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Homes for Rent near Gloucester High School

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    $2,050 - $2,895 per month

    The Heights At Cape Ann

    1-3 Beds

    950 Heights at Cape Ann, Gloucester, MA 01930

    Quietly nestled at the highest point in Gloucester is the Heights at Cape Ann, an exceptional apartment home community. Stop by our onsite management office to view our one, two, and three bedroom floor plans. The Heights at Cape Ann is a pet-friendly apartment community that offers a modern fitness center, swimming pool, fire pit, resident's lounge, Wi-Fi cafe, and units with terraces boasting

    950 Heights at Cape Ann, Gloucester, MA 01930
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    $1,900 per month

    • 2 Beds
    • 2.5 Baths
    • 1,633 Sq Ft
    • Apartment for Rent

    34 Rockport Rd-Winter Rental Unit 6, Gloucester, MA 01930

    Short Term Winter Rental 9/2/2025-5/23/2026- Discover the charm of coastal living with breathtaking water views and stunning sunsets at this multi-level townhome with Long Beach located steps from your door. This spacious fully furnished 2 bedroom, 2.5 bath townhome, boasts a primary en-suite with a balcony and a spacious second bedroom both with ample closet space. The well appointed kitchen

    Angela Cromosini Lyv Realty

    34 Rockport Rd-Winter Rental Unit 6, Gloucester, MA 01930
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    $2,400 per month

    • 2 Beds
    • 1 Bath
    • 1,800 Sq Ft
    • Condo for Rent

    143 Essex Ave Unit 2, Gloucester, MA 01930

    Property Id: 1742683Modern 2 bedroom 1 bathroom high ceilings home. Stainless steel appliances and granite countertops. Large custom tile shower. Large master bedroom with double closet. Laundry hookups conveniently located inside unit. Off-street parking.

    143 Essex Ave Unit 2, Gloucester, MA 01930
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    $3,100 per month

    • 4 Beds
    • 2.5 Baths
    • 1,893 Sq Ft
    • House for Rent

    11 Sleepy Hollow Rd, Gloucester, MA 01930

    Seasonal furnished rental available September 1, 2025 through May 1, 2026 (date could be flexible). This home offers a living room with a fireplace which is open to the kitchen and the dining room (area). The kitchen door leads to a beautiful deck over looking the yard. The first floor also has the main bedroom with a half bathroom attached and one additional bedroom and a full bath. The

    Stephanie Moio J. Barrett & Company

    11 Sleepy Hollow Rd, Gloucester, MA 01930
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    $2,700 per month

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft
    • Condo for Rent

    15 Eastern Ave Unit 15 Eastern Ave unit 2, Gloucester, MA 01930

    East Gloucester sunny, fresh and clean unit available immediately. 2 bedrooms, 1 & 3/4 baths. Walking distance to Good Harbor Beach, downtown shops, restaurants, and more. Very close to route 128, making commuting an ease! Second floor of an owner occupied two family house. Freshly painted, new appliances and refinished hard wood floors. Small sunny deck for your plants and R&R. Plenty of on

    15 Eastern Ave Unit 15 Eastern Ave unit 2, Gloucester, MA 01930
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    $8,000 per month

    • 5 Beds
    • 3 Baths
    • 2,343 Sq Ft
    • House for Rent

    18 Rear Bungalow Rd, Gloucester, MA 01930

    --SHORT TERM RENTAL -- Price is a base price and per week. Inquire for longer stays. Private oceanfront Wingaersheek Beach house features five bedrooms, three bathrooms and has recently been renovated with custom steel front double doors, new wood floors, pine interior paneled walls, new kitchen cabinets, counters, bathrooms, and mini split AC units. The house spans three levels along with an

    Stephen Sassoon Sassoon Group, LLC

    18 Rear Bungalow Rd, Gloucester, MA 01930
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    $2,200 per month

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

    295 Magnolia Ave Unit Rain Gaudreau, Gloucester, MA 01930

    Modern one Bedroom Off street parking lot Fireplace living room 400 sq.Feet Heat and hot water included . Nice Yard . Close to beaches.NO SMOKING.

    295 Magnolia Ave Unit Rain Gaudreau, Gloucester, MA 01930
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    $40,000 per month

    • 5 Beds
    • 2 Baths
    • 3,300 Sq Ft
    • House for Rent

    62 Crafts Rd, Gloucester, MA 01930

    Modern Cape Ann coastal retreat. Sitting on 1.4 waterfront acres with granite outcroppings, mature trees, and gardens. Private deepwater dock, 5 feet at low tide, accommodates 2-3 boats. Riverfront peninsula with sweeping water and marsh views, perfectly located in the middle of the Annisquam River. Take trips out to Ipswich Bay, the bustling Gloucester Harbor and open waters beyond. Features

    John & Cindy Farrell Coldwell Banker Realty - Beverly

    62 Crafts Rd, Gloucester, MA 01930
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    $2,400 per month

    • 1 Bed
    • 1 Bath
    • 672 Sq Ft
    • Townhouse for Rent

    97 Washington St Unit 3rd floor, Gloucester, MA 01930

    Nice restaurants, live music, shops and town are walking distance from this terrific condominium unit. Perfect for a single professional visiting beautiful Gloucester for work or vacation for an extended stay of a minimum of twelve (12) weeks to fifty -two (52) weeks. This fully furnished, new condo unit is small but spacious with an open floor plan and great light. Quiet space. Granite

    97 Washington St Unit 3rd floor, Gloucester, MA 01930
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    $2,700 per month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Apartment for Rent

    366 Main St Unit 3, Gloucester, MA 01930

    Discover a truly unique living experience in the expansive 1500sqfr newly renovated 3 bedroom apartment overlooking the sparkling water of Gloucester. Apartment has a massive brand new kitchen with island and additional sunroom and an abundance of natural light, this home offers an unparalleled sense of space and tranquility. Wake up each morning in the oversized master bedroom to a breathtaking

    366 Main St Unit 3, Gloucester, MA 01930
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    $3,200 per month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    34 Decatur St Unit 8, Gloucester, MA 01930

    This apartment's location provides everything you want in Boston city living without breaking the bank! It is conveniently located in a well-kept building, two blocks from Central Square and only four blocks from the Maverick Square train stop, making city commutes simple. The Maverick Blue Line T stop (Bowdoin line) and Downtown Boston are both conveniently close to Maverick Square properties,

    34 Decatur St Unit 8, Gloucester, MA 01930
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    $2,500 per month

    • 1 Bed
    • 1.5 Baths
    • 940 Sq Ft
    • Apartment for Rent

    3 Atlantic Rd Unit 1, Gloucester, MA 01930

    Enjoy coastal living, Good Harbor Beach and all that East Gloucester has to offer in this newly renovated 1 bedroom, 1.5 bath duplex located 0.2 miles from Good Harbor Beach. The new eat-in kitchen boasts white cabinets, granite countertops and backsplash with stainless steel appliances and opens up to the outdoor deck and living room. The 1st level also includes a walk-in closet and a new half

    Angela Cromosini Lyv Realty

    3 Atlantic Rd Unit 1, Gloucester, MA 01930
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    $7,000 per month

    • 4 Beds
    • 4 Baths
    • 3,567 Sq Ft
    • House for Rent

    39 Decatur St, Gloucester, MA 01930

    WEEKLY SUMMER RENTAL in spacious, well-appointed family home on privately situated, green leafy lot, yet less than half a mile away from the Good Harbor Beach Footbridge. With Bass Rocks Golf Club and tennis courts around the corner and Rocky Neck and downtown Gloucester a short distance away, this is a prime location for fun with friends and family. Generous kitchen opens to family room with

    Amanda Armstrong Compass

    39 Decatur St, Gloucester, MA 01930
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    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    31 Western Ave Unit 16, Gloucester, MA 01930

    Updated one bedroom on the Boulevard with new kitchen,full bath,vinyl plank flooring, heat and hot water included,common laundry,parking for one car.Close distance to the Commuter Rail Station, Downtown shops,restaurants,Stage Fort Park,Half Moon Beach and the Pavilion Beach across the street.

    Emma Fula Coldwell Banker Realty - Boston

    31 Western Ave Unit 16, Gloucester, MA 01930
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    $3,200 per month

    • 3 Beds
    • 1.5 Baths
    • 2,480 Sq Ft
    • House for Rent

    58 Sumner St, Gloucester, MA 01930

    Welcome to Major John Burnham’s historic 17th-century home, a rare opportunity to rent a stately and distinguished property rich in history. This West Gloucester gem showcases original King Pine wood floors, raised paneled walls, exposed beams, and multiple decorative fireplaces, preserving its authentic colonial charm. Enjoy the enclosed three season sunroom, inviting fresh air and tranquil

    Crowell & Frost Realty Group J. Barrett & Company

    58 Sumner St, Gloucester, MA 01930
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    $15,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,483 Sq Ft
    • Apartment for Rent

    6A Stanwood Point Unit A, Gloucester, MA 01930

    ***SHORT TERM RENTAL*** Spend your spring and summer alongside Little River in the seaside city of Gloucester. This property offers beautiful scenery with direct water access. Built in 2023, this townhome offers all modern amenities and upgraded appliances. The open concept first floor makes it a perfect home for summer entertaining, indoors and out! Moments from Stage Fort Park, MBTA and the

    Katelyn Ciaramitaro Engel & Volkers By the Sea

    6A Stanwood Point Unit A, Gloucester, MA 01930
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    $6,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,483 Sq Ft
    • Apartment for Rent

    6A Stanwood Point Unit A, Gloucester, MA 01930

    ***SHORT TERM RENTAL*** Spend your spring and summer alongside Little River in the seaside city of Gloucester. This property offers beautiful scenery with direct water access. Built in 2023, this townhome offers all modern amenities and upgraded appliances. The open concept first floor makes it a perfect home for summer entertaining, indoors and out! Moments from Stage Fort Park, MBTA and the

    Katelyn Ciaramitaro Engel & Volkers By the Sea

    6A Stanwood Point Unit A, Gloucester, MA 01930
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    $2,950 per month

    • 1 Bed
    • 2 Baths
    • 1,250 Sq Ft
    • Apartment for Rent

    2 Spring Street- Summer Rental Unit A, Gloucester, MA 01930

    Welcome to a warm and sunny Cape Ann summer! -SEASONAL RENTAL- This charming, fully furnished 1-bedroom, 2-bath is the perfect retreat for your summer stay. With four spacious rooms—including an extra space ideal for a home office or guest room—plus in-unit laundry and thoughtful furnishings, you’ll feel right at home. Enjoy relaxing on the patio, exploring nearby shops and restaurants (just a

    Alyssa Anderson Keller Williams Realty Evolution

    2 Spring Street- Summer Rental Unit A, Gloucester, MA 01930
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    $4,850 per month

    • 3 Beds
    • 2.5 Baths
    • 1,776 Sq Ft
    • House for Rent

    3 Fort Hill Ave, Gloucester, MA 01930

    WINTER RENTAL on Easten Point. This carriage house is available until April 30, 2025. This new home is fully furnished and outfitted for luxe living in a serene setting. Open concept first floor is chic and comfortable. Three well appointed bedrooms and two baths upstairs with a half bath on the first floor. Deluxe outdoor kitchen, This home is ideal for a winter retreat, a place to call home

    Scott Smith Coldwell Banker Realty - Manchester

    3 Fort Hill Ave, Gloucester, MA 01930
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    $9,000 per month

    • 4 Beds
    • 3 Baths
    • 2,164 Sq Ft
    • House for Rent

    1 Sandy Way, Gloucester, MA 01930

    Wingaersheek Coffin's Beach One Week Summer Rental !! Available 8/20 through 8/27/2025 Coastal living at its finest in this fully furnished home, offers a large open floor plan. First floor has kitchen, living room, dining room, one bedroom, full bath and den. Double sliders allow access to the outside deck. Second floor has a large main bedroom with full bath, two bedrooms and a shared bath. The

    Christine Grammas J. Barrett & Company

    1 Sandy Way, Gloucester, MA 01930
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    $4,500 per month

    • 4 Beds
    • 3.5 Baths
    • 2,900 Sq Ft
    • House for Rent

    17 Fort Hill Ave, Gloucester, MA 01930

    WINTER SEASONAL RENTAL - Flexible lease/price options considered. Charming English Tudor Carriage House privately located in the heart of Eastern Point within walking distance of two sandy beaches, DogBar Breakwater, Eastern Point Light House and many nature paths; only a 10 minute drive to Rt. 128 and all things Gloucester. Only minutes from Rocky Neck Art Colony and Gloucester Stage Company.

    Lois Budrose Advisors Living - Gloucester

    17 Fort Hill Ave, Gloucester, MA 01930
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    $3,900 per month

    • 2 Beds
    • 2 Baths
    • 1,254 Sq Ft
    • Apartment for Rent

    41B Wingaersheek Rd Unit 1, Gloucester, MA 01930

    This is a fully furnished new construction unit located on the private side of Wingaersheek beach. Short term rental from available October 5, 2024 through June 27, 2025. Nothing to do but bring your clothes and move in. Three month minimum rental @$3,900 per mo. Landlord will consider minimum 5 night rental at $300.00 per night.

    Nicholas M Ambeliotis Nicholas M. Ambeliotis Real Estate

    41B Wingaersheek Rd Unit 1, Gloucester, MA 01930
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    $6,500 per month

    • 7 Beds
    • 3.5 Baths
    • 4,267 Sq Ft
    • House for Rent

    24 Wonson St, Gloucester, MA 01930

    Escape to this beautiful Home nestled in the heart of Rocky Neck, a destination that promises to lure you back time & again. Ideal for hosting lg. wedding parties or cherished family reunions. This home boasts newly renovated interiors adorned w/ exquisite finishes & tasteful furnishings. A true haven for vacationers, it features ample outdoor entertainment areas, including outdoor fire pits, a

    Charleen McCarthy Five Mark Realty Group LLC

    24 Wonson St, Gloucester, MA 01930
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    $20,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,518 Sq Ft
    • House for Rent

    14 Sunset Point Rd, Gloucester, MA 01930

    OCEANFRONT IN LANESVILLE SUMMER RENTAL WITH DATES STILL AVAILABLE STARTING IN MID-AUGUST. Idyllic summer retreat in stunning and private oceanfront setting in one of the North Shore’s most scenic communities. This is the perfect base for exploring the many delights of Lanesville, from its rugged shoreline to colorful Lanesville village with its studios and cafes. Head to beautiful Lane’s Cove,

    Amanda Armstrong Compass

    14 Sunset Point Rd, Gloucester, MA 01930
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