Cottage Hill Homes

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  /37

  $879,900

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  100 Cottage Ave, Winthrop, MA 02152

  Ideally located just steps from the Winthrop Yacht Club, The Landing Marina, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace, plus two additional rooms perfect for

  The Reference Group Reference Real Estate

  100 Cottage Ave, Winthrop, MA 02152
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  /8

  $2,000 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  265 Washington Ave Unit 3A, Winthrop, MA 02152

  1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

  265 Washington Ave Unit 3A, Winthrop, MA 02152
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  /42

  $830,000 Sold Jul 18, 2025

  • 2,412 Sq Ft
  • $344/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  27 Crystal Cove Ave, Winthrop, MA 02152

  Nestled in the heart of Winthrop Head, this 4bed, 2bath Colonial blends timeless charm with a prime location just moments from multiple beaches and the scenic Winthrop Golf Club. Enjoy sweeping ocean views from the spacious front porch—an ideal spot for coffee or evening sunsets. Enter inside to a welcoming foyer featuring a bay window, fireplace & gleaming HW floors that flow seamlessly into a

  Lori Lacey Lamacchia Realty, Inc.

  27 Crystal Cove Ave, Winthrop, MA 02152
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  /35

  Est $648,200 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  30 Underhill St Unit 1, Winthrop, MA 02152

  30 Underhill St Unit 1, Winthrop, MA 02152
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  /36

  $829,900

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft

  500 Shirley St, Winthrop, MA 02152

  Located just 3.5 miles from the game-changing Suffolk Downs redevelopment, this fantastic two-family home offers incredible long-term upside in one of the fastest-growing areas north of Boston. The project promises millions of square feet of new housing, retail, parks, and life science space—adding immense value & convenience to the surrounding neighborhoods. Just steps from the beach, this

  Jose Zambrano RE/MAX 360

  500 Shirley St, Winthrop, MA 02152
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  /20

  $2,800 per month

  • 3 Beds
  • 1 Bath
  • 1,153 Sq Ft
  • Apartment for Rent

  64 Prospect Ave Unit 4, Winthrop, MA 02152

  Text Mike for a showing

  Michael Forcillo Coldwell Banker Peggy Carter Team

  64 Prospect Ave Unit 4, Winthrop, MA 02152
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  /28

  $520,000 Sold Jul 11, 2025

  • 1,219 Sq Ft
  • $427/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1880

  30 Crystal Cove Ave Unit 2, Winthrop, MA 02152

  Nestled in Winthrop’s sought-after Crystal Cove neighborhood, this beautifully maintained two-level condo perfectly combines timeless character with stylish comfort. A grand staircase serves as the home’s architectural showpiece, adding elegance and a sense of grandeur. The sun-filled unit features an updated kitchen, two bedrooms and renovated bathrooms offering modern finishes and

  Erica Gore Century 21 Seaport

  30 Crystal Cove Ave Unit 2, Winthrop, MA 02152
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  /40

  Est $500,132 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,139 Sq Ft

  16 Underhill St Unit 2, Winthrop, MA 02152

  16 Underhill St Unit 2, Winthrop, MA 02152
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  /27

  $699,000

  • 3 Beds
  • 1.5 Baths
  • 1,172 Sq Ft

  12 Park Ave, Winthrop, MA 02152

  INTRODUCING 12 PARK AVENUE...This meticulous single family home features 6+ rooms of bright and comfortable living spaces, a private fenced in yard and off street parking. An enclosed sunporch welcomes you to the first floor which has hardwood floors, an open floor plan, a fully applianced kitchen and convenient 1/2 bath. The second floor has three bedrooms with custom built closets and a full

  Mary Ann Cash Charlesgate Realty Group, llc

  12 Park Ave, Winthrop, MA 02152
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  /8

  $1,725 per month

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • Condo for Rent

  64 Moore St Unit 2, Winthrop, MA 02152

  1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

  64 Moore St Unit 2, Winthrop, MA 02152
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  /12

  $290,000 Sold Jun 27, 2025

  • 610 Sq Ft
  • $475/SF
  • 45 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  267 Washington Ave Unit 5, Winthrop, MA 02152

  GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY......Why rent when this 2 bedroom updated unit can give you a start in homeownership? Conveniently located on the Bus Line to the Blue Line and looking out to the harbor and Lewis Lake with just steps to the ocean! Yes, the beach is at the top of the street. This top floor unit has hardwood floors throughout, pretty set of windows in the living

  Sharon Tallent Compass

  267 Washington Ave Unit 5, Winthrop, MA 02152
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  /34

  Est $459,289 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  241 Washington Ave Unit 3, Winthrop, MA 02152

  241 Washington Ave Unit 3, Winthrop, MA 02152
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  /24

  $520,000

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft

  247 Washington Ave Unit 9, Winthrop, MA 02152

  Beautiful corner end-unit condominium in the desirable Nautilus Building offering panoramic views of Boston, the marina, Winthrop Yacht Club, and Elks from every room. This spacious 2-bedroom, 2-bathroom condominium features a private balcony that spans the entire length of the unit, perfect for relaxing and watching the boats go by. Inside this bright and airy unit, is a white kitchen, hardwood

  Erica Gore Century 21 Seaport

  247 Washington Ave Unit 9, Winthrop, MA 02152
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  /14

  $3,400 per month

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Apartment for Rent

  18 Tewksbury St Unit 2, Winthrop, MA 02152

  Absolutely huge apartment for rent that feels like a single family with 2 kitchens and 2 levels of living . This home on Tewksbury street is located between the ocean and Harbor with prime East to West Natural light all day. This home has a private entrance to the unit which boasts 4 large bedrooms, 2 bathrooms along with brand new gas heating system and new windows. Great flow of the apartment

  AD Advisors Team Block Realty

  18 Tewksbury St Unit 2, Winthrop, MA 02152
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  /31

  $680,000 Sold Apr 23, 2025

  • 1,355 Sq Ft
  • $502/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  620 Shirley St Unit 3, Winthrop, MA 02152

  Are you looking for a Bi-level condo with unobstructed Waterfront OCEAN VIEWS into downtown Boston? Look no further, because 620 Shirley Street Unit #3 in Winthrop will be sure to check every single box you're looking for. This 2022 New Construction west facing, spacious, waterfront property boasts 2 levels of living that floods with natural light during the day with breathtaking sunsets over the

  Patrick Fahey Access

  620 Shirley St Unit 3, Winthrop, MA 02152
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  /27

  Est $410,652 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 460 Sq Ft

  241 Washington Ave Unit 1, Winthrop, MA 02152

  241 Washington Ave Unit 1, Winthrop, MA 02152
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  /32

  $549,900

  • 2 Beds
  • 2 Baths
  • 773 Sq Ft

  600 Shirley St Unit 3, Winthrop, MA 02152

  “The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and

  Erika Leigh Pereira Keller Williams Realty Boston Northwest

  600 Shirley St Unit 3, Winthrop, MA 02152
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  /12

  $2,250 per month

  • 1 Bed
  • 1 Bath
  • 799 Sq Ft
  • Condo for Rent

  62 Park Ave Unit 1, Winthrop, MA 02152

  1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

  62 Park Ave Unit 1, Winthrop, MA 02152
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  /40

  $895,000 Sold Mar 07, 2025

  • 3,331 Sq Ft
  • $269/SF
  • 8 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1880

  63 Terrace Ave, Winthrop, MA 02152

  Beautiful Two Family Overlooking The Harbors, Sunsets And The Glamourous And Colorful City Lights Of Boston. This Spectacular Home Does Not Come Up Like This Very Often. Unit #1 Has 4 Good Size Rooms With A Large Bathroom And Private Laundry Space. Unit #2 Has Two Levels Of Living Space With Two Bedrooms And Its Own Laundry Area. Both Units Have Shining Hardwood Floors And Big Windows Throughout,

  Corey Mastrocola Welcome Home Properties, Inc.

  63 Terrace Ave, Winthrop, MA 02152
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  /26

  Est $453,005 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 860 Sq Ft

  235 Washington Ave Unit 5, Winthrop, MA 02152

  235 Washington Ave Unit 5, Winthrop, MA 02152
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  /26

  $525,000

  • 2 Beds
  • 2 Baths
  • 865 Sq Ft

  600 Shirley St Unit 16, Winthrop, MA 02152

  Always wanted to live across from the beach? This might be the place for you! Enjoy breathtaking water and Boston skyline views from this beautifully renovated 2-bed, 2-bath condo at the former Historic Crystal Cove Hotel. Offering first-floor convenience with a private entrance and two deeded parking spaces right outside your door, this home lives like a private residence. The open layout

  Elizabeth Crowley William Raveis R.E. & Home Services

  600 Shirley St Unit 16, Winthrop, MA 02152
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  /39

  $900,000 Sold Feb 14, 2025

  • 2,157 Sq Ft
  • $417/SF
  • 60 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1900

  5 Charles St, Winthrop, MA 02152

  Beautiful Corner lot, half a block from the beach. Well-maintained home in move-in condition, lots of updates. The upper unit has two levels with a loft bedroom,Cathedral ceiling with skylight windows, and a private deck with some ocean view. The lower unit offers a renovated kitchen, bathroom, spacious private yard, and deck. There is an additional living area with a bed and bath. Stainless

  Marisol Aldana Century 21 North East

  5 Charles St, Winthrop, MA 02152
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  /9

  Est $312,785 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 622 Sq Ft

  247 Washington Ave Unit 23, Winthrop, MA 02152

  247 Washington Ave Unit 23, Winthrop, MA 02152
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  /31

  $415,000

  • 1 Bed
  • 2 Baths
  • 604 Sq Ft

  600 Shirley St Unit 1, Winthrop, MA 02152

  WATER VIEWS & PRIVATE DECK! Welcome to The Cove at 600, a premier condominium development in Winthrop, situated on the historic site of the Crystal Cove Hotel. This meticulously renovated first-floor unit features 1 bedroom and 2 baths, epitomizing perfect beach town living. Every detail has been updated finishes, including newer kitchen & bathrooms. Your living room offers stunning water views,

  The Movement Group Compass

  600 Shirley St Unit 1, Winthrop, MA 02152
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  /24

  $480,000 Sold Dec 09, 2024

  • 1,008 Sq Ft
  • $476/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  247 Washington Ave Unit 8, Winthrop, MA 02152

  Welcome to coastal living at its finest. Start your day with a coffee or unwind with a glass of wine, watching the sunset from your private balcony over the serene waters of Winthrop. This 2-bedroom, 2-bath condo has been thoughtfully updated, featuring a spacious living room, a recently renovated kitchen with stainless steel appliances, and newly redone bathrooms. Just steps away from

  Daniel Clucas Reference Real Estate

  247 Washington Ave Unit 8, Winthrop, MA 02152
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  /34

  Est $656,148 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,412 Sq Ft

  10 Perkins St, Winthrop, MA 02152

  10 Perkins St, Winthrop, MA 02152
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  /12

  $1,100,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,308 Sq Ft

  51 Harbor View Ave, Winthrop, MA 02152

  Contractors, Investors, Savvy buyers looking to build equity. This three family on an oversized lot has stunning ocean and bay views! It offers off street parking, separate utilities, spacious two bedroom units and is close to public transportation, Logan Airport and downtown Boston. Whether you're looking to renovate, rent or occupy, this is your opportunity to own a multi family gem in the

  Mary Ann Cash Charlesgate Realty Group, llc

  51 Harbor View Ave, Winthrop, MA 02152
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  /25

  $825,000 Sold Dec 02, 2024

  • 2,212 Sq Ft
  • $373/SF
  • 22 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1890

  19 Moore St, Winthrop, MA 02152

  Grand Victorian Legal Two-Family Home offering the perfect opportunity for owner-occupants or investors alike. With a strong rental history, this property has undergone extensive renovations, including a new roof, gas heating system and electrical upgrades. As you enter, you are greeted by the dramatic staircase and foyer. The main unit is de-leaded and features bi-level living with a large

  Erica Gore Century 21 Seaport

  19 Moore St, Winthrop, MA 02152
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  /38

  Est $608,360 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,378 Sq Ft

  36 Tewksbury St Unit 2, Winthrop, MA 02152

  36 Tewksbury St Unit 2, Winthrop, MA 02152
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  /26

  $375,000 Pending

  • 2 Beds
  • 1 Bath
  • 860 Sq Ft

  235 Washington Ave Unit 6, Winthrop, MA 02152

  WELCOME HOME TO THE WINTHROP CHAMBERS CONDOMINIUM. Penthouse level - 2 bed, 1 bath unit with open floor plan. The views are incredible, whether it be of Lewis Lake and/or the Harbor/City, you will not be disappointed. There are coin operated washer/dryers in the building as well as a storage closet. The condo fee includes heat and hot water and this unit controls its own heat. Enjoy the back

  Cathie Curran Charlesgate Realty Group, llc

  235 Washington Ave Unit 6, Winthrop, MA 02152
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  /14

  $272,000 Sold Nov 14, 2024

  • 555 Sq Ft
  • $490/SF
  • 68 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1900

  483 Shirley St Unit 8, Winthrop, MA 02152

  Your chance to get a condo under $300K this close to Boston just reoccured! Tired of high city prices? This charming 1-bedroom condo is a first-time buyer's dream come true! Completely renovated, it boasts new cabinets, appliances, flooring, and a pristine tub. The location is unbeatable, with grocery, shops, restaurants, and cafes right at your front door! Plus, a leisurely stroll takes you to

  Maghda Amrani Coldwell Banker Realty - Haverhill

  483 Shirley St Unit 8, Winthrop, MA 02152
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  /14

  Est $717,314 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft

  17 Tewksbury St, Winthrop, MA 02152

  17 Tewksbury St, Winthrop, MA 02152
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  /18

  $287,000 Pending

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  265 Washington Ave Unit 2A, Winthrop, MA 02152

  Looking for the perfect balance of city convenience and suburban tranquility? This newly renovated 1-bedroom, 1-bathroom condo is just a quick ride to the Orient Heights T stop, making your commute to downtown Boston easy. Plus, you're only 5 minutes from Boston Logan Airport, perfect for travel. Enjoy stunning views of the Boston skyline and harbor right from your door. Stroll to nearby

  Pareene Group EXIT Premier Real Estate

  265 Washington Ave Unit 2A, Winthrop, MA 02152
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  /35

  $975,000 Sold Oct 31, 2024

  • 2,000 Sq Ft
  • $488/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  11 Perkins St, Winthrop, MA 02152

  Complete gut remodel interior and exterior. This home offers 3 spacious bedrooms and 2 luxurious bathrooms.A 160 sqft. finished bonus room in the basement. A custom dream kitchen awaits, equipped with stainless steel appliances, white shaker cabinets, a wine fridge, pot filler, and a large kitchen island. Off the kitchen, you’ll find a pantry and laundry room with plenty of storage. Main bedroom

  Michael Buscanera Blue Key Realty

  11 Perkins St, Winthrop, MA 02152
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  /42

  Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,536 Sq Ft

  23 Tewksbury St, Winthrop, MA 02152

  23 Tewksbury St, Winthrop, MA 02152
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  /13

  $799,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,777 Sq Ft

  64 Moore St, Winthrop, MA 02152

  Experience the charm of seaside living at 64 Moore Street, a classic 3-family home just steps from Winthrop Beach. The property features two 1-bedroom units and one 2-bedroom unit, all filled with natural light and offering cozy, efficient layouts. Ideal for owner-occupants looking to live near the ocean while generating rental income, or for investors seeking a solid asset in a high-demand

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  64 Moore St, Winthrop, MA 02152
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  /22

  $535,000 Sold Oct 31, 2024

  • 1,228 Sq Ft
  • $436/SF
  • 38 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1850

  90 Terrace Ave Unit 1, Winthrop, MA 02152

  Motivated seller has just reduced this well maintained condo located at 90 Terrace Avenue in the desirable seaside town of Winthrop! It features 2 bedrooms, 2 full baths and finished basement with in-unit laundry. Along with it's spectacular views, this location is walking distance to Winthrop and Yirrel Beaches, Point Shirley, Winthrop Yacht Club and just steps away from the Winthrop Ferry

  John Marino MP Realty Group

  90 Terrace Ave Unit 1, Winthrop, MA 02152
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  /35

  Est $560,811 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,245 Sq Ft

  14 Charles St, Winthrop, MA 02152

  14 Charles St, Winthrop, MA 02152
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  /42

  $699,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft

  831 Shirley St, Winthrop, MA 02152

  Seaside living at its finest...welcome to your dream coastal retreat! This charming 2 bedroom, 2 bath bungalow with garage offers the perfect blend of comfort, style and breathtaking water views offering direct bay water access. Thoughtfully designed with an open floor plan and gleaming Brazilian cherry floors, the property features a warm and inviting sunroom that welcomes you with natural light

  Elaine Akerberg Elite Realty Experts, LLC

  831 Shirley St, Winthrop, MA 02152
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  /38

  $780,000 Sold Sep 10, 2024

  • 4,345 Sq Ft
  • $180/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1900

  39 Cottage Ave, Winthrop, MA 02152

  Welcome to this charming 2-family house nestled in Winthrop’s idyllic Cottage Hill neighborhood. Combining modern comforts with vintage character this beautifully maintained home offers hardwood floors and an abundance of natural light. A versatile kitchen provides plenty of space with an adjacent dining area and separate dining room. The generous master bedroom features water views, ample closet

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  39 Cottage Ave, Winthrop, MA 02152

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