Recently Sold Homes in Litchfield County, CT

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SOLD NOV 10, 2026

ABOUT THIS HOME
Recently Sold Home in Litchfield County, CT:
Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a bygone era. A welcoming foyer leads to the formal living room, formal dining room with pantry, spacious eat-in kitchen, comfortable family room, half bath, and convenient first-floor laundry. The living room features a fireplace that has been sealed but offers the potential to be restored, while the ki

$305,000 Last sold price

4 beds1.5 baths2,722 sq ft

70 Walnut St, Winsted, CT 06098

SOLD SEP 4, 2026

ABOUT THIS HOME
Recently Sold Home in Litchfield County, CT:
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 gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into

$1,850,000 Last sold price

9 beds5.5 baths7,000 sq ft

431 W Wakefield Blvd, Winsted, CT 06098

SOLD AUG 31, 2026

ABOUT THIS HOME
Recently Sold Home in Litchfield County, CT:
PRICE REDUCTION !! 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 in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent majo

$670,000 Last sold price

4 beds3.5 baths2,265 sq ft

121 W Wakefield Blvd, Winsted, CT 06098

SOLD OCT 2, 2026

ABOUT THIS HOME
Recently Sold Home in Litchfield County, CT:
This 4-Acre home is nestled along scenic Kent Road in the heart of charming Warren, Connecticut. Located a short drive from many of Litchfield County's active downtowns and amenities. Whether you seek fine dining, boutique shopping, skiing, hiking, or lakeside leisure, this location is in the heart of it all. This exceptional property offers a rare blend of serene privacy, natural beauty, and limitless potential. The acreage connects to the Warren Land Trust, creating a breathtaking backdrop of classic New England nature. Envision a custom home site with sweeping views, inviting entertaining areas, expanded gardens, and classic stone walls all while maintaining the peaceful, wooded seclusio

$775,000 Last sold price

4 beds2.5 baths3,948 sq ft

34 Kent Rd, Warren, CT 06754

SOLD SEP 23, 2026

ABOUT THIS HOME
Recently Sold Home in Litchfield County, CT:
Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of beautiful wood floors throughout. The open floor plan creates a sense of airiness and flow, while large windows bring the surrounding nature indoors. Whether you're relaxing in the peaceful primary bedroom or gathering in the inviting living area, every space feels serene and connected to the outdoors. The

$710,000 Last sold price

3 beds2.5 baths2,336 sq ft

38 W Mountain Ln, Roxbury, CT 06783

Property at 18 Ranney Hill Rd, Roxbury, CT 06783, 4 beds, 3.5 baths

$1,795,000 Last sold price

4 beds3.5 baths3,198 sq ft

18 Ranney Hill Rd, Roxbury, CT 06783

Property at 286 South St, Roxbury, CT 06783, 5 beds, 4 baths

$995,000 Last sold price

5 beds4 baths2,804 sq ft

286 South St, Roxbury, CT 06783

Property at 28 Garnet Rd, Roxbury, CT 06783, 3 beds, 3.5 baths

$960,000 Last sold price

3 beds3.5 baths3,696 sq ft

28 Garnet Rd, Roxbury, CT 06783

Property at 8 Bayberry Hl, Roxbury, CT 06783, 5 beds, 5 baths

$3,340,000 Last sold price

5 beds5 baths5,940 sq ft

8 Bayberry Hl, Roxbury, CT 06783

Property at 94 Judds Bridge Rd, Roxbury, CT 06783, 2 beds, 1.5 baths

$583,000 Last sold price

2 beds1.5 baths1,990 sq ft

94 Judds Bridge Rd, Roxbury, CT 06783

Property at 188 Bacon Rd, Roxbury, CT 06783, 2 beds, 2 baths

$597,000 Last sold price

2 beds2 baths1,192 sq ft

188 Bacon Rd, Roxbury, CT 06783

Property at 21 Hemlock Rd, Roxbury, CT 06783, 4 beds, 3 baths

$1,525,000 Last sold price

4 beds3 baths2,200 sq ft

21 Hemlock Rd, Roxbury, CT 06783

Property at 20 Wellers Bridge Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$695,000 Last sold price

3 beds2.5 baths2,059 sq ft

20 Wellers Bridge Rd, Roxbury, CT 06783

Property at 692 Kent Rd, Gaylordsville, CT 06755, 2 beds, 1 bath

$329,000 Last sold price

2 beds1 bath1,825 sq ft

692 Kent Rd, Gaylordsville, CT 06755

Property at 20 Timber Ln, New Milford, CT 06776, 4 beds, 3.5 baths

$695,000 Last sold price

4 beds3.5 baths2,347 sq ft

20 Timber Ln, New Milford, CT 06776

Property at 32 Ferris Estates Rd, New Milford, CT 06776, 3 beds, 4 baths

$1,417,000 Last sold price

3 beds4 baths3,800 sq ft

32 Ferris Estates Rd, New Milford, CT 06776

Property at 256 Ridge Rd, New Milford, CT 06776, 2 beds, 1 bath

$410,000 Last sold price

2 beds1 bath1,144 sq ft

256 Ridge Rd, New Milford, CT 06776

Property at 21 Mine Hill Rd, New Milford, CT 06776, 4 beds, 2.5 baths

$540,000 Last sold price

4 beds2.5 baths2,500 sq ft

21 Mine Hill Rd, New Milford, CT 06776

Property at 22 Big Bear Hill Rd, New Milford, CT 06776, 4 beds, 3.5 baths

$712,000 Last sold price

4 beds3.5 baths4,148 sq ft

22 Big Bear Hill Rd, New Milford, CT 06776

Property at 16 Sawyer Hill Rd, New Milford, CT 06776, 2 beds, 1 bath

$200,000 Last sold price

2 beds1 bath744 sq ft

16 Sawyer Hill Rd, New Milford, CT 06776

Property at 25 Maple Dr, New Milford, CT 06776, 2 beds, 3 baths

$420,000 Last sold price

2 beds3 baths1,990 sq ft

25 Maple Dr, New Milford, CT 06776

Redfin Corporation

Property at 99 Great Brook Rd, New Milford, CT 06776, 4 beds, 2.5 baths

$423,000 Last sold price

4 beds2.5 baths2,866 sq ft

99 Great Brook Rd, New Milford, CT 06776

Property at 118 Sherry Ln, New Milford, CT 06776, 3 beds, 2 baths

$725,000 Last sold price

3 beds2 baths912 sq ft

118 Sherry Ln, New Milford, CT 06776

Property at 36 Maple Dr, New Milford, CT 06776, 3 beds, 2 baths

$439,000 Last sold price

3 beds2 baths1,069 sq ft

36 Maple Dr, New Milford, CT 06776

Property at 123 Wynwood Dr, New Milford, CT 06776, 4 beds, 2 baths

$505,000 Last sold price

4 beds2 baths2,448 sq ft

123 Wynwood Dr, New Milford, CT 06776

Property at 128 Carmen Hill Rd, New Milford, CT 06776, 4 beds, 2.5 baths

$707,000 Last sold price

4 beds2.5 baths3,032 sq ft

128 Carmen Hill Rd, New Milford, CT 06776

Property at 8 Pebble Ln, New Milford, CT 06776, 4 beds, 2.5 baths

$580,000 Last sold price

4 beds2.5 baths2,990 sq ft

8 Pebble Ln, New Milford, CT 06776

Property at 7 Treadwell Ave, New Milford, CT 06776, 3 beds, 2 baths

$595,000 Last sold price

3 beds2 baths2,124 sq ft

7 Treadwell Ave, New Milford, CT 06776

Property at 10 Clearview Dr, New Milford, CT 06776, 3 beds, 1 bath

$412,500 Last sold price

3 beds1 bath1,394 sq ft

10 Clearview Dr, New Milford, CT 06776

Property at 14 Paper Mill Rd, New Milford, CT 06776, 3 beds, 2.5 baths

$550,000 Last sold price

3 beds2.5 baths2,259 sq ft

14 Paper Mill Rd, New Milford, CT 06776

Property at 32 Aspetuck Ave, New Milford, CT 06776, 5 beds, 2.5 baths

$805,500 Last sold price

5 beds2.5 baths2,822 sq ft

32 Aspetuck Ave, New Milford, CT 06776

Property at 85 Prospect Hill Rd, New Milford, CT 06776, 12 beds, 8 baths

$1,545,000 Last sold price

12 beds8 baths8,891 sq ft

85 Prospect Hill Rd, New Milford, CT 06776

Property at 16 Jotham Rd, New Milford, CT 06776, 4 beds, 3 baths

$515,000 Last sold price

4 beds3 baths3,098 sq ft

16 Jotham Rd, New Milford, CT 06776

Property at 214 Pumpkin Hill Rd, New Milford, CT 06776, 3 beds, 2 baths

$400,000 Last sold price

3 beds2 baths1,842 sq ft

214 Pumpkin Hill Rd, New Milford, CT 06776

Property at 28 Meetinghouse Ter, New Milford, CT 06776, 3 beds, 2 baths

$553,300 Last sold price

3 beds2 baths1,684 sq ft

28 Meetinghouse Ter, New Milford, CT 06776

Property at 11 Clearview Dr, New Milford, CT 06776, 3 beds, 1 bath

$375,000 Last sold price

3 beds1 bath1,304 sq ft

11 Clearview Dr, New Milford, CT 06776

Property at 255 Aspetuck Ridge Rd, New Milford, CT 06776, 2 beds, 2 baths

$600,000 Last sold price

2 beds2 baths1,410 sq ft

255 Aspetuck Ridge Rd, New Milford, CT 06776

Property at 15 Morey Rd, New Milford, CT 06776, 4 beds, 3 baths

$615,000 Last sold price

4 beds3 baths1,886 sq ft

15 Morey Rd, New Milford, CT 06776

Property at 5 Geiger Rd, New Milford, CT 06776, 3 beds, 2 baths

$385,000 Last sold price

3 beds2 baths1,342 sq ft

5 Geiger Rd, New Milford, CT 06776

Property at 18 Stephanie Dr, New Milford, CT 06776, 3 beds, 2.5 baths

$632,000 Last sold price

3 beds2.5 baths3,695 sq ft

18 Stephanie Dr, New Milford, CT 06776

Property at 23 Cathryn St, New Milford, CT 06776, 4 beds, 1.5 baths

$329,000 Last sold price

4 beds1.5 baths1,836 sq ft

23 Cathryn St, New Milford, CT 06776

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Recently Sold Homes in Litchfield County

There are currently 646 recently sold homes for sale in Litchfield County at a median listing price of $485K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Litchfield County stay on the market for 59 days and receive 2 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 188 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 142 condos, 0 townhouses, and 63 multi-family units for sale in Litchfield County last month. Find your dream home in Litchfield County 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 Litchfield County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Litchfield County. If you're looking to sell your home in the Litchfield County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Litchfield County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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* Data from the last year

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