Winchester, CT homes for sale & real estate

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355 W Lake St, Winchester, CT 06098
355 W Lake St, Winchester, CT 06098
355 W Lake St, Winchester, CT 06098
ABOUT THIS HOME
Winchester, CT Homes 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 positioned beside Holland Beach for the ultimate lake lifestyle. Thoughtfully designed and meticulously maintained, the home spans over 3,200 square feet, delivering both impressive scale and everyday livability. The main level is ideal for one-floor living and entertaining, with an open-concept layout that includes a spacious kitchen with large center island, a sunlit dining area, and a living room that flows seamlessly on

$979,000

5 beds3.5 baths3,216 sq ft

355 W Lake St, Winchester, CT 06098

0.51 acre lot • Car-dependent

150 Mathew Rd, Winchester, CT 06098
150 Mathew Rd, Winchester, CT 06098
150 Mathew Rd, Winchester, CT 06098
ABOUT THIS HOME
Winchester, CT Homes for Sale
Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. Photos to come. 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

$349,000

3 beds2 baths1,480 sq ft

150 Mathew Rd, Winchester, CT 06098

7,405 sq ft lot • Car-dependent

$158,000

1 bed1.5 baths1,172 sq ft

9 John St, Winchester, CT 06098

2,613 sq ft lot • Car-dependent

$995,000

4 beds2 baths3,088 sq ft

469 Platt Hill Rd, Winchester, CT 06098

7.11 acre lot • Car-dependent

$579,999

3 beds2 baths1,744 sq ft

144 Marshall St, Winchester, CT 06098

55 acre lot • 5 garage spots • Car-dependent

Property at 9 Loomis St, Winchester, CT 06098, 3 beds, 2 baths

$165,000

3 beds2 baths1,768 sq ft

9 Loomis St, Winchester, CT 06098

Property at 120 Torrington Rd, Winchester, CT 06098, 5 beds, 2 baths

$260,000

5 beds2 baths1,962 sq ft

120 Torrington Rd, Winchester, CT 06098

Property at 119 W Wakefield Blvd, Winchester, CT 06098, 4 beds, 2 baths

$849,900

4 beds2 baths1,781 sq ft

119 W Wakefield Blvd, Winchester, CT 06098

Property at 51 Pratt St, Winchester, CT 06098, 4 beds, 1.5 baths

$450,000

4 beds1.5 baths2,239 sq ft

51 Pratt St, Winchester, CT 06098

Property at 175 Main St, Winchester, CT 06098, 14 beds, 7 baths

$950,000

14 beds7 baths4,860 sq ft

175 Main St, Winchester, CT 06098

Property at 55 Walnut St, Winchester, CT 06098, 5 beds, 2.5 baths

$525,000

5 beds2.5 baths5,016 sq ft

55 Walnut St, Winchester, CT 06098

Property at 538 Wheelers Pt, Winchester, CT 06098, 4 beds, 3 baths

$1,699,500

4 beds3 baths2,496 sq ft

538 Wheelers Pt, Winchester, CT 06098

Property at 435/434 W Wakefield Blvd, Winchester, CT 06098, 8 beds, 4.5 baths

$1,500,000

8 beds4.5 baths5,231 sq ft

435/434 W Wakefield Blvd, Winchester, CT 06098

Property at 431 W Wakefield Blvd, Winchester, CT 06098, 9 beds, 5.5 baths

$2,600,000

9 beds5.5 baths7,000 sq ft

431 W Wakefield Blvd, Winchester, CT 06098

Property at 711 W Wakefield Blvd, Winchester, CT 06098, 3 beds, 2.5 baths

$1,500,000

3 beds2.5 baths2,664 sq ft

711 W Wakefield Blvd, Winchester, CT 06098

Property at 18-4A Taylor Brook Rd, Winchester, CT 06098, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths2,135 sq ft

18-4A Taylor Brook Rd, Winchester, CT 06098

Property at 129 Shore Dr, Winchester, CT 06098

$225,000

— beds— baths— sq ft

129 Shore Dr, Winchester, CT 06098

Property at Old Robertsville Rd, Winchester, CT 06098

$739,900

— beds— baths2,304 sq ft

Old Robertsville Rd, Winchester, CT 06098

Property at 320 White Oak Trl, Winchester, CT 06098

$17,999

— beds— baths— sq ft

320 White Oak Trl, Winchester, CT 06098

Property at 99 Hubbard St, Winchester, CT 06098

$49,000

— beds— baths832 sq ft

99 Hubbard St, Winchester, CT 06098

Property at 48 Bridge St, Winchester, CT 06098

$23,900

— beds— baths1,428 sq ft

48 Bridge St, Winchester, CT 06098

Property at 124 Rockwell St, Winchester, CT 06098

$29,000

— beds— baths1,882 sq ft

124 Rockwell St, Winchester, CT 06098

Property at 19 Hill St, Winchester, CT 06098

$23,900

— beds— baths— sq ft

19 Hill St, Winchester, CT 06098

Property at 32 norfolk Rd, Winchester, CT 06098

$299,900

— beds— baths360 sq ft

32 norfolk Rd, Winchester, CT 06098

Property at 843-845 (lots - 10A,10 &1 E wakefield Blvd, Winchester, CT 06098

$158,000

— beds— baths— sq ft

843-845 (lots - 10A,10 &1 E wakefield Blvd, Winchester, CT 06098

Property at 256 Colebrook Rd, Winchester, CT 06098

$39,900

— beds— baths— sq ft

256 Colebrook Rd, Winchester, CT 06098

Property at 393 Winchester Rd, Winchester, CT 06098

$295,000

— beds— baths— sq ft

393 Winchester Rd, Winchester, CT 06098

$59,900

— beds— baths— sq ft

105,107 Mountain Rd, Winchester, CT 06098

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Average home prices near Winchester, CT

Cities

Zip Codes
Minor Civil Divisions

Winchester, CT real estate trends

$275K

Sale price

+8.9%
since last year

$171

Sale $/sq ft

+14.0%
since last year

Over list price

0.3%

Days on market

Down payment

20.0%

Total homes sold

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