Winchester CT Homes for Sale
- Type:
- Single Family
- Sq.Ft.:
- 1,824
- Status:
- NEW LISTING
- Beds:
- 3
- Lot size:
- 1.33 Acres
- Year built:
- 1950
- Baths:
- 2.00
- MLS#:
- 24061124
- Subdivision:
- Colebrook Station
ADDITIONAL INFORMATION
Investors, handy person and everyone else! Excellent home to rehab! This 3 bed with 2 bath home has a nice view of the water from the back deck. Well worth the effort!
- Type:
- Condo
- Sq.Ft.:
- 1,204
- Status:
- Active
- Beds:
- 2
- Year built:
- 1987
- Baths:
- 2.00
- MLS#:
- 24060342
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome to 111 Riverton Road, Unit 53-your perfect home just in time for the holidays! This well-maintained Riverwalk end-unit townhouse is nestled in the last building of the complex, offering privacy without through traffic, large open green space, and serene water views of the Still River. This immaculate home features 2 bedrooms, 1.5 baths, and brand-new carpeting installed on November 15th. The bright and inviting kitchen is, equipped with KitchenAid Superba double convection ovens, and a large stainless-steel sink. Natural light pours through the sliding doors, which lead to a spacious deck that spans the length of the unit-an ideal spot to enjoy your morning coffee while taking in the river views. The open concept living and dining area is perfect for entertaining, featuring a pellet stove insert to provide supplemental heat during the colder months and help keep energy costs low. Upstairs, the oversized primary bedroom boasts vaulted ceilings and a walk-in closet with a custom closet system. The full bath is filled with natural light thanks to high ceilings and a skylight. Convenience abounds with a laundry room that includes a newer washer, dryer, and hot water heater. The attached two-car garage is a wintertime game changer-say goodbye to shoveling and snow blowing, and hello to the ease of condo living! Don't miss this opportunity to enjoy the beauty and comfort of Riverwalk before the snow falls!
- Type:
- Single Family
- Sq.Ft.:
- 1,152
- Status:
- Active
- Beds:
- 3
- Lot size:
- 1.35 Acres
- Year built:
- 1989
- Baths:
- 2.00
- MLS#:
- 24060140
- Subdivision:
- N/A
ADDITIONAL INFORMATION
This wonderful Ranch is just waiting for you to call it home! With it's traditional layout 3 beds, 2baths, hardwoods partially finished lower level, and wonderful oversized deck overlooking a great yard. This home is just waiting for you to bring your style and make it yours! Enjoy time with your friends and guests and making tons of memories. Why wait? Being sold as-is.
- Type:
- Single Family
- Sq.Ft.:
- 1,277
- Status:
- Active
- Beds:
- 3
- Lot size:
- 1.3 Acres
- Year built:
- 1940
- Baths:
- 1.00
- MLS#:
- 24059573
- Subdivision:
- Winsted
ADDITIONAL INFORMATION
Home for the Holidays! Enjoy living in your own home nestled in the scenic Litchfield Hills in this newly renovated three-bedroom house with many updates: + Refrigerator, range, microwave, dishwasher, and first floor washer/dryer less than a year old. + Hot water heater 2023. + Updated electrical 2024. + Furnace serviced and updated with new burner 2024. + 3 new exterior doors and 6 new windows. Enjoy the wood-burning stove in the family room, built-ins in the dining room, and storage shed out back. Conveniently located off Route 8 and close to Route 44 --easy commute into Hartford or Bradley International Airport. Close to shopping, restaurants, several parks, pristine lakes with boat launches, and walkable downtown Winchester. Northwest Community College is 4 minutes away and the art scene is up and coming. See it today!
- Type:
- Single Family
- Sq.Ft.:
- 1,186
- Status:
- Active
- Beds:
- 3
- Lot size:
- 7.74 Acres
- Year built:
- 1970
- Baths:
- 2.00
- MLS#:
- 24058232
- Subdivision:
- N/A
ADDITIONAL INFORMATION
This charming, single-level ranch home sits on nearly eight acres of peaceful land, offering plenty of space and privacy. As you enter through the front door, you're welcomed into a stunning, freshly remodeled kitchen with custom cabinetry, brand new appliances all designed by someone with an interior design background. The kitchen flows seamlessly into the main living area, where a unique three-sided fireplace serves as the cozy centerpiece, warming both the kitchen and the spacious living room. In the living room, large windows bring in abundant natural light and provide beautiful views of the property. A sliding glass door opens to a wraparound porch, creating a perfect indoor-outdoor connection for entertainment or relaxing. The home features three comfortable bedrooms, all newly carpeted, providing warmth and comfort. The main bathroom has been fully remodeled with a stand-up shower, while the primary bedroom includes an updated half bath for added convenience. This beautifully updated ranch combines modern design touches with the serenity of country living, making it a true retreat.
$274,999
86 Maple Street Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 1,428
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.24 Acres
- Year built:
- 1880
- Baths:
- 2.00
- MLS#:
- 24058368
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Completely renovated. Brand new appliances. Roof and furnace approx. 10 years old. Nice open yard. New gravel driveway. Walk up attic with plenty of storage. New floors and windows. Large eat-in kitchen with marble counters and stainless steel appliances. Main floor laundry. Two full baths; one upstairs and one on main level. One main level bedroom. 86 Maple St is waiting for you to make it your home!
$480,000
51 Pratt Street Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 2,239
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.21 Acres
- Year built:
- 1901
- Baths:
- 2.00
- MLS#:
- 24057449
- Subdivision:
- Winsted
ADDITIONAL INFORMATION
Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and functionality to the space. Additional highlights include modern stainless steel appliances, with all appliances included, and hardwood flooring throughout the home. The beautifully landscaped yard creates a perfect outdoor space for relaxation and gatherings. Conveniently located near local amenities, this home provides easy access to shopping, dining, and more. Experience this beautiful home firsthand Don't miss the opportunity to make this move-in ready gem your new home.
$1,880,000
538 Wheelers Point Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 2,496
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.7 Acres
- Year built:
- 1930
- Baths:
- 3.00
- MLS#:
- 24052635
- Subdivision:
- Winsted
ADDITIONAL INFORMATION
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!
$399,900
10 Hamill Drive Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 1,476
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.33 Acres
- Year built:
- 1973
- Baths:
- 2.00
- MLS#:
- 24050228
- Subdivision:
- N/A
ADDITIONAL INFORMATION
This single family home has 3 generous bedrooms and 1.5 bathrooms. It features a spacious kitchen with hardwood cabinets and black appliances. There are hardwood floors throughout the entire house, a dedicated laundry room, and a heated finished basement. This home is situated on a cul-de-sac and is close to highways and shopping. It also features a serene backyard that is ready for enjoyment.
$299,999
421 Unity Place Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 1,440
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.12 Acres
- Year built:
- 1927
- Baths:
- 2.00
- MLS#:
- 24048561
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Make this newly renovated house in the sought after Highland Lake community your full time residence or your home away from home! This home has gone through an extensive remodel including brand new roof, insulated siding, energy efficient windows, and LVP flooring. The home features a new large eat-in kitchen with brand new smart stainless steel appliances, living room, and remodeled full bathroom, with a bluetooth enabled exhaust fan, downstairs. Upstairs features 3 bedrooms plus an additional room that can be used as an office or playroom with newly added baseboard heat and partial views of Highland Lake. Make memories with friends and family in the nicely sized, flat yard. Imagine yourself enjoying life in this stunning home close to beach access and boat launch- make it yours today, this won't last long!
- Type:
- Single Family
- Sq.Ft.:
- 2,674
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.32 Acres
- Year built:
- 1890
- Baths:
- 4.00
- MLS#:
- 24047669
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome to 19 Cottage Street, a stunning turnkey Colonial in the heart of Winsted that beautifully blends modern functionality with classic charm. As you enter, a spacious foyer with new tile flooring leads into a bright living room featuring gleaming hardwood floors, create a warm, inviting atmosphere. A dedicated office space presents an ideal setting for productivity, while the heart of the home-the expansive kitchen-boasts custom cabinetry, quartz countertops, and sleek appliances. The large island, which seats four, is perfect for casual dining or gatherings. Just off the kitchen, a sun-drenched sunroom is ideal for enjoying morning coffee with natural light pouring in. The first floor also features a chic half bath and washer/dryer hookups for added convenience. Upstairs, the master bedroom impresses with a spacious walk-in closet, while two additional bedrooms and two full baths make it perfect for family living or hosting guests. The third level also includes three versatile rooms and an additional half bath-perfect for a home office, playroom, or guest suite. Outside, a new driveway and garage doors add curb appeal, while freshly laid masonry lines the front and back yards, offering stylish outdoor spaces. With its blend of modern updates and timeless design, this home is truly move-in ready. Schedule a viewing today and make 19 Cottage Street your new home!
- Type:
- Single Family
- Sq.Ft.:
- 5,231
- Status:
- Active
- Beds:
- 8
- Lot size:
- 1.51 Acres
- Year built:
- 1930
- Baths:
- 5.00
- MLS#:
- 24047556
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring updated appliances, a spacious eat-in area, & an oversized island perfect for meal prep & entertaining. The rest of the main floor is ideal for hosting guests, w/ expansive windows providing stunning views of Highland Lake from every angle. Step outside to a covered front porch, where you can take in breathtaking sunrise views over the water. The second floor is home to the huge Primary bedroom, complete w/ a recently remodeled full bath & two walk-in closets. Four additional spacious bedrooms share Jack & Jill bathrooms, & a second-floor summer porch offers a serene spot to enjoy the natural beauty of the lake. The third floor adds even more space, w/ three additional bedrooms & a full bath that could be updated to reflect your needs. Directly on the lake is a 1/4 acre lot w/ 150+/- ft of water frontage, you'll find a charming lakeside cottage that features a cozy fireplace, kitchenette, full bath, & wrap-around deck. Whether you're relaxing on the dock or enjoying the cottage's amenities, this entire property is perfect for experiencing the best of lakefront living.
$349,900
116 Ashley Road Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 1,491
- Status:
- Active
- Beds:
- 3
- Lot size:
- 13 Acres
- Year built:
- 1830
- Baths:
- 1.00
- MLS#:
- 24044645
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome to a piece of history with this enchanting Cape farmhouse, a true gem nestled in the picturesque town of Winchester. Built in 1830, this home radiates classic charm with its original details and timeless character. The property features two inviting fireplaces, perfect for cozy evenings, and an oversized country kitchen that offers ample space for culinary creativity and family gatherings. The living room exudes warmth and charm, making it an ideal space for relaxation, while the cozy dining room provides a welcoming setting for meals with loved ones. With three bedrooms, this home offers comfortable living spaces that maintain its historical allure. The magnificent and private 13-acre lot presents a rare opportunity for renovation, expansion, or even subdivision. Whether you envision restoring the farmhouse to its former glory, expanding to create your dream estate, or exploring the potential for development, the possibilities are endless. Don't miss out on this unique chance to own a piece of Winchester's history and make it your own. This charming farmhouse is not just a home; it's a canvas for your dreams. Act quickly-opportunities like this are truly one of a kind.
- Type:
- Single Family
- Sq.Ft.:
- 988
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.22 Acres
- Year built:
- 1980
- Baths:
- 1.00
- MLS#:
- 24043032
- Subdivision:
- Winsted
ADDITIONAL INFORMATION
Welcome to 315 East Wakefield Blvd, a charming 3-bedroom, 1-bath ranch offering stunning views and easy access to Highland Lake. This home is in impeccable condition, featuring an updated kitchen and bath, along with newer hard surface flooring. The inviting living room boasts a propane fireplace, wood stove, and a picture window perfectly framing the serene lake views. The updated eat-in kitchen opens to a covered deck and a fenced-in rear yard, providing additional outdoor space with more picturesque views of the lake. This well-cared-for home is not only a cozy retreat but also a gateway to the year-round recreational activities that Highland Lake offers. Spanning 444 acres, the lake is renowned for its watersports, trophy trout and bass fishing, and a marina where you can rent a slip or even a boat. Whether you're seeking a peaceful lakeside residence or an active lifestyle, 315 East Wakefield Blvd is the perfect place to call home.
- Type:
- Single Family
- Sq.Ft.:
- 7,000
- Status:
- Active
- Beds:
- 9
- Lot size:
- 1.9 Acres
- Year built:
- 2002
- Baths:
- 6.00
- MLS#:
- 24042374
- Subdivision:
- N/A
ADDITIONAL INFORMATION
This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter settles in, the lake becomes a playground for ice fishing, skating, and cozy fireside gatherings, making this a year-round sanctuary. With luxury finishes, a gourmet kitchen, and custom craftsmanship in the main home, plus a charming guest bungalow, this property is ideal for hosting family, friends, or even guests. Zoned for a bed and breakfast and featuring an extra subdividable lot, the estate also holds exciting potential for income generation or expansion. Whether you're envisioning a private retreat, an upscale B&B, or future development with a subdividable lot, this versatile property is the perfect setting for those seeking a dynamic, all-season lake life.
- Type:
- Single Family
- Sq.Ft.:
- 3,404
- Status:
- Active
- Beds:
- 5
- Lot size:
- 2.09 Acres
- Year built:
- 1975
- Baths:
- 3.00
- MLS#:
- 24042770
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Welcome home! This inviting residence features an open, airy feel with abundant natural light from big windows and multiple skylights. The main level boasts solid hardwood floors and tiles, while the spacious eat-in kitchen, though older, is well-maintained and perfect for family meals. Enjoy three full bathrooms, a central vacuum system, and tons of storage space throughout. The primary bedroom is a cozy retreat with its own fireplace, and the large living room also includes a fireplace for added charm. Outside, you'll find a deck, mature plantings, flower beds, and a handy shed. With a big 2-car garage and a fantastic laundry room, this home has everything you need! This property is being sold As-Is. All inspections for informational purposes only.
- Type:
- Single Family
- Sq.Ft.:
- 1,781
- Status:
- Active
- Beds:
- 4
- Lot size:
- 0.62 Acres
- Year built:
- 1904
- Baths:
- 2.00
- MLS#:
- 24041356
- Subdivision:
- Winsted
ADDITIONAL INFORMATION
Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-family home can be used as a single family and offers breathtaking water views and modern comforts. Perfect as a family retreat or an income-generating property, the home is fully renovated with upscale finishes throughout and boasts central air, newer appliances, windows, siding, and high-efficiency propane-fueled furnaces. Gorgeous details throughout make this a truly exceptional property. On the first floor, you'll find a rustic custom kitchen w granite, upgraded appliances (sub zero refrigerator and bevg fridge, gas range, dishwasher), a full bathroom w marble and walk-in shower, two spacious bedrooms, and a large family room w French doors leading to a covered wrap around porch to enjoy that view! The second floor unit features a kitchenette with fridge, dishwasher, and range, dining room/office, two bedrooms, and a family room with sliders to a covered porch offering the same amazing landscape! Additional highlights include an oversized two-car detached garage and carport, hot tub(sold as is), level yard area, and side deck. This home is situated just across the street from the water, providing easy access to all lake activities. Rustic yet Upscale! A RARE FIND!
- Type:
- Single Family
- Sq.Ft.:
- 2,664
- Status:
- Active
- Beds:
- 3
- Lot size:
- 0.61 Acres
- Year built:
- 2024
- Baths:
- 3.00
- MLS#:
- 24022821
- Subdivision:
- Winchester Center
ADDITIONAL INFORMATION
Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.
- Type:
- Single Family
- Sq.Ft.:
- 2,687
- Status:
- Active
- Beds:
- 7
- Lot size:
- 1.63 Acres
- Year built:
- 1890
- Baths:
- 4.00
- MLS#:
- 24024787
- Subdivision:
- Sucker Brook
ADDITIONAL INFORMATION
Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong Island for his weekends and vacations away from NYC. Strong Island is one of the largest islands on Highland Lake and has the best views. The position of this island give it the longest view of the lake on a North view and also on an Easterly view. The position of the main house on the island, the various docks, piers and out buildings make this property unable to be duplicated today. Strong Island is a trophy property that needs some polishing, but incredible in so many ways.
$694,000
110 South Road Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 3,870
- Status:
- Active
- Beds:
- 4
- Lot size:
- 2.75 Acres
- Year built:
- 1984
- Baths:
- 3.00
- MLS#:
- 24017090
- Subdivision:
- Winchester Center
ADDITIONAL INFORMATION
Your private oasis nestled in historic Winchester Center, offering serenity, lakes, trails and more. Contemporary Cape w/an abundance of spacious, light-filled and updated rooms. Several options to include; one-floor living, multi-generational home, w 4+ bedrooms and 4 garage bays. Rooms are adorned w/crown molding, beams, skylights and oversized windows, bringing the beauty of the outside in. Gazing out the windows, you'll see mature plantings, flowers, wildlife and private pond. The main level of this home features a spacious kitchen w/ walk-in pantry, mudroom, dining rm, formal living rm, library, den, office, sunroom and spacious great room being used as a primary bedroom. Enjoy the Gunite pool and terrace directly outside the sunroom, with several seating areas overlooking beautiful views - a perfect place for entertainment or to retreat for relaxation, reading and conversation. Upper level boasts a primary suite with spa-like full bath w/soaking tub, additional 2 bedrooms w/en suite full bath, laundry room and a central loft overlooking the formal fireplaced living rm. The 4 garage bays are heated - ideal for car enthusiasts and those desiring an oversized workshop.
$1,100,000
469 Platt Hill Road Winchester, CT 06098
- Type:
- Single Family
- Sq.Ft.:
- 3,088
- Status:
- Active
- Beds:
- 4
- Lot size:
- 7.11 Acres
- Year built:
- 1789
- Baths:
- 2.00
- MLS#:
- 24021622
- Subdivision:
- N/A
ADDITIONAL INFORMATION
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Buyer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, 200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!
- Type:
- Single Family
- Sq.Ft.:
- 2,135
- Status:
- Active
- Beds:
- 3
- Lot size:
- 3.46 Acres
- Year built:
- 2023
- Baths:
- 3.00
- MLS#:
- 170551066
- Subdivision:
- N/A
ADDITIONAL INFORMATION
Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors thru-out, granite tops, stone/marble baths, walk up attic. Large deck off kitchen. Don't miss this incredible opportunity!
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Winchester Real Estate
The median home value in Winchester, CT is $317,000. This is lower than the county median home value of $345,200. The national median home value is $338,100. The average price of homes sold in Winchester, CT is $317,000. Approximately 51.37% of Winchester homes are owned, compared to 34.14% rented, while 14.49% are vacant. Winchester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today!
Winchester, Connecticut has a population of 10,335. Winchester is less family-centric than the surrounding county with 20.73% of the households containing married families with children. The county average for households married with children is 26.17%.
The median household income in Winchester, Connecticut is $65,537. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Winchester is 50.7 years.
Winchester Weather
The average high temperature in July is 80.7 degrees, with an average low temperature in January of 13.6 degrees. The average rainfall is approximately 52.3 inches per year, with 52.6 inches of snow per year.