Connecticut Realtor with experience and knowledge of residential and commercial property in Winchester
173 Smith Hill Road
Winchester, Connecticut 06098
$390,000 | Active
4 Beds | 2 Baths | 1702 Sqft | 4.11 Acres | 3 Days on Market
Property Type: Single Family For Sale
Picture-perfect Cape perched on 4+ private acres, this home boasts 3-4 bedrooms, 2 full bathrooms, hardwood floors, and an abundance of natural light throughout. The main level features a bright and open dining-living room with a fireplace and custom built-ins. Youll enjoy the co...
39 South Main Street
Winchester, Connecticut 06098
$649,900 | Under Contract - Continue
9 Beds | 5 Baths | 4446 Sqft | 4.36 Acres | 123 Days on Market
Property Type: Multi-Family For Sale
Three properties totaling 4.41 acres for one price! 1. 3500 sq ft 2 family home featuring 1800s architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic ...
3 Kittredge Lane
Winchester, Connecticut 06098
$250,000 | Active
4 Beds | 2 Baths | 2190 Sqft | 0.45 Acres | 4 Days on Market
Property Type: Single Family For Sale
Nestled at the end of a tranquil street, this charming Cape offers a perfect blend of indoor comfort and outdoor enjoyment. Sit in your rocker on the inviting front porch or relax on the back deck, where a 2020 Thermospa hot tub awaits you-its included in the sale! Enjoy the gre...
110 South Road
Winchester, Connecticut 06098
$694,000 | Active
4 Beds | 3 Baths | 3870 Sqft | 2.75 Acres | 140 Days on Market
Property Type: Single Family For Sale
Your private oasis nestled in historic Winchester Center, offering serenity, lakes, trails and more. Contemporary Cape w/an abundance of spacious, light-filled and updated rooms. Several options to include; one-floor living, multi-generational home, w 4+ bedrooms and 4 garage bay...
155 Gilbert Avenue
Winchester, Connecticut 06098
$899,900 | Under Contract - Continue
8 Beds | 8 Baths | 3963 Sqft | 1.28 Acres | 18 Days on Market
Property Type: Multi-Family For Sale
Rare opportunity to secure 8 units under one roof! Fantastic location within walking distance of downtown Winsted and Northwestern Community College. Well-maintained and managed, this property presents a new owner the opportunity for cash flow out of the gate, with value to be ad...
220 Gilbert Avenue
Winchester, Connecticut 06098
$379,900 | Active
4 Beds | 2 Baths | 2176 Sqft | 0.25 Acres | 31 Days on Market
Property Type: Multi-Family For Sale
WOW - Welcome to 220 Gilbert Ave! Stop by for a visit and view the amazing transformation of this FABULOUS 2 family dwelling. Home has been completely remodeled inside and out. Relax and enjoy the level, private back yard or the sprawling, open front porch. The open floor plan bo...
239 North Main Street
Winchester, Connecticut 06098
$225,900 | Active
4 Beds | 2 Baths | 2872 Sqft | 0.53 Acres | 6 Days on Market
Property Type: Single Family For Sale
Step into this charming Victorian home, where classic charm blends seamlessly with thoughtful design. Featuring high ceilings and hardwood floors, this 4-bedroom, 2-bath beauty offers spacious living areas with a versatile layout. With its thoughtful layout, the home is primed fo...
421 Unity Place
Winchester, Connecticut 06098
$324,900 | Active
3 Beds | 2 Baths | 1440 Sqft | 0.12 Acres | 21 Days on Market
Property Type: Single Family For Sale
Make this newly renovated house in the sought after Highland Lake community your full time residence or your home away from home! This home has gone through an extensive remodel including brand new roof, insulated siding, energy efficient windows, and LVP flooring. The home featu...
247 North Main Street
Winchester, Connecticut 06098
$499,900 | Active
8 Beds | 5 Baths | 5093 Sqft | 0.84 Acres | 164 Days on Market
Property Type: Multi-Family For Sale
Architectural wonder and great investment opportunity. You will love the entrancing detail and architecture of this lovely building. Huge .84 acre lot and loads of parking. All units are occupied and well cared for. 3 out of 4 tenants are long term and all the tenants love their ...
119 West Wakefield Boulevard
Winchester, Connecticut 06098
$859,900 | Active
4 Beds | 2 Baths | 1781 Sqft | 0.62 Acres | 61 Days on Market
Property Type: Single Family For Sale
Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-fa...
119 West Wakefield Boulevard
Winchester, Connecticut 06098
$859,900 | Active
4 Beds | 2 Baths | 1781 Sqft | 0.62 Acres | 61 Days on Market
Property Type: Multi-Family For Sale
Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-fa...
538 Wheelers Point
Winchester, Connecticut 06098
$1,880,000 | Active
4 Beds | 3 Baths | 2496 Sqft | 0.7 Acres | 11 Days on Market
Property Type: Single Family For Sale
Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360 direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunni...
303 East Wakefield Boulevard
Winchester, Connecticut 06098
$269,900 | Under Contract
2 Beds | 1 Baths | 960 Sqft | 0.12 Acres | 20 Days on Market
Property Type: Single Family For Sale
Year Round Living at Highland Lake! This home has beautiful views and easy access to the beach and Highland Lake. Nominal annual fee gets you access to the clean, private for selected homeowners beach-like and docking area. The home has been freshly painted and has newer flooring...
129 Forest Avenue
Winchester, Connecticut 06098
$679,900 | Under Contract - Continue
3 Beds | 3 Baths | 2400 Sqft | 4.12 Acres | 164 Days on Market
Property Type: Single Family For Sale
Welcome to your serene retreat nestled in the heart of Winchester, CT! This stunning, single owner, post and beam style house, at 129 Forest Ave offers a perfect blend of tranquility and convenience, inviting you to experience the best of both worlds. Situated amidst lush greene...
111 Riverton Road
Winchester, Connecticut 06098
$215,000 | Active
2 Beds | 2 Baths | 1204 Sqft | 0 Acres | 12 Days on Market
Property Type: Condo/Co-Op For Sale
Rarely Available End Unit at Riverwalk Condos! This pristine 2-bedroom, 1.5-bath condo offers a move-in ready experience with stunning river views and modern upgrades. The open-concept living space is filled with natural light and features crown molding and recessed lighting, add...
354 Platt Hill Road
Winchester, Connecticut 06098
$444,900 | Active
4 Beds | 3 Baths | 2486 Sqft | 1.5 Acres | 13 Days on Market
Property Type: Single Family For Sale
Welcome to your dream home in Winchester, Connecticut, just minutes from the serene Highland Lake. Park your boat o. Your property and use the public boat launch! This charming residence boasts a large, flat wooded lot, offering plenty of space for outdoor activities and privacy....
10 Hamill Drive
Winchester, Connecticut 06098
$399,900 | Active
3 Beds | 2 Baths | 1476 Sqft | 0.33 Acres | 21 Days on Market
Property Type: Single Family For Sale
This single family home has 3 generous bedrooms and 1.5 bathrooms. It features a spacious kitchen with hardwood cabinets and black appliances. There are hardwood floors throughout the entire house, a dedicated laundry room, and a heated finished basement. This home is situated on...
80 Colony Drive
Winchester, Connecticut 06098
$290,000 | Under Contract
4 Beds | 2 Baths | 1530 Sqft | 0.4 Acres | 10 Days on Market
Property Type: Single Family For Sale
Welcome to 80 Colony Drive in Winsted, CT! This inviting 4-bedroom, 2-bathroom home perfectly blends modern updates with classic charm. As you enter, youll be greeted by hardwood floors that flow throughout the main living areas. The cozy wood stove adds warmth and character, cre...
102 West Road
Winchester, Connecticut 06098
$499,900 | Under Contract - Continue
2 Beds | 2 Baths | 2144 Sqft | 2.7 Acres | 31 Days on Market
Property Type: Single Family For Sale
Discover the enchanting David Alvord Home, a beautifully restored saltbox antique nestled just off the green in Winchester Center. This historic gem, built in 1776, seamlessly combines classic New England charm w/ modern comforts, making it an ideal sanctuary for those seeking bo...
115 Moore Avenue
Winchester, Connecticut 06098
$449,900 | Active
3 Beds | 3 Baths | 2240 Sqft | 4.92 Acres | 38 Days on Market
Property Type: Single Family For Sale
If you are looking for a mini estate look no further. This completely remodeled home has everything you need. New eat in kitchen with a bay window overlooking the rear yard. Quartz c/tops and new appliances. Formal dining room, den with fireplace and wood stove insert. Sliders to...
19 Cottage Street
Winchester, Connecticut 06098
$399,999 | Active
4 Beds | 4 Baths | 2674 Sqft | 0.32 Acres | 32 Days on Market
Property Type: Single Family For Sale
Welcome to 19 Cottage Street, a stunning turnkey Colonial in the heart of Winsted that beautifully blends modern functionality with classic charm. As you enter, a spacious foyer with new tile flooring leads into a bright living room featuring gleaming hardwood floors, create a wa...
441 Platt Hill Road
Winchester, Connecticut 06098
$650,000 | Active
5 Beds | 3 Baths | 3404 Sqft | 2.09 Acres | 54 Days on Market
Property Type: Single Family For Sale
Welcome home! This inviting residence features an open, airy feel with abundant natural light from big windows and multiple skylights. The main level boasts solid hardwood floors and tiles, while the spacious eat-in kitchen, though older, is well-maintained and perfect for family...
350 Walnut Street
Winchester, Connecticut 06098
$120,000 | Active
2 Beds | 1 Baths | 720 Sqft | 0.56 Acres | 25 Days on Market
Property Type: Single Family For Sale
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....
224 Smith Hill Road
Winchester, Connecticut 06098
$329,000 | Under Contract - Continue
3 Beds | 2 Baths | 1178 Sqft | 2.25 Acres | 45 Days on Market
Property Type: Single Family For Sale
If you love country you are going to love this Chalet styled ranch! 3 bedrooms, 1.5 baths, 2 car garage attached. Lovely, enclosed porch looking over a beautiful rear lot. 2.25 acres! Close to Rt. 8 and amenities while offering the tranquility of this beautiful location. A true d...
296 Colebrook Road
Winchester, Connecticut 06098
$525,000 | Active
7 Beds | 4 Baths | 4253 Sqft | 9.87 Acres | 21 Days on Market
Property Type: Single Family For Sale
. The Main house features a Huge Stone fire-placed family room , plus a fire-placed Living room,for cozier gatherings. The home also includes a walk-out basement,. There is finished space ideal for an in-law suite on the second floor, located above the oversized attached 2-car ga...
184 Newfield Road
Winchester, Connecticut 06098
$349,900 | Under Contract
2 Beds | 2 Baths | 1598 Sqft | 10.15 Acres | 45 Days on Market
Property Type: Single Family For Sale
This country escape home is located in Litchfield County, just outside of quaint Winchester Center. If a quiet setting is what youre seeking, then this is the home for you. Situated on over 10 acres, you travel over a bridge and up a long driveway to find yourself immersed in com...
36 Whiting Street
Winchester, Connecticut 06098
$189,000 | Under Contract - Continue
3 Beds | 3 Baths | 1608 Sqft | 0.22 Acres | 125 Days on Market
Property Type: Single Family For Sale
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...
435 West Wakefield Boulevard
Winchester, Connecticut 06098
$1,700,000 | Active
8 Beds | 5 Baths | 5231 Sqft | 1.51 Acres | 24 Days on Market
Property Type: Single Family For Sale
Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ h...
182 Florence Street
Winchester, Connecticut 06098
$269,900 | Under Contract - Continue
3 Beds | 2 Baths | 1982 Sqft | 0.34 Acres | 31 Days on Market
Property Type: Single Family For Sale
Welcome to this charming 3-bedroom, 1.5-bath Raised Ranch located in a serene Winsted neighborhood, set on a lightly wooded, level lot. This inviting home features a spacious living room with beautiful wood floors, a cathedral ceiling, and skylights, creating an airy atmosphere f...
114 Moore Avenue
Winchester, Connecticut 06098
$399,900 | Under Contract - Continue
6 Beds | 4 Baths | 2580 Sqft | 1.61 Acres | 67 Days on Market
Property Type: Single Family For Sale
Impeccably Remodeled 6 Bedroom, 3+ Bath Colonial Farmhouse on 1.6 Acres Features 2 Kitchens on Main Level with Seperate Full Baths, Bedroom and Living Area for Possible In-Law or Extra Income Apartment. Both Kitchens & All 3 Baths Have Been Totally Renovated with New Cabinetry, G...
178 Torringford Street
Winchester, Connecticut 06098
$315,000 | Under Contract - Continue
3 Beds | 2 Baths | 2112 Sqft | 0.62 Acres | 37 Days on Market
Property Type: Single Family For Sale
Charming 3-bedroom, 2-bathroom Cape Cod home nestled in the heart of Winsted! This beautifully maintained property features gleaming hardwood floors throughout and an updated kitchen with modern appliances, perfect for cooking and entertaining. Enjoy outdoor living on the new dec...
231 Jewett Street
Winchester, Connecticut 06098
$559,000 | Active
3 Beds | 3 Baths | 2052 Sqft | 0.41 Acres | 101 Days on Market
Property Type: Single Family For Sale
A Perfect Year Round or Vacation Home where you can have all the enjoyment offered of lake living with a water front lot yet a home with privacy. This Beautiful home features 3/4 Bedroom with 3 Full Bathrooms. The Main Floor with open plan features Brazilian Cherry flooring in Li...
25 Hillside Avenue
Winchester, Connecticut 06098
$575,000 | Under Contract - Continue
6 Beds | 5 Baths | 5001 Sqft | 0.62 Acres | 179 Days on Market
Property Type: Multi-Family For Sale
Wow, this handsome Historic Manson is a rare beauty. It was coverted into 5 units and has original woodwork, stunning history and details. This updated, stately home has gas hot water and gas heat. Gorgeous common areas and porches. New front steps, 2 new oven ranges, 4 new hot w...
74 Strong Terrace
Winchester, Connecticut 06098
$260,000 | Under Contract - Continue
3 Beds | 2 Baths | 1032 Sqft | 1.71 Acres | 45 Days on Market
Property Type: Single Family For Sale
Three bedroom Ranch with fireplace on the main level, and set on three lots totaling 1.71 acres near the center of Winsted. Close to Rt.8. There are three lots, and the taxes reflect this. Public Water and Sewer and Natural Gas. Lower level has a wood burning fireplace and is stu...
315 East Wakefield Boulevard
Winchester, Connecticut 06098
$299,900 | Active
3 Beds | 1 Baths | 988 Sqft | 0.22 Acres | 53 Days on Market
Property Type: Single Family For Sale
Welcome to 315 East Wakefield Blvd, a charming 3-bedroom, 1-bath ranch offering stunning views and easy access to Highland Lake. This home is in impeccable condition, featuring an updated kitchen and bath, along with newer hard surface flooring. The inviting living room boasts a ...
153 Mathew Road
Winchester, Connecticut 06098
$279,900 | Under Contract - Continue
2 Beds | 2 Baths | 1544 Sqft | 0.13 Acres | 110 Days on Market
Property Type: Single Family For Sale
Price Reduced! This charming two-bedroom, one and one half -bathroom house is situate in Highland Lake community. The property boasts a generous 1,278 square feet of living space, with an open floor plan that creates a spacious and airy feel. New split system air conditioning. Cu...
160 Glendale Avenue
Winchester, Connecticut 06098
$249,900 | Under Contract - Continue
3 Beds | 2 Baths | 1114 Sqft | 0.56 Acres | 77 Days on Market
Property Type: Single Family For Sale
Dont miss out on this well kept, roomy cape with a very large yard in a great neighborhood, off the beaten path but moments away from routes 8,44 and 183. There is a beautiful backyard with a shed and a nice stone wall, lots of extra space for gardening or outdoor activities. The...
116 Ashley Road
Winchester, Connecticut 06058
$349,900 | Active
3 Beds | 1 Baths | 1491 Sqft | 13 Acres | 46 Days on Market
Property Type: Single Family For Sale
Welcome to a piece of history with this enchanting Cape farmhouse, a true gem nestled in the picturesque town of Winchester. Built in 1830, this home radiates classic charm with its original details and timeless character. The property features two inviting fireplaces, perfect fo...
431 West Wakefield Boulevard
Winchester, Connecticut 06098
$2,800,000 | Active
9 Beds | 6 Baths | 7000 Sqft | 1.9 Acres | 47 Days on Market
Property Type: Single Family For Sale
DIRECT WATERFRONT PROPERTY!!!! The estate at 431 W. Wakefield Blvd in Winchester, CT, is truly a gem with its stunning views of Highland Lake and unique amenities. The combination of a main home with high-end finishes, Gourmet kitchen, Custom craftsmanship throughout, a guest bun...
522 West Wakefield Boulevard
Winchester, Connecticut 06098
$650,000 | Active
2 Beds | 1 Baths | 1134 Sqft | 1 Acres | 568 Days on Market
Property Type: Single Family For Sale
LOCATION! LOCATION! LOCATION! Direct Waterfront Lake Property on a VERY RARE 1 ACRE level & private CORNER LOT with tons of parking on the highly sought after pristine, glistening & scenic Highland Lake in Winsted, Litchfield County, CT This property has approx 400 ft of waterfro...
711 West Wakefield Boulevard
Winchester, Connecticut 06098
$1,500,000 | Active
3 Beds | 3 Baths | 2664 Sqft | 0.61 Acres | 70 Days on Market
Property Type: Single Family For Sale
Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Dont miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents....
175 Main Street
Winchester, Connecticut 06098
$1,100,000 | Active
14 Beds | 7 Baths | 4860 Sqft | 0.13 Acres | 79 Days on Market
Property Type: Multi-Family For Sale
Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Nolis Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident...
508 West Wakefield Boulevard
Winchester, Connecticut 06098
$1,650,000 | Active
7 Beds | 4 Baths | 2687 Sqft | 1.63 Acres | 124 Days on Market
Property Type: Single Family For Sale
Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alt...
469 Platt Hill Road
Winchester, Connecticut 06098
$1,100,000 | Active
4 Beds | 2 Baths | 3088 Sqft | 7.11 Acres | 140 Days on Market
Property Type: Single Family For Sale
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Buyer, whether Youre an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 178...
18-4A Taylor Brook Road
Winchester, Connecticut 06098
$650,000 | Active
3 Beds | 3 Baths | 2135 Sqft | 3.46 Acres | 611 Days on Market
Property Type: Single Family For Sale
Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors thru-out, granite tops, stone/marble baths, walk up attic. Large deck off kitchen. Dont miss this incredible o...