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Winchester CT Real Estate & Homes for Sale

89 Properties Found

The median home value in Winchester, CT is $95,000 This is lower than the county median home value of $225,300. The national median home value is $185,800. The average price of homes sold in , is $. Approximately 51.53% of Winchester homes are owned, compared to 33.6% rented, while 14.87% 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 Winchester real estate agent to arrange a tour today !
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1-25 of 89 properties displayed
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$129,900

112 Meadow St Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
1,842
Status:
NEW LISTING
MLS#:
W10214288
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.2 Acres
Year built:
1873
Courtesy: Weichert REALTORS Briotti Group
View additional info

Great investment opportunity! Don’t miss this very well maintained 2 family house with very low taxes . Spacious bedrooms,new 2016 built country porch, hardwood floors, newer kitchen, remodeled dining room w/beams. Great decent size level yard, a detached carriage house garage for 2 cars. Plenty of parking spaces. Call at 203-558-9101 to schedule Showing.

$324,900

158 Torringford St Winchester, CT 06098

Beds:
3
Baths:
3.00
Sq.Ft.:
2,520
Status:
NEW LISTING
MLS#:
G10214594
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
1.37 Acres
Year built:
2004
Courtesy: CutTheCommission.com
View additional info

Well maintained Colonial built in 2004. 2520 sf featuring 2 story foyer leading to large kitchen, dining room and living room with stone fireplace. 3 large BR plus office/nursery, 2.5 baths. Full basement, large walk-up attic, attached oversized 2 car garage. Sliders from LR lead to 16x28 stamped concrete patio overlooking beautifully landscaped 1.37 acres with nice views.

$695,000

254 Perch Rock Trl Winchester, CT 06098

Beds:
4
Baths:
4.00
Sq.Ft.:
2,564
Status:
NEW LISTING
MLS#:
L10214475
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.16 Acres
Year built:
1929
Courtesy: Northwest CT Realty
View additional info

Located on the shores of Highland Lake in the much sought after neighborhood of Perch Rock Trail. This year round 4 bedroom, 3.5 bath home is in impeccable condition and offers space for everyone. There are 3 full levels of living. The lower level contains a large family room with fireplace and sliders leading out to the expansive waterfront. Main level contains large eat in kitchen, dining area, oversized living room with fireplace and opens up to enclosed 3 season porch overlooking the lakefront. Upstairs there are 4 modest bedrooms with gleaming hardwood floors and 2 full baths. The waterfront contain a large deck overlooking the lake. There is a detached two car garage with plenty of storage for all the toys. This property receives late afternoon sun and western exposure for lasting sunsets.

$139,900

151 Main St Winchester, CT 06098

Beds:
8
Baths:
4.00
Sq.Ft.:
4,817
Status:
NEW LISTING
MLS#:
W10211099
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.43 Acres
Year built:
1895
Courtesy: West View Properties, LLC
View additional info

Beautiful Victorian On Main Street in a Commercial Zone (CB2) Built in 1895 and over the years has been used for various things and in most cases occupied by the owners and their families. The primary use for the last 25 years on and off has been as a Bed & Breakfast. Each owner had invested in various aspects of restoration yet the most comprehensive renovation was completed in 2004 and 2005 by the current owner. During that time all the systems were completely refreshed and/or updated. Tenant Requires 24 HR Notice......

$69,900

25 Riveredge Dr UNIT 25 Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
1,000
Status:
NEW LISTING
MLS#:
G10214264
Type:
Condo
Subdivision:
Winsted (136)
Year built:
1986
Courtesy: RE/MAX Communities
View additional info

Great riverfront location close to Town Center. End unit townhouse with 2 large bedrooms. 1.5 bathrooms. Large kitchen with all appliances included, backsplash, & cheerful eat-in area. Combined living/dining area complete with large built-in shelving. Private patio backs to River adding to the serene setting. Attic storage accessible from pull down staircase in bedroom. Upstairs Washer & Dryer included. New Water Heater. Parking offers open space directly in front of unit plus spacious 1 car garage with extra storage area for bikes, etc.

$379,000

111 Mundry Rd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,872
Status:
NEW LISTING
MLS#:
D10213821
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
3.03 Acres
Year built:
1976
Courtesy: The Higgins Group
View additional info

Traditional charm with today's amenities! Superbly maintained, this outstanding 3 bdrm/1.5 bath family residence exudes warmth and grace with hardwood floors, built-ins, sunny exposure in the fireplace anchored living room, and the home's lower level finished for relaxation and recreation. The rear yard includes an oversized deck for entertaining, screened in porch for dining, 100x130 fencing, and additional electric perimeter fencing - plus paddocks for horses with functional sheds for living quarters, storage, tack and equipment.

$144,900

40 Oak Street Winchester, CT 06098

Open House:

Sunday, 4/23 1:00-3:00PM

Beds:
4
Baths:
2.00
Sq.Ft.:
1,674
Status:
NEW LISTING
MLS#:
G10213438
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.16 Acres
Year built:
1870
Courtesy: Coldwell Banker Res Brokerage
View additional info

Enjoy summer evenings sitting on your covered front porch sipping lemonade or gather with your friends around the stone fire pit in the backyard to roast marshmallows. This charming vintage colonial in the heart of Winchester gives the feeling of yesteryear while providing the conveniences of 2017, and is only steps away from downtown Winchester and one mile from Highland Lake! Freshly painted interior and refinished hardwood floors are a plus. The living room opens to an oversized dining room, and the first floor office can also double as a 4th bedroom. Don't miss the half bath with its custom stained and sealed concrete sink and vanity. The kitchen, with its new appliances, has many custom features with artfully installed tile floor and the stained glass mosaic back door which leads to the back porch. Delightful artistic panels guide you down the stairs to the backyard. Walk up the stairs and discover the huge master bedroom along with two additional bedrooms. You will love the spacious full bath with custom-tiled shower, new “old” vanity with hand-thrown sink and waterfall faucet. The walkout basement houses the laundry, new furnace and new energy-efficient hybrid heat pump water heater. Also extensive new plumbing, new insulation, new electrical, new bathrooms, are just a few of the updates which have been completed in the past year. Truly a unique and special home!

$379,000

111 Mundry Road Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,872
Status:
NEW LISTING
MLS#:
99182303
Type:
Single Family
Subdivision:
Winchester Center
Lot size:
3.03 Acres
Year built:
1976
A broker reciprocity listing Courtesy: Higgins Group Real Estate
View additional info

Traditional charm with today's amenities! Superbly maintained, this outstanding 3 bdrm/1.5 bath family residence exudes warmth and grace with hardwood floors, built-ins, sunny exposure in the fireplace anchored living room, and the home's lower level finished for relaxation and recreation. The rear yard includes an oversized deck for entertaining, screened in porch for dining, 100x130 fencing, and additional electric perimeter fencing - plus paddocks for horses with functional sheds for living quarters, storage, tack and equipment.

$139,900

275 Florence St Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,008
Status:
NEW LISTING
MLS#:
L10213594
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.17 Acres
Year built:
1979
Courtesy: Northwest CT Realty
View additional info

Well cared for Ranch on corner lot. Nice side yard for playing or gardening. This home features 3 bedrooms, an oak kitchen with center island/breakfast bar and stainless appliances, thermopane widows, efficient gas boiler and newer roof. Additional space in basement makes for a nice spare bedroom or family room. Very nice home. Wood stove in basement does not convey.

$759,900

126 East Wakefield Blvd Winchester, CT 06098

Beds:
3
Baths:
4.00
Sq.Ft.:
2,186
Status:
NEW LISTING
MLS#:
G10208979
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.16 Acres
Courtesy: BHHS New England Properties
View additional info

Stunning, Turn Key, Water Front, Year Round Dream Home on Highland Lake, a 444 acre lake with 2 beaches, a boat launch with swimming, stocked lake for fishing, water skiing, boating, kayaking and so much more - year round fun. Completely re-built in 2009+, this quality, custom gem has it all! Open Main level with granite kitchen, stainless appliances, lots of cabinet space, and breakfast bar. The Great Room with cathedral ceiling is incredible---the wall of windows and water views are truly amazing. The master bedroom is located on the first floor with a full bath and tile steam shower. First floor laundry room with sink and an additional half bath. The second floor offers 2 additional generously sized bedrooms with ample closet space and an additional full bath. The lower level offers a kitchen area, half bath and lots of storage. The patio is the perfect spot to relax and enjoy lake living. The professionally landscaped grounds are gorgeous leading right to your private dock! Some of the many special features include gleaming hardwood floors throughout, public water, public sewer, central air, generator hook-up, security system and an irrigation system. This fabulous location offers quick access to Route 44, Route 8 to New Haven and New York, approximately 40 minutes to Hartford, and close to Infinity Music Hall and the Warner Theater. Start making your memories here -- a place in the sun for fun and laughter every day with your family and friends!

$219,900

182 Shore Dr Winchester, CT 06098

Beds:
1
Baths:
1.00
Sq.Ft.:
900
Status:
NEW LISTING
MLS#:
L10209305
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.18 Acres
Year built:
2007
Courtesy: The D'Amore Agency, LLC
View additional info

Just in time for Summer. Bring all your toys and make memories enjoying all that Highland Lake and surrounding areas have to offer. New Kitchen and Bath, Stone patio and outdoor fire pit. A must see waterfront Home

$133,500

171 Elm St Winchester, CT 06098

Beds:
3
Baths:
1.00
Sq.Ft.:
1,455
Status:
NEW LISTING
MLS#:
L10213173
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.12 Acres
Year built:
1900
Courtesy: Northwest CT Realty
View additional info

Magnificent Victorian style home with open foyer and sparkling wood floors. This home features oak kitchen with center isle/breakfast bar, thermopane windows, second floor laundry room and approx 400 sq ft (not included in total sq ft) master bedroom with enormous walk in closet. There truly is nothing to do but move right in. Very easy walk to shopping, recreation and schools.

$449,000

332 East Wakefield Blvd Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
900
Status:
Active
MLS#:
L10211145
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.21 Acres
Year built:
1900
Courtesy: Hunter Real Estate, LLC
View additional info

Welcome to beauty of a Lake front home. This updated home, with it's breath taking views, has a newer roof, thermal paned windows and vinyl siding. This seasonal cottage is equipped with a gas fireplace for those chilly summer nights with the cool air running off the lake. This home is fully applianced including washer and dryer, fully furnished with furniture, tables, and beds, etc... One of the best available lots, has direct waterfront, plenty of off street parking and on a level landscaped yard. This home includes a pump-up waterfall coming from the lake. Meticulously maintained and ready for the new summer season. Dont miss this opportunity to own a piece of heaven with gorgeous sunsets! Second bedroom was originally 2 bedrooms so very large bedroom with office or use with 2 sets of bunk beds for family gatherings! House could easily be converted to year round by adding electric heat or furnace. Alot of storage space under the house.

$254,900

283 Grantville Road Winchester, CT 06098

Open House:

Sunday, 4/23 12:00-2:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
1,459
Status:
Active
MLS#:
G10211098
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
1.96 Acres
Year built:
1987
Courtesy: Coldwell Banker Res Brokerage
View additional info

Come experience the beauty and tranquility that this country Cape has to offer! Meticulously maintained, warm and comfortable, home features a gorgeous stone chimney, expansive oversized rooms and exposed beams everywhere. This quality built, rock solid home is sited on a quiet country road directly across from a beautiful meadow. There are three generously sized bedrooms, two full baths, hardwood floors on the main level and a first floor bedroom/den that could also serve as the master. The eat-in kitchen offers ample space for any cook with tile floor and granite tops that lead to a sunny dining room for the more formal gatherings. There is a huge deck right off the country kitchen which overlooks a backyard paradise with stone walls and gardens, a great entertaining space for large parties or small gatherings. On the second floor you will find two oversized, light and bright bedrooms with cathedral ceilings, ample storage space and a center hall full bath. Just minutes to picturesque Winchester Lake and the heart of historic Winchester Village, home is a private retreat yet a stone's throw away from everything. You will enjoy beautiful views from every window. This is the ultimate home to build family memories or escape to your dreams.

$124,900

29 Crescent St Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
1,386
Status:
Active
MLS#:
L10211339
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.23 Acres
Year built:
1894
Courtesy: Northwest CT Realty
View additional info

Nicely maintained and updated in-town Colonial with easy walk to downtown shopping and schools. This 4 bedroom 1.5 bath home offers room for everyone and features natural gas heating, updated kitchen, thermopane windows, first floor laundry and hardwood floors along with other recent updates.

$649,900

39 Lake St Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
2,182
Status:
Active
MLS#:
G10211156
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.69 Acres
Year built:
1900
Courtesy: Realty World Hometown
View additional info

Direct Waterfront on Highland Lake! Great house with lots of updates. 71 ft. of lakefront. Property includes a waters edge boathouse with bar and refrigerator, 2 docks, sprawling backyard, & wonderful back deck with an awning. perfect place for a party! Inside has had lots of updates including hardwood floors, kitchen updated, bathroom updates & more. Garden area on side of house. Very tranquil setting to spend your days. Central air is included for hot summer days. also the hot tub is included.

$350,000

6 Stadler Hts Winchester, CT 06098

Beds:
4
Baths:
3.00
Sq.Ft.:
2,726
Status:
Active
MLS#:
L10210777
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
3.22 Acres
Year built:
1990
Courtesy: Sullivan Real Estate Inc
View additional info

Meticulously Maintained Custom Built Contemporary/Colonial on a Private Cul-De-Sac, Beautifully Nestled on 3.22 Acres in the Woods of Winchester Being Offered by the Original Owners. Enjoy the Serenity while still Convenient to Major Routes and Area Shopping. From the Welcoming Foyer to the Soaring Ceilings Enjoy All This Special Home has to Offer. Four Spacious and Bright Bedrooms along with Two and a Half Baths. Master Bedroom Suite with Walk-in Closet. Kitchen with full accompaniment of Cabinets and Breakfast Bar. Formal Living Room and Family Room with see-through Fireplace. Walk-Out Basement Awaiting Your Finishing Touches. High-end Furnace with Tandem Oil Tanks. Central Air. Wired for Generator Hook-up. Attached Two-Car Garage. Large Deck Overlooking Private Backyard. 12X24 Shed for Extra Storage.

$520,000

160 E Wakefield Blvd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,508
Status:
Active
MLS#:
L10210124
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.15 Acres
Year built:
1968
Courtesy: Elyse Harney Real Estate
View additional info

DIRECT WATERFRONT ON HIGHLAND LAKE - The living is easy in this impeccably cared for year round 3 bedroom home. The large covered Porch faces peaceful Sandy Cove, and it is just steps to your private dock and boat lift. A major renovation/addition added a spacious Master Bedroom with views over the water. The Living Room features a cathedral ceiling, a brick hearth fireplace, exposed beams. Mechanicals are state of the art, including 200 amp service and a newer Buderus boiler and water heater. Wall A/C units in four rooms, a generator hook up, Speed Queen commercial heavy duty washer/dryer, and much more. Your summer is waiting!

$120,000

141 Williams Ave Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,485
Status:
Active
MLS#:
F10208171
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.35 Acres
Year built:
1951
Courtesy: William Pitt Sotheby's International Realty
View additional info

Well maintained 3 Bedroom 1.5 Bathroom Cape Cod with formal dining room, living room with fireplace. Large backyard and rear deck, also has attached car garage. *** HUD Home.Property is NOT located in a FEMA Special Flood Hazard Area but is listed as a moderate to low flood risk. Please refer to website for additional information regarding flood zones and insurance, State law requires Smoke/ Carbon Monoxide detectors be installed for properties having combustible fuel heaters/furnaces, fireplaces, hot water heaters, clothes dryers, cooking appliances, or an attached garage, but seller (HUD) is exempt from this requirement as a Federal Entity. Repairs: Treat and paint interior / exterior defective paint surfaces, Repair damaged exterior trim where needed.

$29,900

112 Sterling Trl Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
960
Status:
Active
MLS#:
G10207860
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.22 Acres
Year built:
1942
Courtesy: Property Works Connecticut
View additional info

Beautiful cottage right next to the Lake. Newer windows, Fire place for the cold nights. This year round Bungalow has charm and the space to accommodate. Will not last long. Set up your showing today. See attachment for PAS requirements and WFHM offer submittal information in MLS document section. Please submit all offers to the listing broker/agent. To report any concerns with a listing broker/agent, or to report any property condition or other concern needing escalation (including concerns related to a previously submitted offer), please see attached.

$929,900

504 W. Wakefield Blvd Winchester, CT 06098

Beds:
3
Baths:
3.00
Sq.Ft.:
2,249
Status:
Active
MLS#:
L10205624
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.57 Acres
Year built:
1995
Courtesy: Northwest CT Realty
View additional info

Privacy, views and 350' +/- of waterfrontage-Contemporary lakehouse with 2250 SF. Great floor plan for entertaining. Boathouse, dock, swimming area, stone walls, vinyl decking, patios, expansive lawns and nicely landscaped property. A large, sunny, level parcel (over half acre) which is rare find at Highland Lake! The house features a large kitchen w/breakfast bar, granite countertops, tile floors; hardwood floor in LR w/cathedral ceiling and stunning lake views. DR has coffered ceiling. All bedrooms have walk in closets plus three full baths; separate laundry room; walk up attic; family room w/tile floors and antique wood stove w/access to patio area. Additional room used as office/exercise area. Stone stairs access the swimming area. Owner/Agent

$899,900

25 East Lake St Winchester, CT 06098

Beds:
4
Baths:
5.00
Sq.Ft.:
3,099
Status:
Active
MLS#:
L10206319
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.74 Acres
Year built:
1960
Courtesy: The D'Amore Agency, LLC
View additional info

125+ ft highland Lake direct waterfront with dock,large shed and 1/2 bath with outside access ,paved RV site with electric hook-up, nice large level yard...full in law set-up with bedroom,great room with stainless appliances laundry, french doors to patio with great lake views..main level has foyer, mud room and great room with large island stainless appliances pantry, and awesome lake views, den/dining room/office with wood fired pizza oven and 1/2 bath master bedroom suite with full bath and laundry area two additional bedrooms full bath car garage with second floor workshop,studio...agent owner related

$199,900

44 Spencer St Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
2,008
Status:
Active
MLS#:
L10206405
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.41 Acres
Year built:
1889
Courtesy: Sullivan Real Estate Inc
View additional info

Beautifully maintained and updated Victorian with Charm and Character. Foyer, Great Natural Lighting, Crown Molding, Numerous Built-ins including an Archway, French doors, Fireplace, Period Woodwork, Stained Glass. Maple and Oak Hardwood Floors. Updated Kitchen with Pantry. Three large bedrooms on second floor with possibility of one on first floor. Garage underneath and enough parking for five cars. Picturesque patio with a brook at the back property line.

$169,000

58 Overlook Rd Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
L10205663
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
1.44 Acres
Year built:
1890
Courtesy: The D'Amore Agency, LLC
View additional info

1890 Colonial with many updates! Newer kitchen. Great room looks out over the spacious back yard. 2 bedrooms, 1 bath, formal living room with fireplace/stove, 2 car garage and barn! Winchester Residents Highland Lake Beach Pass Access available.

$149,500

173 Gilbert Ave Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
1,664
Status:
Active
MLS#:
L10205876
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.23 Acres
Year built:
1927
Courtesy: Northwest CT Realty
View additional info

Unique Cape with charm and character. Located in walking distance to conveniences this home offers 4 modest size bedrooms, front to back living room with decorative, period fireplace and a formal dining room. Enclosed side porch. Very solid structure and mechanicals. This will make a great comfortable home.

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The data relating to real estate for sale on this website comes in part from the GFC CMLS IDX Program. Real estate listings held by brokerage firms other than this broker are marked with an “IDX Logo” (a little black house surrounding the letters “IDX”) and detailed information about those listings includes the name of the listing broker.
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