Recent sales in Winchester
5,629 parcels, median assessed value $138,600. 230 sales recorded in the 12 months to April 14, 2026, median $290,000.
| Address | Date | Price | Assessed | Use |
|---|---|---|---|---|
| 35 Glendale Ave | April 14, 2026 | $410,000 | $176,050 | Single Family |
| 35 Glendale Ave | April 14, 2026 | $410,000 | $176,050 | Single Family |
| 35 Glendale Ave | April 14, 2026 | $410,000 | $176,050 | Single Family |
| 35 Glendale Ave | April 14, 2026 | $410,000 | $176,050 | Single Family |
| 35 Glendale Ave | April 14, 2026 | $410,000 | $176,050 | Single Family |
| 35 Glendale Ave | April 14, 2026 | $410,000 | $176,050 | Single Family |
| Maloney Ct Ext | April 14, 2026 | $410,000 | $2,310 | Resvac Unb |
| 25 Center St | April 10, 2026 | $315,000 | $104,020 | Res/Com |
| 95 Colony Dr | April 9, 2026 | $316,000 | $110,740 | Single Family |
| 9 John St | April 8, 2026 | $225,000 | $104,790 | Single Family |
| 44 Lewis St | April 8, 2026 | $340,000 | $134,680 | Single Family |
| 9 Central Ave | April 7, 2026 | $266,500 | $115,990 | Single Family |
| 9 Central Ave | April 7, 2026 | $266,500 | $115,990 | Single Family |
| 171 Wallens St | March 30, 2026 | $370,000 | $119,910 | Single Family |
| 256 Colebrook Rd | March 23, 2026 | $33,500 | $39,620 | Res Vacant |
| 181 Torringford St | March 19, 2026 | $310,000 | $176,260 | Single Family |
| 106 Rockwell St | March 19, 2026 | $230,000 | $125,300 | Three Family |
| 604 W Wakefield Blvd | March 18, 2026 | $309,741 | $303,380 | Waterfront |
| 38 Upland Rd | March 16, 2026 | $240,000 | $136,220 | Single Family |
| 21 Riveredge Dr | March 13, 2026 | $160,000 | $82,950 | Condo |
| Riveredge Dr #G3 | March 13, 2026 | $160,000 | $6,510 | Condo |
| 155 Rockwell St | March 13, 2026 | $151,000 | $137,900 | Single Family |
| 157 Elm St | March 11, 2026 | $330,000 | $120,050 | Single Family |
| 8 Oak St | March 9, 2026 | $154,600 | $62,370 | Single Family |
| 52 White St | March 5, 2026 | $33,000 | $121,450 | Res Vacant |
| 11 Gibbs St #9 | March 5, 2026 | $101,600 | $49,910 | Condo |
| 123 Wetmore Ave | March 4, 2026 | $330,000 | $98,980 | Single Family |
| 148 Danbury Quarter Rd | March 3, 2026 | $320,000 | $166,250 | Single Family |
| 197 Spencer Hill Rd | March 3, 2026 | $475,000 | $273,420 | Single Family |
| 187 Torringford St | March 3, 2026 | $360,000 | $303,100 | Single Family |
| 311 Taylor Brook Rd | March 3, 2026 | $425,000 | $246,470 | Single Family |
| 43 Wallens St | March 3, 2026 | $250,000 | $153,580 | Two Family |
| 150 Ashley Rd | February 12, 2026 | $412,894 | $184,170 | Single Family |
| 440 Platt Hill Rd | February 12, 2026 | $440,000 | $407,190 | Multi Hses |
| 817 E Wakefield Blvd | February 12, 2026 | $231,000 | $337,050 | Direct Water Access |
| E Wakefield Blvd | February 12, 2026 | $231,000 | $18,550 | Resvac Unb |
| 18 Curtice St | February 12, 2026 | $229,000 | $114,590 | Single Family |
| 375 Platt Hill Rd | February 11, 2026 | $370,000 | $236,670 | Single Family |
| 151 Losaw Rd | February 10, 2026 | $690,000 | $361,550 | Single Family |
| 117 South Rd | February 9, 2026 | $375,000 | $282,730 | Single Family |
| 107 Peck Rd | February 9, 2026 | $309,250 | $122,500 | Single Family |
| 50 Benton St | February 3, 2026 | $275,000 | $121,310 | Two Family |
| 208 Spencer Hill Rd | January 27, 2026 | $385,000 | $201,950 | Single Family |
| 24 Riveredge Dr | January 27, 2026 | $20,000 | $82,950 | Condo |
| Riveredge Dr #G8 | January 27, 2026 | $20,000 | $6,510 | Condo |
| 45 Riveredge Dr | January 22, 2026 | $185,000 | $82,950 | Condo |
| Riveredge Dr #G22 | January 22, 2026 | $185,000 | $6,510 | Condo |
| 61 Rock St | January 14, 2026 | $240,000 | $94,990 | Single Family |
| 216 Perch Rock Trail | January 12, 2026 | $1,000,000 | $567,770 | Waterfront |
| 216 Perch Rock Trail | January 12, 2026 | $1,000,000 | $567,770 | Waterfront |
| Blue St | January 8, 2026 | $500,000 | $272,580 | Res Vacant |
| 10 Crescent St | January 8, 2026 | $280,000 | $119,980 | Two Family |
| 111 Riverton Rd #90 | January 6, 2026 | $171,000 | $98,140 | Condo |
| 409 W Wakefield Blvd | January 6, 2026 | $500,000 | $249,690 | Direct Water Access |
| W Wakefield Blvd | January 6, 2026 | $500,000 | $19,670 | Resvac Unb |
| 49 Walnut St | December 31, 2025 | $305,000 | $141,960 | Two Family |
| 183 Main St | December 30, 2025 | $780,000 | $215,250 | Res/Com |
| 175 Main St | December 30, 2025 | $780,000 | $195,370 | Res/Com |
| 99 Norfolk Rd | December 29, 2025 | $180,000 | $120,400 | Single Family |
| 73 Norfolk Rd | December 23, 2025 | $260,000 | $169,610 | Single Family |
| 68 Wetmore Ave | December 23, 2025 | $190,000 | $149,310 | Two Family |
| 142 Main St | December 23, 2025 | $255,000 | $263,130 | Four Family |
| 28 Spring St | December 18, 2025 | $260,000 | $228,760 | Single Family |
| 142 Mountain Rd | December 17, 2025 | $206,000 | $121,170 | Single Family |
| 38 Riveredge Dr | December 15, 2025 | $135,800 | $64,400 | Condo |
| Riveredge Dr #G29 | December 15, 2025 | $135,800 | $6,510 | Condo |
| 32 Charles St | December 11, 2025 | $225,000 | $123,130 | Single Family |
| 111 Riverton Rd #61 | December 9, 2025 | $194,900 | $99,120 | Condo |
| 819 E Wakefield Blvd | December 8, 2025 | $439,900 | $271,880 | Single Family |
| 101 Norfolk Rd | December 4, 2025 | $270,000 | $128,590 | Single Family |
| 39 Orchard St | December 3, 2025 | $290,000 | $137,830 | Single Family |
| 30 Rock St | November 26, 2025 | $235,000 | $123,620 | Two Family |
| 135-137 Elm St | November 24, 2025 | $324,900 | $190,540 | Two Family |
| 147 Smith Hill Rd | November 19, 2025 | $362,000 | $200,550 | Single Family |
| 22 Curtice St | November 19, 2025 | $243,000 | $156,800 | Single Family |
| 331 Colebrook Rd | November 18, 2025 | $300,000 | $131,320 | Single Family |
| 166 Torringford St | November 17, 2025 | $370,000 | $210,700 | Single Family |
| 28 Union St | November 17, 2025 | $280,000 | $115,080 | Three Family |
| 14 Pratt St | November 17, 2025 | $167,900 | $75,810 | Single Family |
| 548 E Wakefield Blvd | November 10, 2025 | $425,000 | $311,080 | Waterfront |
| 21 Thibault Ave | November 10, 2025 | $389,900 | $13,930 | ResVac Po |
| 21 Thibault Ave | November 10, 2025 | $389,900 | $13,930 | ResVac Po |
| 27 Thibault Ave | November 10, 2025 | $389,900 | $185,360 | Multi Hses |
| 132 Alpha Ave | November 10, 2025 | $29,000 | $5,320 | ResVac Po |
| 132 Alpha Ave | November 10, 2025 | $29,000 | $5,320 | ResVac Po |
| 130 Alpha Ave | November 10, 2025 | $29,000 | $2,170 | Resvac Unb |
| 130 Alpha Ave | November 10, 2025 | $29,000 | $2,170 | Resvac Unb |
| 126 Bayview Rd | November 10, 2025 | $29,000 | $2,170 | Resvac Unb |
| 126 Bayview Rd | November 10, 2025 | $29,000 | $2,170 | Resvac Unb |
| 124 Bayview Rd | November 10, 2025 | $29,000 | $2,100 | Resvac Unb |
| 124 Bayview Rd | November 10, 2025 | $29,000 | $2,100 | Resvac Unb |
| 152 East Lake St | November 5, 2025 | $310,000 | $115,500 | Single Family |
| 152 East Lake St | November 5, 2025 | $310,000 | $115,500 | Single Family |
| 179 Pratt St | November 5, 2025 | $300,000 | $328,230 | School |
| 212 Torringford St | November 4, 2025 | $282,000 | $197,400 | Single Family |
| 212 Torringford St | November 4, 2025 | $282,000 | $197,400 | Single Family |
| 12 Cherry St | November 4, 2025 | $277,000 | $151,830 | Single Family |
| 40 Colony Dr | November 4, 2025 | $205,000 | $132,720 | Single Family |
| 62-64 Fruit St | November 3, 2025 | $336,000 | $139,650 | Two Family |
| 115 Wallens St | November 3, 2025 | $345,000 | $181,160 | Single Family |
| 131-133 Willow St | November 3, 2025 | $293,000 | $93,590 | Two Family |
| 113 Old North Rd | October 31, 2025 | $388,750 | $50,750 | Res Vacant |
| 111 Old North Rd | October 31, 2025 | $388,750 | $164,780 | Single Family |
| 111 Riverton Rd #37 | October 30, 2025 | $198,000 | $98,140 | Condo |
| 15 John St | October 30, 2025 | $288,557 | $145,740 | Single Family |
| 126 Forest Ave | October 29, 2025 | $375,000 | $182,280 | Single Family |
| 649 Jewell Rd | October 28, 2025 | $8,400 | $5,180 | ResVac Po |
| 210 Walnut St | October 24, 2025 | $240,000 | $139,440 | Single Family |
| 160 Walnut St | October 22, 2025 | $320,000 | $116,480 | Single Family |
| 115 Laurel Way | October 21, 2025 | $261,000 | $99,260 | Single Family |
| 538 Wheelers Pt | October 15, 2025 | $1,500,000 | $938,560 | Waterfront |
| 36 Whiting St | October 8, 2025 | $310,000 | $128,310 | Single Family |
| 128 Danbury Quarter Rd | October 1, 2025 | $320,000 | $132,650 | Single Family |
| 17 Adams St | September 30, 2025 | $315,000 | $110,670 | Single Family |
| 50 Manchester Hgts | September 29, 2025 | $330,000 | $134,820 | Single Family |
| 22 Stanton Ave | September 29, 2025 | $270,000 | $112,070 | Single Family |
| 3 Stadler Heights | September 26, 2025 | $340,000 | $268,240 | Single Family |
| 226 E Wakefield Blvd | September 26, 2025 | $380,000 | $154,210 | Single Family |
| 226 E Wakefield Blvd | September 26, 2025 | $380,000 | $154,210 | Single Family |
| 1 Hamill Dr | September 24, 2025 | $180,000 | $134,610 | Single Family |
| 129 Forest Ave | September 23, 2025 | $112,000 | $255,780 | Single Family |
| 20 Case Ave | September 22, 2025 | $300,000 | $96,110 | Four Family |
| 920 Main St | September 19, 2025 | $275,000 | $212,870 | Res/Com |
| 740 Lake Dr | September 17, 2025 | $880,000 | $525,770 | Waterfront |
| 740 Lake Dr | September 17, 2025 | $880,000 | $525,770 | Waterfront |
| 179 Gilbert Ave | September 15, 2025 | $275,000 | $112,630 | Single Family |
| 267 Rockwell St | September 15, 2025 | $302,500 | $160,300 | Three Family |
| 39 Colony Dr | September 15, 2025 | $279,900 | $150,710 | Single Family |
| 435 W Wakefield Blvd | September 11, 2025 | $1,215,000 | $546,560 | Direct Water Access |
| 434 W Wakefield Blvd | September 11, 2025 | $1,215,000 | $307,440 | Waterfront |
| 41 Lovely St | September 11, 2025 | $383,000 | $164,360 | Two Family |
| 155 Spencer St | September 10, 2025 | $455,000 | $240,380 | Two Family |
| 185 Stanton Ave | September 10, 2025 | $262,000 | $166,740 | Single Family |
| 42 Maloney Ct | September 10, 2025 | $240,000 | $130,200 | Single Family |
| 409 N Main St | September 5, 2025 | $388,000 | $141,470 | Two Family |
| 107 Old North Rd | September 4, 2025 | $320,000 | $172,130 | Single Family |
| 279 Pratt St | September 2, 2025 | $290,000 | $166,670 | Single Family |
| 30 Mountain Ave | September 2, 2025 | $178,500 | $121,590 | Single Family |
| 53 Norfolk Rd | August 28, 2025 | $250,000 | $128,870 | Single Family |
| 415 N Main St | August 26, 2025 | $172,500 | $107,660 | Single Family |
| 29 Walnut St | August 26, 2025 | $321,000 | $230,860 | Three Family |
| 233 Grantville Rd | August 25, 2025 | $250,000 | $141,610 | Single Family |
| 343 W Wakefield Blvd | August 25, 2025 | $236,434 | $150,150 | Single Family |
| 440 Main St | August 21, 2025 | $230,000 | $184,730 | Res/Com |
| Holabird Ave | August 18, 2025 | $1,900,000 | $28,700 | Land Mft |
| 210 Holabird Ave | August 18, 2025 | $1,900,000 | $348,460 | Warehouse |
| 50 Lakeview Rd | August 15, 2025 | $425,000 | $208,040 | Single Family |
| 141 Maloney Ct | August 13, 2025 | $320,000 | $122,850 | Single Family |
| 710 W Wakefield Blvd | August 12, 2025 | $281,000 | $28,910 | Resvac Unb |
| 711 W Wakefield Blvd | August 12, 2025 | $281,000 | $126,630 | Res Vacant |
| 711 W Wakefield Blvd | August 12, 2025 | $281,000 | $126,630 | Res Vacant |
| 144 Marshall St | August 7, 2025 | $540,000 | $403,270 | Single Family |
| 266 Perch Rock Trail | August 5, 2025 | $800,000 | $402,990 | Waterfront |
| 17 Woodland Ave | August 4, 2025 | $410,000 | $218,960 | Single Family |
| 17 Woodland Ave | August 4, 2025 | $410,000 | $218,960 | Single Family |
| 102 Hollow Hill Rd | August 1, 2025 | $639,000 | $298,270 | Single Family |
| 126-128 Williams Ave | July 28, 2025 | $292,000 | $158,340 | Two Family |
| 101 Ridge St | July 28, 2025 | $280,000 | $140,910 | Single Family |
| 200 Perch Rock Trail | July 24, 2025 | $1,200,000 | $618,310 | Waterfront |
| 896 Main St | July 23, 2025 | $250,000 | $74,410 | Store/Shop |
| 898 Main St | July 23, 2025 | $250,000 | $94,780 | Rest/Club |
| 112 Shore Dr | July 23, 2025 | $862,500 | $456,540 | Waterfront |
| 100 Norfolk Rd | July 22, 2025 | $160,000 | $176,260 | Single Family |
| 284 Gilbert Ave | July 18, 2025 | $325,000 | $161,350 | Single Family |
| 273 Florence St | July 17, 2025 | $275,000 | $105,000 | Single Family |
| 273 Florence St | July 17, 2025 | $275,000 | $105,000 | Single Family |
| 273 Florence St | July 17, 2025 | $275,000 | $105,000 | Single Family |
| 88 Strong Terrace | July 17, 2025 | $282,000 | $165,130 | Single Family |
| 232 Torringford St | July 14, 2025 | $100,000 | $95,130 | Single Family |
| 335 Colebrook Rd | July 11, 2025 | $160,000 | $133,840 | Single Family |
| 208 Walnut St | July 10, 2025 | $378,000 | $213,080 | Single Family |
| 11 Gibbs St #7 | July 8, 2025 | $120,000 | $49,700 | Condo |
| 39 Baker St | July 8, 2025 | $225,000 | $120,540 | Two Family |
| 150 Mathew Rd | July 3, 2025 | $314,000 | $131,950 | Single Family |
| 150 Mathew Rd | July 3, 2025 | $314,000 | $131,950 | Single Family |
| 150 Mathew Rd | July 3, 2025 | $314,000 | $131,950 | Single Family |
| 508 W Wakefield Blvd | July 1, 2025 | $1,575,000 | $1,141,630 | Waterfront |
| 355 W Lake St | June 30, 2025 | $950,000 | $380,590 | Single Family |
| 105 W Wakefield Blvd | June 30, 2025 | $950,000 | $114,240 | Res Vacant |
| 19 Riveredge Dr | June 27, 2025 | $157,500 | $82,950 | Condo |
| W Wakefield Blvd | June 23, 2025 | $500,000 | $18,830 | Resvac Unb |
| 531 W Wakefield Blvd | June 23, 2025 | $500,000 | $480,550 | Direct Water Access |
| W Wakefield Blvd | June 23, 2025 | $500,000 | $20,580 | Resvac Unb |
| 288 Torringford St | June 23, 2025 | $460,000 | $294,350 | Single Family |
| 85 Oak St | June 23, 2025 | $315,000 | $208,180 | Res/Com |
| 174 Boyd St | June 18, 2025 | $280,000 | $108,640 | Single Family |
| 704 W Wakefield Blvd | June 16, 2025 | $495,000 | $246,330 | Waterfront |
| 103 Forest Ave | June 16, 2025 | $495,000 | $3,500 | Resvac Unb |
| Rowley St | June 12, 2025 | $10,000 | $20,020 | Land Pot |
| 421 Unity Place | June 10, 2025 | $286,000 | $102,410 | Single Family |
| 421 Unity Place | June 10, 2025 | $286,000 | $102,410 | Single Family |
| 461 E Wakefield Blvd | June 10, 2025 | $286,000 | $3,500 | Resvac Unb |
| 461 E Wakefield Blvd | June 10, 2025 | $286,000 | $3,500 | Resvac Unb |
| 461 E Wakefield Blvd | June 10, 2025 | $286,000 | $3,500 | Resvac Unb |
| 355 St Catherine St | June 9, 2025 | $250,000 | $1,960 | Resvac Unb |
| 323 E Wakefield Blvd | June 5, 2025 | $397,000 | $162,260 | Single Family |
| 323 E Wakefield Blvd | June 5, 2025 | $397,000 | $162,260 | Single Family |
| 323 E Wakefield Blvd | June 5, 2025 | $397,000 | $162,260 | Single Family |
| 323 E Wakefield Blvd | June 5, 2025 | $397,000 | $162,260 | Single Family |
| 323 E Wakefield Blvd | June 5, 2025 | $397,000 | $162,260 | Single Family |
| 323 E Wakefield Blvd | June 5, 2025 | $397,000 | $162,260 | Single Family |
| 269 Walnut St | June 5, 2025 | $45,000 | $33,530 | Municipal |
| 150 Meadow St | June 5, 2025 | $255,000 | $128,030 | Single Family |
| 125 Ridge St | June 5, 2025 | $400,000 | $27,580 | Res Vacant |
| 155 Mathew Rd | June 2, 2025 | $314,000 | $115,360 | Single Family |
| 155 Mathew Rd | June 2, 2025 | $314,000 | $115,360 | Single Family |
| 9 Loomis St | May 29, 2025 | $144,000 | $103,950 | Single Family |
| 104 Norfolk Rd | May 22, 2025 | $8,000 | $45,500 | Municipal |
| 47 Moore Ave | May 22, 2025 | $322,000 | $125,370 | Single Family |
| 154 Wallens St | May 19, 2025 | $190,000 | $110,320 | Two Family |
| 37 Riveredge Dr | May 12, 2025 | $160,000 | $82,950 | Condo |
| 39 Finn St | May 8, 2025 | $269,000 | $94,850 | Single Family |
| 244 Colebrook Rd | May 5, 2025 | $379,000 | $190,330 | Single Family |
| 14 Riveredge Dr | May 5, 2025 | $160,000 | $82,950 | Condo |
| Riveredge Dr #G2 | May 5, 2025 | $160,000 | $6,510 | Condo |
| 50-52 Cottage St | May 2, 2025 | $70,000 | $140,280 | Two Family |
| 110 South Rd | May 1, 2025 | $679,000 | $360,920 | Single Family |
| 18 Upland Rd | May 1, 2025 | $290,000 | $125,160 | Two Family |
| 18 Upland Rd | May 1, 2025 | $290,000 | $125,160 | Two Family |
| 109 Marshall St | April 28, 2025 | $90,000 | $98,420 | Single Family |
| 52 Lakeview Rd | April 28, 2025 | $410,000 | $229,320 | Single Family |
| 151 Elm St | April 28, 2025 | $275,000 | $158,970 | Single Family |
| 315 E Wakefield Blvd | April 23, 2025 | $289,900 | $112,420 | Single Family |
| 315 E Wakefield Blvd | April 23, 2025 | $289,900 | $112,420 | Single Family |
| 315 E Wakefield Blvd | April 23, 2025 | $289,900 | $112,420 | Single Family |
| 315 E Wakefield Blvd | April 23, 2025 | $289,900 | $112,420 | Single Family |
| 493 N Main St | April 21, 2025 | $275,000 | $130,900 | Single Family |
| 139-141 Main St | April 17, 2025 | $250,000 | $173,880 | Rest/Club |
| 58 Cherry St | April 17, 2025 | $275,000 | $139,160 | Single Family |
| 47 Orchard St | April 15, 2025 | $395,000 | $174,720 | Single Family |