My Info

Professional Experience: Dave began his career in the Keys in sales and marketing at Newfound Harbor Marine Institute on Big Pine Key in 1983. Over the past 20 years he has become intimate with Lower Keys real estate, neighborhoods, and the surrounding waters while operating a successful flats fishing business. Dave’s commitment to sellers and buyers will be to “provide amazing customer service”, and a “high level of communication” resulting in successful closings.

Additional bio info: University of Delaware '83 alumnus

Welcome

"I Introduced Thousands to the Thrill of Fishing The Florida Keys...I Can Help Make The Florida Keys Your Home!"

Specialties

  • Luxury Island Water Front Homes
  • Second Homes and Vacation Homes
  • Commercial Sales & Leasing

Specialty Markets

  • Luxury Island Properties
  • Military Markets
  • Vacation/Second
  • Retirement
  • Buyer Representative
  • First Time Buyers
  • Recreational

Credentials

  • Top 100 Agents in the Keys ~ Elite Circle
  • E-Pro Realtor


What my clients are saying (30)

My Service Ratings

03/17/2026 - Genicarmen N.

Dave assisted me in originally purchasing the property and it was a positive experience that I contacted him to sell the property.


My Service Ratings

05/16/2023 - Hollia & Brad W.

Dave was so helpful as he navigated the sale of my home.


My Service Ratings

03/22/2022 - Thomas McCormick

Dave Wiley provided us with excellent market knowledge as well as the exceptional advice about Key West Real Estate that comes with decades of experience. As far as service, Dave has walked through homes when we weren't available to travel, he's also provided facetime video of various properties throughout our journey. Dave kept us completely up to date with all the new properties coming into the market through the e-portal. We have had countless phone calls and showings over a two year period. Dave helped my wife and I finally land our dream condo! It was a pleasure to work with Dave Wiley - we think you will like him too - give him a call today !

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Active Listings (3)

Property Address Details
29555 Enterprise Avenue Property Photo 1
29555 Enterprise Avenue
Big Pine, FL 33043
Bed(s): 3
Bath(s): 2
sqft: 1,352
83 Sugarloaf Drive Property Photo 1
83 Sugarloaf Drive
Sugarloaf, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,225
Lot 8 Little Knockemdown Key Aka Parcel 23 Property Photo 1
Lot 8 Little Knockemdown Key Aka Parcel 23
Summerland, FL 33042
OS - Offshore Island District Zoning | 4.00 Acre(s)

Recent Listings Sold (45)

Property Address Details
20864 W 4th Avenue Property Photo 1
20864 W 4th Avenue
Cudjoe, FL 33042
Bed(s): 3
Bath(s): 4
sqft: 3,056
27450 W Indies Drive Property Photo 1
27450 W Indies Drive
Ramrod, FL 33042
Bed(s): 2
Bath(s): 4
sqft: 1,968
1183 E Caribbean Drive Property Photo 1
1183 E Caribbean Drive
Summerland, FL 33042
Bed(s): 3
Bath(s): 4
sqft: 3,019
27367 Martinique Lane Property Photo 1
27367 Martinique Lane
Ramrod, FL 33042
Bed(s): 4
Bath(s): 3
sqft: 2,080
2237 San Remo Drive Property Photo 1
2237 San Remo Drive
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,244
2131 Coral Way Property Photo 1
2131 Coral Way
Big Pine, FL 33043
Bed(s): 4
Bath(s): 3
sqft: 2,100
30830 Watson Boulevard, A & B Property Photo 1
30830 Watson Boulevard, A & B
Big Pine, FL 33043
Bed(s): 5
Bath(s): 2
sqft: 2,400
521 Blackbeard Road Property Photo 1
521 Blackbeard Road
Little Torch, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,758
29809 Newfound Boulevard Property Photo 1
29809 Newfound Boulevard
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,414
25359 2nd Street Property Photo 1
25359 2nd Street
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,352
953 Flagship Drive Property Photo 1
953 Flagship Drive
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,656
687 30th Street Property Photo 1
687 30th Street
Marathon, FL 33050
Bed(s): 3
Bath(s): 3
sqft: 1,776
22841 Buccaneer Lane Property Photo 1
22841 Buccaneer Lane
Cudjoe, FL 33042
Bed(s): 3
Bath(s): 3
sqft: 1,920
27367 Martinique Lane Property Photo 1
27367 Martinique Lane
Ramrod, FL 33042
Bed(s): 4
Bath(s): 3
sqft: 2,080
22774 Cudjoe Drive Property Photo 1
22774 Cudjoe Drive
Cudjoe, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,216
20896 7th Avenue Property Photo 1
20896 7th Avenue
Cudjoe, FL 33042
Bed(s): 3
Bath(s): 3
sqft: 1,956
306 N Anglers Drive B Property Photo 1
306 N Anglers Drive B
Marathon, FL 33050
Bed(s): 2
Bath(s): 2
sqft: 984
28548 Peg Leg Road Property Photo 1
28548 Peg Leg Road
Little Torch, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,324
2421 Linda Avenue Property Photo 1
2421 Linda Avenue
Key West, FL 33040
Bed(s): 2
Bath(s): 1
sqft: 1,127
27439 St. Vincent Lane Property Photo 1
27439 St. Vincent Lane
Ramrod, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,232
747 W Shore Drive Property Photo 1
747 W Shore Drive
Summerland, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 2,102
340 Spanish Main Drive Property Photo 1
340 Spanish Main Drive
Cudjoe, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,188
27451 Saint Croix Lane Property Photo 1
27451 Saint Croix Lane
Ramrod, FL 33042
Bed(s): 3
Bath(s): 3
sqft: 1,824
27363 St Martin Lane Property Photo 1
27363 St Martin Lane
Ramrod, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,200
27311 Saint Croix Lane Property Photo 1
27311 Saint Croix Lane
Ramrod, FL 33042
Bed(s): 3
Bath(s): 3
sqft: 1,172
30912 Bay Shore Drive Property Photo 1
30912 Bay Shore Drive
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,760
27388 Saint Vincent Lane Property Photo 1
27388 Saint Vincent Lane
Ramrod, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,092
57 W Sandy Circle Property Photo 1
57 W Sandy Circle
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,250
135 Cutlass Lane Property Photo 1
135 Cutlass Lane
Cudjoe, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 960
770 Carolyn Avenue Property Photo 1
770 Carolyn Avenue
Little Torch, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 952
27458 Haiti Lane Property Photo 1
27458 Haiti Lane
Ramrod, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,160
20874 W 4th Avenue Property Photo 1
20874 W 4th Avenue
Cudjoe, FL 33042
IS - Improved Subivision Zoning | 0.29 Acre(s)
19540 Tequesta Street Property Photo 1
19540 Tequesta Street
Sugarloaf, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,300
27994 Winsom Avenue Property Photo 1
27994 Winsom Avenue
Little Torch, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,288
3746 Driftwood Street Property Photo 1
3746 Driftwood Street
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,036
641 W Indies Drive Property Photo 1
641 W Indies Drive
Ramrod, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,232
247 W Shore Drive Property Photo 1
247 W Shore Drive
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,032
27983 Temple Avenue Property Photo 1
27983 Temple Avenue
Little Torch, FL 33042
Bed(s): 1
Bath(s): 1
sqft: 768
27431 W Indies Drive Property Photo 1
27431 W Indies Drive
Ramrod, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 2,372
27329 St Vincent Lane Property Photo 1
27329 St Vincent Lane
Ramrod, FL 33042
IS - Improved Subivision Zoning | 0.14 Acre(s)
No Listing Photos
701 Spanish Main Drive #647
Cudjoe Key, FL 33042
URML-L - Urban Res Mobile Home L Zoning | 0.05 Acre(s)
Acosta Trail Property Photo 1
Acosta Trail
Sugarloaf, FL 33042
NA - Native Area District Zoning | 0.31 Acre(s)
No Listing Photos
Tract B Helen Street
Big Pine Key, FL 33043
IS - Improved Subivision Distric Zoning | 0.43 Acre(s)
Lot 8 Little Knockemdown Key, Aka Parcel 23 Property Photo 1
Lot 8 Little Knockemdown Key, Aka Parcel 23
Summerland, FL 33042
OS - Offshore Island District Zoning | 4.00 Acre(s)
27404 W Indies Drive Property Photo 1
27404 W Indies Drive
Ramrod, FL 33042
Story(s) | 6,000 sqft | 0 Office SqFt

Recent Buyer Sales (29)

Property Address Details
281 Trumbo Road, 203 Property Photo 1
281 Trumbo Road, 203
Key West, FL 33040
Bed(s): 3
Bath(s): 4
sqft: 2,851
1183 Caribbean Drive Property Photo 1
1183 Caribbean Drive
Summerland, FL 33042
Bed(s): 3
Bath(s): 4
sqft: 3,119
937 Ocean Drive Property Photo 1
937 Ocean Drive
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,112
2237 San Remo Drive Property Photo 1
2237 San Remo Drive
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,244
113 Pirates Cove Drive Property Photo 1
113 Pirates Cove Drive
Marathon, FL 33050
Bed(s): 3
Bath(s): 3
sqft: 2,902
25359 2nd Street Property Photo 1
25359 2nd Street
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,352
230 Airport Drive Property Photo 1
230 Airport Drive
Summerland, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,900
953 Flagship Drive Property Photo 1
953 Flagship Drive
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,656
833 Elizabeth Street Property Photo 1
833 Elizabeth Street
Key West, FL 33040
Bed(s): 5
Bath(s): 4
sqft: 2,083
1901 S Roosevelt Boulevard, 406s Property Photo 1
1901 S Roosevelt Boulevard, 406s
Key West, FL 33040
Bed(s): 2
Bath(s): 2
sqft: 1,099
656 W Shore Drive Property Photo 1
656 W Shore Drive
Summerland, FL 33042
Bed(s): 3
Bath(s): 3
sqft: 1,748
27367 Martinique Lane Property Photo 1
27367 Martinique Lane
Ramrod, FL 33042
Bed(s): 4
Bath(s): 3
sqft: 2,080
2601 S Roosevelt Boulevard, 117c Property Photo 1
2601 S Roosevelt Boulevard, 117c
Key West, FL 33040
Bed(s): 3
Bath(s): 2
sqft: 1,221
2421 Linda Avenue Property Photo 1
2421 Linda Avenue
Key West, FL 33040
Bed(s): 2
Bath(s): 1
sqft: 1,127
747 W Shore Drive Property Photo 1
747 W Shore Drive
Summerland, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 2,102
27363 St Martin Lane Property Photo 1
27363 St Martin Lane
Ramrod, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,200
517 Heck Avenue Property Photo 1
517 Heck Avenue
Little Torch, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,417
57 W Sandy Circle Property Photo 1
57 W Sandy Circle
Big Pine, FL 33043
Bed(s): 2
Bath(s): 2
sqft: 1,250
22774 Cudjoe Drive Property Photo 1
22774 Cudjoe Drive
Cudjoe, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,216
1509 George Street Property Photo 1
1509 George Street
Key West, FL 33040
Bed(s): 3
Bath(s): 2
sqft: 1,200
19540 Tequesta Street Property Photo 1
19540 Tequesta Street
Sugarloaf, FL 33042
Bed(s): 3
Bath(s): 2
sqft: 1,300
641 W Indies Drive Property Photo 1
641 W Indies Drive
Ramrod, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,232
247 W Shore Drive Property Photo 1
247 W Shore Drive
Summerland, FL 33042
Bed(s): 2
Bath(s): 2
sqft: 1,032
2nd Street Property Photo 1
2nd Street
Summerland, FL 33042
IS - Improved Subivision Zoning | 0.16 Acre(s)
27329 St Vincent Lane Property Photo 1
27329 St Vincent Lane
Ramrod, FL 33042
IS - Improved Subivision Zoning | 0.14 Acre(s)
501 W Sandy Circle Property Photo 1
501 W Sandy Circle
Big Pine, FL 33043
Bed(s): 2
Bath(s): 1
sqft: 936
Lot 7 Jamaica Lane Property Photo 1
Lot 7 Jamaica Lane
Ramrod, FL 33042
IS - Improved Subivision Distric Zoning | 0.14 Acre(s)
No Listing Photos
Tract B Helen Street
Big Pine Key, FL 33043
IS - Improved Subivision Distric Zoning | 0.43 Acre(s)
Lot 8 Little Knockemdown Key, Aka Parcel 23 Property Photo 1
Lot 8 Little Knockemdown Key, Aka Parcel 23
Summerland, FL 33042
OS - Offshore Island District Zoning | 4.00 Acre(s)

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