Winchester CT Real Estate & Homes for Sale

70 Properties Found

The median home value in Winchester, CT is $152,000. This is lower than the county median home value of $207,900. The national median home value is $177,414. The average price of homes sold in Winchester, CT is $152,000. Approximately 73.89% of Winchester homes are owned, compared to 21.68% rented, while 4.43% 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!
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$79,900

26 Riveredge UNIT 26 Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
997
Status:
NEW LISTING
MLS#:
L10190886
Type:
Condo
Subdivision:
Winsted (136)
Year built:
1987
Courtesy: The D'Amore Agency, LLC
View additional info

Completely remodeled end unit in brand new condition right down to the Kitchen, bath and appliances. You won't believe your eyes... Move right in as everything has been done!

$319,000

159 West Rd Winchester, CT 06098

Beds:
3
Baths:
3.00
Sq.Ft.:
2,062
Status:
Active
MLS#:
W10182686
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
2.41 Acres
Year built:
2000
Courtesy: G & W Real Estate
View additional info

Beautiful setting on 2.4 acres. Drive up to a 2,062 sqft ranch with fabulous wrap around deck. Views of Winchester Lake walking distance to boat launch. Heated oversized two car garage. Open floor plan kitchen, dining and living room with lots of windows surrounded by mother nature at her best. Two full baths includes master bedroom. Gleaming hardwood flooring through out. Large family room with walk out - laundry room with half bath and utility sink. Living room has access to wrap around as well as dining area. Gas fireplace can be enjoyed in living room and dining room. Garage has electric panel for a generator. House wired for Hot Tub. Can't ask for more bring in your offers!

$89,900

22 Curtice St Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
1,334
Status:
NEW LISTING
MLS#:
L10191299
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.09 Acres
Year built:
1900
Courtesy: Realty Experts LLC
View additional info

Colonial style home with a great layout and a large living room on a level fully fenced lot on a dead end street. Peace and quiet.

$194,900

128 Florence St Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,770
Status:
NEW LISTING
MLS#:
L10191061
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
3.26 Acres
Year built:
1977
Courtesy: Northwest CT Realty
View additional info

Totally updated 3 bedroom, 2 full bath ranch on 3+ acre in town lot. This home sits on a very unique in town parcel facing west with long reaching views and fabulous sunsets. In the last 10 years this home has seen a complete make over and features an open floor plan with bamboo flooring throughout. Efficient natural gas heating and hot water, central air, generator transfer switch and natural gas log set in FP. This is one not to miss.

$54,900

111 Riverton Rd UNIT 36 Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
1,204
Status:
Active
MLS#:
G10190794
Type:
Condo
Subdivision:
Winsted (136)
Year built:
1987
Courtesy: Century 21 A-Gold Action Rlty
View additional info

Invest in your future with this spacious end unit townhouse located in the country. Nice open floor plan includes living room combo dining room with fireplace and sliders to deck. Galley kitchen with sliders. Large master bedroom and 1 1/2 baths. Potentially 2 car garage. Great wooded views off back.

$124,900

29 Bridge St Winchester, CT 06098

Beds:
8
Baths:
3.00
Sq.Ft.:
3,343
Status:
Active
MLS#:
L10189998
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.24 Acres
Year built:
1890
Courtesy: Realty Experts LLC
View additional info

Beautiful victorian house with original woodwork, beautiful fireplaces, hardwood floors, and a large yard.

$399,900

113 Chapel Rd Winchester, CT 06098

Beds:
4
Baths:
3.00
Sq.Ft.:
1,843
Status:
Active
MLS#:
L10189429
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
2.3 Acres
Year built:
1974
Courtesy: Sullivan Real Estate Inc
View additional info

Very well maintained country home. Peace and quiet surround this hidden gem. Open floor plan including a fire placed living room that is open to the dining area. Large eat in kitchen, family room. The garage is heated and would make a great place to enjoy your hobbies. To show is to sell.

$149,900

358 Demonstranti Rd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
L10188689
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.23 Acres
Year built:
2002
Courtesy: Northwest CT Realty
View additional info

Newer, vinyl sided ranch with additional 400 square feet of heated space in lower level. Freshly painted with all new carpeting and flooring throughout. Lower level also has a half bath in utility room. Home is located on private road in a quite neighborhood near Highland Lake.

$379,000

103 South Rd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
2,848
Status:
Active
MLS#:
L10188710
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
4 Acres
Year built:
1974
Courtesy: The D'Amore Agency, LLC
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Country home near historic Winchester Center on 4 acres with recreation inside and out! Located in beautiful Litchfield County this makes a great getaway home from NYC area-a little over 2 hours to get to! Beautiful pond surrounded by nice open land for daytime activities and well lit at night for outdoor entertaining. This 3 bedroom home features a wonderful two-tiered deck for enjoying the views! Relax year round with the indoor heating swimming pool, wet bar and gas grill in downstairs entertainment area. Main floor features the 3 bedrooms, diing room and living room with cathedral ceiling, Casablanca fans, fieldstone fireplace and oak wood detail. Unfinished approx. 400sf of space off dining room with potential. Home can be heated by woodstove or oil furnace. Ample storage spaces in the lower level. Newer roof and vinyl siding for easy maintenance! Extra large 2 car garage and 3rd oversized bay. Contractor's dream with wide entrance driveway and plenty of room in the driveway for any and all vehicles! 5 foot high Red Brand non-climbing fence already surrounds most of the property for your horses!

$145,000

191 Spencer Hill Rd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,472
Status:
Active
MLS#:
G10188742
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
4.25 Acres
Year built:
1988
Courtesy: Nutmeg Properties
View additional info

Excellent opportunity to own a roomy 3 bedroom 2 bathroom split level on with a fully finished lower level, huge 2 car attached garage, above ground pool with fixed deck around it, huge deck right off of the dining room area and a floor to ceiling wood burning brick fireplace. You will find excellent craftsmanship and detail starting from the clapboard wood siding on the outside to the details on the front porch. Truly a great opportunity to own an excellent home at a great price!

$325,000

124 Huntington Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
2,229
Status:
Active
MLS#:
L10181618
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
2.59 Acres
Year built:
1984
Courtesy: Elyse Harney Real Estate
View additional info

Privacy and convenience in a park like setting,this impressive 4 bedroom 2 bath cape features an open floor plan with a fully remodeled kitchen complete with quartz counters, custom cherry cabinets, and stainless steel appliances. Beautiful butterscotch oak floors, and a cozy fireplace in the large living room and a coal stove fireplace insert in the dinning room. Relax in the Hot tub on the deck outside the family room which is accentuated by a cathedral ceiling. Fire pit, gardens and a brook highlight the yard. This desirable location is just 2 miles from Riverton village and state forests, also convenient to rt. 8

$165,000

135 Prospect St Winchester, CT 06098

Beds:
4
Baths:
2.00
Sq.Ft.:
2,268
Status:
Active
MLS#:
L10188360
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.17 Acres
Year built:
1700
Courtesy: Hunter Real Estate, LLC
View additional info

Great opportunity to own a large 4 bedroom home with 1.5 baths connected to an oversized heated 2 car garage and workshop with commercial zoning (MDL-96, MDL-01). This large 2268 sqft Colonial offers formal fireplaced living room, great room, and dining area. Complete with 1st floor Laundry, wood floors and all new thermal paned windows. New roof on main house and garage. Built in 1700 but no sloping floors and offers new sheet rocked walls with new insulation. Overlooks the Mad River Dam. Enjoy the towns parades from your front porch!

$55,000

46 Riveredge Dr UNIT 46 Winchester, CT 06098

Beds:
2
Baths:
2.00
Sq.Ft.:
992
Status:
Active
MLS#:
P10187988
Type:
Condo
Subdivision:
Winchester (136)
Year built:
1986
Courtesy: Coldwell Banker Premier Real Estate
View additional info

Well cared for unit with lots of upgrades. Newer kitchen cabinets, appliances and tile. Newer walk-in shower, tile and fixtures. All newer wood interior doors. Private and peaceful deck. 1 Car detached garage with storage.

$105,000

268 Walnut St Winchester, CT 06098

Beds:
4
Baths:
1.00
Sq.Ft.:
1,174
Status:
Active
MLS#:
F10187926
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.2 Acres
Year built:
1950
Courtesy: William Pitt Sotheby's International Realty
View additional info

Cape Cod home set on .20 acres, featuring 4 bedrooms, living room w/ fireplace and a full basement, Larger back yard makes this an ideal purchase. Minor work required but well worth the effort for this centrally located home. 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, Uses an oil tank. Repairs: Repair/replace damaged kitchen floor, Repair defective paint surface.

$399,900

372 East Wakefield Blvd Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
780
Status:
Active
MLS#:
L10187223
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.46 Acres
Year built:
1952
Courtesy: Northwest CT Realty
View additional info

Perched on a nubble overlooking the expands of 2nd bay at Highland Lake. This property offers much privacy as it is located at the end of a private road with only 3 other homes on it.Plenty of room for guest parking. It appears enough room to tear down the cottage and build one of the most private year round homes on the lake. Property faces due west for stunning sunsets. Abutted by 3 acres of preserved land.

$229,900

113 Peck Rd Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,686
Status:
Active
MLS#:
L10185962
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
4.79 Acres
Year built:
1986
Courtesy: Northwest CT Realty
View additional info

Set on a secluded 4.79 acre lot, this home is in the final stages of a complete makeover. This home features new hardwood floors in the main living area, new kitchen with granite. Both bathrooms have been remodeled. There is a brand new high efficiency propane heating system. Driveway has been resurfaced with asphalt road millings and will last for years to come. Buyer can still have choice in carpeting.

$4,700,000

139 Grantville Rd Winchester, CT 06098

Beds:
6
Baths:
5.00
Sq.Ft.:
2,872
Status:
Active
MLS#:
S10183520
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
412.09 Acres
Year built:
1830
Courtesy: Global Real Estate Network LLC
View additional info

Amazing opportunity to own 419 acres along the quiet countryside of Winstead/Winchester in Litchfield County CT. As you take-in the endless scenery of land, water and sky you can see why this tranquil setting is like no other. Enjoy a peaceful walk around the lake or explore the endless fields along the winding creek. The property is divided into three parcels; 251 acres, 160 acres and 7 acres, providing opportunity for conservation or partial development. It also includes a historic colonial home built in 1830 which features 6 bedrooms, 4 full baths, 1 partial bath and multiple fireplaces. Love life on this picturesque 419 acre country property.

$164,900

101 Oakdale Ave Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
1,896
Status:
Active
MLS#:
L10184929
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.97 Acres
Year built:
1984
Courtesy: Northwest CT Realty
View additional info

Solid 3 bedroom 2 full bathroom one owner Colonial located on 1 acre lot in semi rural neighborhood. You get the feeling of being totally secluded yet accessible to all conveniences. Less than a mile to Rte's 44 and 8. Main living level has hardwood floors and laundry with full bath. Lower level offers additional living space and 2 car garage. New Weil Maclean Gold series boiler installed 11/16.

$189,000

124 Norfolk Rd Winchester, CT 06021

Beds:
2
Baths:
2.00
Sq.Ft.:
1,524
Status:
Active
MLS#:
L10183924
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
3 Acres
Year built:
1810
Courtesy: Elyse Harney Real Estate
View additional info

Historic Norfolk Road Landmark - circa 1810 but believed to be mid 1700's early stage coach stop with 3 acres open, mature trees and water views. Wide board floors, period details, 4 fireplaces, winder staircase with rare curved rod iron railing and a spacious new kitchen, 2/3 bedrooms and 1/ 1/2 baths . A delightful home with a strong traffic count for possible additional uses.

$80,000

407 Winchester Rd Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
1,267
Status:
Active
MLS#:
P10184794
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
4.23 Acres
Year built:
1976
Courtesy: DB Associates of CT, LLC
View additional info

OPPORTUNITY EXISTS IN THIS LOG CABIN SITUATED ON 4 + ACRES OF LAND. LARGE DECKS ON FRONT AND SIDE. MASTER BEDROOM ON MAIN FLOOR. FAMILY ROOM OFF KITCHEN, LOFT WITH ADDITIONAL ROOMS. HUD Home. Sold “AS IS” by elec. bid only Prop avail 12-16-16. Bids due daily by 11:59 PM Central Time until sold. FHA Case #061-309997. Uninsured. Eligible for FHA 203K. . Buyer to verify all info. LBP . PLEASE SEE ATTACHMENTS FOR ADDITIONAL INFORMATION.

$59,900

13 Riveredge UNIT 13 Winchester, CT 06098

Beds:
1
Baths:
1.00
Sq.Ft.:
634
Status:
Active
MLS#:
G10182994
Type:
Condo
Subdivision:
Winsted (136)
Year built:
1986
Courtesy: Revolution Properties, LLC
View additional info

Priced to Sale! This single bedroom condo offers plenty of privacy and a quiet setting with easy access to Route 8 and 202 is just up the road. This unit is clean warm and ready for its new owners. Appliances include a dishwasher oven electric range refrigerator garbage disposal and the washer and dryer is in the unit.

$149,000

421 North Main St Winchester, CT 06098

Beds:
4
Baths:
3.00
Sq.Ft.:
2,031
Status:
Active
MLS#:
L10182375
Type:
Single Family
Subdivision:
Winsted (136)
Lot size:
0.25 Acres
Year built:
1880
Courtesy: William Raveis Real Estate
View additional info

Newly renovated home in a super convenient location. Bright interior features updated kitchen, living room with custom field stone fireplace, new floors, new half bath, new roof, main level freshly painted waiting for your custom touches. 4 bedrooms, 2 full baths and 1 new half bath. Minutes to the Winsted Green, Northwestern CT Community College, shopping, restaurants and beautiful Highland Lake.

$299,900

159 West Wakefield Blvd Winchester, CT 06098

Beds:
2
Baths:
1.00
Sq.Ft.:
593
Status:
Active
MLS#:
L10182274
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. This very spacious and private parcel of land appears to have enough room to build your dream home and keep the cottage. Over 150' of beautiful waterfront that includes boat lift area, aluminum dock, boat launch ramp along with level fire pit and picnic area. Recently remodeled kitchen and bath along with fresh 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!!!!

$399,900

246 Old Waterbury Tpke Winchester, CT 06098

Beds:
3
Baths:
2.00
Sq.Ft.:
2,300
Status:
Active
MLS#:
L10182035
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
45.32 Acres
Year built:
1980
Courtesy: The D'Amore Agency, LLC
View additional info

Extremely Private 45 +/- acres .Pond, Bridge , 2 streams & Stone walls . This Contemporary Cape has Stone & Shingle Exterior and covered porch . Open floor plan with circular center chimney Fireplace . Master suite has balcony loft . Newer heating , Kitchen & Flooring . Hunter's or nature lovers paradise .

$299,000

109 Newfield Rd Winchester, CT 06098

Beds:
4
Baths:
4.00
Sq.Ft.:
2,802
Status:
Active
MLS#:
L10180537
Type:
Single Family
Subdivision:
Winchester (136)
Lot size:
5 Acres
Year built:
2003
Courtesy: Northwest CT Realty
View additional info

Built in 2003, this custom built saltbox reproduction has modern flair. Placed elegantly on 5 acres with spectacular sunset views. It features a gourmet kitchen with granite countertops, maple cabinets, stainless steel appliances, gas cooktop and 2 built-in wall ovens. There are 2 master bedroom suites, 1 on each level of the house; each with their own full bath and walk in closets and 1 has a fireplace. Hardwood floors throughout, as well as 9 ft ceilings and crown moldings. Some of the other features are a state of the art heating system, central air, whole house generator and enhanced invisible fencing. There is a detached 3 car garage which features the potential for additional living space, suitable for an apt or guest quarters. This home offers a tranquil and serene setting in rural and historic Winchester Center. This location not only makes it convenient to shopping and highways but also Park Pond, Burr Pond, Lake Winchester and other area outdoor activity destinations as well as Bradley Airport. This home is an incredible value.

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