flexibility and offers the potential for an in-law suite, home office, or additional living space. Whether you're looking for comfort, convenience, or versatility, this home delivers it all. Don't wait-this one is here today and gone tomorrow.

44 Lewis St, Winchester
$330,000
4 Beds ⋅ 2 Baths ⋅ 24150199 MLS
What a wonderful Home! Walk in and be Wowed! This 4 bedroom home built in 1900 has been meticulously redone inside and out in 2020. Featuring gleaming hardwood floors on all 3 floors. Thermal paned windows through out. Spacious 12x10 foyer makes a great sitting room or office. First floor has the open floor plan with formal dining, living room and kitchen all in one. Comes with a full bath and laundry room on the first floor. New kitchen with gas stove. Second floor features 4 large bedrooms with wood floors, freshly painted and a full bath. Primary bedroom has a large walk-in closet. Walk up to the 3rd floor and enjoy a playroom with walk in closet, home office or studio. Energy efficient windows, tankless hot water heater and gas furnace. The numerous windows offer a very bright and inviting natural light source. Complete with central air and wrap around porch. Nothing to do but move on in and relax. Located within the school zone and walking distance to elementary, middle and high schools, as well as, the local playground, Main Street parades and town green with summer activities. Dont forget to get your parking pass for town residents to the well known Highland lake with 2 beaches and boating activities.

123 Wetmore Ave, Winchester
$326,000
6 Beds ⋅ 2 Baths ⋅ 24121764 MLS
62-64 Fruit Street in Winchester offers a rare opportunity to acquire a turnkey property located in one of the town's most desirable neighborhoods. This expansive residence is characterized by its classic New England architecture, making it a perfect fit for those seeking both charm and functionality. Both units offer spacious layouts and maintained interiors, ideal for entertaining and living comfortably. The large backyard offers ample space for outdoor activities or potential for expansion, providing flexibility to accommodate various needs. Use your imagination to finish the attic and potentially use it as a third unit.

62 Fruit St, Winchester
$325,000
4 Beds ⋅ 2 Baths ⋅ 24189235 MLS
Excellent opportunity for both owner-occupants and investors! This well-maintained two-family home features two spacious units, each offering 5 rooms, 2 bedrooms, and 1 full bath. Both apartments showcase beautiful hardwood flooring throughout and are served by separate natural gas heating systems for efficiency and convenience. The upper-level unit includes a charming enclosed porch, providing additional seasonal living space and a perfect spot to relax. Situated on a generous .66-acre lot, the property offers seasonal views of Highland Lake and is within walking distance of two public beaches, making it an ideal location to enjoy all that the area has to offer. Additional features include a detached three-car garage, ample outdoor space, and a desirable setting close to recreation, shopping, dining, and other local amenities. Whether you're looking to generate rental income or occupy one unit while offsetting your mortgage with the other, this is an outstanding opportunity.

120 E Lake St, Winchester
$324,900
4 Beds ⋅ 2 Baths ⋅ 24134631 MLS
Welcome to 135-137 Elm Street! This well-maintained two-family home offers an excellent opportunity for owner-occupants or investors alike. The main level unit features 5 rooms, including 2 bedrooms and 1 full bath, and is in excellent condition. It's equipped with a natural gas warm-air furnace that also provides central air for year-round comfort. The second-floor unit mirrors the first-floor layout with 5 rooms, 2 bedrooms, and 1 full bath, but includes additional finished space on the third level, offering several more rooms and a second full bath-the perfect setup for a 4-bedroom, 2-bath unit or flexible living arrangements. A detached two-car garage adds convenience and storage space, and the property's location offers easy access to downtown amenities, shopping, restaurants, and area schools. Whether you're looking to live in one unit and rent the other or add to your investment portfolio, this versatile property is a great find in a convenient location.

135 Elm St, Winchester
$320,000
2 Beds ⋅ 1 Baths ⋅ 24190178 MLS
Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where every day feels like a vacation. Perfectly positioned on one of Connecticut's most sought-after lakes. This home needs some love, but has great bones! Bring your vision and create your dream home!

729 W Wakefield Blvd, Winchester

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