| 3-13 Crest Ave. - Built: 1920s |
|
| Now |
| 5 - Pomona Café & Wine Bar/Piccolo Piatti - 2020 |
| |
| Earlier |
| 3 - Governor's Garden Florist - 2005 |
| 3 - Winthrop Highlands Service - 1986 |
| 3 - Tony's Auto Service - Texaco - 1984 |
| 3-13 - Sweeney's Citgo (Jenney) Service Station - 1972-1975 |
| 3-13 - McEwen Filling Station - 1947 |
| 3-13 - McEwen & Meharg Filling Station - 1942 |
| 3-13 - Jenney Mfg. - 1936 |
| 3-13 - M. Cherney Hardware and Heating - 1922 |
| 5 - Hot Diggity - 2006-2014 |
| 7 - Mark Gross Real Estate - 1929 |
|
| 19-29 Crest Ave. |
 |
| Now |
| 19 - Antique Table Restaurant - 2015 |
| 23 - Elite Hair Design - 2015 |
| 29 - Crest Ave. Wine and Spirits - 2015 |
| 29 - J.A.C.'s Café - 200 |
| |
| Earlier |
| 19 - Millie's Kitchen - 2012 |
| 19 - Bob's Bait Shop - 2010 |
| 19 - Business Forms Plus - 2000 |
| 19 - Village Market - 1994 |
| 19 - Treats Fine Food Store - 1987-1988 |
| 19 - North Shore Lab for Podiatric Orthotics - 1984-1986 |
| 19-25 - Lewis Kasanof Co. Toys - 1967-1976 |
| 19 - Highland Barber Shop - 1942 |
| 21 - Winthrop Taxi - 2012 |
| 21 - Winthrop Community Health Center - 2006 |
| 21 - Dr. Deepa Jhaveri Podiatry - 2006-2010 |
| 21 - Dr. Donald W. Clayman - 1996-2000 |
| 21 - Todo's TLC Pet Grooming (House of Fido) - 1984 |
| 21 - Ocean News - 1967-1976 |
| 21 - John's Television Repair Service - 1957 |
| 21 - Highland Town Cab - 1947 |
| 21 - Hilda's Beauty Salon - 1942 |
|
| 21 - Snider's Fish Market - 1936 |
| 21 - Arthur McLean's Fish Market - 1929-1931 |
| 21A - Samual Braff Grocer - 1929-1947 |
| 21 - Highland Hand Laundry - 1918 |
| 21 - A. J. Connor Co. Groceries - 1918 |
| 23-25 - Andiamo's New Image - 1996-2009 |
| 23 - Travalot Ltd. Travel Arangements - 1986-1989 |
| 23-25 - Ad Mat - 1986 |
| 23 - Marion's Specialty Shop Dry Goods - 1942-1947 |
| 23 - Great Atlantic & Pacific Tea Co. - 1929-1936 |
| 25 - Statik Hair Salon - 2012 |
| 25 - Crest Flower Shop - 1942 |
| 25 - Frank Lacaronza Shoe Repair - 1929-1931 |
| 25 - Stone's Food Shop - 1921-1922 |
| 27 - Alvin Cleaners - 1947 |
| 27A - Charlie Lee Hand Laundry - 1929-1942 |
| 27 - Jacob Silverman Tailor - 1918-1942 |
| 29 - Fab's Liquors - 2003-2015 |
| 29 - Joe's Highland Liquor - 2000 |
| 29 - Seaside Liquors Inc. - 1994 |
| 29 - Aljay's Ice Cream - 1984-1992 |
| 29 - G&M Liquors - 1986 |
| 29A - Kay's 5c to $1 - 1936 |
| 29 - Harry & Sam's Crest Market (Crest Cash Market) - 1929-1984 |
| 29A - Alice Cook Dry Goods - 1919-1931 |
| 29 - Everybody's Cash Market - 1921 |
|
| 31-35 Crest Ave. |
 |
| Now |
| 31 - Precious Pets - 2009-2022 |
| 35 - Bridges Nepali Cuisine - 2020 |
| |
| Earlier |
| 31 - J. Silverman Cleansers and Dyers - 1943-1957 |
| 31 - Leonard Perroni Barber - 1929-1936 |
| 31 - G. Wong Laundry - 1918 |
| 31 - Highland Hand Landry - 1916 |
|
| 33 - Jean Harris Beauty Shoppe - 1931-1936 |
| 33 - Mrs Dorothy T Wadley Beauty Parlor - 1929 |
| 33 - Dr. Merwin K. Fox Dentist - 1923 |
| 33 - The Highland - Mrs. E. J. Partington - 1918 |
| 35 - Crest Ave. Pizza - 1993 |
| 35 - Upper Krust Pizza & Deli - 1984-1986 |
| 35 - Braff's Food Mart & Delicatessen - 1967-1976 |
| 35 - Hilda's Beauty Salon - 1947 |
| 35 - Highland Hardware - 1929-1936 |
| 35 - J. Silverman Tailor - 1916 |
|
| 37-39 Crest Ave. |
|
| Now |
| 37 - Reds Hair Salon - 2000 |
| 37 - Highland Convenient Mart - 1986 |
| 37 - ATS Alarm Systems - 1996 |
| |
| Earlier |
| 37 - il Pastaio Pasta - 2000-2004 |
| 37 - Seaside Liquors Inc. - 1995 |
| 37 - Winthrop Beauty Lounge - 1967-1994 |
| 37 - Charles Cobbler Shop - 1985-1993 |
| 37 - Budd's Sub Shop - 1975-1986 |
| 37 - The Bargain Hunter - 1976 |
|
| 37A - Crest Ave. Beauty Shop - 1967-1972 |
| 37B - Highland Barber Shop - 1947 |
| 37 - First National Stores - 1931-1947 |
| 37 - Franks Shoe Repair - 1942 |
| 37B - Crest Ave. Beauty Salon - 1942 |
| 37B - Highland Beauty Salon - 1936 |
| 35 - J. Silverman Tailor - 1931-1947 |
| 37 - Morrow & Torrey Real Estate, Insurance - 1931 |
| 37B - Goodyear Shoe Rebuilt - 1931 |
| 37 - Charles Dutton Bakery - 1929 |
| 37 - Fred H. Wegener Delicatessen - 1925-1926 |
|
| 41-45 Crest Ave. |
 |
| Now |
| 41 - Sliver Clean Inc. - 1967 |
| 45 - CrossFit Tradewinds - 2015 |
| |
| Earlier |
| 41 - Atkinson Hardware Co. - 1947-1951 |
| 41 - Highland Restaurant - 1936 |
| 41 - Swett's Bakery - 1931 |
| 41 - Priscilla Restaurant - 1929 |
| 41 - H. R. Henderson Groceries - 1918 |
| 41 - Louis Raca Shoe Repair - 1916 |
|
| 45 - Bronze Tanning Salon - 2012 |
| 45 - Ultimate Tan & Juice Bar - 2000-2006 |
| 45 - A Total Touch Tanning, Nails - 1996 |
| 45 - Bronze Tanning Salon - 2012 |
| 45 - All Seasons Tanning - 1994 |
| 45 - Total Touch Toning and Tanning - 1989-1994 |
| 45 - LVR Contact Lens Lab, Inc. - 1984-1986 |
| 45 - Buy Better Inc. - 1976 |
| 45 - Highland Presciption Pharmacy - H. Frank Pharmacist - 1942-1972 |
| 45 - Leonard E. Hubbard Pharmacy - 1923-1937 |
| 45 - J. P. Martin Pharmacist - 1921 |
| 45 - B. F. Connor Druggist - 1916-1918 |
|
| 50 Crest Ave. |
 |
| Now |
| 50 - Top Quality Barbershop - 2022 |
| |
|
| Earlier |
| 50 - Star Nails - 2010 |
| 50 - Nana's Pantry - 2000 |
| 50 - Designer Optical II (Winthrop Optician) - 2000 |
| 50 - Brian Perrin Law Office - 1999-2002 |
| 50 - Beachcomber Hair Design - 1972-1988 |
| 50 - Ham's Confectionery - 1915-1957 |
|
| 64-66 Crest Ave. |
 |
| Now |
| 64 - BB's Hair Design - 2010-2022 |
| 66 - Richard Honan Sign Co. - 1976-2022 |
| |
| Earlier |
| 64 - Nana's Pantry - 2000-2006 |
| 64 - Winthrop Karate Academy - 1994 |
| 64 - The Ultimate Stained Glass Shoppe - 1992 |
| 64 - V&M Woodworking - 1986 |
| 64 - Cerbone's Upholstering - 1954-1984 |
| 64 - Highlands Market - 1947 |
| 64 - W. R. Tibbetts Groceries - 1916-1942 |
|
| 66 - John's Television Repair Service - 1967-1974 |
| 66 - Tibbetts Bakery - 1936 |
| 66 - The Coffee Cup Restaurant - 1929-1931 |
| 66 - Mall's (Highland) Restaurant - 1916-1947 |
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