Cheap homes for sale & real estate in Winchester, CT

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ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Beautifully renovated 1870 Colonial offering 1,172 sq. ft. of updated and functional living space. The home features hardwood floors in the living room and both bedrooms, adding warmth and durability throughout. A convenient first-floor bedroom provides flexibility, while the spacious primary bedroom is located on the second level. The kitchen has been completely refreshed with new flooring, skylights that bring in excellent natural light, an eat-in area, and all-new stainless steel appliances. The first-floor laundry room adds everyday convenience and includes a remodeled half bath. The full bathroom has also been fully updated with modern finishes. Fresh interior paint and all-new lightin

$230,000

2 beds1.5 baths1,172 sq ft

9 John St, Winsted, CT 06098

Updated kitchen • Hardwood floors • First floor bedroom

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Turnkey 3 Bedroom, 1 bathroom home on almost an acre in Winchester. The home is sited up a long driveway in a quiet, wooded setting across from state land. Completely renovated by current owner, top to bottom. Updated kitchen & bath, new roof, new hot water heater, new Trex deck, new pellet stove, new ductless mini splits in living area and primary bedroom and much more! Attached one car garage and shed. Must see! Minutes from Burr Pond State Park for hiking & swimming and Highland Lake, a popular recreation destination.

$329,000

3 beds1 bath960 sq ft

107 Peck Rd, Winsted, CT 06098

0.94 acre lot • Garage • Built 1983

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern cooking space. The carpet (installed in 2024) has been well maintained, and the home includes a hot water heater installed in 2022 for added peace of mind. Recent major updates include a new roof installed in 2023 with a 15-year transferable warranty, providing long-term value and security. Outside,

$159,000

2 beds1.5 baths832 sq ft

8 Oak St, Winsted, CT 06098

Hot water heater • New refrigerator • New gas stove

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm, inviting space for cooking and gathering. Adjacent to the kitchen is a cozy breakfast nook with a bay window, opening seamlessly into the living room for easy everyday living. Across the hall, you'll find a generous family room and a separate dining room, offering plenty of room for entertaining and host

$419,000

4 beds1.5 baths2,365 sq ft

187 Torringford St, Winsted, CT 06098

Wood beams • Upper loft • Living room

OPEN JAN 4, 2PM TO 4PM

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal f

$269,999

3 beds2 baths1,652 sq ft

118 Meadow St, Winsted, CT 06098

7,405 sq ft lot • Built 1860 • Listed 30 days

Property at 148 Danbury Quarter Rd, Winsted, CT 06098, 4 beds, 2 baths

$329,900

4 beds2 baths1,999 sq ft

148 Danbury Quarter Rd, Winsted, CT 06098

Property at 157 Elm St, Winsted, CT 06098, 6 beds, 2.5 baths

$339,000

6 beds2.5 baths2,376 sq ft

157 Elm St, Winsted, CT 06098

Property at 38 Upland Rd, Winsted, CT 06098, 3 beds, 1.5 baths

$269,000

3 beds1.5 baths1,736 sq ft

38 Upland Rd, Winsted, CT 06098

Property at 720 Main St, Winsted, CT 06098, 3 beds, 1.5 baths

$395,000

3 beds1.5 baths1,909 sq ft

720 Main St, Winsted, CT 06098

Property at 32 Norfolk Rd, Winsted, CT 06098

$299,900

— beds— baths— sq ft

32 Norfolk Rd, Winsted, CT 06098

Property at 7 Stadler Hts, Winsted, CT 06098

$389,000

— beds— baths— sq ft

7 Stadler Hts, Winsted, CT 06098

Property at 124 Rockwell St, Winsted, CT 06098

$29,000

— beds— baths1,882 sq ft

124 Rockwell St, Winsted, CT 06098

Property at 503 N Main St, Winsted, CT 06098

$69,000

— beds— baths— sq ft

503 N Main St, Winsted, CT 06098

Property at 48 Bridge St, Winsted, CT 06098

$23,900

— beds— baths1,428 sq ft

48 Bridge St, Winsted, CT 06098

Property at 256 Colebrook Rd, Winsted, CT 06098

$39,900

— beds— baths— sq ft

256 Colebrook Rd, Winsted, CT 06098

Property at 99 Hubbard St, Winsted, CT 06098

$49,000

— beds— baths832 sq ft

99 Hubbard St, Winsted, CT 06098

Property at 843-845 (lots - 10A,10 &1 E wakefield Blvd, Winsted, CT 06098

$158,000

— beds— baths— sq ft

843-845 (lots - 10A,10 &1 E wakefield Blvd, Winsted, CT 06098

Property at 00 Chapel Rd, Winchester, CT 06098

$300,000

— beds— baths8,862 sq ft

00 Chapel Rd, Winchester, CT 06098

$59,900

— beds— baths— sq ft

105,107 Mountain Rd, Winchester, CT 06098

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NEW 17 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
This GREAT, move-in ready, 3Bed/2.1Bath Contemporary Colonial is ready for a new owner! The lovely front porch has lots of curb appeal & is just the spot for a morning coffee or afternoon beverage. Enter into the sunny LR, with hardwood floors & cozy FP, w/ stone surround. Continue into the kitchen w/ plentiful wood cabinets & SS appliances, plus access to the attached garage & partly-finished walk-out basement. Just beyond is the DR w/ more hardwood floors & sliders to the deck - perfect for warm weather outdoor dining! Also on this main level you'll find a convenient half-bath. On the upper level are 3 generous bedrooms & 2 full baths. The primary bedro

$369,900

3 beds2.5 baths1,544 sq ft

94 Colin Dr, Torrington, CT 06790

Convenient half-bath • Front porch • Sliders to the deck

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
This beautiful Cape style home offers 3 bedrooms and 2 full bathrooms with flexible living space throughout. The main level features a spacious eat-in kitchen with built-in cabinetry and a wood-burning fireplace, perfect for everyday living and entertaining. A full bathroom and a versatile additional room ideal for an office, dining room, or guest space complete the first floor and is currently used as a fourth bedroom. Upstairs, all bedrooms offer ample closet space, including two walk-in closets in the primary bedroom. Hardwood floors and warm wood accents enhance the inviting living room. The fully finished basement, completed in 2023, provides additional living or recreational space and

$359,000

3 beds2 baths2,124 sq ft

478 Greenwoods Rd, Torrington, CT 06790

Mini-split system • Finished basement • Eat-in kitchen

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Adorable 2-bedroom Hideaway model full of light. Living area opened up with vaulted ceiling and two large skylights. Corner stone fireplace has been fitted with an electric fireplace. Bedroom and full bathroom on main level. The primary, with vaulted ceiling, has a walk in closet and full bath. The entrance has been enclosed with side window and storage closet. The deck has been super enlarged and is perfect for grilling and entertaining in the summer months. Quilted window shades have been installed on many of the windows. Short path and only two steps to enter home.

$214,000

2 beds2 baths1,154 sq ft

207 Ledge Dr, Torrington, CT 06790

Large skylights • Enclosed entrance • Vaulted ceiling

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Want to feel like you are on vacation. .. everyday? Move-in ready 2 bedroom and 2 bath END UNIT in Lakeridge, a pristine gated community. Property features an open floor plan with cathedral ceilings, and combined living/dining/kitchen space with a slider to a private deck. Lightly wooded setting with nearby owner/guest parking. Outstanding amenities including a heated pool, lake access, horseback riding, skiing, playground, tennis/basketball courts and MORE! Ideal for year-round living or a weekend retreat.

$215,000

2 beds2 baths1,154 sq ft

65 Woodside Cir #65, Torrington, CT 06790

$349 HOA • Pool • Built 1975

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Welcome home to 109 Winterberry Way, a beautifully maintained 3-bedroom, 1.5 bath residence tucked away on a quiet cul-de-sac in one of Torrington's most inviting neighborhoods. Built in 1997, this home combines the warmth of New England tradition with modern comfort and thoughtful updates throughout. Step inside to a bright, open living space with neutral tones and natural light that create an inviting atmosphere. The spacious kitchen offers generous counter space and cabinetry, ideal for entertaining or everyday living. The primary bedroom features two walk-in closets, providing abundant storage and convenience. The lower-level family room includes a slider to the private back deck-perfec

$360,000

3 beds1.5 baths1,464 sq ft

109 Winterberry Way, Torrington, CT 06790

Private back deck • Quiet cul-de-sac • Two walk-in closets

ABOUT THIS HOME
Cheap Home for sale in Winchester, CT:
Welcome to The Ledge: a home for every season, offering elegant Adirondak-style living in a serene setting surrounded by majestic pines & lush perennial landscaping. The exterior & interior have been newly updated & freshly painted, giving the entire property a fresh, modern look while retaining its timeless charm. Step inside & be greeted by a beautifully remodeled kitchen, featuring high-end cabinets, sleek quartz countertops, & state-of-the-art GE Profile appliances, making it a chef's dream. The bathrooms have been upgraded w/ luxurious finishes that include double vanities & mirrors w/ high end fixtures, providing a spa-like experience every day. Addi

$349,000

3 beds2 baths1,612 sq ft

174 Ledge Dr #174, Torrington, CT 06790

Quartz countertops • High end cabinets • Remodeled kitchen

Property at 431 Trailsend Dr Unit + Garage G128, Torrington, CT 06790, 3 beds, 2.5 baths

$289,000

3 beds2.5 baths1,978 sq ft

431 Trailsend Dr Unit + Garage G128, Torrington, CT 06790

Property at 230 White Oak Way, Torrington, CT 06790, 3 beds, 1.5 baths

$360,000

3 beds1.5 baths1,863 sq ft

230 White Oak Way, Torrington, CT 06790

Property at 389 Trailsend Dr, Torrington, CT 06790, 3 beds, 2.5 baths

$250,000

3 beds2.5 baths1,584 sq ft

389 Trailsend Dr, Torrington, CT 06790

Property at 390 Trailsend Dr #390, Torrington, CT 06790, 4 beds, 3.5 baths

$270,000

4 beds3.5 baths2,284 sq ft

390 Trailsend Dr #390, Torrington, CT 06790

Property at 239 Ledge Dr, Torrington, CT 06790, 3 beds, 3 baths

$300,000

3 beds3 baths1,612 sq ft

239 Ledge Dr, Torrington, CT 06790

Property at 225 Ledge Dr, Torrington, CT 06790, 3 beds, 2.5 baths

$225,000

3 beds2.5 baths1,584 sq ft

225 Ledge Dr, Torrington, CT 06790

Property at 353A Hayden Hill Rd, Torrington, CT 06790, 3 beds, 1 bath

$29,900

3 beds1 bath945 sq ft

353A Hayden Hill Rd, Torrington, CT 06790

Property at 174 Old North Rd, Barkhamsted, CT 06063

$195,000

— beds— baths— sq ft

174 Old North Rd, Barkhamsted, CT 06063

Property at Hayden Hill Rd, Torrington, CT 06790

$40,000

— beds— baths— sq ft

Hayden Hill Rd, Torrington, CT 06790

Property at 18 Niles Rd, New Hartford, CT 06057

$299,000

— beds— baths— sq ft

18 Niles Rd, New Hartford, CT 06057

Property at 3222 Torringford St, Torrington, CT 06790

$225,000

— beds— baths— sq ft

3222 Torringford St, Torrington, CT 06790

Property at 408 New Hartford Rd, Barkhamsted, CT 06063

$45,000

— beds— baths— sq ft

408 New Hartford Rd, Barkhamsted, CT 06063

Property at 408 A Niles Rd, New Hartford, CT 06057

$119,000

— beds— baths2,134 sq ft

408 A Niles Rd, New Hartford, CT 06057

Property at 00 Ramsgate Ln, Barkhamsted, CT 06063

$299,900

— beds— baths— sq ft

00 Ramsgate Ln, Barkhamsted, CT 06063

Cheap Homes for Sale in Winchester

There are currently 19 cheap homes for sale in Winchester at a median listing price of $329K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 65 days and receive 1 offers. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 12 homes have been sold in Winchester. In addition to houses in Winchester, there were also 5 condos, 0 townhouses, and 7 multi-family units for sale in Winchester last month. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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