Newest Homes for Sale in Winchester, CT

Q: What are the most popular zip codes in Winchester, CT?

The most popular zip codes in Winchester, CT include 06098 , 06790 , 06021 , 06058 and 06063 .

/40
$349,900

Open Sat 10AM - 12PM
- 3 Beds
- 1.5 Baths
- 1,466 Sq Ft
405 N Main St, Winsted, CT 06098

Move right into this absolutely charming Colonial with incredible curb appeal & pride of ownership throughout! Lovingly maintained & impeccably clean, this true dollhouse is set on .31 acres in the scenic, beautiful Litchfield Hills & just minutes to Northwestern Community College, the town green, shopping, restaurants, walking trails, biking, & endless outdoor recreation. From the moment you

Nancy Reardon Berkshire Hathaway NE Prop.

405 N Main St, Winsted, CT 06098
Explore Winchester
/2
$49,000
- Land
- 2 Acres
- $24,500 per Acre
18 Pine Rd, Colebrook, CT 06021

Discover the perfect setting for your dream home on this private 2.0-acre parcel in the scenic hills of Colebrook. Featuring 236 feet of road frontage on quiet Pine Road, this property offers a beautiful building site situated on a gently elevated plateau with desirable southern and western exposures, providing excellent sunlight and the potential for stunning sunset views. Surrounded by nature

David Sartirana

Northwest CT Realty

(860) 345-5479

18 Pine Rd, Colebrook, CT 06021
/39
$369,000
- 2 Beds
- 1.5 Baths
- 1,440 Sq Ft
212 Spencer Hill Rd, Winsted, CT 06098

Nestled on a private lot in scenic Winchester, this beautifully maintained home offers a wonderful blend of comfort, character, and natural surroundings. Hardwood floors welcome you into the bright and inviting interior, where the custom kitchen serves as the heart of the home with hickory cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. The second floor features

David Sartirana

Northwest CT Realty

(860) 452-3419

212 Spencer Hill Rd, Winsted, CT 06098
/29
$325,000
- 3 Beds
- 1.5 Baths
- 1,118 Sq Ft
188 Glendale Ave, Winsted, CT 06098

Welcome to 188 Glendale Avenue! This charming 3-4 bedroom ranch sits on a quiet cul-de-sac. This home boasts of beautiful evening sunsets and quiet mornings sipping coffee on a secluded backyard patio. There have been many updates added, including vinyl windows, a new circuit panel and a new walk-in shower. Entering the home, you find a cozy living room with a working fireplace. The

Mary Anne Casey D. Beckley Realty

188 Glendale Ave, Winsted, CT 06098
/19
$349,000
- 3 Beds
- 1.5 Baths
- 1,888 Sq Ft
107 Roberts Ave, Winsted, CT 06098

Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the

Mary Anne Casey D. Beckley Realty

107 Roberts Ave, Winsted, CT 06098
/2
$29,900
- Land
- 5,662 Sq Ft
- $230,000 per Acre
17 Birdsall St, Winsted, CT 06098

Rare opportunity to build in a convenient in-town location! This level 0.13-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

David Sartirana

Northwest CT Realty

(860) 295-4250

17 Birdsall St, Winsted, CT 06098
/2
$29,000
- Land
- 5,227 Sq Ft
- $241,667 per Acre
82-84 Rockwell St, Winchester, CT 06098

Rare opportunity to build in a convenient in-town location! This level 0.12-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

David Sartirana

Northwest CT Realty

(860) 419-2496

82-84 Rockwell St, Winchester, CT 06098
/2
$45,000
- Land
- 1.07 Acres
- $42,056 per Acre
132 Florence St, Winsted, CT 06098

Rare opportunity to build your dream home on this 1.07-acre vacant lot conveniently located close to downtown shopping, dining, and everyday amenities. Situated in an established neighborhood, this property offers season-long westerly views and spectacular sunset vistas, creating the perfect backdrop for your future home. Public water and public sewer are available in the street (buyer to verify

David Sartirana

Northwest CT Realty

(860) 217-5758

132 Florence St, Winsted, CT 06098
/2
$45,000
- Land
- 17,859 Sq Ft
- $109,756 per Acre
32 Hubbard St, Winsted, CT 06098

Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available

David Sartirana

Northwest CT Realty

(860) 217-3265

32 Hubbard St, Winsted, CT 06098
/17
$450,000
- 8 Beds
- 4 Baths
- 2,000 Sq Ft
71-73 Wheeler St, Winchester, CT 06098

A positive income even if you live in one of the units. Two 2 family homes(4 units total) on one parcel. Good parking. Large lot. Residential setting. Second floor of back house has a private deck, back yard and woods, yet is convenient to downtown.

Ida Chaplinski The DIY Listing

71-73 Wheeler St, Winchester, CT 06098
/25
$474,900

$25K PRICE DROP
- 5 Beds
- 3 Baths
- 3,404 Sq Ft
441 Platt Hill Rd, Winsted, CT 06098

Tucked away on 2.09 private acres in the desirable Platt Hill area of Winchester, this custom-built contemporary offers the perfect blend of architectural character, space, and recent updates. With over 3,400 square feet, 5 bedrooms, 3 full baths, and a 2-car garage, this home provides flexibility for everyday living, entertaining, or multi-generational needs. Inside, you'll find a thoughtfully

Meagan Albert Tier 1 Real Estate

441 Platt Hill Rd, Winsted, CT 06098
/5
$70,000
- Land
- 5,227 Sq Ft
- $583,333 per Acre
319 White Oak Trail, Winchester, CT 06098

Wooded interior lot located at the end of a dead-end street, offering a private setting. The parcel is slightly sloped and accessed from the end of the road. Clients, do your homework , including but not limited to surveys, zoning, and building approvals. Convenient location with approximately a 15-minute walk to Resha Beach on Highland Lake for recreational enjoyment. Lake rights are granted to

Matt Tearman Coldwell Banker Realty

319 White Oak Trail, Winchester, CT 06098
/7
$499,900
- 6 Beds
- 5 Baths
- 2,864 Sq Ft
205 Old New Hartford Rd, Winchester, CT 06098

Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing

TK Krumm Berkshire Hathaway NE Prop.

205 Old New Hartford Rd, Winchester, CT 06098
/28
$349,999
- 6 Beds
- 2.5 Baths
- 2,555 Sq Ft
68 Wetmore Ave, Winsted, CT 06098

Extremely well-cared-for two-family home located on a desirable street! This property offers plenty of off-street parking, a rear lot, a 3-car garage with basement adds potential for additional income. Large back yard with gazebo.The first floor is unoccupied, while the second floor is tenant-occupied, making this a great opportunity for an owner-occupant or investor. Come take a look while it

Alex King Lock and Key Realty, Inc

68 Wetmore Ave, Winsted, CT 06098
/26
$220,000
- 4 Beds
- 2 Baths
- 1,844 Sq Ft
30 Upland Rd, Winsted, CT 06098

Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a private outdoor setting to enjoy year round. This home also features a beautiful enclosed second-floor sun porch, perfect for

Jeffrey Liskin

Northwest CT Realty

(860) 854-8201

30 Upland Rd, Winsted, CT 06098
/2
$795,000
- Land
- 10,018 Sq Ft
- $3,456,522 per Acre
535,538 W Wakefield Blvd, Winchester, CT 06098

This waterfront property is ideal for contractors or individuals who want to build a year-round home on Highland Lake's West side. The property is being sold as a package (3 lots have been approved for construction, parking, and a well ). The lots consist of .10 acres across the street from the water and .023 acres on the water.

chris marino Cohen Agency

535,538 W Wakefield Blvd, Winchester, CT 06098
/24
$544,000
- 1 Bed
- 1.5 Baths
- 1,308 Sq Ft
736 W Wakefield Blvd, Winsted, CT 06098

Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family room with a stone fireplace, and an efficient kitchen with storage. The lower walk-out level can be accessed by the

Ed Richman Lakefront Living Realty, LLC

736 W Wakefield Blvd, Winsted, CT 06098
/29
$299,900
- 2 Beds
- 1 Bath
- 702 Sq Ft
147 E Wakefield Blvd, Winsted, CT 06098

Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

Mary Mary LeBlanc Realty

147 E Wakefield Blvd, Winsted, CT 06098
/19
$469,900

Open Sat 3:30PM - 5:30PM
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
9 Loomis St, Winsted, CT 06098

Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on

Marshall Cohen Cohen Agency

9 Loomis St, Winsted, CT 06098
/24
$174,900

$25K PRICE DROP
- Land
- 5,227 Sq Ft
- $1,457,500 per Acre
624 Wynne Rd, Winsted, CT 06098

Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a

AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

624 Wynne Rd, Winsted, CT 06098
/26
$284,000

Open Sun 1PM - 3PM $5K PRICE DROP
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
104 Maloney Ct, Winsted, CT 06098

Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak

Lisa Garten Johnson Turning Point Realty, LLC

104 Maloney Ct, Winsted, CT 06098
/5
$200,000
- Land
- 15.9 Acres
- $12,579 per Acre
00 Chapel Rd, Winchester, CT 06098

Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.

Linda Ganem Borla & Associates Real Estate

00 Chapel Rd, Winchester, CT 06098
/40
$895,000
- 4 Beds
- 2 Baths
- 3,088 Sq Ft
469 Platt Hill Rd, Winsted, CT 06098

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

Marshall Cohen Cohen Agency

469 Platt Hill Rd, Winsted, CT 06098
/26
$239,000
- 7 Beds
- 3 Baths
- 2,400 Sq Ft
Unlisted Address

Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space.

Frank J. Berg Broker/Owner Town & Country Real Estate

Unlisted Address
/19
$579,000
- 11 Beds
- 5.5 Baths
- 5,233 Sq Ft
150 Oak St, Winsted, CT 06098

150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3-4 bedroom, 1 1/2 bath unit with electric

Pamela Silvestri Turning Point Realty, LLC

150 Oak St, Winsted, CT 06098
/38
$749,000

$20K PRICE DROP
- 4 Beds
- 3.5 Baths
- 2,265 Sq Ft
121 W Wakefield Blvd, Winsted, CT 06098

Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

Elizabeth Stockwell Coldwell Banker Realty

121 W Wakefield Blvd, Winsted, CT 06098
/36
$1,850,000
- 9 Beds
- 5.5 Baths
- 7,000 Sq Ft
431 W Wakefield Blvd, Winsted, CT 06098

Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

Lisa Ogren Berkshire Hathaway NE Prop.

431 W Wakefield Blvd, Winsted, CT 06098
/15
$799,000

$60K PRICE DROP
- Land
- 65.29 Acres
- $12,238 per Acre
257-259 Torringford St, Winchester, CT 06098

Uncover this hidden gem - 65.29 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views and incredible sunsets can be enjoyed from the property. Much site work has been done to date. A driveway with a binder course is already in place offering easy access into and throughout the property. Many acres have

Lisa Toczko Home Valley Realty, LLC

257-259 Torringford St, Winchester, CT 06098
/2
$299,900
- Land
- 34 Acres
- $8,821 per Acre
00 Ramsgate Ln, Barkhamsted, CT 06063

30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

00 Ramsgate Ln, Barkhamsted, CT 06063
/21
$879,990
- Land
- 131.5 Acres
- $6,692 per Acre
000000 Norfolk Rd, Winchester, CT 06098

Rare Multi-Parcel Land Opportunity 5 Contiguous Parcels | Colebrook & Winchester, CT Discover an exceptional land offering spanning five contiguous parcels across two of Litchfield County's most desirable rural towns. This unique property features a strong presence in highly sought-after Colebrook, known for its scenic beauty, low-density living, and unspoiled New England charm-paired with the

John Harney William Pitt Sotheby's Int'l

000000 Norfolk Rd, Winchester, CT 06098
/8
$389,000
- Land
- 20.87 Acres
- $18,639 per Acre
7 Stadler Heights, Winsted, CT 06098

Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39 minutes

Hector Ortiz KW Legacy Partners

7 Stadler Heights, Winsted, CT 06098
/9
$850,000

$149K PRICE DROP
- Land
- 116.5 Acres
- $7,296 per Acre
82 Riverton Rd, Colebrook, CT 06021

Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

Suzie Larson Turning Point Realty, LLC

82 Riverton Rd, Colebrook, CT 06021
/5
$1,350,000
- Land
- 124.92 Acres
- $10,807 per Acre
0 Winsted Norfolk Rd Unit 24089254, Colebrook, CT 06021

Intriguing Litchfield County / Colebrook CT Location: Great Opportunity to Own this Surveyed 124.92 Acre Site. Excellent Visible Corner Location. Lightly Wooded with Good Road Frontage. Potential as a Commercial / Residential Development, Private Estate Style Compound, Agricultural Use. Put your imagination to work here. Includes an existing Golf Driving Range at the Corner of Route 44

Marshall Cohen Cohen Agency

0 Winsted Norfolk Rd Unit 24089254, Colebrook, CT 06021
/37
$449,000

$101K PRICE DROP
- 5 Beds
- 4 Baths
- 5,016 Sq Ft
55 Walnut St, Winsted, CT 06098

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 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

David Sartirana

Northwest CT Realty

(860) 390-5071

55 Walnut St, Winsted, CT 06098
/5
$158,000

$3K PRICE INCREASE
- Land
- 1.18 Acres
- $133,898 per Acre
843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

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

David D'Amore Northwest CT Realty

843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
/2
$59,900

$9K PRICE DROP
- Land
- 17,859 Sq Ft
- $146,098 per Acre
105,107 E Mountain Rd, Winchester, CT 06098

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

David D'Amore Northwest CT Realty

105,107 E Mountain Rd, Winchester, CT 06098
/5
$295,000
- Land
- 51 Acres
- $5,784 per Acre
393 Winchester Rd, Winsted, CT 06098

WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

Tom McGowan Elyse Harney Real Estate

393 Winchester Rd, Winsted, CT 06098

Connecticut Litchfield County Winchester

Frequently Asked Questions

What is the average home price in Winchester, CT?

Homes for sale in Winchester, CT have an average home price of $347,425.

Are home prices dropping in Winchester?

Yes, home prices in Winchester are down 13% in the last 12 months.

How many homes have sold over the last 12 months in Winchester, CT?

4 homes have sold in Winchester, CT over the last 12 months.

What is the average household income in Winchester, CT?

The average household income in Winchester, CT is $87K.

What are the most popular zip codes in Winchester, CT?

The most popular zip codes in Winchester, CT include 06098, 06790, 06021, 06058 and 06063.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $349,900. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $1,770 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $76K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $87K.

How are the schools in Winchester, CT?

Winchester, CT has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Colebrook Consolidated School, Lakeview High School and Northwestern Regional High School. Browse all the schools in Winchester, CT to learn more.

Home Prices in Winchester, CT

The median home sale price in Winchester, CT is $345,000, down 10% year-over-year. Homes in Winchester sell in 50 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $345,000	Median Single Family Sale Price $345,000
Median 2 Bedroom Sale Price $370,000	Average Price Per Sq Ft $248
Number of Homes for Sale 0	Last 12 months Home Sales 4
Months of Supply 0.00	Median List Price $349,900
Median Change From 1st List Price -2%	Median Home Sale Price YoY Change -10%

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Winchester Types of Homes for Sale

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