Winchester CT Real Estate & Homes for Sale

18 Properties Found

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Beds:
2
Baths:
1.00
Sq.Ft.:
500
Status:
Active
MLS#:
24086525
Type:
Single Family
Subdivision:
N/A
Lot size:
0.26 Acres
Year built:
1954
Courtesy: Mary LeBlanc Realty 860-689-2689
View additional info

ADDITIONAL INFORMATION

Welcome to your Lake side escape. This year round home on Highland Lake offers stunning views of the lake and just a few steps to your very own water front parcel where you can lounge water side or launch your kayak or make a boat stop . This cozy ranch home features a large deck for relaxing, sliders to let in the warm sunlight or the cool lake breeze, open living room with electric fireplace and kitchen area with updated cabinets, appliances and vinyl flooring, full bath and 2 bedrooms with newer carpeting and stackable washer/dryer. New Roof and new Hardie board siding, propane heat, public water and sewer, on private road, also just a short walk to the public beach. Own your slice of Lake Paradise just in time for Summer! Owner related to listing agent and broker.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
24085643
Type:
Single Family
Subdivision:
N/A
Lot size:
0.12 Acres
Year built:
1927
Courtesy: Premier Re Group LLC 860-335-0681
View additional info

ADDITIONAL INFORMATION

UPDATED SERENE CHARMING 2 LOTS This Highland Lake retreat is ideal for the 1st time homeowner, getaway retreat or investment opportunity. Nestled in New England's natural beauty, you are sure to enjoy your lush surroundings & stunning views, truly a nature lovers delight. 3+ generous bedrooms, 2 full bathrooms, dining room, fireplaced living room, updated kitchen with stainless appliances, 1st flr laundry, plenty of parking & lake views. 2ND LOT: 461 E. Wakefield Blvd, Winsted (Additional Lot) to convey with purchase of 421 Unity Place. Property Card reads 2bed/1bath but is a 3bed/2bath. UPDATES INCLUDE: Newer Roof ('24), flooring, paint, energy efficient windows, kitchen, bathrooms and MORE! LOCATION: public lake access w/Resha Beach, 4min. away & Holland Beach (boat launch, 7min. away. Platt Hill State Park (78 acres of outdoor activities), 10 min. away. Steven's Reserve of the Winchester Land Trust.**Buyers must do their research if choosing this property as an investment opportunity

Beds:
2
Baths:
2.00
Sq.Ft.:
1,536
Status:
Active
MLS#:
24085896
Type:
Single Family
Subdivision:
Winsted
Lot size:
0.13 Acres
Year built:
1979
Courtesy: Sullivan Real Estate Inc 860-738-1902
View additional info

ADDITIONAL INFORMATION

Situated on a private road with views of Highland Lake, this beautifully updated home offers a perfect blend of modern comfort and quiet surroundings. Boasting a brand-new roof, siding, windows, as well as new front and back porches this home is ready to go for anyone looking for a great home. Step inside to discover an inviting, light-filled interior with contemporary finishes throughout. The spacious kitchen is perfect for cooking and entertaining, and finished basement for additional space This home includes private water access for residents on Mathew Rd as well as a public beach only a short walk from the front door. Basement living area will be added to overall living space once permit is closed.

Beds:
2
Baths:
2.00
Sq.Ft.:
992
Status:
Active
MLS#:
24084787
Type:
Condo
Subdivision:
Wallen'S Hill
Year built:
1986
Courtesy: Turning Point Realty, LLC 860-909-1162
View additional info

ADDITIONAL INFORMATION

Come see this wonderful sought after condo in a great neighborhood that has been freshly painted and all new appliances in the kitchen as well as a newer water heater that is just a few years old. Close proximity to town and route 8 and just down the street from the Northwestern Connecticut Community College. This unit has a garage that is directly across from the condo and has an additional parking spot right in front of the door; there are visitor spots as well. These condos do not last long, so get your time in for a showing quickly!

Open House:

Saturday, 4/19 11:00-1:00PM

More Open House Info >

Beds:
5
Baths:
2.00
Sq.Ft.:
1,962
Status:
Active
MLS#:
24084424
Type:
Single Family
Subdivision:
Winsted
Lot size:
1 Acres
Year built:
1900
Courtesy: Bolduc Realty Group 203-464-1479
View additional info

ADDITIONAL INFORMATION

This spacious 5-bedroom, 2-bath Colonial offers incredible flexibility and room to grow. The first floor features a large eat-in kitchen, a sun-filled dining room with a charming brick hearth fireplace, a massive family room, two bedrooms, and a full bath with laundry. Upstairs you'll find three generously sized bedrooms and a freshly painted second full bath. Set on a nice lot with a newer septic system (installed approx. 2022), this home has great bones and the space you've been looking for. Some updates and personal touches will make it shine. Not eligible for FHA financing due to some exterior condition items. Audio/video recording devices are in use on the property. Professional pictures to be uploaded. Being sold As-Is.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,870
Status:
Active
MLS#:
24076783
Type:
Single Family
Subdivision:
N/A
Lot size:
2.75 Acres
Year built:
1984
Courtesy: Regency Real Estate, LLC 860-945-9868
View additional info

ADDITIONAL INFORMATION

Discover your private sanctuary in the heart of historic Winchester Center, where tranquility meets nature! This contemporary Cape-style home boasts spacious, light-filled rooms that have been thoughtfully updated throughout. Elegant details such as crown molding, beams, skylights & oversized windows invite the beauty of the outdoors in-all showcasing your private pond! The main floor is designed for comfort & functionality, featuring a chef's kitchen with walk-in pantry, dining room, formal living room, library, den, office & generous great room currently used as a primary bedroom. A sunroom finishes off the main level & as you step outside to the terrace, you'll find a Gunite pool surrounded by seating areas with sweeping views-the perfect setting for entertaining or relaxing. Upstairs, the primary suite offers a spa-like retreat with a soaking tub. Two additional bedrooms w/ bath provide privacy & comfort. A central loft overlooks the living room, while a dedicated laundry room adds convenience. For car enthusiasts or those in need of extra space, the 4 heated garage bays provide ample room for vehicles and a large workshop. This exceptional home is ideally located near Winchester & Highland Lakes, four state parks (including Burr Pond), the private Park Pond Club, ski resorts, cultural attractions & is in walking distance of Winchester Land Trust trails. Just 2.5 hours from NYC and Boston, this property truly offers the best of seclusion & accessibility. A must-see!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,781
Status:
Active
MLS#:
24075940
Type:
Single Family
Subdivision:
Winsted
Lot size:
0.62 Acres
Year built:
1904
Courtesy: KW Legacy Partners 860-313-0700
View additional info

ADDITIONAL INFORMATION

Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating investment. Featuring modern upgrades throughout, the home boasts C/A, high-efficiency propane furnaces, newer appliances, windows, and siding-all designed for comfort and style. Inside, you'll find gorgeous details at every turn. The first-floor unit showcases a custom rustic kitchen with granite countertops, a Sub-Zero refrigerator, beverage fridge, gas range, and dishwasher. A luxurious marble-accented bathroom with a walk-in shower, two spacious bedrooms, and a large family room with French doors leading to a wraparound covered porch complete this level-perfect for soaking in those incredible views! The second-floor unit offers flexibility, featuring a kitchenette, dining room/office space, two additional bedrooms, and a family room with sliding doors opening to another covered porch-all with the same stunning lake vistas! Addt'l highlights include an oversized two-car detached garage with a carport, a hot tub (sold as-is), a level yard area, and a side deck. Situated just steps from the water, this home provides easy access to all lake activities. Rustic charm meets upscale living!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,021
Status:
Active
MLS#:
24067951
Type:
Single Family
Subdivision:
N/A
Lot size:
4.6 Acres
Year built:
1875
Courtesy: RE/MAX Right Choice 860-659-3343
View additional info

ADDITIONAL INFORMATION

Welcome to this charming four-bedroom antique home that is beautifully renovated to blend timeless character with modern comforts. As you step inside you'll be greeted by the warmth of refinished hardwood floors and an inviting living room featuring a cozy fireplace and built-in bookcases perfect for relaxing or entertaining. The heart of the home is the brand-new kitchen boasting sleek granite countertops, stainless steel appliances and plenty of cabinet space for all your culinary needs. The adjacent dining room is ideal for gatherings or hosting guests. This home offers three fully remodeled bathrooms each showcasing contemporary finishes and thoughtful design. A new second-floor laundry room adds convenience to daily living keeping chores organized and easily accessible. For added versatility, the property includes an in-law apartment providing privacy and comfort for extended guests. Additional upgrades include a new boiler, energy-efficient windows, a new roof and a modern engineered septic system ensuring the home is both efficient and well-maintained. Outside, enjoy the tranquility of a spacious four-acre lot complete with a patio for outdoor dining and relaxation. The large barn with three bays offers ample space for car storage, hobbies, or potential workshop use. With its perfect blend of antique charm and modern updates this home is truly a rare find. Don't miss your chance to experience the best of both worlds.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,239
Status:
Active
MLS#:
24073605
Type:
Single Family
Subdivision:
Winsted
Lot size:
0.21 Acres
Year built:
1901
Courtesy: Coldwell Banker Realty 203-272-1633
View additional info

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.

Beds:
5
Baths:
4.00
Sq.Ft.:
5,016
Status:
Active
MLS#:
24071827
Type:
Single Family
Subdivision:
Winsted
Lot size:
0.56 Acres
Year built:
1880
Courtesy: Northwest CT Realty 860-379-7245
View additional info

ADDITIONAL INFORMATION

Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,424
Status:
Active
MLS#:
24066803
Type:
Single Family
Subdivision:
N/A
Lot size:
0.22 Acres
Year built:
1900
Courtesy: Elyse Harney Real Estate 860-435-0120
View additional info

ADDITIONAL INFORMATION

A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is large and spacious and off the kitchen in the back is a lovely sunroom with a fireplace (natural gas) that has sliders that lead to the deck and the back yard. The laundry room is located on the first floor, the 3 bedrooms upstairs have hard wood floors as well the downstairs with the exception of the kitchen.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,496
Status:
Active
MLS#:
24052635
Type:
Single Family
Subdivision:
Winsted
Lot size:
0.7 Acres
Year built:
1930
Courtesy: William Pitt Sotheby's Int'l 860-567-0806
View additional info

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!

Beds:
8
Baths:
5.00
Sq.Ft.:
5,231
Status:
Active
MLS#:
24047556
Type:
Single Family
Subdivision:
N/A
Lot size:
1.51 Acres
Year built:
1930
Courtesy: Berkshire Hathaway NE Prop. 860-489-1772
View additional info

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.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,491
Status:
Active
MLS#:
24044645
Type:
Single Family
Subdivision:
N/A
Lot size:
13 Acres
Year built:
1830
Courtesy: Vylla Home (CT) LLC 860-656-0555
View additional info

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.

Beds:
9
Baths:
6.00
Sq.Ft.:
7,000
Status:
Active
MLS#:
24042374
Type:
Single Family
Subdivision:
N/A
Lot size:
3 Acres
Year built:
2002
Courtesy: Berkshire Hathaway NE Prop. 860-677-7321
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,664
Status:
Active
MLS#:
24022821
Type:
Single Family
Subdivision:
Winchester Center
Lot size:
0.61 Acres
Year built:
2024
Courtesy: The Washington Agency 860-482-7044
View additional info

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.

Beds:
7
Baths:
4.00
Sq.Ft.:
2,687
Status:
Active
MLS#:
24024787
Type:
Single Family
Subdivision:
Sucker Brook
Lot size:
1.63 Acres
Year built:
1890
Courtesy: William Pitt Sotheby's Int'l 860-567-0806
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,135
Status:
Active
MLS#:
170551066
Type:
Single Family
Subdivision:
N/A
Lot size:
3.46 Acres
Year built:
2023
Courtesy: The Washington Agency 860-482-7044
View additional info

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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Davis E. Owen, Sr., License REB.0754414, Xome CT LLC, License REB.0790146 , Davis.Owen@xome.com, 844-400-XOME (9663), 2083 Main Street, Stratford, CT 06615

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Winchester Real Estate

Winchester is located in Connecticut. 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.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $268,000
    14.1%
    change since last quarter
  • # Active listings

    43
    30-day change

Winchester Schools and Demographics

Education near Winchester, CT

City County
High School Graduates 93.76 93.89
College Degree - 2 year 11.55 9.19
College Degree - 4 year 27.21 36.19
Graduate Degree 8.81 11.56
Expenditures per Student 26,218 26,218
Students per Teacher 11.5 11.5

Elementary Schools near Winchester, CT

Grades Students P/T Ratio ZIP
Batcheller Early Education Center PK - 01 186 12.6 06098
Botelle Elementary School PK - 06 115 12 06058
East School KG - 05 361 12.9 06790
Forbes School KG - 05 373 11 06790
Goshen Center School KG - 06 150 10.7 06756
Mary P. Hinsdale School 02 - 04 241 11.9 06098
Torringford School KG - 05 615 13.4 06790
Vogel-Wetmore/Outreach PREK PK - PK 7 06790

Middle Schools near Winchester, CT

Grades Students P/T Ratio ZIP
Northwestern Regional Middle School 07 - 08 332 10.9 06098
Pearson Middle School 05 - 08 149 11.5 06098
Torrington Middle School 06 - 08 1,012 13.1 06790

High Schools near Winchester, CT

Grades Students P/T Ratio ZIP
Explorations 09 - 12 88 9 06098
Northwestern Regional High School 09 - 12 693 12.9 06098
The Gilbert School 07 - 12 552 11.8 06098
Torrington High School 09 - 12 1,003 12.4 06790

Ungraded Schools near Winchester, CT

Grades Students P/T Ratio ZIP
* Migeon Academy 09 - 12 12 06790
Batcheller - Bridges 1 UG - UG 0 06098
Connecticut Mental Health Center UG - UG 0 06790
Intensive Learning Program UG - UG 0 06098
Links 06 - 12 13 13 06098

Real estate near Winchester