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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ā˜…ā˜…ā˜…ā˜…ā˜…
"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."

ā˜…ā˜…ā˜…ā˜…ā˜…
"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."

ā˜…ā˜…ā˜…ā˜…ā˜…
"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."

ā˜…ā˜…ā˜…ā˜…ā˜…
"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!"

ā˜…ā˜…ā˜…ā˜…ā˜…
"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."


ā€‹ā€‹
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

$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
$2,575,000 | 443 Central Avenue, Needham, MA 02494
1/41
Listed By Compass

$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

$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
$1,429,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176
1/40
Listed By CompassUnder Agreement

$1,429,000

6
Bedrooms
4,094
Square Feet

12-14 Sylvan Street, Unit 4, Melrose, MA 02176

a living room with furniture a table and a potted plant
a view of entryway with furniture
a living room with furniture and a rug
a living room with furniture and a large window
a dining room with furniture and wooden floor
a living room with furniture and a table
a dining room with furniture and a kitchen view
a kitchen with stainless steel appliances granite countertop chairs and white cabinets
a kitchen with stainless steel appliances a refrigerator a sink a stove a microwave a dining table and chairs
a kitchen with kitchen island a sink a counter top space and stainless steel appliances
a kitchen with white cabinets and chairs
a view of entryway with wooden floor and stairs
a bathroom with a sink a toilet and shower
a living room with furniture and a window
a living room with furniture a window and a table
a view of a hallway with windows and stairs
a view of staircase with railing and a window
a living room with furniture and a wooden floor
a view of a room with a window and a kitchen
a bedroom with a bed and a large window
a bedroom with bed and a couch
a spacious bedroom with a bed a dresser and mirror
a bathroom with a sink a shower and mirror
a bathroom with a sink a toilet and shower
a bed room with a bed and a window
a bedroom with a bed and a window
a bedroom with a bed and a large window
a bathroom with a double vanity sink toilet and shower
a bedroom with furniture and a window
a bedroom with a bed and a table
a bedroom with furniture and a window
a living room with furniture
a living room with furniture and a large window
a bedroom with a bed and a window
a bathroom with a sink toilet and shower
a view of garage
a view of backyard with barbeque grill and plants
a view of a yard with a table and chair and potted plants
a view of a house with wooden fence and large windows
1/39
Listed By CompassUnder Agreement

$1,299,000

6
Bedrooms
3,530
Square Feet

12-14 Sylvan Street, Unit 3, Melrose, MA 02176

$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
$1,188,888 | 7 Trinity Road, Winchester, MA 01890
1/42
Listed By Compass

$1,188,888

3
Bedrooms
2,130
Square Feet
0.38
Acres

7 Trinity Road, Winchester, MA 01890

a front view of a house with garden
a front view of a house with garden
front view of house that has a lot of plants
a living room with furniture a large window and a wooden floor
a living room with furniture and a flat screen tv
a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop a stove sink and cabinets
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a view of a dining room with furniture
a view of a dining room with furniture window and outside view
a view of an entryway
a kitchen with granite countertop a stove cabinets and wooden floor
a view of a livingroom with furniture and wooden floor
a view of a bedroom with wooden floor and windows
a view of a bedroom with wooden floor and windows
a bathroom with a granite countertop toilet sink and mirror
an empty room with wooden floor chandelier fan and windows
a view of a room with wooden floor and window
a view of a hallway with wooden floor and closet
wooden floor in an empty room with a window
wooden floor in an empty room with a window
a bathroom with a granite countertop sink toilet and shower
an empty room with wooden floor closet and windows
wooden floor in an empty room with a window
a bedroom with a large bed and a large window
a bedroom with a bed and wooden floor
a bedroom with a large bed and a chandelier
a bathroom with a sink a toilet and a mirror
a view of empty room with wooden floor and fan
wooden floor in an empty room
a view of a room with furniture and a window
a view of a kitchen with utility and utility
a living room with furniture and a flat screen tv
a living room with furniture and a window
a view of a white house with a yard
a backyard of a house with lots of green space
a view of a house with backyard and sitting area
a view of a white house with a yard
a backyard of house
1/39
Listed By Compass

$1,099,888

5
Bedrooms
2,511
Square Feet
0.12
Acres

35 Fells Avenue Terrace, Medford, MA 02155

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 CompassContingent

$1,099,000

4
Bedrooms
2,249
Square Feet

11 Bonner Avenue, Unit 2, Medford, MA 02155

$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
$1,049,000 | 109 Meadow Creek Drive, Dracut, MA 01826
1/40
Listed By Compass

$1,049,000

4
Bedrooms
3,618
Square Feet
0.91
Acres

109 Meadow Creek Drive, Dracut, MA 01826

$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
$725,000 | 44-46 Woods Avenue, Unit 44, Somerville, MA 02144
1/35
Listed By Compass

$725,000

2
Bedrooms
872
Square Feet

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