Connecticut Realtor with experience and knowledge of residential and commercial property in Winchester
409 Main Street
Winchester, Connecticut 06098
$388,000 | Active
5 Beds | 2 Baths | 2403 Sqft | 0.4 Acres | 0 Days on Market
Property Type: Multi-Family For Sale
This versatile 2-family home would make a perfect owner occupant first floor unit with 3 bedrooms, with a 2 bedroom second floor apartment. Private entrances with separate utilities. Let your rental income help pay your mortgage. Each unit comes with formal living and dining...
409 Main Street
Winchester, Connecticut 06098
$388,000 | Active
5 Beds | 2 Baths | 2403 Sqft | 0.4 Acres | 0 Days on Market
Property Type: Single Family For Sale
Adorable Family home with 3 bedrooms and a separate 2 bedroom in-law; each with formal living and dining rooms. Refinished original wide pine flooring. Large main Kitchen with lots of cabinet space which walks out to a beautiful Trex patio overlooking a manicured lawn. Main home ...
115 Old Robertsville Road
Winchester, Connecticut 06098
$649,900 | Active
5 Beds | 2 Baths | 2304 Sqft | 41.23 Acres | 1 Days on Market
Property Type: Single Family For Sale
Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near...
141 Maloney Court
Winchester, Connecticut 06098
$270,000 | Under Contract - Continue
4 Beds | 3 Baths | 1752 Sqft | 0.37 Acres | 8 Days on Market
Property Type: Single Family For Sale
A charming ranch-style home, located in a desirable area, offers the convenience of single-level living. It features 4 bedrooms and 3 bathrooms, making it perfect for families or anyone in need of extra space. Upon entering the main floor, youll find a spacious living room filled...
343 Wakefield Boulevard
Winchester, Connecticut 06098
$249,000 | Active
2 Beds | 1 Baths | 674 Sqft | 0.28 Acres | 18 Days on Market
Property Type: Single Family For Sale
Your oasis awaits!!! Schedule your appointment today and come view this adorable Bungalow. There is so much potential to be made here. Bring your ideas and creativity as the seller is motivated, bring all offers!!!...
126 Williams Avenue
Winchester, Connecticut 06098
$285,000 | Active
6 Beds | 2 Baths | 2225 Sqft | 0.63 Acres | 2 Days on Market
Property Type: Multi-Family For Sale
Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income. The property has been completely overhauled in the past few years with almost everything updated. It is located in a great neighborhood in walking distance to...
102 Hollow Hill Road
Winchester, Connecticut 06098
$589,900 | Active
3 Beds | 3 Baths | 2692 Sqft | 2.78 Acres | 3 Days on Market
Property Type: Single Family For Sale
First time to the market this turnkey 2,692 sq ft Grand Ranch is nestled in on 2.78 bucolic acres surrounded by nature & mature trees. Lovingly maintained, this home provides the perfect set up for stress free living & entertaining boasting a large eat in kitchen with center isla...
181 Torringford Street
Winchester, Connecticut 06098
$375,000 | Coming Soon
3 Beds | 2 Baths | 2160 Sqft | 0.88 Acres | Days on Market
Property Type: Single Family For Sale
Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviti...
38 Upland Road
Winchester, Connecticut 06098
$299,000 | Coming Soon
3 Beds | 2 Baths | 1736 Sqft | 0.34 Acres | Days on Market
Property Type: Single Family For Sale
Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24 ...
50 Lakeview Road
Winchester, Connecticut 06098
$425,000 | Active
4 Beds | 3 Baths | 2086 Sqft | 0.63 Acres | 4 Days on Market
Property Type: Single Family For Sale
Located just a short stroll from Holland Beach and only a 3-minute drive to the public boat launch, this charming Colonial offers the perfect blend of comfort, convenience, and year-round recreation. Nestled on a level corner lot in a well-established neighborhood, this home invi...
200 Perch Rock Trail
Winchester, Connecticut 06098
$989,000 | Under Contract
3 Beds | 3 Baths | 2407 Sqft | 0.21 Acres | 1 Days on Market
Property Type: Single Family For Sale
Exceptional Waterfront Living on Highland Lake - Your Dream Home Awaits! Seize this rare opportunity to own a stunning YEAR-ROUND WATERFRONT property on the highly sought-after EAST SIDE of Highland Lake! This turnkey gem is move-in ready and packed with modern features, offering...
88 Strong Terrace
Winchester, Connecticut 06098
$289,900 | Under Contract
5 Beds | 2 Baths | 2470 Sqft | 0.2 Acres | 9 Days on Market
Property Type: Single Family For Sale
This solid 5-bedroom colonial in Winsted has been in the same hands for over 40 years and been well taken care of the whole time. With almost 2,500 square feet theres plenty of space for whatever you need, whether its family, guests, or just room to spread out. Inside, youll fin...
284 Gilbert Avenue
Winchester, Connecticut 06098
$319,900 | Active
4 Beds | 1 Baths | 1849 Sqft | 0.24 Acres | 9 Days on Market
Property Type: Single Family For Sale
Welcome to 284 Gilbert Avenue-a charming 4-bedroom Cape that combines efficient updates with inviting living spaces. Approximately 1,849 sq ft of sun-splashed interiors begin with a spacious eat-in kitchen featuring generous cabinetry, a dining area, and sliders that open to an e...
112 Shore Drive
Winchester, Connecticut 06098
$889,000 | Active
3 Beds | 3 Baths | 2113 Sqft | 0.13 Acres | 24 Days on Market
Property Type: Single Family For Sale
Live like youre on vacation every day! This beautifully updated lakefront home sits directly on the water in Highland Lakes first Bay, offering a level backyard & a private dock just steps from your door. With 50+ feet of direct waterfront and a fenced, low-maintenance yard, this...
117 South Road
Winchester, Connecticut 06098
$499,000 | Active
3 Beds | 3 Baths | 2747 Sqft | 3.37 Acres | 31 Days on Market
Property Type: Single Family For Sale
Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home w...
19 Riveredge Drive
Winchester, Connecticut 06098
$159,999 | Under Contract
2 Beds | 2 Baths | 992 Sqft | 0 Acres | 4 Days on Market
Property Type: Condo/Co-Op For Sale
Dont miss your chance to own this beautiful Riveredge condo as these condos go under contract within hours! In the kitchen you will find brand new Stainless Steel appliances as well as brand new cupboards and counters! Freshly painted throughout and new carpet on stairs and secon...
11 Gibbs Street
Winchester, Connecticut 06098
$109,900 | Under Contract
1 Beds | 1 Baths | 570 Sqft | 0 Acres | 3 Days on Market
Property Type: Condo/Co-Op For Sale
Welcome to easy, one-level living in this rarely available unit at Gilbert Commons! This well-maintained 1 bedroom, 1 full bathroom condo offers approximately 570 square feet of comfortable living space with plenty of natural light and privacy. Inside, youll find a spacious livin...
29 Walnut Street
Winchester, Connecticut 06098
$310,000 | Under Contract
3 Beds | 5 Baths | 2623 Sqft | 0.37 Acres | 7 Days on Market
Property Type: Single Family For Sale
Introducing 29 Walnut: a grand Victorian home with a front porch view complimented by perennial rose gardens, a terrace fit for garden parties, and a large back yard. Upon entry, look upward to high ceilings, a spacious entryway and a grand, swirling staircase. Note precise finis...
30 Mountain Avenue
Winchester, Connecticut 06098
$229,900 | Active
5 Beds | 2 Baths | 2310 Sqft | 0.41 Acres | 16 Days on Market
Property Type: Single Family For Sale
Not afraid of some peeling paint or rotting wood? This is the house for you! 30 Mountain Ave with 5 beds, 1.5 baths is your opportunity to bring a vision to life. Located in a welcoming neighborhood, it offers a generous layout ready for customization and renovation. Whether your...
711 Wakefield Boulevard
Winchester, Connecticut 06098
$1,500,000 | Under Contract
3 Beds | 3 Baths | 2664 Sqft | 0.61 Acres | 287 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....
115 Stanton Avenue
Winchester, Connecticut 06098
$269,900 | Under Contract - Continue
2 Beds | 1 Baths | 1424 Sqft | 0.51 Acres | 24 Days on Market
Property Type: Single Family For Sale
Step inside this charming Cape Cod style home as you walk in the front door your in a large living room with wood floors, big picture window and lots of sunshine and seasonal views. The kitchen is bright and sunny and has room for a large table. The master bedroom is also on the ...
50 Manchester Heights
Winchester, Connecticut 06098
$335,000 | Active
3 Beds | 1 Baths | 1287 Sqft | 1.05 Acres | 17 Days on Market
Property Type: Single Family For Sale
Charming Country Cape with Cottagecore appeal on just over an acre of land and situated on a culd-de-sac. Located off the beaten path in the quiet hills of Winchester, this storybook Cape-style home offers the perfect blend of rustic charm and modern comfort. Convenient to Route ...
11 Gibbs Street
Winchester, Connecticut 06098
$109,900 | Under Contract
1 Beds | 1 Baths | 570 Sqft | 0 Acres | 10 Days on Market
Property Type: Condo/Co-Op For Sale
Welcome to easy, one-level living in this rarely available first-floor end unit at Gilbert Commons! This well-maintained 1 bedroom, 1 full bathroom condo offers approximately 570 square feet of comfortable living space with plenty of natural light and privacy. Inside, youll find ...
203 Holabird Avenue
Winchester, Connecticut 06098
$369,900 | Under Contract
5 Beds | 4 Baths | 3690 Sqft | 0.36 Acres | 6 Days on Market
Property Type: Multi-Family For Sale
Exceptional Mixed-Use Investment Opportunity Discover the perfect blend of charm, functionality, and income potential at 203 Holabird Avenue in the heart of Winsted, CT. This well-maintained riverfront property features a versatile mixed-use layout with two residential apartments...
355 Lake Street
Winchester, Connecticut 06098
$979,000 | Under Contract - Continue
5 Beds | 4 Baths | 3216 Sqft | 0.51 Acres | 44 Days on Market
Property Type: Single Family For Sale
Sweeping Views, Exceptional Craftsmanship, and Lake Life at Its Finest.Set on a rare half-acre double lot across from Highland Lake, this custom-built 5-6 bedroom home offers panoramic views over First Bay and deeded dock access just steps from your front door-perfectly positione...
150 Mathew Road
Winchester, Connecticut 06098
$329,000 | Active
3 Beds | 2 Baths | 1480 Sqft | 0.17 Acres | 47 Days on Market
Property Type: Single Family For Sale
Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. 6,500 watt whole house generator. 8x12 shed with power, 35 Amp out side outlet for camper, working chimney for wood stove on lower level, ASSUMABLE M...
144 Marshall Street
Winchester, Connecticut 06098
$559,999 | Active
3 Beds | 2 Baths | 1744 Sqft | 55 Acres | 52 Days on Market
Property Type: Single Family For Sale
Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-lev...
424 Wakefield Boulevard
Winchester, Connecticut 06098
$1,595,000 | Active
5 Beds | 2 Baths | 3693 Sqft | 0.59 Acres | 24 Days on Market
Property Type: Single Family For Sale
Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure ...
39 Baker Street
Winchester, Connecticut 06098
$225,000 | Under Contract - Continue
5 Beds | 2 Baths | 1612 Sqft | 0.2 Acres | 51 Days on Market
Property Type: Multi-Family For Sale
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 porch...
435/434 Wakefield Boulevard
Winchester, Connecticut 06098
$1,400,000 | Active
8 Beds | 5 Baths | 5231 Sqft | 1.51 Acres | 261 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...
39 Orchard Street
Winchester, Connecticut 06098
$230,000 | Active
3 Beds | 2 Baths | 1200 Sqft | 0.26 Acres | 98 Days on Market
Property Type: Single Family For Sale
Back on the market, buyers financing fell through. 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 update...
288 Torringford Street
Winchester, Connecticut 06098
$460,000 | Under Contract - Continue
4 Beds | 3 Baths | 3021 Sqft | 4.6 Acres | 123 Days on Market
Property Type: Single Family For Sale
Welcome to this charming four-bedroom antique home that is beautifully renovated to blend timeless character with modern comforts. As you step inside youll be greeted by the warmth of refinished hardwood floors and an inviting living room featuring a cozy fireplace and built-in b...
55 Walnut Street
Winchester, Connecticut 06098
$525,000 | Active
5 Beds | 4 Baths | 5016 Sqft | 0.56 Acres | 136 Days on Market
Property Type: Single Family For Sale
Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900s. Nestled in the TCR Zone, this versatile building offers a wealth of potential....
51 Pratt Street
Winchester, Connecticut 06098
$450,000 | Active
4 Beds | 2 Baths | 2239 Sqft | 0.21 Acres | 125 Days on Market
Property Type: Single Family For Sale
Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home bo...
508 Wakefield Boulevard
Winchester, Connecticut 06098
$1,650,000 | Under Contract
7 Beds | 4 Baths | 2687 Sqft | 1.63 Acres | 315 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...
174 Boyd Street
Winchester, Connecticut 06098
$289,000 | Under Contract
3 Beds | 1 Baths | 1424 Sqft | 0.22 Acres | 105 Days on Market
Property Type: Single Family For Sale
A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is la...
469 Platt Hill Road
Winchester, Connecticut 06098
$995,000 | Active
4 Beds | 2 Baths | 3088 Sqft | 7.11 Acres | 52 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 Customer, 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 ...
538 Wheelers Point
Winchester, Connecticut 06098
$1,699,500 | Active
4 Beds | 3 Baths | 2496 Sqft | 0.7 Acres | 248 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...
110 Rugg Brook Road
Winchester, Connecticut 06098
$400,000 | Under Contract - Continue
3 Beds | 3 Baths | 2209 Sqft | 3.32 Acres | 82 Days on Market
Property Type: Single Family For Sale
Wow! Check out this beautiful, modern, colonial built in 1998 with over 2,000 square feet on 3+ level acres with an inground pool and an attached garage. Enjoy the comfortable feel and the beautiful hardwood floors, vaulted ceiling in the primary bedroom suite. With views of Winc...
39 Main Street
Winchester, Connecticut 06098
$749,900 | Active
7 Beds | 3 Baths | 3486 Sqft | 4.36 Acres | 81 Days on Market
Property Type: Multi-Family For Sale
THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 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 ...
431 Wakefield Boulevard
Winchester, Connecticut 06098
$2,600,000 | Active
9 Beds | 6 Baths | 7000 Sqft | 3 Acres | 284 Days on Market
Property Type: Single Family For Sale
This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating...
119 Wakefield Boulevard
Winchester, Connecticut 06098
$849,900 | Active
4 Beds | 2 Baths | 1781 Sqft | 0.62 Acres | 110 Days on Market
Property Type: Single Family For Sale
Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay,...
119 Wakefield Boulevard
Winchester, Connecticut 06098
$849,900 | Active
4 Beds | 2 Baths | 1781 Sqft | 0.62 Acres | 110 Days on Market
Property Type: Multi-Family For Sale
Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay,...
175 Main Street
Winchester, Connecticut 06098
$950,000 | Active
14 Beds | 7 Baths | 4860 Sqft | 0.13 Acres | 127 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...
77 Hubbard Street
Winchester, Connecticut 06098
$299,900 | Under Contract
6 Beds | 2 Baths | 2699 Sqft | 0.28 Acres | 33 Days on Market
Property Type: Multi-Family For Sale
Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, f...
18-4A Taylor Brook Road
Winchester, Connecticut 06098
$650,000 | Active
3 Beds | 3 Baths | 2135 Sqft | 3.46 Acres | 848 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...