Gail Underwood, REALTOR®

Office Location: 3801 W Bay to Bay Boulevard, Tampa

Office Phone Number: (813) 839-3800

Cell Phone Number: 813-767-0676

About Gail

Gail Underwood is a fifth generation Floridian. Born and raised on Florida’s East Coast, Gail has made Tampa her home since graduating from the School of Human Sciences at Florida State University nearly 20 years ago. Whether you are buying or selling, Gail’s extensive knowledge of the area, vast community contacts, and innovative methods translate to a client-centric approach that maintains focus on achieving client goals as her first priority. Clients cruise through transactions with a Gail-Force wind at their backs.

Watch This Video to Learn More About Gail



Prior to entering Real Estate, Gail achieved success in professional client relationship fields. Starting in retail merchandising with a major national brand, she later transitioned to a successful recruiting career in the medical industry. Along the way, Gail paused from professional advancement for the birth of her children, but the drive within her again found success. While working as a stay at home mom, Gail accidentally became a highly sought after personal trainer; training a Who’s-Who list of clients in boxing and crossfit style regimens. Together with her husband-to-be, a third-generation Tampa native and a second-generation local business owner, Gail’s intense local knowledge and customer focused industry experience made her transition to client focused real estate transactions market seamless.


Gail feels blessed to have found and made Tampa her home. She loves Tampa and one of her greatest joys is being able to share her story and introduce new families or individuals to everything this great city and its surrounding areas has to offer. Gail has a daughter, a son, and two stepdaughters. Together, her family leads a very active South Tampa lifestyle.


Community involvement plays a major role in Gail’s life. She is active in school and extracurricular organizations including the St John’s Episcopal School, St Mary’s Episcopal School, Academy of the Holy Names High School, and Jesuit High School communities as well as involvement with Tampa Bay Little League and serving as a board member of Bayshore Little League. Gail is a Guardian Ad Litem in Hillsborough County, advocating for the rights of abused and neglected children. She also regularly participates in volunteer opportunities events benefiting children, the homeless, battered women for organizations including No Strings Attached, The Spring, and Feeding Tampa Bay. Gail also enjoys professional and social affiliations including Greater Tampa Realtors, the Pi Beta Phi Alumni Association, Carlouel Yacht Club, and her Smith & Associates family!

Sold Listings.

Sold
6025 Beacon Shores Street, TAMPA

$4,500,000

6025 Beacon Shores Street, TAMPA

5 Beds 8 Baths 6,517 SqFt Residential TB8456639
Sold
19730 Gulf Boulevard 500, INDIAN SHORES

$4,500,000

19730 Gulf Boulevard 500, INDIAN SHORES

5 Beds 5 Baths 5,100 SqFt Residential TB8474767
Sold
10520 Broadland Pass, THONOTOSASSA

$2,950,000

10520 Broadland Pass, THONOTOSASSA

6 Beds 8 Baths 6,379 SqFt Residential TB8316565
Sold
913 South Bruce Street, TAMPA

$1,350,000

913 South Bruce Street, TAMPA

4 Beds 3 Baths 1,680 SqFt Residential TB8312092
Sold
6421 3rd Palm Point, ST. PETE BEACH

$1,099,000

6421 3rd Palm Point, ST. PETE BEACH

3 Beds 3 Baths 1,874 SqFt Residential U8237256
Sold
4965 Bayshore Boulevard 4965, TAMPA

$1,050,000

4965 Bayshore Boulevard 4965, TAMPA

3 Beds 3 Baths 2,675 SqFt Residential TB8406492
Sold
502 69th Street, HOLMES BEACH

$999,000

502 69th Street, HOLMES BEACH

2 Beds 2 Baths 1,380 SqFt Residential A4645230
Sold
5210 Covesound Way, APOLLO BEACH

$989,000

5210 Covesound Way, APOLLO BEACH

4 Beds 4 Baths 2,900 SqFt Residential TB8478602
Sold
809 South Oregon Avenue A, TAMPA

$950,000

809 South Oregon Avenue A, TAMPA

3 Beds 4 Baths 1,860 SqFt Residential TB8348066
Sold
1000 Gulf Boulevard 108, INDIAN ROCKS BEACH

$899,000

1000 Gulf Boulevard 108, INDIAN ROCKS BEACH

3 Beds 2 Baths 1,300 SqFt Residential TB8347547
Sold
2 Adalia Avenue 502, TAMPA

$825,000

2 Adalia Avenue 502, TAMPA

3 Beds 2 Baths 1,592 SqFt Residential TB8337437
Sold
2510 West Cleveland Street 2, TAMPA

$725,000

2510 West Cleveland Street 2, TAMPA

3 Beds 4 Baths 1,936 SqFt Residential TB8301041
Sold
4518 West Gray Street, TAMPA

$599,000

4518 West Gray Street, TAMPA

3 Beds 3 Baths 1,799 SqFt Residential TB8491197
Sold
1023 West Ohio Avenue, TAMPA

$599,000

1023 West Ohio Avenue, TAMPA

3 Beds 2 Baths 1,751 SqFt Residential TB8334230
Sold
1338 Kinsmere Drive, TRINITY

$440,000

1338 Kinsmere Drive, TRINITY

3 Beds 2 Baths 2,032 SqFt Residential W7866934
Sold
32674 Osprey Peak Way, SAN ANTONIO

$434,990

32674 Osprey Peak Way, SAN ANTONIO

5 Beds 3 Baths 2,605 SqFt Residential TB8379685
Sold
3381 19th Place Sw, LARGO

$409,900

3381 19th Place Sw, LARGO

3 Beds 2 Baths 1,709 SqFt Residential TB8398849
Sold
3420 Rugby Court, PALM HARBOR

$407,999

3420 Rugby Court, PALM HARBOR

2 Beds 2 Baths 1,420 SqFt Residential TB8305740
Sold
1040 Summer Breeze Drive, BRANDON

$399,900

1040 Summer Breeze Drive, BRANDON

4 Beds 2 Baths 1,665 SqFt Residential TB8377949
Sold
1906 West Dekle Avenue H, TAMPA

$379,900

1906 West Dekle Avenue H, TAMPA

2 Beds 2 Baths 873 SqFt Residential TB8438582
Sold
1124 Sousa Drive, LARGO

$372,000

1124 Sousa Drive, LARGO

2 Beds 2 Baths 1,182 SqFt Residential TB8426281
Sold
4851 West Gandy Boulevard 14c, TAMPA

$325,000

4851 West Gandy Boulevard 14c, TAMPA

2 Beds 2 Baths 960 SqFt Residential TB8353439
Sold
4911 Rock Island Court, WIMAUMA

$319,500

4911 Rock Island Court, WIMAUMA

3 Beds 2 Baths 1,888 SqFt Residential TB8396118
Sold
1997 Searay Shore Drive, CLEARWATER

$289,999

1997 Searay Shore Drive, CLEARWATER

3 Beds 2 Baths 1,429 SqFt Residential TB8424745
Smith Background image

Contact Gail to help you with your next home.

Smith & Associates watermark