Refine Search
Map
Sort by
424 E Wakefield Blvd, Winchester
$1,600,000
5 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
878 W Wakefield Blvd, Winchester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
674 E Wakefield Blvd, Winchester
$1,050,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
204 E Wakefield Blvd, Winchester
$960,000
2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
359 Winchester Rd, Winchester
$850,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24208872 MLS
Breathtaking water views and master craftsmanship await in this pristine Colonial offering nearly 3,000 SF overlooking serene Highland Lake. This entertainer's dream home opens from an inviting two-story foyer into an airy, open layout where the living and dining rooms are joined by a floor-to-ceiling fieldstone fireplace. The spacious dining room easily accommodates large gatherings and flows seamlessly onto a delightful screened-in porch to enjoy the beautiful calm setting with distant lake views. The gourmet kitchen is a master craftsman renovation featuring custom white birch cabinetry, rich soapstone countertops, stone subway tile backsplash, a farmhouse sink with a view and a Sub-Zero refrigerator. Dedicated home office off front foyer, mudroom, laundry room, and half bath complete the main level. Upstairs features an en-suite primary bedroom, two additional nice-sized bedrooms, and a full guest bath. Accessed via a private second staircase off the kitchen, the expansive 27' x 21' "Skybox" family room (finished over the garage in 2017) boasts its own heating/cooling system, surround sound, and live music performance hook-ups. Property is flanked by a magnificent stone wall, emerald green meadows including a two-stall run-in shed with tack room. Hardwood floors main level, bamboo engineered floors upper level, oversized 2 car garage, walk-out basement. New well pump 2020, new whole house generator 2023. EZ commute to NYC & Boston from this ideal retreat. Rare opportunity

359 Winchester Rd, Winchester
354 Main St, Winchester
$825,000
3 Baths ⋅ CLOSED Status ⋅ 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
156 Shore Dr, Winchester
$691,000
5 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
736 W Wakefield Blvd, Winchester
$525,000
1 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
123 Old North Rd, Winchester
$475,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
5 Stadler Hts, Winchester
$475,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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
136 Losaw Rd, Winchester
$430,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24202969 MLS
Welcome to 136 Losaw Rd! Built in 1984, this nicely maintained and updated home offers 1,977 sq. ft. of living space with 4 bedrooms, 2 full baths, and a comfortable open floor plan, all set on 1.76 acres. The main living level features an open dining area and kitchen with breakfast bar overlooking the sunken living room, highlighted by a beautiful arched fieldstone fireplace with propane log set. Two modest-sized bedrooms and a full bath complete this level. Upstairs, you'll find two generously sized bedrooms, a second full bath, and a large storage closet. The lower level features a fieldstone hearth and approximately 400 sq. ft. of additional space ready to be finished to suit your needs. Outside, the property offers a two-stall horse barn with additional room for hay and storage, adding great versatility for equestrian use, hobbies, or additional storage. Nicely maintained and thoughtfully updated over the years, this property offers plenty of space both inside and out. Don't let this one slip away!

136 Losaw Rd, Winchester
217 Walnut St, Winchester
$420,000
5 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 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
195 Reaching Hill Rd, Winchester
$400,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
102 Wallens St, Winchester
$368,500
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
320 Colebrook Rd, Winchester
$365,000
2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24206905 MLS
Private Country Living on 16 Acres! Enjoy the peace and privacy of this charming ranch nestled on expansive acreage, offering the feel of a true country compound. Features include 2 bedrooms, a family room with fireplace, kitchen, three-season enclosed porch, heated possible office, and large deck. Plenty of cleared land surrounds the homesite while mature trees provide exceptional privacy. Possible subdivision potential adds even more opportunity. Buyer to verify with the town. A rare opportunity for those seeking space, privacy, and endless possibilities!

320 Colebrook Rd, Winchester
262 Holabird Ave, Winchester
$365,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
50 High St, Winchester
$350,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24199721 MLS
Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.

50 High St, Winchester
9 Colony Dr, Winchester
$350,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
1 Hamill Dr, Winchester
$340,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
120 E Lake St, Winchester
$325,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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
729 W Wakefield Blvd, Winchester
$320,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 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
621 Wynne Rd, Winchester
$320,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24161635 MLS
Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of thoughtfully designed living space, including two bedrooms and one full bath, all in pristine condition. The dining area opens to the outdoors through sliding doors, leading to a rear deck that directly abuts the preserved land-an ideal spot to relax, entertain, or simply take in the quiet surroundings.Enjoy a coveted location near Highland Lake, offering boating, fishing, and year-round recreation, with seasonal lake views that add a subtle yet distinctive layer of charm and serenity. Whether you're looking for a year-round residence or a weekend retreat, this move-in ready home offers a rare opportunity to enjoy low-maintenance living in a truly special location.

621 Wynne Rd, Winchester
230 E Wakefield Blvd, Winchester
$300,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24150574 MLS
This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

230 E Wakefield Blvd, Winchester
350 Walnut St, Winchester
$285,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24170101 MLS
Fully remodeled from top to bottom, 350 Walnut St offers the perfect blend of modern updates, efficient living, and outdoor space. This move-in-ready 2-bedroom, 1-bath ranch has been beautifully reimagined with a fresh, stylish feel and all the major improvements already done for you. Inside, you will find a brand-new kitchen with quartz countertops and stainless-steel appliances, a fully updated bathroom, oak floors, new windows, new roof, new mechanicals, new electrical, and new plumbing. Built in 1950, this home offers 720 square feet of thoughtfully designed living space that feels comfortable, practical, and easy to maintain. A full basement with garage access and a 1-car attached garage adds valuable storage and utility, while natural gas heat adds everyday convenience. Set on an oversized 0.56-acre lot, this property offers a rare size of land for a home of this size, giving you room to relax, garden, entertain, or simply enjoy having open space around you. Its location near Tatro Park and local recreation adds to the appeal, making it easy to enjoy the outdoors close to home. Whether you are a first-time purchaser, downsizing, or looking for a turnkey alternative to condo living, this home delivers exceptional value. Why rent or settle when you can own a fully renovated single-family home with land, a garage, and major system updates already completed? Small in size but big on quality, comfort, and lifestyle, this is a home that is easy to love.Photos enhanced

350 Walnut St, Winchester
1 Division St, Winchester
$280,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24202478 MLS
Well-maintained and move-in ready, this charming one-level ranch offers 912 square feet of comfortable living space with 2 bedrooms and 1 full bath. Features include a one-car garage and convenient main-level laundry. The functional layout offers easy one-level living. Conveniently located close to town and local amenities. A great opportunity for buyers looking for a manageable home in a convenient location.

1 Division St, Winchester
64 Wheeler St, Winchester
$280,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24194728 MLS
Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch, providing additional seasonal living space and a relaxing retreat. Outside, you'll find a level lot and a unique two-story barn with a full basement, offering exceptional storage, workshop space, or endless possibilities for hobbyists and contractors alike. Conveniently located just minutes from downtown, schools, shopping, dining, and everyday conveniences, this property is ideal whether you're looking to build your investment portfolio or live in one unit while generating rental income from the other. A rare opportunity to own a versatile multi-family property with timeless Victorian charm!

64 Wheeler St, Winchester
57 Bridge St, Winchester
$276,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24167580 MLS
Step into the charm of this 1880 Colonial, featuring 4 bedrooms and 1.5 baths, just a short walk to the shops, dining, and conveniences of downtown. The main level offers a spacious eat-in kitchen, inviting living room, and a versatile bonus room that could serve as a home office or, with a little creativity, an additional bedroom, along with a half bath for added convenience. Upstairs includes four comfortable bedrooms, a full bath, and a walk-up attic offering great storage or future potential. Outside, enjoy an open lot with plenty of off-street parking, a ground-level deck/patio for entertaining, and a brick fire pit-perfect for relaxing evenings. A covered front porch and classic details add to the home's timeless appeal.

57 Bridge St, Winchester
147 E Wakefield Blvd, Winchester
$260,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24175908 MLS
Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring throughout, new roof, HW heater is only 4 years old, vinyl siding & fire pit. Year round lake living.

147 E Wakefield Blvd, Winchester
94 Holabird Ave, Winchester
$255,000
3 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24158795 MLS
Welcome to this charming New England Colonial that blends classic character with comfortable living. Step inside to an inviting, oversized living room featuring beautiful new vinyl flooring-perfect for relaxing, entertaining guests, or gathering with family. The main living level offers two convenient bedrooms and a laundry area, making everyday living easy and practical. Upstairs, you'll find two additional bedrooms that provide flexible space for family, guests, a home office, or hobbies. Outside, the backyard truly shines through the seasons, offering a peaceful setting to enjoy spring blooms, summer gatherings, colorful fall foliage, and quiet winter views. With its warm layout, timeless Colonial style, and inviting spaces inside and out and easy heating with natural gas, this home offers the perfect blend of New England charm and everyday functionality.

94 Holabird Ave, Winchester
111 Riverton Road Unit 79, Winchester
$222,000
2 Beds ⋅ 2 Baths ⋅ CLOSED 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. FINAL & BEST BY 5:30 10/5/26

111 Riverton Road Unit 79, Winchester

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!