$8,000 Per Month
- 4 Beds
- 3 Baths
- 2,000 Sq Ft
- Condo for Rent
14 Riverside Rd, Gloucester, MA 01930
14 Riverside Rd, Gloucester, MA 01930
68
Homes for Rent near Ralph B O'maley Middle School
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Explore Ralph B O'maley Middle School
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$1,800
Total Monthly Price
- 1 Bed
- 1 Bath
- 872 Sq Ft
- House for Rent
143 Prospect St Unit 2, Gloucester, MA 01930
143 Prospect St Unit 2, Gloucester, MA 01930$1800 per month,1 bedroom- 1 BR Apartment, downtown 143 Prospect Street Gloucester MA. 1 year lease.Nice size 872 Sq ft 1 bedroom 2nd floor of two family house , on street parking,Walking distance to Train, Bus, Main St and Gloucester harbor.One block from Destino’s and Our Lady of Good Voyage Church.The apartment is ideal for a single or couple. The kitchen is equipped with a
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$2,700 Per Month
- 2 Beds
- 1 Bath
- 1,574 Sq Ft
- Condo for Rent
8 Brightside Ave Unit 1, Gloucester, MA 01930
8 Brightside Ave Unit 1, Gloucester, MA 01930 -
Starting at $2,050
Total Monthly Price
- 1 - 3 Beds
950 Heights at Cape Ann, Gloucester, MA 01930
950 Heights at Cape Ann, Gloucester, MA 01930Quietly 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
The Heights At Cape Ann
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$2,900
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- House for Rent
540 Washington St, Gloucester, MA 01930
540 Washington St, Gloucester, MA 01930On the River with views. 2 bedroom, 2 bath single family. Utilities included, except Oil. Waterfront. 2 Private Decks. Driveway. Large Kitchen, Dining Room, Living Room. Breathtaking Sunsets. Grills. Fire Pit. Washer Dryer In unit. No past evictions. Includes electricity, hot water, cable, and WiFi. Spacious. Year Round Property
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$2,700
Total Monthly Price
- 3 Beds
- 1.5 Baths
- 1,000 Sq Ft
- Condo for Rent
117 Western Ave Unit 2, Gloucester, MA 01930
117 Western Ave Unit 2, Gloucester, MA 01930Short term rental-winter furnished rental. Enjoy this beautiful costal apartment by the ocean in an amazing location! This apartment offers 3 bedrooms, 1.5 bedrooms, nice size living room and kitchen with parking up to 3 cars ! Feel the luxury of leaving in this beautiful decorated apartment and with the comfort of have Landry in unit. Also offers a private patio with breathtaking ocean views!
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$3,200
Total Monthly Price
- 3 Beds
- 1 Bath
- 1,800 Sq Ft
- Condo for Rent
21 Addison St Unit 21 Addison street unit. 2, Gloucester, MA 01930
21 Addison St Unit 21 Addison street unit. 2, Gloucester, MA 01930Freshly painted and packed with space! This 3-bedroom, 1-bath apartment offers classic hardwood floors, a huge living room, a separate dining room, and a dedicated home office. The Space: Generous room sizes, fresh neutral paint, and abundant natural light. The Extras: Private office space for remote work/studying, formal dining area, and beautiful hardwoods throughout. The Location:
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$1,800
Total Monthly Price
- Studio
- 1 Bath
- 425 Sq Ft
- Condo for Rent
50R Maplewood Ave Unit 212, Gloucester, MA 01930
50R Maplewood Ave Unit 212, Gloucester, MA 01930New apartment with all new appliances. Washer/dryer combo. First and last due at signing.
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$3,500
Total Monthly Price
- 2 Beds
- 1 Bath
- 1,500 Sq Ft
- Condo for Rent
115 Western Ave Unit 3, Gloucester, MA 01930
115 Western Ave Unit 3, Gloucester, MA 01930Seasonal Winter rental at 115 western ave. Entire top floor. Furnished. nov 1-April 30.
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$2,500
Total Monthly Price
- 1 Bed
- 1 Bath
- 790 Sq Ft
- Condo for Rent
4 Lighthouse Way Unit 1, Gloucester, MA 01930
4 Lighthouse Way Unit 1, Gloucester, MA 01930Ground floor unit walking distance to Niles beach. Open concept with spacious outdoor area and parking.
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$4,750
Total Monthly Price
- 4 Beds
- 2 Baths
- 1,700 Sq Ft
- House for Rent
48 Rowley Shore, Gloucester, MA 01930
48 Rowley Shore, Gloucester, MA 01930Winter Rental | November 2 – April 1Oceanfront Winter Retreat in Lanesville, GloucesterEscape to the peaceful seaside village of Lanesville and enjoy a comfortable winter stay in this beautifully remodeled oceanfront home. With stunning views of Ipswich Bay, spacious living areas, four bedrooms, two remodeled bathrooms, and a fully equipped kitchen, this home is ideal for a winter
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$2,600
Total Monthly Price
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
60 Eastern Ave Unit 2, Gloucester, MA 01930
60 Eastern Ave Unit 2, Gloucester, MA 01930 -
$1,500
Total Monthly Price
- 1 Bed
- 1 Bath
- 950 Sq Ft
- Condo for Rent
7 Ellery St Unit 2, Gloucester, MA 01930
7 Ellery St Unit 2, Gloucester, MA 01930- Available October 1st.- Well-kept 1 Bedroom, 1 Bath Apartment.- Open kitchen and living room, separate bedroom, and tile floors throughout.- Includes smooth top stove, fridge, washer/dryer, walk in tiled shower, and hot water.- Electricity paid by tenant.- On street parking with off street parking during snow storms.- Easy 1/2-mile commute to Route 128.- No smoking
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$2,400
Total Monthly Price
- 1 Bed
- 2 Baths
- 1,250 Sq Ft
- Condo for Rent
2 Spring St Unit A, Gloucester, MA 01930
2 Spring St Unit A, Gloucester, MA 01930Enjoy comfortable first-floor living in this charming, fully furnished one-bedroom, two-full-bath apartment. The unit also features an additional room with closet space, offering flexible space for storage, an office, or other uses. Relax and enjoy the outdoor patio, with convenient access to nearby shops, restaurants, and multiple Gloucester-area beaches. The property also offers easy highway
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$1,750 Per Month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Apartment for Rent
9 Eastern Ave Unit 1, Gloucester, MA 01930
9 Eastern Ave Unit 1, Gloucester, MA 01930Updated 1 bedroom unit in a very convenient location with close proximity to Downtown, Good Harbor Beach and Route 128.
Anthony Stanton Boston Realty Company
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$2,775
Total Monthly Price
- 2 Beds
- 1.5 Baths
- 996 Sq Ft
- Condo for Rent
19 Atlantic Rd, Gloucester, MA 01930
19 Atlantic Rd, Gloucester, MA 01930Winter Rental Available: October 1, 2026-May 31, 2027Welcome to this modern two-story condo located in the desirable Bass Rocks neighborhood. This home boasts beautiful views of the Bass Rocks Golf Course while being just .2 miles from the Good Harbor Beach Footbridge. This 2-bedroom, 1.5-bath home combines contemporary style with comfortable living.The open floor plan is filled
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$2,800 Per Month
- 2 Beds
- 1 Bath
- 840 Sq Ft
- Apartment for Rent
6 Cabo Dr Unit Winter, Gloucester, MA 01930
6 Cabo Dr Unit Winter, Gloucester, MA 01930*WINTER RENTAL*Available Nov 1st -May 31, with some flexibility* Nestled on a quiet cul-de-sac, this beautifully renovated and fully furnished 2-bedroom, 1-bath home is just a short stroll to both Good Harbor Beach & Long Beach and close to shopping, restaurant's and everything Gloucester and Rockport have to offer. This home offers the perfect retreat to enjoy coastal living during the
Lane Burnham Team LAER Realty Partners
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$2,495
Total Monthly Price
- 2 Beds
- 1 Bath
- 660 Sq Ft
- Condo for Rent
45 Western Ave Unit 2, Gloucester, MA 01930
45 Western Ave Unit 2, Gloucester, MA 01930Prime waterfront Year-Round Two-Bedroom plus office Rental at the historic Stacey Boulevard and renowned Gloucester Fisherman's Statue! Enjoy the southern exposure of this five-room, two-bedroom apartment as you overlook Gloucester's Historic Harbor from your living room window/private deck while the sun and moon glisten on its waters. This second-floor unit with single-level living offers
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$1,800 Per Month
- 1 Bed
- 1 Bath
- 699 Sq Ft
- Apartment for Rent
31 Western Ave Unit 19, Gloucester, MA 01930
31 Western Ave Unit 19, Gloucester, MA 01930SEPTEMBER RENT FREE! Qualified applicants may also be eligible for a reduced $500 security deposit. Updated one-bedroom on the Boulevard featuring an open-concept kitchenette and living room, full bath, and vinyl plank flooring. Heat and hot water are included, with common laundry and parking for one car. Conveniently located near the Commuter Rail station, downtown Gloucester shops and
Emma Fula Charlesgate Realty Group, llc
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$3,850
Total Monthly Price
- 2 Beds
- 2.5 Baths
- 1,319 Sq Ft
- House for Rent
660 Washington St, Gloucester, MA 01930
660 Washington St, Gloucester, MA 01930Winter Rental Available: November 3, 2026-May 15, 2027Waterfront on the Annisquam River in Gloucester, this exceptional winter rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo.This home has a custom kitchen, spacious open concept living/dining room and lots of windows. There are
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$2,100 Per Month
- 2 Beds
- 1 Bath
- 1,026 Sq Ft
- Apartment for Rent
9 Friend St Unit 1, Gloucester, MA 01930
9 Friend St Unit 1, Gloucester, MA 01930This year-round, sunlit four-room apartment rental includes heat and hot water. Meticulously maintained first-floor unit has an open concept eat-in kitchen, living room, and outside deck with views of our working harbor. A heated front porch, a slider to a large 19' x 8' deck at the back that overlooks the working harbor, polished hardwood floors, period coffered ceilings, a washer and dryer, a
Ana Silveira J. Barrett & Company
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$3,000
Total Monthly Price
- 2 Beds
- 1 Bath
- 852 Sq Ft
- Condo for Rent
5 Pirates Ln, Gloucester, MA 01930
5 Pirates Ln, Gloucester, MA 01930WINTER RENTAL - Available: Now-June 15, 2027 (Utilities Included)Tucked away along the harbor, this charming East Gloucester end-unit condo is part of a classic coastal Victorian-era complex overlooking picturesque Smith Cove and Gloucester Harbor. With its private entrance and two spacious decks, this light-filled retreat is the perfect seaside escape.Step inside from the side
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$2,600 Per Month
- 1 Bed
- 1 Bath
- 966 Sq Ft
- House for Rent
41 E Main St, Gloucester, MA 01930
41 E Main St, Gloucester, MA 01930Charming Coastal Cottage in East GloucesterMoments from beaches, downtown Gloucester & Rocky NeckAvailable December 1, 2026 through May 31, 2027Enjoy the best of coastal living in this bright, thoughtfully furnished 966-square-foot cottage in East Gloucester. With great proximity to sandy beaches, downtown Gloucester, and the Rocky Neck Art Colony, this home offers a rare combination of comfort,
Caroline Noonan Corcoran Property Advisors
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$2,300
Total Monthly Price
- 2 Beds
- 1 Bath
- 688 Sq Ft
- House for Rent
10 Josephs Way, Gloucester, MA 01930
10 Josephs Way, Gloucester, MA 01930Winter Rental Available: October 1, 2026 - May 15, 2027Just a half mile from Gloucester's Good Harbor Beach, Joseph's Way is a delightful two-bedroom rental nestled on a quiet hidden side street with just four other houses.Freshly renovated and decorated, enjoy the ease of one-level living with a spacious open plan dining/living room which expands to the fully-applianced kitchen
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$5,000 Per Month
- 4 Beds
- 3.5 Baths
- 2,900 Sq Ft
- House for Rent
17 Fort Hill Ave, Gloucester, MA 01930
17 Fort Hill Ave, Gloucester, MA 01930SEASONAL and FlEXIBLE TERM RENTAL - 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. Just minutes from Rocky Neck Art Colony and Gloucester Stage Company. Bicycle to town or around Cape
Lois Budrose Lois Budrose Realty
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$4,000
Total Monthly Price
- 3 Beds
- 3 Baths
- 2,700 Sq Ft
- Condo for Rent
37 Rocky Neck Ave Unit Winter Rental: The Gallery, Gloucester, MA 01930
37 Rocky Neck Ave Unit Winter Rental: The Gallery, Gloucester, MA 01930Winter Rental Available: October 1,2026-May 31, 2027One-of-a-kind waterfront multi-level property on Rocky Neck, America's oldest art colony. Enjoy views of Smith Cove and the Gloucester skyline.The main living area is on the second floor where there is a spacious living room overlooking the cove. Also on this level is a fully equipped kitchen with granite countertops and
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$2,500 Per Month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Apartment for Rent
16 Magnolia Ave Unit 7, Gloucester, MA 01930
16 Magnolia Ave Unit 7, Gloucester, MA 01930Charming renovated 2-bedroom apartment available now! This well-maintained unit features modern updates throughout, a bright and inviting living space, and the convenience of off-street parking. Heat and hot water is included in the rent. Conveniently located near Gloucester’s shops, restaurants, beaches, and commuter routes.
Desiree Taylor Desired Homes Realty LLC
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$3,150
Total Monthly Price
- 3 Beds
- 2 Baths
- 1,596 Sq Ft
- House for Rent
31 Chester Square, Gloucester, MA 01930
31 Chester Square, Gloucester, MA 01930Winter Rental: Available October 1, 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 runs
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$1,900 Per Month
- 1 Bed
- 1 Bath
- Apartment for Rent
16 Magnolia Ave Unit 11, Gloucester, MA 01930
16 Magnolia Ave Unit 11, Gloucester, MA 01930Charming renovated 1-bedroom apartment available now! This well-maintained unit features modern updates throughout, a bright and inviting living space, and the convenience of off-street parking. Heat and hot water is included in the rent. Conveniently located near Gloucester’s shops, restaurants, beaches, and commuter routes.
Desiree Taylor Desired Homes Realty LLC
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$3,400
Total Monthly Price
- 4 Beds
- 1 Bath
- Condo for Rent
75 Friend St Unit 1, Gloucester, MA 01930
75 Friend St Unit 1, Gloucester, MA 01930Welcome to Unit #1 at 75 Friend Street, Gloucester, MA 01930, where comfort meets convenience. This charming apartment offers four spacious bedrooms, providing ample space for relaxation and personal retreat. The unit features a well-appointed full bathroom, designed with modern fixtures and a soothing color palette to enhance your daily routine.The living area is bright and inviting,
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$2,300 Per Month
- 2 Beds
- 1.5 Baths
- 1,400 Sq Ft
- Apartment for Rent
124 Mount Pleasant Ave Unit 1, Gloucester, MA 01930
124 Mount Pleasant Ave Unit 1, Gloucester, MA 01930Beautifully furnished winter rental available September 15, 2026–May 30, 2027. This bright, two-level East Gloucester townhouse lives like a single-family home and is tucked away on a quiet dead-end street near Niles and Good Harbor Beaches, Rocky Neck, and Bass Rocks Golf Club. The open-concept main level features a granite and cherry kitchen with an oversized island, spacious living room with
Patricia McCormick J. Barrett & Company
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$3,975
Total Monthly Price
- 3 Beds
- 2.5 Baths
- 1,520 Sq Ft
- House for Rent
206 Atlantic St, Gloucester, MA 01930
206 Atlantic St, Gloucester, MA 01930Winter Rental Available: October 1, 2026- May 31, 2027This private contemporary furnished house is perched on a hilltop near Wingaersheek Beach. Inside is an open plan living/dining room with vaulted ceilings, hardwood floors, and large oversized windows which fills the room of natural light. The dining area includes a large table with plenty of seating. The eat-in kitchen with breakfast
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$2,975 Per Month
- 3 Beds
- 1.5 Baths
- 1,402 Sq Ft
- House for Rent
16 Warwick Rd Unit WINTER, Gloucester, MA 01930
16 Warwick Rd Unit WINTER, Gloucester, MA 01930WINTER RENTAL: Ideally situated between two of Cape Ann's most beautiful beaches; Long Beach and Good Harbor, this impeccable one level home features an open-plan kitchen/dining area with granite countertops, stainless steel appliances, and gas range. It's comfortable living room features large windows and a flat screen tv over the decorative fireplace. There are 3 bedrooms: the primary has a
Carole Sharoff AVH Realty
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$3,150
Total Monthly Price
- 2 Beds
- 1.5 Baths
- 1,462 Sq Ft
- House for Rent
42 Rocky Neck Ave, Gloucester, MA 01930
42 Rocky Neck Ave, Gloucester, MA 01930WINTER RENTAL: Available October 27, 2026 - May 31, 2027Perched high above Rocky Neck, Painter’s Perch offers sweeping views of the Neck and scenic Smith Cove. This charming 2-bedroom, 1.5-bath retreat is an ideal getaway near Gloucester’s vibrant arts district.Enjoy the coastal air from the spacious backyard, private patio for al fresco dining, main-level deck, or the
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$2,975 Per Month
- 2 Beds
- 1.5 Baths
- 996 Sq Ft
- Condo for Rent
19 Atlantic Rd Unit 16, Gloucester, MA 01930
19 Atlantic Rd Unit 16, Gloucester, MA 01930OFF SEASON RENTAL: Welcome to this modern two-story condo located in desirable Bass Rocks neighborhood boasting beautiful views of the golf course yet just .2 miles from Good Harbor Beach and its fabled footbridge. This 2-bedroom, 1.5-bath home combines contemporary style with comfortable living. Its open floor plan is filled with natural light, creating a warm and inviting atmosphere throughout.
Jonathan Fonvielle AVH Realty
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$3,950
Total Monthly Price
- 6 Beds
- 2.5 Baths
- 2,282 Sq Ft
- House for Rent
64 Riverview Rd, Gloucester, MA 01930
64 Riverview Rd, Gloucester, MA 01930Winter Rental Available: December 1, 2026-May 31, 2027Welcome to Tidebend, a beautifully crafted 6-bedroom, 2.5-bath home offering serene views of the Annisquam River. This thoughtfully designed home blends quality craftsmanship with comfort and practicality, featuring custom woodwork and built-ins throughout that enhance both character and functionality. The home’s inviting
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$3,700 Per Month
- 4 Beds
- 3 Baths
- 2,164 Sq Ft
- House for Rent
1 Sandy Way, Gloucester, MA 01930
1 Sandy Way, Gloucester, MA 01930Winter Rental: 10/1/2026-5/15/2026. This serene retreat is perfect for sunsets and seaside relaxation. Available week September 21-27 $7,500 Discover the best of coastal living with this beautifully furnished and equipped weekly rental, deeded access to Coffins Beach. Whether you enjoy peaceful walks along the shoreline, stunning sunsets or the serenity of living by the sea, this home provides
Kimberly Tipert Noyes Engel & Volkers By the Sea
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$2,975
Total Monthly Price
- 3 Beds
- 2.5 Baths
- 1,717 Sq Ft
- House for Rent
11 S Kilby St, Gloucester, MA 01930
11 S Kilby St, Gloucester, MA 01930Winter Rental Available: November 3, 2026 - May 15, 2027 (Dogs Welcome!)Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers seasonal views of Ipswich Bay from the balcony of the second-floor bedroom. Decorated with a European sensibility, this home is bright and comfortable with hardwood floors throughout.A Queen Anne-style house, you can access the
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$1,900 Per Month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Apartment for Rent
16 Magnolia Ave Unit 12, Gloucester, MA 01930
16 Magnolia Ave Unit 12, Gloucester, MA 01930Charming renovated 1-bedroom apartment available now! This well-maintained unit features modern updates throughout, a bright and inviting living space, and the convenience of off-street parking. Heat and hot water is included in the rent. Conveniently located near Gloucester’s shops, restaurants, beaches, and commuter routes.
Desiree Taylor Desired Homes Realty LLC
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$3,675 Per Month
- 4 Beds
- 2 Baths
- 1,400 Sq Ft
- Condo for Rent
98 Maplewood Ave Unit 2, Gloucester, MA 01930
98 Maplewood Ave Unit 2, Gloucester, MA 01930Lots of natural light fills this updated 4 bedroom, 2 bath condo that is conveniently located within walking distance of the train, shopping, restaurants and parks. Freshly painted throughout with a new full bathroom, new dishwasher, new washer/dryer, new floors, new roof. Two assigned parking spaces in the driveway and a big patio and garden area. Plenty of storage in the basement. Please Note:
Timothy Collins Boston Metropolitan Realty
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