55 Connecticut Properties

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Contract Signed
Property for Sale at E Wakefield Boulevard, Winchester, Connecticut - Bedrooms: 2 
Bathrooms: 2 
Rooms: 5  - $260,000 Previous PhotoNext Photo

E Wakefield Boulevard
$260,000

Winchester, CT
House
Rooms: 5
Bedrooms: 2
Bathrooms: 2
Web ID: 24071795

Enjoy water views from this charming Colonial located just across the street from Highland Lake. This cozy retreat blends historic charm with modern updates, offering a perfect escape for year-round living or a weekend getaway. Inside, refinished wide-plank hardwood floors add warmth and character, while the freshly painted interior enhances the bright and inviting atmosphere. The living room features French doors that open to a lovely porch-an ideal spot to sip your morning coffee while soaking in the lake views. The galley kitchen is efficiently designed, and a first-floor half bath with laundry adds convenience. The room off the living room on the 1st floor could serve as an office or third bedroom. Upstairs, you'll find two comfortable bedrooms with cathedral ceilings and an updated full bath. Recent upgrades include a newer heating system (2020) and a brand-new water heater, with efficient propane heat to keep you cozy during colder...

(203) 253-1800

Meadow Street
$249,900

Winchester, CT
House
Rooms: 8
Bedrooms: 4
Bathrooms: 2
Web ID: 24079880

Steeped in history and charm, this 1860-built home offers a blend of classic character and modern updates. With 8 rooms, 4 bedrooms, and 2 baths, this spacious home provides versatile living options. The main level features a kitchen with recent updates, a dining room, a cozy living room, a primary bedroom with an en-suite bath, and a home office. Upstairs, you'll find three bedrooms, a study area, and a full bath (currently not functioning), with potential for reconfiguring a larger bedroom while still maintaining ample storage and closet space. Recent improvements include a new kitchen and back door, updated roofs, a high-efficiency Viessmann boiler, and electrical upgrades in 2022, along with new flooring and fresh paint in several rooms in 2023 and 2024. A detached two-plus-car garage provides excellent storage and workspace. Conveniently located near Main Street, this home offers easy access to shops, dining, and local amenities. A fantastic...

(203) 253-1800

Orchard Street
$230,000

Winchester, CT
House
Rooms: 6
Bedrooms: 3
Bathrooms: 2
Web ID: 24079182

Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends classic charm with modern conveniences, featuring a spacious layout, abundant natural light, and stylish updates throughout. The inviting living room offers a cozy atmosphere perfect for gatherings. The updated kitchen boasts sleek countertops, stainless steel appliances, and ample cabinet space. Upstairs, you'll find three generously sized bedrooms and a refreshed full bath. Additional highlights include a convenient half bath on the main level as well as a cozy den. The backyard provides plenty of space for outdoor entertaining or gardening. Located in a desirable neighborhood close to local shops, restaurants, and parks, this move-in-ready gem won't last long! Schedule your showing today! Available financing: FHA, FHA 203k ($100 down), Conventional, Cash. Insured w Escrow Repair (IE).

(203) 253-1800
Contract Signed
Property for Sale at Main Street, Winchester, Connecticut - Bedrooms: 5 
Bathrooms: 3.5 
Rooms: 11  - $225,000 Previous PhotoNext Photo

Main Street
$225,000

Winchester, CT
House
Rooms: 11
Bedrooms: 5
Bathrooms: 3.5
Web ID: 24074006

Large side by side duplex with 1 and half baths on each side and a finished attic on each side. Lots of potential here but freeze damage as well. As is sale or repairs possible.

(203) 253-1800
Contract Signed
Property for Sale at Baker Street, Winchester, Connecticut - Bedrooms: 5 
Bathrooms: 2 
Rooms: 10  - $225,000 Previous PhotoNext Photo

Baker Street
$225,000

Winchester, CT
House
Rooms: 10
Bedrooms: 5
Bathrooms: 2
Web ID: 24067033

Wonderful opportunity to own a 2 family with a newer 2 car garage. Home has gas heat. Wood floors thru out, in need of refinishing. Updated cabinets in kitchens; in need of flooring and appliances. Units each have their own heat and laundry hook ups. Wonderful front covered porches. Private back deck 12x12. Thermal paned windows thru out. Property in need of cosmetic updates, TLC. Subject to Probate Approval. Wont go VA, FHA or CHFA. Chfa Conventional will work.

(203) 253-1800
Contract Signed
Property for Sale at Riverton Road Apt 9, Winchester, Connecticut - Bedrooms: 2 
Bathrooms: 2 
Rooms: 4  - $205,000 Previous PhotoNext Photo

Riverton Road Apt 9
$205,000

Winchester, CT
Townhouse
Rooms: 4
Bedrooms: 2
Bathrooms: 2
Web ID: 24067668

This 3-story condominium boasts two large bedrooms, and 1.5 bathrooms, as well as a 2-car garage with a private indoor entrance. The primary bedroom provides lofty ceilings, a walk-in closet, and its own entry way into the full bath. On the main level, the pellet stove is powerful enough to heat the entire living space whilst having its own thermostat to ensure a comfortable temperature throughout. Upon entering the back deck, you are greeted by beautiful views of the wooded area surrounding the condominium. The two sliding glass doors that lead to the deck area ensure that the main floor is booming with natural light. Whether it be the brand-new wall to wall carpeting, the heated floors in the master bathroom, or the fully updated kitchen, this condo is a must see if you are looking to buy in the area.

(203) 253-1800
Contract Signed
Property for Sale at Riverton Road Apt 17, Winchester, Connecticut - Bedrooms: 2 
Bathrooms: 2 
Rooms: 5  - $199,900 Previous PhotoNext Photo

Riverton Road Apt 17
$199,900

Winchester, CT
Townhouse
Rooms: 5
Bedrooms: 2
Bathrooms: 2
Web ID: 24051317

Two bedroom, 1 & 1/2 bath end unit Townhouse with wood floors throughout, living room with fireplace and sliders to deck, primary bedroom with walk in closet, deck has just been painted, Spacious 2 car garage. Unit has lower-level laundry room with entry into garage. Great space and ready for New Owner.

(203) 253-1800

Grove Street
$199,000

Winchester, CT
House
Rooms: 8
Bedrooms: 4
Bathrooms: 3
Web ID: 24069013

ADDITIONAL ADJACENT BONUS LOT INCLUDED! A single family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!! CASH OR HARD MONEY ONLY. HOME WILL NOT PASS GOVT BACKED FINANCING. SUBJECT TO PROBATE COURT APPROVAL!

(203) 253-1800

Whiting Street
$189,000

Winchester, CT
House
Rooms: 6
Bedrooms: 3
Bathrooms: 3
Web ID: 24026928

Great opportunity for Investors. This is a total renovation project being offered to serious qualified buyers only. 1608 sqft incl. 3 bedroom and 2.5 baths, dining and living room open concept, patio in backyard and water feature in front yard. Interior mix of tiled and HW floors. Located within walking distance downtown Winsted, Northwestern Community College, Whiting Mills building home to various artists, craftsman, retail shops. Property has amazing opportunities to rejuvenate this New England colonial back to its unique original charm once again. Perfect setting for an Airbnb rental, weekender or simply a year-round home. Just minutes away to beautiful lakes, rivers, skiing, various unique eateries, cultural events and endless outdoor activities. Just minutes away to beautiful Highland Lake, fishing, kayaking, bicycling and walking trails and endless adventures to explore. Cash or 203K Renovation Loan financing.

(203) 253-1800
Contract Signed
Property for Sale at Riveredge Drive 37, Winchester, Connecticut - Bedrooms: 2 
Bathrooms: 2 
Rooms: 5  - $160,000 Previous PhotoNext Photo

Riveredge Drive 37
$160,000

Winchester, CT
Townhouse
Rooms: 5
Bedrooms: 2
Bathrooms: 2
Web ID: 24073529

Enjoy the private and peaceful setting of Still River right from your bedroom window or private patio all the while being close to the many amenities offered in town. Inside this well-maintained condo you'll find an abundance of natural light flowing in every room, a bright slider opening up to your own patio, all new paint throughout, lots of storage and durable like-new flooring on the main and upper levels. Perfect for easy maintenance. Parking within steps to your front door and extra spaces available nearby. Outdoor activities abound with fishing, kayaking, golf nearby and a variety of shopping within a mile. Don't miss this opportunity!

(203) 253-1800

E Wakefield Boulevard
$158,000

Winchester, CT
Vacant Land
Web ID: 24003236

1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL CONSIDER HOLDING A 2 YEAR BALLOON MORTGAGE WITH 15% DOWN

(203) 253-1800
Contract Signed
Property for Sale at Riveredge Drive 13, Winchester, Connecticut - Bedrooms: 1 
Bathrooms: 1 
Rooms: 4  - $140,000 Previous PhotoNext Photo

Riveredge Drive 13
$140,000

Winchester, CT
Condominium
Rooms: 4
Bedrooms: 1
Bathrooms: 1
Web ID: 24068577

This is your chance to experience turnkey condo-style living with modern upgrades and unbeatable comfort. The remodeled kitchen boasts newer appliances, sleek granite countertops, and stylish flooring, perfect for everyday living and entertaining. Enjoy peace of mind with a five-year-old water heater with a 10-year warranty. Imagine waking up to the serene, calming sounds of the river through your bedroom windows, providing an atmosphere of tranquility every day. With individual thermostats in each room, you'll enjoy customized comfort while also helping to keep your energy costs down. This condo is also part of a well-maintained community, offering low-maintenance living, where exterior upkeep and lawn care are taken care of. Please take advantage of its proximity to local parks, dining, and shopping, or enjoy the peaceful surroundings outside your door. This opportunity is rare, and homes like this don't last long. Take swift action to make this move-in-ready condo yours...

(203) 253-1800
Contract Signed
Property for Sale at Walnut Street, Winchester, Connecticut - Bedrooms: 2 
Bathrooms: 1 
Rooms: 4  - $120,000 Previous PhotoNext Photo

Walnut Street
$120,000

Winchester, CT
House
Rooms: 4
Bedrooms: 2
Bathrooms: 1
Web ID: 24049352

Attention investors! This 2-bedroom, 1-bathroom single ranch style home is a prime opportunity for a complete rehab. The property was involved in a fire and requires a full rehab with a 1-car garage and is being sold as-is. Subject to probate approval.

(203) 253-1800
Contract Signed
Property for Sale at Marshall Street, Winchester, Connecticut - Bedrooms: 3 
Bathrooms: 1 
Rooms: 6  - $89,000 Previous PhotoNext Photo

Marshall Street
$89,000

Winchester, CT
House
Rooms: 6
Bedrooms: 3
Bathrooms: 1
Web ID: 24073884

Charming bungalow with great potential! This 936 sq. ft. home features 6 rooms, including 3 bedrooms and 1 full bath, situated on a spacious 0.80-acre lot. A detached one-car garage provides additional storage or parking. While this home is in poor condition and will require significant renovation, it presents an excellent opportunity for investors or buyers looking to restore and customize. Will not qualify for traditional financing-rehab loan or cash purchase required. Sold as-is. Don't miss the chance to bring this property back to life!

(203) 253-1800
Property for Sale at 105 Mountain Road, Winchester, Connecticut -  - $59,900

105 Mountain Road
$59,900

Winchester, CT
Vacant Land
Web ID: 170616672

105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON MORTGAGE @7.5% WITH A 30 YEAR AMORTIZATION SCHEDULE .

(203) 253-1800
Property for Sale at Walnut Street, Winchester, Connecticut -  - $49,000

Walnut Street
$49,000

Winchester, CT
Vacant Land
Web ID: 24073691

Prime Building Lot Near Downtown & Tatro's Pond!-Discover the perfect setting for your dream home on this level and open .50-acre lot at 269 Walnut St. Nestled on a lightly traveled street, this property offers a peaceful atmosphere while maintaining easy access to downtown amenities. The lot is flat and fully cleared, providing a generous building envelope to accommodate your vision. A pre-existing asphalt driveway remains in place, adding convenience and value. With city water and sewer available at the street, utility connections are easily accessible. Plus, outdoor enthusiasts will appreciate the close proximity to Tatro's Pond and recreation area. Don't miss this opportunity to build in a prime location-schedule a visit today!

(203) 253-1800
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