442

Annisquam Homes

Section Image
  • /39

    $995,000

    $355K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,902 Sq Ft

    65 Leonard St, Gloucester, MA 01930

    One of the oldest surviving homes in Annisquam, this historic First Period Colonial (circa 1717) is part of the property known as "The Old Castle." On Lobster Cove, this waterfront residence showcases a seasonal dock providing direct access. Located on the North Shore in Gloucester, the historic village of Annisquam offers a distinct coastal experience, distinguished by its narrow winding lanes,

    John Farrell Coldwell Banker Realty - Beverly

    65 Leonard St, Gloucester, MA 01930
  • /15

    $3,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    4 Diamond Ave, Gloucester, MA 01930

    Charming Annisquam Village Home. This seasonal rental starts 9/1 through 6/1Discover this cozy retreat nestled in the heart of Gloucester's coveted Annisquam Village, just a short drive from Boston.Enjoy easy access to Diamond Cove, a stunning rocky beach, located just across the lane.This delightful home offers a perfect blend of comfort and coastal charm. The open-concept living and dining area

    Brian Rothe Coldwell Banker Realty - Manchester

    4 Diamond Ave, Gloucester, MA 01930
  • /37

    $860,000

    Sold Sep 10, 2026

    136 Leonard St, Gloucester, MA 01930

    • 3 Beds
    • 2 Baths
    • 2,216 Sq Ft
    • Built 1920

    Last Sold Summary

    • 14% Below List Price
    • $388/SF
    • 119 Days On Market

    Current Estimated Value $934,484

    Last Listing Agent Karen Bernier Churchill Properties

    136 Leonard St, Gloucester, MA 01930
    • /39

      Est $1,123,820

      Not Listed For Sale

      142 Leonard St, Gloucester, MA 01930

      • 3 Beds
      • 2.5 Baths
      • 2,251 Sq Ft
      • Built 1920
      142 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Paula Polo-Filias J. Barrett & Company

  • /47

    $3,150

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • House for Rent

    31 Chester Square, Gloucester, MA 01930

    Winter Rental: Available October 14, 2026-May 31, 2027 (Utilities Included)Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect off-season home. The bright and airy ground floor has many windows, letting in lots of natural light. The full bathroom on the main level has a shower over tub. A three-season sunroom

    31 Chester Square, Gloucester, MA 01930
  • /30

    $1,900,000

    Sold Dec 09, 2025

    6 River Rd, Gloucester, MA 01930

    • 3 Beds
    • 3.5 Baths
    • 2,418 Sq Ft
    • Built 1920

    Last Sold Summary

    • 4% Below List Price
    • $786/SF
    • 42 Days On Market

    Current Estimated Value $1,899,329

    Last Listing Agent Scott Smith Coldwell Banker Realty - Manchester

    6 River Rd, Gloucester, MA 01930
    • /23

      Est $1,138,530

      Not Listed For Sale

      134R Leonard St, Gloucester, MA 01930

      • 3 Beds
      • 1.5 Baths
      • 1,860 Sq Ft
      • Built 1940
      134R Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Scott Smith Coldwell Banker Realty - Manchester

  • /17

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • House for Rent

    138 Leonard St, Gloucester, MA 01930

    Seasonal Furnished Two-Bedroom House Rental available now through June 15, 2027. Situated in the desirable neighborhood of Annisquam Village, this well-maintained, fully furnished gambrel-style Colonial is situated on a private lot surrounded by mature plantings. Enter through the heated four-season sunroom, and through French doors you’ll find a spacious living room that flows into a

    Jackelyn Enslow Cameron Real Estate Group

    138 Leonard St, Gloucester, MA 01930
  • /34

    $1,700,000

    Sold Oct 15, 2025

    4 Lane Rd, Gloucester, MA 01930

    • 3 Beds
    • 3.5 Baths
    • 3,882 Sq Ft
    • Built 1920

    Last Sold Summary

    • 21% Below List Price
    • $438/SF
    • 147 Days On Market

    Current Estimated Value $1,817,567

    Last Listing Agent Lynda Surdam Coldwell Banker Realty - Manchester

    4 Lane Rd, Gloucester, MA 01930
    • /38

      Est $1,191,855

      Not Listed For Sale

      121 Leonard St, Gloucester, MA 01930

      • 4 Beds
      • 2 Baths
      • 2,576 Sq Ft
      • Built 1920
      121 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Linda Hayes William Raveis R.E. & Home Services

  • /30

    $3,500 Per Month

    • 5 Beds
    • 2 Baths
    • 2,081 Sq Ft
    • Condo for Rent

    11 Leonard St Unit 2, Gloucester, MA 01930

    SEASONAL WINTER RENTAL WITH WATER VIEWS! Spend the off-season in one of Annisquam's most picturesque settings, perched in the heart of the village with sweeping views of the Annisquam River and the pristine shores of Wingaersheek Beach beyond. This beautifully preserved period home blends timeless New England charm with modern comforts, featuring exposed beams, hardwood floors, multiple

    Paula Polo-Filias J. Barrett & Company

    11 Leonard St Unit 2, Gloucester, MA 01930
  • /42

    $4,805,000

    Sold Sep 01, 2026

    77 Norwood Heights, Gloucester, MA 01930

    • 5 Beds
    • 7 Baths
    • 5,526 Sq Ft
    • Built 2007

    Last Sold Summary

    • 2% Below List Price
    • $870/SF
    • 44 Days On Market

    Current Estimated Value $4,764,927

    Last Listing Agent Sara Seber Engel & Volkers By the Sea

    77 Norwood Heights, Gloucester, MA 01930
    • /37

      Est $3,558,508

      Not Listed For Sale

      50 Norwood Heights, Gloucester, MA 01930

      • 4 Beds
      • 3.5 Baths
      • 3,246 Sq Ft
      • Built 2005
      50 Norwood Heights, Gloucester, MA 01930

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Lynda Surdam Coldwell Banker Realty - Manchester

    • /16

      Est $1,883,021

      Not Listed For Sale

      23 Norwood Heights, Gloucester, MA 01930

      • 3 Beds
      • 3 Baths
      • 2,300 Sq Ft
      • Built 1959
      23 Norwood Heights, Gloucester, MA 01930

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent McClelland Del Rio Group Gibson Sotheby's International Realty

    • /41

      Est $1,139,291

      Not Listed For Sale

      11 Rockholm Rd, Gloucester, MA 01930

      • 3 Beds
      • 2 Baths
      • 1,698 Sq Ft
      • Built 1984
      11 Rockholm Rd, Gloucester, MA 01930

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Brackett Janis Group Engel & Volkers By the Sea

    • /23

      Est $790,361

      Not Listed For Sale

      860 Washington St, Gloucester, MA 01930

      • 2 Beds
      • 1 Bath
      • 1,140 Sq Ft
      • Built 1941
      860 Washington St, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Kathryn Tully Century 21 North East

    • /42

      Est $1,388,154

      Not Listed For Sale

      37 Walnut St, Gloucester, MA 01930

      • 4 Beds
      • 3 Baths
      • 2,368 Sq Ft
      • Built 1800
      37 Walnut St, Gloucester, MA 01930

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /39

      Est $2,190,070

      Not Listed For Sale

      25 Adams Hill Rd, Gloucester, MA 01930

      • 3 Beds
      • 2.5 Baths
      • 2,499 Sq Ft
      • Built 2003
      25 Adams Hill Rd, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Judith Toner The Proper Nest Real Estate

    • /38

      Est $1,047,953

      Not Listed For Sale

      5 River Rd, Gloucester, MA 01930

      • 3 Beds
      • 1.5 Baths
      • 1,050 Sq Ft
      • Built 1920
      5 River Rd, Gloucester, MA 01930

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Nancy Goodick Gibson Sotheby's International Realty

    • /35

      Est $2,938,549

      Not Listed For Sale

      15 Norrock Rd, Gloucester, MA 01930

      • 4 Beds
      • 3.5 Baths
      • 2,490 Sq Ft
      • Built 2009
      15 Norrock Rd, Gloucester, MA 01930

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Scott Smith Coldwell Banker Realty - Manchester

    • /40

      Est $1,667,368

      Not Listed For Sale

      152 Leonard St, Gloucester, MA 01930

      • 3 Beds
      • 3.5 Baths
      • 2,934 Sq Ft
      • Built 1800
      152 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Andree Robert Engel & Volkers By the Sea

    • /40

      Est $2,588,559

      Not Listed For Sale

      21 Norwood Heights, Gloucester, MA 01930

      • 3 Beds
      • 4 Baths
      • 3,311 Sq Ft
      • Built 1945
      21 Norwood Heights, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent McDermott Group Gibson Sotheby's International Realty

    • /23

      Est $1,290,646

      Not Listed For Sale

      9 Mechanics Place, Gloucester, MA 01930

      • 2 Beds
      • 1 Bath
      • 1,190 Sq Ft
      • Built 1920
      9 Mechanics Place, Gloucester, MA 01930

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /26

      Est $1,322,215

      Not Listed For Sale

      7 Mechanics Place, Gloucester, MA 01930

      • 3 Beds
      • 2 Baths
      • 1,553 Sq Ft
      • Built 1920
      7 Mechanics Place, Gloucester, MA 01930

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /32

      Est $1,374,392

      Not Listed For Sale

      2 Lane Rd, Gloucester, MA 01930

      • 3 Beds
      • 2.5 Baths
      • 2,509 Sq Ft
      • Built 1920
      2 Lane Rd, Gloucester, MA 01930

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Nancy Goodick Gibson Sotheby's International Realty

    • /26

      Est $2,065,591

      Not Listed For Sale

      62 Leonard St, Gloucester, MA 01930

      • 4 Beds
      • 3 Baths
      • 2,286 Sq Ft
      • Built 1999
      62 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /31

      Est $2,784,938

      Not Listed For Sale

      19 Chester Square, Gloucester, MA 01930

      • 5 Beds
      • 4.5 Baths
      • 3,259 Sq Ft
      • Built 1880
      19 Chester Square, Gloucester, MA 01930

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /29

      Est $1,735,755

      Not Listed For Sale

      11 Adams Hill Rd, Gloucester, MA 01930

      • 3 Beds
      • 2.5 Baths
      • 2,061 Sq Ft
      • Built 1920
      11 Adams Hill Rd, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Senkler, Pasley & Dowcett Coldwell Banker Realty - Concord

    • /42

      Not Listed For Sale

      53 Leonard St, Gloucester, MA 01930

      • 4 Beds
      • 3.5 Baths
      • 2,368 Sq Ft
      • Built 1830
      53 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Karen Bernier Churchill Properties

    • /33

      Est $1,867,303

      Not Listed For Sale

      54 Adams Hill Rd, Gloucester, MA 01930

      • 3 Beds
      • 2.5 Baths
      • 1,273 Sq Ft
      • Built 1920
      54 Adams Hill Rd, Gloucester, MA 01930

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Scott Smith Coldwell Banker Realty - Manchester

    • /27

      Est $2,712,747

      Not Listed For Sale

      4 Cambridge Ave, Gloucester, MA 01930

      • 3 Beds
      • 3 Baths
      • 2,759 Sq Ft
      • Built 1991
      4 Cambridge Ave, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /36

      Est $1,267,361

      Not Listed For Sale

      18 Leonard St, Gloucester, MA 01930

      • 6 Beds
      • 3 Baths
      • 2,365 Sq Ft
      • Built 1900
      18 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Peter Lane North Shore's Gold Coast Realty

    • /24

      Est $899,328

      Not Listed For Sale

      20 Leonard St Unit 4, Gloucester, MA 01930

      • 2 Beds
      • 1.5 Baths
      • 1,633 Sq Ft
      • Built 2000
      20 Leonard St Unit 4, Gloucester, MA 01930

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Lynda Surdam Coldwell Banker Realty - Manchester

    • /30

      Est $1,073,217

      Not Listed For Sale

      20 Leonard St Unit 1, Gloucester, MA 01930

      • 2 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 2000
      20 Leonard St Unit 1, Gloucester, MA 01930

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Lynda Surdam Coldwell Banker Realty - Manchester

    • /42

      Est $2,531,783

      Not Listed For Sale

      28 River Rd, Gloucester, MA 01930

      • 3 Beds
      • 2 Baths
      • 1,752 Sq Ft
      • Built 1920
      28 River Rd, Gloucester, MA 01930

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lynda Hemeon Coldwell Banker Realty - Manchester

    • /23

      Est $1,361,929

      Not Listed For Sale

      17 Leonard St, Gloucester, MA 01930

      • 2 Beds
      • 2.5 Baths
      • 1,867 Sq Ft
      • Built 1920
      17 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Amanda Armstrong Compass

    • /23

      Not Listed For Sale

      33 Leonard St, Gloucester, MA 01930

      • 3 Beds
      • 1 Bath
      • 1,116 Sq Ft
      • Built 1829
      33 Leonard St, Gloucester, MA 01930

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Mark Ventimiglia Vadala Real Estate

    • /35

      Est $684,668

      Not Listed For Sale

      1 Vale Ct, Gloucester, MA 01930

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1974
      1 Vale Ct, Gloucester, MA 01930

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Holly Chiancola Holly C & Co. Fine Homes

    • /2

      Est $1,194,526

      Not Listed For Sale

      24 Leonard St Unit WINTER, Gloucester, MA 01930

      • 3 Beds
      • 2 Baths
      • 1,278 Sq Ft
      • Built 1900
      24 Leonard St Unit WINTER, Gloucester, MA 01930

    • /2

      Est $1,507,812

      Not Listed For Sale

      18 River Rd Unit WINTER, Gloucester, MA 01930

      • 3 Beds
      • 2 Baths
      • 1,147 Sq Ft
      • Built 1920
      18 River Rd Unit WINTER, Gloucester, MA 01930

Showing Results 1 - 40, Page 1 of 12

Home Price Trends

Median Sale Price
$1,800,000
Median Single Family Sale Price
$1,800,000
Average Price Per Sq Ft
$620
Number of Homes for Sale
442
Last 12 months Home Sales
4
Months of Supply
0.00
Median List Price
$2,067,500
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
23%
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