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 view of a white house and large windows
a dining room with wooden floor a chandelier a wooden table and chairs
a living room with furniture and a large window
a living room with furniture fireplace and window
1/4
Compass Coming Soon

$3,450,000

5
Bedrooms
5,295
Square Feet
0.47
Acres

18 Ridge Street, Winchester, MA 01890

a front view of a building with a street
a view of a house with a street
a view of a entryway door of the house
a living room with furniture and a dining table with rug
a living room with furniture and a dining table with wooden floor
a living room with furniture rug and window
a view of a balcony with toilet and a deck
a view of a building from a balcony
a living room with furniture and wooden floor
a living room with furniture and wooden floor
a dining room with furniture and wooden floor
a kitchen with stainless steel appliances a sink and a refrigerator
a kitchen with stainless steel appliances a stove a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a kitchen with sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a sink
a view of a hallway with wooden floor and a bathroom
a bedroom with bed and a potted plant
a bedroom with a bed and a potted plant
a bathroom with a sink a toilet and a mirror
a bathroom with a sink a toilet and a bathtub
a bedroom with a bed and wooden floor
a bedroom with a bed and a dresser
a bedroom with a bed and a mirror
a bathroom with a sink toilet and shower
a view of walk in closet with empty racks
a bedroom with a bed and wooden floor
a bedroom with a bed and wooden floor
a front view of a house with parking space
a view of a backyard of the house
a view of outdoor space yard and patio
a view of a house with a wooden fence
a front view of a house with garden
a view of a backyard with a garden
a view of a garden with plants
a bunch of flowers in a garden
1/36
Listed By CompassUnder Agreement

$960,000

3
Bedrooms
1,109
Square Feet

14 Carlton Street, Unit B, Somerville, MA 02143

a view of a chair and table in the back yard of the house
a view of a house with a yard and large tree
a living room with furniture and a table
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a dining room with furniture and window
a view of a dining room with furniture and a potted plant
a view of a dining room with furniture window and outside view
a dining room with furniture and window
a kitchen with granite countertop white cabinets and white appliances
a kitchen with granite countertop white cabinets and white appliances
a kitchen with a refrigerator a stove and white cabinets with wooden floor
workspace with wooden floor and glass door
a view of a patio with a table and chairs and a barbeque with wooden fence
a view of a chairs and table in backyard of the house
a view of a room with wooden floor and stairs
a bedroom with a large bed and wooden floor
a bedroom with a bed and a painting on the wall
a spacious bedroom with a bed and a large window
a bedroom with a bed and a night stand
a view of a hallway with a window
a bathroom with a sink a toilet and shower
a view of a hallway with living room and furniture
a bedroom with a bed and a night lamp
a spacious bedroom with a bed and a chair
a spacious bedroom with a bed and a couch
a bedroom with a bed and a large window
a view of an empty room
an empty room with windows
a bathroom with a sink toilet and vanity
a view of a backyard
a view of a backyard space with trees
a front view of a house with garage
$799,000 | 4 Drummer Boy Way, Unit 4, Lexington, MA 02420
1/37
Listed By CompassUnder Agreement

$799,000

3
Bedrooms
1,509
Square Feet

4 Drummer Boy Way, Unit 4, Lexington, MA 02420

Gayle Wintersā€™ Transactions

Past Sales
$1,560,000 | 17 Cranston Road, Winchester, MA 01890

$1,560,000

4
Bedrooms
2,578
Square Feet
0.17
Acres

17 Cranston Road, Winchester, MA 01890

a front view of a house with a yard and garage

$640,000

5
Bedrooms
2,210
Square Feet
0.20
Acres

9 Russ Street, Methuen, MA 01844

a front view of a house with a garden

$870,000

3
Bedrooms
2,040
Square Feet

70 Sylvan Street, Unit 70, Melrose, MA 02176

$1,150,000 | 10 Bradshaw Street, Medford, MA 02155

$1,150,000

6
Bedrooms
2,749
Square Feet
0.10
Acres

10 Bradshaw Street, Medford, MA 02155

$2,112,500 | 4 Adams Street, Wakefield, MA 01880

$2,112,500

6
Bedrooms
5,400
Square Feet
0.32
Acres

4 Adams Street, Wakefield, MA 01880

a view of an entryway with wooden floor

$1,030,000

4
Bedrooms
3,618
Square Feet
0.91
Acres

109 Meadow Creek Drive, Dracut, MA 01826

a view of a house with a yard

$2,500,000

7
Bedrooms
6,600
Square Feet
1.47
Acres

443 Central Avenue, Needham, MA 02494

a living room with furniture a flat screen tv and a fireplace

$1,055,000

3
Bedrooms
2,130
Square Feet
0.38
Acres

7 Trinity Road, Winchester, MA 01890

a view of a white house with large windows and refrigerator

$1,100,000

4
Bedrooms
2,314
Square Feet
0.46
Acres

17 Wakefield Street, Reading, MA 01867

$1,410,000 | 12-14 Sylvan Street, Unit 2, Melrose, MA 02176

$1,410,000

6
Bedrooms
3,611
Square Feet

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

$1,439,000 | 12-14 Sylvan Street, Unit 1, Melrose, MA 02176

$1,439,000

6
Bedrooms
3,593
Square Feet

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

a kitchen with a sink appliances and cabinets

$1,060,000

4
Bedrooms
2,249
Square Feet

11 Bonner Avenue, Unit 2, Medford, MA 02155

a living room with furniture a table and a potted plant

$1,408,000

6
Bedrooms
3,530
Square Feet

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

$1,430,000 | 12-14 Sylvan Street, Unit 4, Melrose, MA 02176

$1,430,000

6
Bedrooms
4,094
Square Feet

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

a front view of a house with a yard

$1,191,000

4
Bedrooms
2,126
Square Feet
0.48
Acres

189 High Street, Winchester, MA 01890

$475,500 | 8 Crowninshield Street, Unit 111, Peabody, MA 01960

$475,500

2
Bedrooms
1,177
Square Feet

8 Crowninshield Street, Unit 111, Peabody, MA 01960

a front view of a house with garden

$932,000

4
Bedrooms
2,239
Square Feet
0.24
Acres

25 Murdoch Road, Stoneham, MA 02180

$1,825,000 | 45 Hancock Street, Lexington, MA 02420

$1,825,000

5
Bedrooms
3,768
Square Feet
0.36
Acres

45 Hancock Street, Lexington, MA 02420

Past Rentals
a view of a white house with a large tree

$2,900

2
Bedrooms

11 Symonds Street, Unit 2, Salem, MA 01970

a view of a big house with a yard

$3,000

2
Bedrooms

32 Watts Street, Unit 1, Malden, MA 02148

a living room with furniture and a potted plant

$3,000

2
Bedrooms

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

a front view of a house with garden

$4,700

4
Bedrooms

176 Washington Street, Unit 176, Reading, MA 01867

a house view with a garden

$3,800

3
Bedrooms

196 Waverley Road, North Andover, MA 01845

$5,200 | 61 Prince Street, Unit 3B, Boston, MA 02113

$5,200

3
Bedrooms

61 Prince Street, Unit 3B, Boston, MA 02113

a kitchen with stainless steel appliances granite countertop a stove a sink and white cabinets with wooden floors

$3,650

2
Bedrooms

2 Stratton Drive, Unit 106, Woburn, MA 01801

$4,600 | 176 Washington Street, Unit 176, Reading, MA 01867

$4,600

4
Bedrooms

176 Washington Street, Unit 176, Reading, MA 01867

a front view of a house with garden

$4,500

4
Bedrooms

176 Washington Street, Unit 176, Reading, MA 01867

a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher a microwave oven with granite countertops and cabinets

$2,900

3
Bedrooms

22 Auburn Street, Unit 5, Malden, MA 02148

a view of a kitchen with a sink and wooden floor

$4,000

4
Bedrooms

91 Haverhill Street, North Reading, MA 01864

a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher a microwave oven with granite countertops and cabinets

$3,000

4
Bedrooms

22 Auburn Street, Unit 5, Malden, MA 02148

a kitchen with stainless steel appliances granite countertop a stove a sink and white cabinets with wooden floors

$3,650

2
Bedrooms

2 Stratton Drive, Unit 106, Woburn, MA 01801

a front view of a house with a yard

$4,695

3
Bedrooms

139 Johnson Woods Drive, Unit 139, Reading, MA 01867

a view of a dining room with furniture large window and wooden floor

$4,500

3
Bedrooms

907-1 Main Street, Unit 1, Winchester, MA 01890

a front view of a house with garden

$3,000

2
Bedrooms

44 Woods Avenue, Unit 44, Somerville, MA 02144

a front view of a residential apartment building with a yard

$3,200

4
Bedrooms

22 Auburn Street, Unit 3, Malden, MA 02148

a front view of a house with a garden and yard

$4,300

3
Bedrooms

9 Upland Road, Winchester, MA 01890