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  1. Photo of 7 Wainwright Rd #22, Winchester, MA 01890 (MLS # 73274235)
    $1,495,000
    Photo of 7 Wainwright Rd #22, Winchester, MA 01890 (MLS # 73274235)
    Photo of 7 Wainwright Rd #22, Winchester, MA 01890 (MLS # 73274235)
    27
     
    7 Wainwright Rd #22, Winchester, MA
    7 Wainwright Rd #22
    Winchester, MA
    • 2 Beds
    • 3 Baths
    • 3,350 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  2. Photo of 70 Canal Street, Winchester, MA 01890 (MLS # 73286762)
    $4,000
    Photo of 70 Canal Street, Winchester, MA 01890 (MLS # 73286762)
    Photo of 70 Canal Street, Winchester, MA 01890 (MLS # 73286762)
    18
     
    70 Canal Street, Winchester, MA
    70 Canal Street
    Winchester, MA
    • 4 Beds
    • 2 Baths
    • 1,765 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Quintess Real Estate
  3. Photo of 50 Winford Way, Winchester, MA 01890 (MLS # 73288818)
    $2,599,000
    Photo of 50 Winford Way, Winchester, MA 01890 (MLS # 73288818)
    Photo of 50 Winford Way, Winchester, MA 01890 (MLS # 73288818)
    41
     
    50 Winford Way, Winchester, MA
    50 Winford Way
    Winchester, MA
    • 5 Beds
    • 5 Baths
    • 4,270 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
    Listed with Compass
  4. Photo of 40 Church St #40, Winchester, MA 01890 (MLS # 73293542)
    $4,000
    Photo of 40 Church St #40, Winchester, MA 01890 (MLS # 73293542)
    Photo of 40 Church St #40, Winchester, MA 01890 (MLS # 73293542)
    23
     
    40 Church St #40, Winchester, MA
    40 Church St #40
    Winchester, MA
    • 2 Beds
    • 3 Baths
    • 1,700 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Real Estate by Hughes & Assoc. Inc.
  5. Photo of 40 Church St #C, Winchester, MA 01890 (MLS # 73293540)
    $8,500
    Photo of 40 Church St #C, Winchester, MA 01890 (MLS # 73293540)
    Photo of 40 Church St #C, Winchester, MA 01890 (MLS # 73293540)
    38
     
    40 Church St #C, Winchester, MA
    40 Church St #C
    Winchester, MA
    • 5 Beds
    • 4 Baths
    • 4,200 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Real Estate by Hughes & Assoc. Inc.
  6. Photo of 15 Churchill Road, Winchester, MA 01890 (MLS # 73298854)
    $2,699,000
    Photo of 15 Churchill Road, Winchester, MA 01890 (MLS # 73298854)
    Photo of 15 Churchill Road, Winchester, MA 01890 (MLS # 73298854)
    42
     
    15 Churchill Road, Winchester, MA
    15 Churchill Road
    Winchester, MA
    • 4 Beds
    • 5 Baths
    • 5,501 Home (sqft)
    • 5 Baths
    • 20,038 Lot (sqft)
    Listed with Compass
  7. Photo of 8 Chestnut St, Winchester, MA 01890 (MLS # 73305360)
    $3,299,000
    Photo of 8 Chestnut St, Winchester, MA 01890 (MLS # 73305360)
    Photo of 8 Chestnut St, Winchester, MA 01890 (MLS # 73305360)
    41
     
    8 Chestnut St, Winchester, MA
    8 Chestnut St
    Winchester, MA
    • 5 Beds
    • 6 Baths
    • 5,366 Home (sqft)
    • 6 Baths
    • 16,553 Lot (sqft)
    Listed with Coldwell Banker Realty - Lexington
  8. Photo of 7 Conant Rd #60, Winchester, MA 01890 (MLS # 73307969)
    $749,000
    Photo of 7 Conant Rd #60, Winchester, MA 01890 (MLS # 73307969)
    Photo of 7 Conant Rd #60, Winchester, MA 01890 (MLS # 73307969)
    20
     
    7 Conant Rd #60, Winchester, MA
    7 Conant Rd #60
    Winchester, MA
    • 2 Beds
    • 3 Baths
    • 1,634 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Matahari Real Estate LLC
  9. Photo of 186 Ridge Street, Winchester, MA 01890 (MLS # 73309181)
    $15,000
    Photo of 186 Ridge Street, Winchester, MA 01890 (MLS # 73309181)
    Photo of 186 Ridge Street, Winchester, MA 01890 (MLS # 73309181)
    20
     
    186 Ridge Street, Winchester, MA
    186 Ridge Street
    Winchester, MA
    • 5 Beds
    • 5 Baths
    • 5,820 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
    Listed with Skylight Real Estate, LLC
  10. Photo of 71 Church Street #2, Winchester, MA 01890 (MLS # 73309963)
    $5,250
    Photo of 71 Church Street #2, Winchester, MA 01890 (MLS # 73309963)
    Photo of 71 Church Street #2, Winchester, MA 01890 (MLS # 73309963)
    23
     
    71 Church Street #2, Winchester, MA
    71 Church Street #2
    Winchester, MA
    • 3 Beds
    • 2 Baths
    • 1,620 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Better Homes and Gardens Real Estate - The Shanahan Group
  11. Photo of 3 Lewis Rd #3, Winchester, MA 01890 (MLS # 73310841)
    $3,695
    Photo of 3 Lewis Rd #3, Winchester, MA 01890 (MLS # 73310841)
    Photo of 3 Lewis Rd #3, Winchester, MA 01890 (MLS # 73310841)
    21
     
    3 Lewis Rd #3, Winchester, MA
    3 Lewis Rd #3
    Winchester, MA
    • 2 Beds
    • 1 Bath
    • 1,400 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Better Homes and Gardens Real Estate - The Shanahan Group
  12. Photo of 64 Wildwood St, Winchester, MA 01890 (MLS # 73310488)
    $2,985,000
    Photo of 64 Wildwood St, Winchester, MA 01890 (MLS # 73310488)
    Photo of 64 Wildwood St, Winchester, MA 01890 (MLS # 73310488)
    42
     
    64 Wildwood St, Winchester, MA
    64 Wildwood St
    Winchester, MA
    • 5 Beds
    • 5 Baths
    • 4,400 Home (sqft)
    • 5 Baths
    • 10,455 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  13. Photo of 200 Swanton St #L32, Winchester, MA 01890 (MLS # 73311612)
    $2,100
    Photo of 200 Swanton St #L32, Winchester, MA 01890 (MLS # 73311612)
    Photo of 200 Swanton St #L32, Winchester, MA 01890 (MLS # 73311612)
    15
     
    200 Swanton St #L32, Winchester, MA
    200 Swanton St #L32
    Winchester, MA
    • 1 Bed
    • 1 Bath
    • 602 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Denkar Realty Group
  14. Photo of 40 Church St #B, Winchester, MA 01890 (MLS # 73312723)
    $6,000
    Photo of 40 Church St #B, Winchester, MA 01890 (MLS # 73312723)
    Photo of 40 Church St #B, Winchester, MA 01890 (MLS # 73312723)
    23
     
    40 Church St #B, Winchester, MA
    40 Church St #B
    Winchester, MA
    • 3 Beds
    • 3 Baths
    • 3,500 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Real Estate by Hughes & Assoc. Inc.
  15. Photo of 7 Thornberry Road #0, Winchester, MA 01890 (MLS # 73316303)
    $8,500
    Photo of 7 Thornberry Road #0, Winchester, MA 01890 (MLS # 73316303)
    Photo of 7 Thornberry Road #0, Winchester, MA 01890 (MLS # 73316303)
    34
     
    7 Thornberry Road #0, Winchester, MA
    7 Thornberry Road #0
    Winchester, MA
    • 5 Beds
    • 2 Baths
    • 3,033 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with TAJ Mahal Realty LLC
  16. Photo of 64 Highland Avenue #4, Winchester, MA 01890 (MLS # 73317083)
    $3,200
    Photo of 64 Highland Avenue #4, Winchester, MA 01890 (MLS # 73317083)
    Photo of 64 Highland Avenue #4, Winchester, MA 01890 (MLS # 73317083)
    12
     
    64 Highland Avenue #4, Winchester, MA
    64 Highland Avenue #4
    Winchester, MA
    • 1 Bed
    • 1 Bath
    • 800 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Media Realty Group Inc.
  17. Photo of 27 Ledyard Road #SF, Winchester, MA 01890 (MLS # 73318120)
    $5,000
    Photo of 27 Ledyard Road #SF, Winchester, MA 01890 (MLS # 73318120)
    Photo of 27 Ledyard Road #SF, Winchester, MA 01890 (MLS # 73318120)
    36
     
    27 Ledyard Road #SF, Winchester, MA
    27 Ledyard Road #SF
    Winchester, MA
    • 3 Beds
    • 2 Baths
    • 2,364 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Plunkett Properties
  18. Photo of 7 Conant Rd #24, Winchester, MA 01890 (MLS # 73318457)
    $719,897
    Photo of 7 Conant Rd #24, Winchester, MA 01890 (MLS # 73318457)
    Photo of 7 Conant Rd #24, Winchester, MA 01890 (MLS # 73318457)
    42
     
    7 Conant Rd #24, Winchester, MA
    7 Conant Rd #24
    Winchester, MA
    • 2 Beds
    • 2 Baths
    • 1,196 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Beaudoin & Associates, REALTOR®
  19. Photo of 848 Main St #848, Winchester, MA 01890 (MLS # 73320481)
    $4,050
    Photo of 848 Main St #848, Winchester, MA 01890 (MLS # 73320481)
    Photo of 848 Main St #848, Winchester, MA 01890 (MLS # 73320481)
    25
     
    848 Main St #848, Winchester, MA
    848 Main St #848
    Winchester, MA
    • 4 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Real Broker MA, LLC
  20. Photo of 7 Conant Rd #60, Winchester, MA 01890 (MLS # 73321512)
    $3,300
    Photo of 7 Conant Rd #60, Winchester, MA 01890 (MLS # 73321512)
    Photo of 7 Conant Rd #60, Winchester, MA 01890 (MLS # 73321512)
    10
     
    7 Conant Rd #60, Winchester, MA
    7 Conant Rd #60
    Winchester, MA
    • 2 Beds
    • 3 Baths
    • 1,634 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Matahari Real Estate LLC
  21. Photo of 8 Pepper Hill Dr, Winchester, MA 01890 (MLS # 73321949)
    $2,100,000
    Photo of 8 Pepper Hill Dr, Winchester, MA 01890 (MLS # 73321949)
    Photo of 8 Pepper Hill Dr, Winchester, MA 01890 (MLS # 73321949)
    8 Pepper Hill Dr, Winchester, MA
    8 Pepper Hill Dr
    Winchester, MA
    • 4 Beds
    • 4 Baths
    • 3,800 Home (sqft)
    • 4 Baths
    • 23,523 Lot (sqft)
    Listed with Core Property Group, LLC
  22. Photo of 20 Amberwood Dr, Winchester, MA 01890 (MLS # 73322357)
    $3,898,000
    Photo of 20 Amberwood Dr, Winchester, MA 01890 (MLS # 73322357)
    Photo of 20 Amberwood Dr, Winchester, MA 01890 (MLS # 73322357)
    34
     
    20 Amberwood Dr, Winchester, MA
    20 Amberwood Dr
    Winchester, MA
    • 6 Beds
    • 7 Baths
    • 8,866 Home (sqft)
    • 7 Baths
    • 23,087 Lot (sqft)
    Listed with Keller Williams Realty
  23. Photo of 23 Olde Village Dr, Winchester, MA 01890 (MLS # 73323471)
    $1,879,000
    Photo of 23 Olde Village Dr, Winchester, MA 01890 (MLS # 73323471)
    Photo of 23 Olde Village Dr, Winchester, MA 01890 (MLS # 73323471)
    42
     
    23 Olde Village Dr, Winchester, MA
    23 Olde Village Dr
    Winchester, MA
    • 3 Beds
    • 4 Baths
    • 4,997 Home (sqft)
    • 4 Baths
    • 1.01 Lot (ac)
    Listed with Keller Williams Realty Boston Northwest
  24. Photo of 171 Swanton St #13, Winchester, MA 01890 (MLS # 73323582)
    $3,800
    Photo of 171 Swanton St #13, Winchester, MA 01890 (MLS # 73323582)
    Photo of 171 Swanton St #13, Winchester, MA 01890 (MLS # 73323582)
    26
     
    171 Swanton St #13, Winchester, MA
    171 Swanton St #13
    Winchester, MA
    • 2 Beds
    • 3 Baths
    • 1,427 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Lexington
  25. Photo of 49 Amberwood Dr, Winchester, MA 01890 (MLS # 73324069)
    $8,000
    Photo of 49 Amberwood Dr, Winchester, MA 01890 (MLS # 73324069)
    Photo of 49 Amberwood Dr, Winchester, MA 01890 (MLS # 73324069)
    29
     
    49 Amberwood Dr, Winchester, MA
    49 Amberwood Dr
    Winchester, MA
    • 4 Beds
    • 4 Baths
    • 3,220 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Senne
  26. Photo of 27 Everett Ave, Winchester, MA 01890 (MLS # 73324581)
    $3,899,000
    Photo of 27 Everett Ave, Winchester, MA 01890 (MLS # 73324581)
    Photo of 27 Everett Ave, Winchester, MA 01890 (MLS # 73324581)
    41
     
    27 Everett Ave, Winchester, MA
    27 Everett Ave
    Winchester, MA
    • 6 Beds
    • 6 Baths
    • 7,431 Home (sqft)
    • 6 Baths
    • 27,879 Lot (sqft)
    Listed with Advisors Living - Winchester
  27. Photo of 3 Lagrange St, Winchester, MA 01890 (MLS # 73324754)
    $2,749,000
    Photo of 3 Lagrange St, Winchester, MA 01890 (MLS # 73324754)
    Photo of 3 Lagrange St, Winchester, MA 01890 (MLS # 73324754)
    38
     
    3 Lagrange St, Winchester, MA
    3 Lagrange St
    Winchester, MA
    • 4 Beds
    • 4 Baths
    • 4,060 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
    Listed with Advisors Living - Winchester
  28. Photo of 30 Bellevue Ave, Winchester, MA 01890 (MLS # 73324918)
    $1,198,000
    Photo of 30 Bellevue Ave, Winchester, MA 01890 (MLS # 73324918)
    Photo of 30 Bellevue Ave, Winchester, MA 01890 (MLS # 73324918)
    21
     
    30 Bellevue Ave, Winchester, MA
    30 Bellevue Ave
    Winchester, MA
    • 3 Beds
    • 2 Baths
    • 2,052 Home (sqft)
    • 2 Baths
    • 23,958 Lot (sqft)
    Listed with Fairview Partners International LLC
  29. Photo of 410 Main St, Winchester, MA 01890 (MLS # 73326415)
    $1,545,000
    Photo of 410 Main St, Winchester, MA 01890 (MLS # 73326415)
    Photo of 410 Main St, Winchester, MA 01890 (MLS # 73326415)
    42
     
    410 Main St, Winchester, MA
    410 Main St
    Winchester, MA
    • 3 Beds
    • 3 Baths
    • 2,075 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
    Listed with Barrett Sotheby's International Realty
  30. Photo of 200 Swanton St #607, Winchester, MA 01890 (MLS # 73326729)
    $2,680
    Photo of 200 Swanton St #607, Winchester, MA 01890 (MLS # 73326729)
    Photo of 200 Swanton St #607, Winchester, MA 01890 (MLS # 73326729)
    23
     
    200 Swanton St #607, Winchester, MA
    200 Swanton St #607
    Winchester, MA
    • 2 Beds
    • 1 Bath
    • 600 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Keller Williams Realty Evolution
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About Alexa

Alexa Dealy is a seven-year residential real estate veteran, having successfully represented hundreds of clients through a wide array of real estate transactions. Born and raised in the Boston area, Alexa has an intrinsic and unteachable understanding of the local real estate market. She comes from a family of real estate investors; it’s no surprise that Alexa began her career in the real estate industry at age 20 – after buying and selling her first investment property for a profit.

Contact Alexa

Alexa Dealy, Realtor® RE/MAX Andrew Realty Services Hours: 9:00 am – 7:00 pm

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