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Winchester CT Real Estate & Homes for Sale

107 Properties Found

The median home value in Winchester, CT is $163,500 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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$219,000

78 Wheeler St Winchester, CT 06098

Beds:
5
Baths:
3.00
Sq.Ft.:
2,916
Status:
NEW LISTING
MLS#:
L10239532
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.28 Acres
Year built:
1900
Courtesy: Elite Realty
View additional info

Large Victorian style colonial with 15 rooms that was converted to a 2 family home. It can easily be converted back to a single family by turning the upstairs kitchen into a laundry room. It also has a walk up attic with 3 large rooms that need updating. Lots of potential. It offers a car port to the side of house and a oversized 2 car garage with a storage loft upstairs and a circular driveway. Close to shopping Town hall has it listed as a duplex.

$148,900

219 Wakefield Blvd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,510
Status:
NEW LISTING
MLS#:
G10238115
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.12 Acres
Year built:
1977
Courtesy: RE/MAX Premier REALTORS
View additional info

Move-in condition! Across the street from Highland Lake. Take a look at this newer house that has a freshly painted interior, new carpeting throughout, newer kitchen cabinets with a new floor and new stainless steel appliances. There is a balcony off the living room and master bedroom plus a large deck at the back/left side of the house. The lower level room can be finished off for additional living space. This is a Fannie Mae HomePath property.

$55,000

111 Riverton Rd UNIT 39 Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
1,204
Status:
NEW LISTING
MLS#:
G10238038
Type:
Condo
Subdivision:
Winchester (136)
Year built:
1987
Courtesy: Nutmeg Properties
View additional info

Must see value, this condo offers over 1200 square feet with a large, open living room with a fireplace. Private balcony off the living room. Partially finished basement with patio walk out. Attached garage is a plus. Priced well below assessment. Make sure to schedule 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.

$115,700

162 Wilcox Ave Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
858
Status:
Active
MLS#:
L10237456
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.17 Acres
Year built:
1953
Courtesy: Northwest CT Realty
View additional info

Charming cottage with water views in Highland Lake community

$169,900

119 Rugg Brook Rd Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
1,509
Status:
Active
MLS#:
L10237707
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
1.75 Acres
Year built:
1950
Courtesy: Northwest CT Realty
View additional info

This 1500 square foot very well cared for 2 bedroom Cape is minutes from town and is on 1.75 acres with a huge deck ready for summer gatherings with room for parking two vehicles under (could possibly enclose for garage). There is a beautiful updated kitchen open to the dining area which boasts a fireplace with sliders to the deck. The living room is front to back for plenty of room. A spacious full bath along with a large 4 season porch rounds out the main level. Upstairs there are two nice sized bedrooms. The basement has a laundry room, usable space for an office or work shop, and plenty of storage space. There is also a shed for more storage. A brand new septic was installed in 2015 and the foot valve on the well was just replaced this spring. Along with cable being available, but there is an antenna which delivers about 30 HD channels for free. A generator transfer switch is also included. The house is move-in ready and if needed, there are several options for a third bedroom

$169,000

109 Old Colebrook Rd Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
936
Status:
Active
MLS#:
L10237706
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.75 Acres
Year built:
1963
Courtesy: Turning Point Realty, LLC
View additional info

Perfect First Time Home Buyer Home! Well maintained, newer Navien propane boiler, very energy efficient home, plenty of storage, possible in-law in lower level walk out. Newer roof. Two fireplaces! Wood stove insert in basement fireplace. Private setting. Hardwood floors. Great price!

$147,500

123 Shore Dr Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
779
Status:
Active
MLS#:
L10236244
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.14 Acres
Year built:
1900
Courtesy: Northwest CT Realty
View additional info

Adorable seasonal cottage on and with deeded access to Highland Lake. Beautiful oak kitchen with quartz counters. The living/great room is adorned with a handsome brick fireplace. There is a modest deck and patio with fire pit for great outdoor living and views of the lake. There currently is one bedroom on the first floor and could easily be made into 2 and the walk up attic provides sleeping space for an additional 4-6 people. Vacant and ready to enjoy the rest of the summer and fall.

$114,900

101 South Rd Winchester, CT 06098

Beds:
6
Baths:
3.00
Sq.Ft.:
3,898
Status:
Active
MLS#:
B10236248
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
1.25 Acres
Year built:
1785
Courtesy: Carrington Real Estate Services (CT) LLC
View additional info

Large 6-8 bedroom antique colonial in need of some rehab. Well priced to restore it back to its former glory.

$240,000

289 Colebrook Rd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
2,062
Status:
Active
MLS#:
G10236206
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
2 Acres
Year built:
1971
Courtesy: RE/MAX Compass
View additional info

Beautiful well maintained Cape close to downtown amenities yet secluded and quiet. This home has everything you are looking for, 3 Bedrooms, 2 full bathrooms, and with just over 2,000 sq. ft there is room to grow. This home boasts a remodeled kitchen complete with breakfast bar and dining room with a wood stove that can be used to heat the space or just admire. There is a second formal dining room that abuts the gorgeous family room with vaulted ceilings, sky lights, french doors and a slider onto your large deck with room for a hot tub! There is a large front to back living room with built in bookcases, a gorgeous fireplace and lots of windows. The laundry is right off of the kitchen by the garage entrance keeping it close by and handy yet out of the way! All three good sized bedrooms have large closets, hardwood floors and share a remodeled bath. The basement is partially finished with a drop ceiling and lots of light with an abundance of storage. An oversized two car garage set on a large 2 acre lot surrounded by wildlife finishes off this beautiful home. Motivated Seller, schedule your showing today!

$178,900

127 Shore Dr Winchester, CT 06098

Beds:
3
Baths:
1.00
Sq.Ft.:
1,084
Status:
Active
MLS#:
G10235916
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.12 Acres
Year built:
1948
Courtesy: Haynes Real Estate Services
View additional info

Highland Lake Living! Lake views, large level lot, with garage (not many homes on lake have garages!!!)l Short walk to Rescha Beach, open bright home. New roof!! Recently added dormers provide lake views,and full length front porch ideal for morning coffee or afternoon retreat! Large private, level rear yard ideal for family gatherings, barbecues and year around enjoyment. Will consider selling furnished (some decorative items excluded). Excellent location, close to beach, marina and state boat launch and easy access from town center. Shore Drive is one of the most desirable locations. Year around home, with some original cottage charm. Seller will consider allowance for new carpet on second floor. Owner/Broker

$130,000

6 Central Ave Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
785
Status:
Active
MLS#:
L10235191
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.2 Acres
Year built:
1958
Courtesy: Realty Experts LLC
View additional info

Move in ready, two bedroom, one bath, one level home with a one car garage on a large corner lot. There is a walk up attic for storage and a nice deck off the side of the house.

$329,000

6 Stadler Hts Winchester, CT 06098

Beds:
4
Baths:
3.00
Sq.Ft.:
2,726
Status:
Active
MLS#:
G10235028
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
3.22 Acres
Year built:
1990
Courtesy: BHHS New England Properties
View additional info

Welcome to this open, light and airy one owner home. This property has been meticulously maintained and nicely updated. Located in a private neighborhood off the beaten path yet convenient to EVERYTHING! This colonial home with contemporary flair features an open floor plan that is great for entertaining. The kitchen has been updated with newer appliances and granite counter tops and overlooks the family room. They both open to an expansive deck overlooking the private, level rear yard. The rest of the main level has a formal living room with cathedral ceilings and a 2 sided fire place, formal dining room, mud room, 1/2 bath and 1st floor laundry. The 2nd floor features 4 bedrooms and 2 full baths. The master bedroom overlooks the living room and the rear yard and has private full bath and walk-in closet. 3 additional bedrooms and another full bath complete the 2nd floor. Enjoy nature from every square inch of this property. Gardening will be a snap with all the outdoor area available that includes an outbuilding perfect for all your tools and equipment. If privacy and convenience is what you are looking for then all this home is missing is you!!

$175,000

8 Woodland Ave Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
1,775
Status:
Active
MLS#:
G10234463
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.26 Acres
Year built:
1913
Courtesy: Keller Williams Realty
View additional info

CHARMING COLONIAL HOME NESTLED ON A LUSH LOT AND SURROUNDED BY BEAUTIFUL GARDENS! This lovely home features 4 bedrooms, 2 FULL baths and hardwood floors throughout! Remodeled eat in kitchen with built ins, granite countertops, pantry, center island AND lots of storage for all your kitchen gadgets! Grab some popcorn and watch the latest action flick in your spacious family room OR have a quiet night in with a cup of tea and find out how that new mystery novel ends! Master bedroom with walk in closet, laundry/mudroom AND option for a den or that home office you have always wanted! NEW roof in 2010, NEW gutters in 2012 and a detached 2 car garage! Minutes from local shopping, restaurants, Highland Lake, state parks and SO much more!

$1,199,000

512 West Wakefield Blvd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
G10234290
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.86 Acres
Year built:
1910
Courtesy: BHHS New England Properties
View additional info

RARE OPPORTUNITY TO OWN ONE OF HIGHLAND LAKES GEMS. PINE KNOLL IS AN AMAZING AND CLASSIC, UPDATED TURN KEY WATERFRONT HOME LOCATED ON THE CRESTED AREA OF A PENINSULA. BEAUTIFUL VIEWS FROM EVERY WINDOW, MOST WITH WATER VIEW. SALE INCLUDES PRIVATE ISLAND, 2 DOCKS, EXTENSIVE LANDSCAPING, MOST FURNISHINGS AND WATER TOYS INCLUDING BOATS. PLENTY OF ROOM TO EXPAND IF NEEDED IN WALK-UP ATTIC AREA. RECENT UPDATES INCLUDE KITCHEN WITH GRANITE, SPA QUALITY FULL BATH ON THE FIRST FLOOR, HARDWOOD, AND BEAUTIFUL MILL WORK ON EXTERIOR WINDOWS. ENJOY LONG LAZY SUMMER DAYS ON THE EXPANSIVE WRAPAROUND DECK AND SWEEPING COVERED FRONT PORCH. ONE LOOK AND YOUR HOME ALL YOU NEED TO DO IS UNPACK.

$59,900

13 Riveredge Dr UNIT 13 Winchester, CT 06098

Beds:
1
Baths:
1.00
Sq.Ft.:
643
Status:
Active
MLS#:
L10234204
Type:
Condo
Subdivision:
Winsted (136)
Year built:
1986
Courtesy: Northwest CT Realty
View additional info

Second floor 1 bedroom ranch unit. Nice, clean and efficient unit. Great investment opportunity.

$389,000

546 Wakefield Blvd Winchester, CT 06098

Beds:
3
Baths:
1.00
Sq.Ft.:
1,340
Status:
Active
MLS#:
G10232682
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.05 Acres
Year built:
1936
Courtesy: The Greene Realty Group
View additional info

This unique property is built literally on a lake. It is like living on a houseboat -- great for people looking for a low-maintenance vacation home. It could be used year-round. Outside: The cottage is on the desirable east side of Highland Lake that gets sun all day until sunset. Do some early morning swimming or fishing -- the spring-fed lake is perfect for both. Step out the back door right onto your deck, get in your boat, and take off waterskiing and tubing. Sit out on the deck under a retractable awning, host a late afternoon barbecue, and then watch an amazing sunset. Inside: The newly renovated kitchen has stainless steel appliances and granite countertops. The living room has a beautiful stone fireplace two stories high. The master bedroom has breathtaking views of the lake. Two additional bedrooms are ready for guests. The cottage is located just two hours from NYC.

$65,000

35 Boyd St Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
1,082
Status:
Active
MLS#:
L10232633
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.32 Acres
Year built:
1926
Courtesy: Realty Experts LLC
View additional info

Cute two bedroom house located near Highland Lake with hardwood floors and a nice level back yard. The kitchen has been removed so this will not wisdom for FHA. This is a short sale.

$239,000

29 Griswold Ln Winchester, CT 06098

Beds:
3
Baths:
1.00
Sq.Ft.:
600
Status:
Active
MLS#:
G10231854
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
0.67 Acres
Year built:
1959
Courtesy: Morrow Realty, LLC
View additional info

1 of only 15 parcels on an private lake. includes dock and 200 ft of lake frontage. Price below appraised value. Must be seen to be appreciated. Very private and clean, great fire pit on property and fenced in. Plenty of room for parking. New pump for water source. Make this your next vacation home. Seller financing available to qualified buyers. Annual membership fee is determined at end of season meeting. ($400 - $800 usually)

$249,900

222 Smith Hill Rd Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
1,560
Status:
Active
MLS#:
L10231510
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
19.9 Acres
Year built:
1947
Courtesy: Northwest CT Realty
View additional info

This level 20 acre property on the Winsted/Colebrook border has a little something for everyone. The level meadows offer opportunity for farming and horses, there is frontage on Rowley Pond for canoeing and fishing and wooded acreage for the outdoor enthusiast. The modest 2 bedroom ranch has a fireplace in both the large great room and living room.

$374,000

185 Marshall St Winchester, CT 06098

Beds:
3
Baths:
3.00
Sq.Ft.:
1,776
Status:
Active
MLS#:
L10229626
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
17.11 Acres
Year built:
2005
Courtesy: Marrin Santore Realty LLC
View additional info

Well maintained and solidly built 3 bedroom 2 bath colonial home. There are over 17 acres located in the heart of NWCT, Winchester Connecticut. The home is conveniently located off RT 8 which allows easy access to the rest of Litchfield County and the Berkshires. Less than two hours from NYC this home is move in ready and prepared for New England living. The open floor plan kitchen provides access to the living room with fireplace, the dining room, the rear enclosed porch and the center staircase to the second floor. There are Brazilian hardwood floors, tile floors, and carpeting. All of the bedrooms are generously sized. The master bedroom has a walk-in closet, recessed ceiling and a whirlpool tub. There is an over-sized 3 car attached garage which has been insulated, sheetrocked, has 100 amp electrical service, and is heated. It is heated with both a wood burning and oil burning furnace, and a 9 ft basement The property is structurally and mechanically immaculate and is ready for a new home owner.

$499,999

110 Shore Dr Winchester, CT 06098

Beds:
4
Baths:
3.00
Sq.Ft.:
2,164
Status:
Active
MLS#:
G10230088
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.14 Acres
Year built:
1979
Courtesy: BHHS New England Properties
View additional info

Highland Lake - This beautiful, direct waterfront, all-season lake home w/ 4 Bedrooms, 2.5 baths & over 2100 sq ft, incl. 700+/- in LL, has everything you want in a lake house and more! The main level features an Open Floor plan w/a spacious kitchen w/ tons of cabinets and counterspace, Living Room w/gorgeous stone fireplace, Dining Room w/sliders to deck overlooking well-manicured, level yard, gardens & Your Own Lake Front. A full bath and large bedroom complete the main floor. The upper level offers an oversized MBR, with bay window for Amazing Water Views, sun porch, dressing area and his/her closets. 2 add'l bedrooms and a full bath w/ skylight finish off the upper level. The finished Walk-out Lower Level provides even more living space w/ its combination recreation/family room, kitchen area, half bath, laundry & plenty of storage. Public Water & Sewer. Quiet Street. Sandy waterfront w/ large dock. Great yard for relaxing, lawn games & space to launch kayaks, jet skis, etc. Off street parking for 3+ cars. Outbuilding w/ 2 levels of storage. Front Porch. Home was rebuilt in 1979 except for the fireplace. All this on Highland Lake, a full recreational lake offering marina, 2 beaches, all-weather activities, award winning fishing, water skiing, kayaking, tubing & in winter, show-shoeing, ice skating, snowmobiling, ice fishing & more! Close to amenities. Short commute to Hartford, EZ trip to Boston/New York. One look and you won't want to leave!

$124,900

132 Ridge St Winchester, CT 06098

Beds:
4
Baths:
1.00
Sq.Ft.:
1,218
Status:
Active
MLS#:
L10229306
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.25 Acres
Year built:
1947
Courtesy: Northwest CT Realty
View additional info

Well cared for Cape on .25 acre lot 1 block from Highland Lake. There are 2 first floor bedroom and 2 on the upper level. Home has newer natural gas warm air heat. Other features include thermo pane windows, natural gas H20, private deck, stonewalls and long reaching mountain views to the north and of Soldiers Monument. Great starter or home to downsize in to.

$995,000

129 E Lake Street Winchester, CT 06098

Beds:
3
Baths:
4.00
Sq.Ft.:
2,559
Status:
Active
MLS#:
99189421
Type:
Single Family
Lot size:
0.6 Acres
Year built:
2016
A broker reciprocity listing Courtesy: Higgins Group
View additional info

Take advantage of the opportunity to own this trophy property of Highland Lake. Hop on your motor boat, take a sail, or paddle board right from your private dock and boat launch. The heated dock house offers a full sized refrigerator and wet bar directly on the water. The lawn is superior to all other water front properties and has one of the largest water fronts on Highland Lake. The construction of the home is unmatched in quality, offering hardwood floors and high end finishes throughout. Open the folding doors to enjoy the lake activity from your living room, the over-sized deck or while relaxing in the hot tub. This property truly has everything you need to entertain family and friends, and is the premier option for lake front living.

$79,900

22 Curtice St Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
1,334
Status:
Active
MLS#:
L10227624
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.09 Acres
Year built:
1900
Courtesy: Northwest CT Realty
View additional info

Quaint Colonial on Dead End street located close to schools, recreation and downtown. Private fence rear and side yard. Large living room, formal dining room and kitchen on main level. Upper level contains 2 bedroom and what could be a third bedroom or nursery along with a full bath.

$289,900

159 West Wakefield Blvd Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
593
Status:
Active
MLS#:
L10227314
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
1.07 Acres
Year built:
1937
Courtesy: Northwest CT Realty
View additional info

Come for the summer or stay for the whole year. This pristine cottage will give you the taste of lake living and enough room to build your dream home with a sunrise view over the entire first bay on this 1.07 acre lot. The very spacious and private parcel includes a boat lift area, boat launch ramp along with a level fire pit and picnic area. Recently remodeled kitchen and bath along with paint inside and out. Square footage does not include walk up attic area that has been used for sleeping quarters and is easily dormered for even more room. Don't miss this one as there are very few lots left that meet current zoning to build on. Also listed as vacant lot L10235742

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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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