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Heather Winter
REALTOR®

A corporate attorney from Manhattan who was drawn by her love of the sun and beach to permanently call Southwest Florida home, Heather Winter is the ultimate go-getter. With over 16 years working in mergers & acquisitions and technology transactions for Fortune 100 companies and multinational law firms, negotiations, marketing, contracts and relationship-building are her thing! Her love for real estate stems from a childhood spent visiting open houses and listening to her grandparents chat about their own thriving real estate business.   Heather has always enjoyed acting as a liaison for her customers to facilitate one of the largest transactions of their lives.  

When not working, you can find Heather refining her negotiating and athletic skills chasing around her two young boys, jogging on the beach, swimming with the Naples masters swim team, playing tennis or watching her boys play various sports around town.   Often you can find Heather and her boys at the Naples airport viewing deck watching the planes take off and land - reminding them of their U.S. Navy Captain Dad who is in Naples when he is not flying for the Navy.

A former Division I swimmer, multi marathoner and a successful attorney, Heather is a true professional and master multitasker who thrives under pressure and offers nothing but the best in service with a smile!

Heather Winter
REALTOR®

A corporate attorney from Manhattan who was drawn by her love of the sun and beach to permanently call Southwest Florida home, Heather Winter is the ultimate go-getter. With over 16 years working in mergers & acquisitions and technology transactions for Fortune 100 companies and multinational law firms, negotiations, marketing, contracts and relationship-building are her thing! Her love for real estate stems from a childhood spent visiting open houses and listening to her grandparents chat about their own thriving real estate business.   Heather has always enjoyed acting as a liaison for her customers to facilitate one of the largest transactions of their lives.  

When not working, you can find Heather refining her negotiating and athletic skills chasing around her two young boys, jogging on the beach, swimming with the Naples masters swim team, playing tennis or watching her boys play various sports around town.   Often you can find Heather and her boys at the Naples airport viewing deck watching the planes take off and land - reminding them of their U.S. Navy Captain Dad who is in Naples when he is not flying for the Navy.

A former Division I swimmer, multi marathoner and a successful attorney, Heather is a true professional and master multitasker who thrives under pressure and offers nothing but the best in service with a smile!

About about Heather ...
Fun Facts

What is McQuaid and Company to you?

From the moment I first entered the McQuaid and Company office, I was struck but the vivacity, warmth, and congenial energy in each person I met and in every corner of the office.

What is your favorite local restaurant?

Sea monkey

What is your guilty pleasure?

A few hours on the beach with a good book and a glass of wine

What is your proudest moment?

Watching my boys love and protect each other.

What is your alarm clock in the morning? 

My boys jumping into my bed at 5am on the regular!

What would you say your superhero power is? 

My energy and persistence

What inspires you?

My children and fighting for freedom so they may enjoy it.

Let Us Connect
Office Properties
$44,880,000 For Sale 6111 Sanibel Captiva Road Sanibel, FL  33957
Development: Metes And Bounds, Status: A-Active
MLS#: 224050501
  • area" role="presentation icon 11068 Sqft
  • bedrooms" role="presentation icon 6
  • bathrooms" role="presentation icon 5
  • key" role="presentation icon Save
$3,676,800 1301 3Rd Avenue Naples, FL  34102
Development: Bayfront, Status: Pending
MLS#: 221083320
  • area" role="presentation icon 3064 Sqft
  • bedrooms" role="presentation icon 4
  • bathrooms" role="presentation icon 4
  • key" role="presentation icon Save
$3,675,000 For Sale 4602 Pond Apple Drive Naples, FL  34119
Development: Quail Creek, Status: A-Active
MLS#: 224035741
  • area" role="presentation icon 6300 Sqft
  • bedrooms" role="presentation icon 5
  • bathrooms" role="presentation icon 6
  • key" role="presentation icon Save
$3,400,000 For Sale 9715 Gulf Shore Drive Naples, FL  34108
Development: Vanderbilt Beach, Status: A-Active
MLS#: 224092138
  • area" role="presentation icon 2353 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
$2,750,000 For Sale 980 Cape Marco Drive Marco Island, FL  34145
Development: Cape Marco, Status: A-Active
MLS#: 223092912
  • area" role="presentation icon 2368 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
$2,688,000 For Sale 4724 Oak Leaf Drive Naples, FL  34119
Development: Quail Creek, Status: A-Active
MLS#: 224034252
  • area" role="presentation icon 4674 Sqft
  • bedrooms" role="presentation icon 4
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
$2,339,044 1320 3Rd Avenue Naples, FL  34102
Development: Bayfront, Status: Pending
MLS#: 221083176
  • area" role="presentation icon 2081 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
$2,135,320 1301 3Rd Avenue Naples, FL  34102
Development: Bayfront, Status: Pending
MLS#: 221083303
  • area" role="presentation icon 2110 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
$2,090,000 3779 Bayshore Drive Naples, FL  34112
Development: The Grove Bayshore, Status: Pending
MLS#: 224048202
  • area" role="presentation icon 2668 Sqft
  • bedrooms" role="presentation icon 4
  • bathrooms" role="presentation icon 4
  • key" role="presentation icon Save
$2,090,000 3771 Bayshore Drive Naples, FL  34112
Development: The Grove Bayshore, Status: Pending
MLS#: 224063091
  • area" role="presentation icon 2668 Sqft
  • bedrooms" role="presentation icon 4
  • bathrooms" role="presentation icon 4
  • key" role="presentation icon Save
$2,082,696 1320 3Rd Avenue Naples, FL  34102
Development: Bayfront, Status: Pending
MLS#: 221083166
  • area" role="presentation icon 2254 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
$1,983,520 1301 3Rd Avenue Naples, FL  34102
Development: Bayfront, Status: Pending
MLS#: 221083298
  • area" role="presentation icon 2254 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save

 

Office Rental Properties
Season Rate: $15,500 1135 3Rd Avenue Naples, FL  34102
Development: Naples Square, Status: A-Active
MLS#: 223095617
  • area" role="presentation icon 1476 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $15,500 Off-Season Rate: $8,500 1135 3Rd Avenue Naples, FL  34102
Development: Naples Square, Status: A-Active
MLS#: 223094919
  • area" role="presentation icon 1476 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $15,500 1115 Central Avenue Naples, FL  34102
Development: Eleven Eleven Central, Status: A-Active
MLS#: 224009658
  • area" role="presentation icon 1407 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $14,000 115 Cambria Lane Naples, FL  34112
Development: Cambria, Status: A-Active
MLS#: 224086781
  • area" role="presentation icon 2937 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save
Season Rate: $13,500 Off-Season Rate: $5,000 451 Bayfront Place Naples, FL  34102
Development: Bayfront, Status: A-Active
MLS#: 224030311
  • area" role="presentation icon 1800 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $11,000 Off-Season Rate: $6,400 3295 Tahoe Court Naples, FL  34119
Development: Riverstone, Status: A-Active
MLS#: 224068530
  • area" role="presentation icon 3359 Sqft
  • bedrooms" role="presentation icon 5
  • bathrooms" role="presentation icon 4
  • key" role="presentation icon Save
Season Rate: $10,000 Off-Season Rate: $4,500 410 Bayfront Place Naples, FL  34102
Development: Bayfront, Status: A-Active
MLS#: 224043169
  • area" role="presentation icon 1511 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $9,000 Off-Season Rate: $3,500 333 4Th Avenue Naples, FL  34102
Development: Olde Naples, Status: A-Active
MLS#: 224004212
  • area" role="presentation icon 1050 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $8,500 Off-Season Rate: $5,500 564 107Th Avenue Naples, FL  34108
Development: Naples Park, Status: A-Active
MLS#: 224031589
  • area" role="presentation icon 1500 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
1135 3Rd Avenue Naples, FL  34102
Development: Naples Square, Status: A-Active
MLS#: 223092988
  • area" role="presentation icon 1476 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $8,000 3420 Gulf Shore Boulevard Naples, FL  34103
Development: Moorings, Status: A-Active
MLS#: 224069505
  • area" role="presentation icon 1345 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save
Season Rate: $7,000 410 Bayfront Place Naples, FL  34102
Development: Bayfront, Status: A-Active
MLS#: 224086789
  • area" role="presentation icon 1511 Sqft
  • bedrooms" role="presentation icon 2
  • bathrooms" role="presentation icon 2
  • key" role="presentation icon Save

 

Office Properties
Sold Price: $2,400,000 Asking Price: $2,400,000 Date Closed: 06/11/2024 27760 Riverwalk Way Bonita Springs, FL  34134
Development: Bonita Bay, Status: CS-Closed Sale
MLS#: 224033152
  • area" role="presentation icon 3719 Sqft
  • bedrooms" role="presentation icon 3
  • bathrooms" role="presentation icon 3
  • key" role="presentation icon Save

 


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