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."


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

$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
$995,000 | 35 Fells Avenue Terrace, Medford, MA 02155
1/38
Listed By CompassNew

$995,000

5
Bedrooms
2,511
Square Feet
0.12
Acres

35 Fells Avenue Terrace, Medford, MA 02155

$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
$975,000 | Address Upon Request, Somerville, MA 02143
1/45
Compass Coming Soon

$975,000

3
Bedrooms
1,109
Square Feet

Address Upon Request, Somerville, MA 02143

Gayle Wintersā€™ Transactions

Past Sales
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

$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 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

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

a living room with furniture and a flat screen tv

$405,000

1
Bedrooms
673
Square Feet

235 Winthrop Street, Unit 2210, Medford, MA 02155

$960,000 | 11 Bonner Avenue, Unit 1, Medford, MA 02155

$960,000

4
Bedrooms
2,057
Square Feet

11 Bonner Avenue, Unit 1, Medford, MA 02155

a living room with furniture and a couch

$639,000

3
Bedrooms
1,775
Square Feet

659 Moody Street, Unit 2, Waltham, MA 02453

an aerial view of a house with swimming pool and garden space

$2,100,000

4
Bedrooms
3,044
Square Feet
1.08
Acres

55 Pleasant Street, Lexington, MA 02421

an aerial view of a house

$650,000

3
Bedrooms
2,733
Square Feet
2.08
Acres

68 Mt Lebanon Street, Pepperell, MA 01463

Past Rentals
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

a living room with furniture a fireplace and a dining table with wooden floor

$4,500

3
Bedrooms

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