Gayle Winters

Gayle Winters

REALTORĀ®
gayle.winters@compass.com
M: 617-699-0310

Specialties

Buyer's Agent, Listing Agent, Relocation, Investment Properties, New Construction, Renovations

Education

Salem State University - Bachelors, Accounting and Business/Management
Johnson & Wales University


Client Testimonials

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"Gayle was fantastic. She helped us purchase a single family home and sell our condo (which went for well above asking). She had deep knowledge of the market and the real estate field. She connected us to relevant contractors who could do the work we needed to prepare our condo for market. She was also a great negotiator. She helped us find a home in a community that we love. We are very grateful for her help and support. I would definitely recommend Gayle to others."

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"Gayle helped my wife and I with our search through the pandemic, and we could not have asked for a better agent. We looked at a few different home styles, conditions, and locations; Gayle guided us through it all flawlessly with her knowledge of the area and the market. Once we found our home Gayle helped us with a creative offer and through challenging situations to get us to close. Would highly recommend Gayle for your search."

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"She was a joy to work with. Her attitude and demeanor are top notch. She was able to guide us through the process with ease and make a stressful period tolerable. She had a firm grasp on the local market and was able to quickly identify potential homes. She will be the first person we call if we ever decide to list. You will not be disappointed if you have the opportunity to work with her."

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"Gayle will tell you what you need to do in order to move your home smoothly, and quickly! No one in the business beats her marketing skills, which go above, and beyond! Sheā€™s confident, knowledgeable, and choosing her as a realtor was the best decision Iā€™ve ever made! A#1 for sure!"

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"I really donā€™t have the word to describe how great she is. Iā€™m forever grateful I had you as my agent, being a first time home buyer I got exactly the right person to help me through this. I would recommend her to everyone she will put her clients best interest before hers. Thank you Gayle."


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About Gayle
                                       The logo of Gayle Winters & Co.

As a premier Massachusetts Real Estate Agent ranking in the top 1% of all REALTORSĀ® nationwide, I am responsible for a wide range of sales and management duties with The Gayle Winters Team. I am an industry-leading real estate agent and a true professional, experienced specialist providing a comprehensive real estate experience for buyers, sellers, investors and builders.

I have an awesome team of folks behind me that work closely together so we can provide nothing short of top notch service to all of our clients. We have offices throughout Massachusetts and across the country.

I have a very strong finance background with excellent negotiation skills, business planning, sales, management, and seller/buyer/investor representation. With my previous experience as Controller/CFO on the finance side of real estate, fueled by market research and insight, I am able to be your trusted local resource.

Gayle Wintersā€™ Listings

a front view of a house with garden
Listed By Compass

$3,100,000

6
Bedrooms
5,500
Square Feet
0.24
Acres

135 Hartman Road, Newton, MA 02459

a view of a house with a yard
an aerial view of a house
a view of an empty room with wooden floor and stairs
a living room with furniture a window and wooden floor
a bathroom with a sink a toilet and a mirror
a living room with furniture and view of kitchen
a living room with furniture a window and a chandelier
a living room with furniture a fireplace and a chandelier
a living room with furniture and a large window
a living room with furniture and a view of kitchen
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances kitchen island granite countertop a refrigerator a stove a dining table and chairs with wooden floor
a large kitchen with stainless steel appliances granite countertop a lot of counter space and wooden floors
a large kitchen with stainless steel appliances a lot of counter space and wooden floors
a living room with furniture and a wooden floor
a view of white cabinets and a wooden floor
a bedroom with a large bed and a potted plant
a bedroom with a bed and a window
a bathroom with a sink and a mirror
a kitchen with a sink and cabinets
a spacious bedroom with a bed a chandelier and large window with outer view
a bedroom with a bed and a chandelier
a view of walk in closet with clothes
a room with gym equipment and a potted plant
a bathroom with a sink mirror and window
a bathroom with a sink and a mirror
an empty room with wooden floor and a bathroom
an empty room with wooden floor cabinet and windows
a bathroom with a double vanity sink a toilet and a mirror
a view of an empty room and wooden floor
a white toilet sitting next to a bathroom sink
a view of an empty room with stairs and furniture
a living room with furniture and wooden floor
a living room with furniture and a table
a view of a house with wooden floor
a view of a house with a yard
an aerial view of residential house with outdoor space and trees all around
front view of a house with a yard
an aerial view of multiple house
$2,575,000 | 443 Central Avenue, Needham, MA 02494
1/41
Listed By CompassUnder Agreement

$2,575,000

7
Bedrooms
6,600
Square Feet
1.47
Acres

443 Central Avenue, Needham, MA 02494

$1,439,000 | 12-14 Sylvan Street, Unit 1, Melrose, MA 02176
Listed By CompassUnder Agreement

$1,439,000

6
Bedrooms
3,593
Square Feet

12-14 Sylvan Street, Unit 1, Melrose, MA 02176

a front view of a house with street
a view of a building with glass windows and door
a living room with furniture and a large window
a living room with furniture and a large window
a kitchen with a sink cabinets and window
a living room with furniture and a large window
a dining room with furniture and wooden floor
a kitchen with a dining table chairs and refrigerator
a view of a dining room with furniture and window
a living room with furniture and window
a view of a livingroom with furniture and a potted plant
a view of a hallway with windows and stairs
a view of a hallway with a bedroom
a bedroom with a large bed and a window
a bed room with a bed and a lamp
a bedroom with bed and a window
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a bedroom with bed and a window
a bedroom with a bed and a large window
a bedroom with a bed and a window
a bedroom with a bed and dresser
a view of an empty room with a window
a bathroom with a tub shower sink and mirror
a bedroom with a bed and a cabinets
a living room with furniture
a white bath tub sitting next to a white toilet
a view of a livingroom with storage and utility
a view of a livingroom with a hardwood floor
a bedroom with a bed and a couch
a living room with furniture and view of kitchen
a living room with furniture and a painting
a living room with furniture and a wooden floor
a bathroom with a sink a toilet and shower
a living room with furniture and a large window
a bathroom with a sink a toilet and shower
a view of an outdoor space
a view of a house with a yard
a view of a house with a barbeque and wooden stairs
$1,410,000 | 12-14 Sylvan Street, Unit 2, Melrose, MA 02176
1/40
Listed By CompassUnder Agreement

$1,410,000

6
Bedrooms
3,611
Square Feet

12-14 Sylvan Street, Unit 2, Melrose, MA 02176

a living room with furniture a flat screen tv and a fireplace
a front view of a house with a yard
a view of a room with wooden floor and white walls
a view of entryway and hall with wooden floor
a bathroom with a sink a toilet and mirror
a view of a bathroom with a tub and shower
wooden floor in a gallery
a living room with furniture a flat screen tv and a fireplace
a living room with furniture a rug and a painting on the wall
an empty room with wooden floor and windows
an empty room with wooden floor
a bathroom with a sink and a mirror
a living room with furniture and a large window
a living room with furniture and a flat screen tv
a living room with furniture a flat screen tv and a large window
a living room with furniture a flat screen tv and a fireplace
a living room with furniture and a wooden floor
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture window and wooden floor
a dining room with furniture and wooden floor
a kitchen with stainless steel appliances kitchen island granite countertop a sink a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a refrigerator sink and stove
an empty room with wooden floor and windows
a view of an empty room with wooden floor and a window
a bathroom with a granite countertop sink a toilet and shower
a bathroom with a granite countertop sink and a mirror
a bedroom with a bed and a painting on the wall
a large white bed in a white room
a large white bed in a white room
a bathroom with a sink a toilet and a mirror
a view of a room with wooden floor
a view of an empty room with wooden floor and a window
a view of empty room with wooden floor
a view of empty room with wooden floor and fan
a backyard of a house
a view of a tree in a yard
a view of city and mountain
an aerial view of multiple house
a view of covered with green space
a backyard of a house with lots of green space
$1,125,000 | 7 Trinity Road, Winchester, MA 01890
$1,125,000 | 7 Trinity Road, Winchester, MA 01890
1/42
Listed By CompassUnder Agreement

$1,125,000

3
Bedrooms
2,130
Square Feet
0.38
Acres

7 Trinity Road, Winchester, MA 01890

a kitchen with a sink appliances and cabinets
a kitchen with kitchen island a counter top space cabinets and stainless steel appliances
a view of a house with a yard and deck
a view of a white building among the yard
a view of a house with a yard and wooden fence
a view of an empty room with a window
an empty room with wooden floor closet and windows
a view of a livingroom with a fireplace
a kitchen with kitchen island a sink stainless steel appliances and cabinets
a kitchen with a stove and a wooden floor
a kitchen with stainless steel appliances a refrigerator sink and microwave
a view of an empty room with a window and a fireplace
a view of walk in closet with empty racks
a bathroom with a sink and a mirror
a kitchen with stainless steel appliances granite countertop a sink a stove a refrigerator and a cabinets
a view of a storage & utility room with washer and dryer
a utility room with dryer and washer
a bathroom with a toilet a sink and shower
a view of an empty room with a window
a view of an empty room
a view of an empty room
a view of an empty room with a window and wooden floor
a view of an empty room with wooden floor and a window
a view of empty room with wooden floor
an empty room with wooden floor and windows
a bathroom with a tub a sink and glass door shower
a bathroom with a shower and a sink
a view of a kitchen with wooden floor and a ceiling fan
a bathroom with a granite countertop sink toilet and shower
a bathroom with a shower
a view of an empty room with wooden floor
a view of a deck with a small yard
a view of a house with backyard and a tree
1/33
Listed By CompassUnder Agreement

$1,099,000

4
Bedrooms
2,249
Square Feet

11 Bonner Avenue, Unit 2, Medford, MA 02155

a view of an entryway with wooden floor
front view of a house with a yard
a front view of a house with a yard
a view of a city and mountains in the background
a sign on the side of a building
a view of empty room with wooden floor and fan
a view of an empty room with wooden floor and a window
a view of an empty room with a window
a view of an empty room with a window
a view of an empty room with wooden floor and a fireplace
a view of an empty room with window and fire place
a view of a room with wooden floor and windows
a view of an empty room with wooden floor and a window
a kitchen with stainless steel appliances granite countertop wooden cabinets a sink and dishwasher a stove with wooden floor
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher and a microwave oven with wooden cabinets
a kitchen with stainless steel appliances granite countertop a stove microwave and refrigerator
a view of a closet and wooden floor
a utility room with dryer and washer
a view of empty room with wooden floor and fan
wooden floor in an empty room with a window
a spacious bathroom with a mirror a sink and a mirror
a bathroom with a bathtub sink and mirror
a view of a room with wooden floor staircase and a wooden door
an empty room with windows and cabinet
a bathroom with a sink a toilet and a mirror
a view of an empty room with a window
a bathroom with a double vanity sink and a mirror
an empty room with a bathroom
a view of a room with racks on the wall
a view of an outdoor space
a view of a house with a balcony
a front view of a house with a yard
a view of white house with a yard and large tree
a view of empty room with entertaining space
a view of a garage
an aerial view of a house with yard swimming pool and outdoor seating
a view of a city with ocean view
a bathroom with a sink mirror and vanity
an aerial view of a houses with a yard
a front view of multiple houses with yard
1/41
Listed By Compass

$1,049,000

4
Bedrooms
3,618
Square Feet
0.91
Acres

109 Meadow Creek Drive, Dracut, MA 01826

$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$720,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
1/35
Listed By Compass

$720,000

2
Bedrooms
872
Square Feet

44-46 Woods Avenue, Unit 44, Somerville, MA 02144