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The DiPinto Group

Local Expertise, Globally Connected

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We are a team of local real estate experts boasting over 80 years of collective experience in Real Estate, committed to family values and personalized service.  Operating in the market where we live, work and play our expertise covers acquisitions, new construction, waterfront properties and condominium developments.  We ensure a smooth experience for our clients from start to finish, leveraging our renowned negotiations skills and a focus on quality and attention to detail.  Our track record speaks for itself, with a low inventory and a select focus on high-quality properties.  At The DiPinto Group, the only vanity statistic we care about is our client being #1.

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Featured Properties

Explore our exclusive listings.

Sold

4136 HIGEL AVE
$16,995,000

4136 HIGEL AVE, SARASOTA, FL 34242

  • 5 BEDS
  • 7 BATHS
  • 8,964 Sq.Ft.

Inactive

6489 GULFSIDE RD
$16,995,000

6489 GULFSIDE RD, LONGBOAT KEY, FL 34228

  • 4 BEDS
  • 4.5 BATHS
  • 6,614 Sq.Ft.

For Sale

6489 GULFSIDE RD
$16,995,000

6489 GULFSIDE RD, LONGBOAT KEY, FL 34228

  • 4 BEDS
  • 5 BATHS
  • 6,616 Sq.Ft.

Sold

1325 WESTWAY DRIVE
$12,800,000

1325 WESTWAY DR, SARASOTA, FL 34236

  • 5 BEDS
  • 8 BATHS
  • 6,590 Sq.Ft.

Inactive

109 N WARBLER LN
$11,750,000

109 N WARBLER LN, SARASOTA, FL 34236

  • 4 BEDS
  • 4 BATHS
  • 5,292 Sq.Ft.

For Sale

109 N WARBLER LN
$9,975,000

109 N WARBLER LN, SARASOTA, FL 34236

  • 4 BEDS
  • 5 BATHS
  • 3,700 Sq.Ft.

For Sale

3621 SAN REMO TER
$9,750,000

3621 SAN REMO TER, SARASOTA, FL 34239

  • 5 BEDS
  • 6 BATHS
  • 5,328 Sq.Ft.

For Sale

1540 HILLVIEW DR
$8,850,000

1540 HILLVIEW DR, SARASOTA, FL 34239

  • 4 BEDS
  • 7 BATHS
  • 7,074 Sq.Ft.

Inactive

1212 CENTER PL
$6,995,900

1212 lot 6 CENTER PL, SARASOTA, FL 34236

  • 5 BEDS
  • 6.5 BATHS
  • 4,750 Sq.Ft.

Inactive

1212 CENTER PL
$6,595,000

1212 CENTER PL, SARASOTA, FL 34236

  • 5 BEDS
  • 6 BATHS
  • 4,750 Sq.Ft.

Sold

1160 CENTER PLACE
$5,353,000

1160 CENTER PLACE, SARASOTA, FL 34236

  • 4 BEDS
  • 6 BATHS
  • 4,000 Sq.Ft.

Sold

1160 CENTER PLACE
$4,750,000

1160 CENTER PLACE, SARASOTA, FL 34236

  • 4 BEDS
  • 5 BATHS
  • 3,700 Sq.Ft.

Inactive

610 YARDARM LN
$4,699,999

610 YARDARM LN, LONGBOAT KEY, FL 34228

  • 4 BEDS
  • 5 BATHS
  • 4,138 Sq.Ft.

For Sale

109 N WARBLER LN
$4,549,000

109 N WARBLER LN, SARASOTA, FL 34236

Sold

3480 BAYOU SOUND
$4,000,000

3480 BAYOU SOUND, LONGBOAT KEY, FL 34228

  • 5 BEDS
  • 5 BATHS
  • 3,926 Sq.Ft.

For Sale

560 SCHOONER LN
Open House: 7/9/2025, 3:00 PM - 5:00 PM
$3,999,999

560 SCHOONER LN, LONGBOAT KEY, FL 34228

  • 4 BEDS
  • 4 BATHS
  • 3,666 Sq.Ft.

Sold

551 S POLK DR
$3,400,000

551 S POLK DR, SARASOTA, FL 34236

  • 3 BEDS
  • 3 BATHS
  • 2,565 Sq.Ft.

Sold

1131 MORNINGSIDE PL
$3,300,000

1131 MORNINGSIDE PL, SARASOTA, FL 34236

  • 4 BEDS
  • 3.5 BATHS
  • 2,814 Sq.Ft.

Sold

1121 MORNINGSIDE PL
$3,075,000

1121 MORNINGSIDE PL, SARASOTA, FL 34236

  • 4 BEDS
  • 5 BATHS
  • 3,454 Sq.Ft.

Inactive

3408 FAIR OAKS LN
$2,999,999

3408 FAIR OAKS LN, LONGBOAT KEY, FL 34228

  • 5 BEDS
  • 5 BATHS
  • 4,510 Sq.Ft.

Inactive

585 CUTTER LN
$2,999,999

585 CUTTER LN, LONGBOAT KEY, FL 34228

  • 4 BEDS
  • 4 BATHS
  • 3,602 Sq.Ft.

For Sale

148 N POLK
$2,995,000

148 N POLK, SARASOTA, FL 34236

  • 3 BEDS
  • 3 BATHS
  • 3,115 Sq.Ft.

Sold

129 TAFT DRIVE Unit: W201
$2,620,000

129 TAFT DR #W201, SARASOTA, FL 34236

  • 3 BEDS
  • 3 BATHS
  • 2,460 Sq.Ft.

Sold

159 TAFT DRIVE Unit: E206
$2,450,000

159 TAFT DR #E206, SARASOTA, FL 34236

  • 3 BEDS
  • 3 BATHS
  • 2,460 Sq.Ft.

For Sale

129 TAFT DR #W102
$2,350,000

129 TAFT DR #W102, SARASOTA, FL 34236

  • 3 BEDS
  • 3 BATHS
  • 2,445 Sq.Ft.

Sold

3927 SOMERSET DR
$2,100,000

3927 SOMERSET DR, SARASOTA, FL 34242

  • 3 BEDS
  • 4 BATHS
  • 2,758 Sq.Ft.

Inactive

3060 GRAND BAY BLVD #154
$1,999,999

3060 GRAND BAY BLVD #154, LONGBOAT KEY, FL 34228

  • 3 BEDS
  • 4 BATHS
  • 2,369 Sq.Ft.

Inactive

3131 BAYOU SOUND
$1,999,999

3131 BAYOU SOUND, LONGBOAT KEY, FL 34228

  • 3 BEDS
  • 3 BATHS
  • 3,023 Sq.Ft.

Sold

109 GARFIELD DR #201
$1,800,000

109 GARFIELD DR #201, SARASOTA, FL 34236

  • 3 BEDS
  • 2 BATHS
  • 1,993 Sq.Ft.

For Sale

3318 BAYOU SOUND
$1,495,000

3318 BAYOU SOUND, LONGBOAT KEY, FL 34228

  • 3 BEDS
  • 2 BATHS
  • 2,675 Sq.Ft.

Inactive

569 CHANNEL LN
$1,050,000

569 CHANNEL LN, LONGBOAT KEY, FL 34228

Sold

1050 LONGBOAT CLUB RD #704
$935,000

1050 LONGBOAT CLUB RD #704, LONGBOAT KEY, FL 34228

  • 2 BEDS
  • 2 BATHS
  • 1,409 Sq.Ft.

Sold

569 CHANNEL LN
$900,000

569 CHANNEL LN, LONGBOAT KEY, FL 34228

  • 2,381 Sq.Ft.

For Sale

131 GARFIELD DR #4D
$775,000

131 GARFIELD DR #4D, SARASOTA, FL 34236

  • 2 BEDS
  • 2 BATHS
  • 1,161 Sq.Ft.

Sold

2402 PALMETTO ST
$632,000

2402 PALMETTO ST, NOKOMIS, FL 34275

  • 3 BEDS
  • 3 BATHS
  • 1,833 Sq.Ft.

Sold

5552 EAGLE CREEK RD
$628,000

5552 EAGLE CREEK RD, SARASOTA, FL 34238

  • 3 BEDS
  • 2 BATHS
  • 2,110 Sq.Ft.

Sold

4519 TROUT RIVER XING
$456,617

4519 TROUT RIVER XING, ELLENTON, FL 34222

  • 4 BEDS
  • 4 BATHS
  • 2,909 Sq.Ft.

Sold

4938 72ND CT E
$408,000

4938 72ND CT E, BRADENTON, FL 34203

  • 3 BEDS
  • 2 BATHS
  • 1,646 Sq.Ft.

Sold

2525 ARAPAHO ST
$388,000

2525 ARAPAHO ST, SARASOTA, FL 34231

  • 3 BEDS
  • 2 BATHS
  • 1,337 Sq.Ft.
View All Properties

Looking to buy or sell a home in Lido Key, Longboat Key, Siesta Key, or the surrounding areas?

Contact The DiPinto Group, your expert real estate professionals in the region. With our deep knowledge of the local market and commitment to exceptional service, we are your go-to resource for navigating the real estate process with ease and confidence.

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WHAT MY CLIENTS SAY

Kerry McCarthy showed me all the special spots that I never knew existed. Well educated in the entire market and what a wonderful person to work with. She’s got good MoJo !!!!!

— Taryn M

WHAT MY CLIENTS SAY

Kerry is the President of our HOA in Sarasota. Her attention to detail and knowledge of the ever-changing laws in FL are second to none. She is a tireless worker. She always meets our needs. She is solution driven. She is a joy to work with.

— Scott

WHAT MY CLIENTS SAY

Kerry’s competitive edge combined with her big heart makes her the ideal broker to work with when searching for your next home. Her knowledge of the market is expansive and she’s an excellent listener - she’ll make you her priority. Kerry always makes me laugh and helps me keep everything in perspective - for all of these reasons, I highly recommend her!

— Tori K

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Areas of Expertise

Longboat Key

Longboat Key

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Lido Shores

Lido Shores

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St. Armands

St. Armands

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Siesta Key

Siesta Key

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West of the Trail

West of the Trail

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Downtown Sarasota & Bay Front

Downtown Sarasota & Bay Front

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Work With Us

One would be hard-pressed to find a real estate group more attuned to the opulent offerings of Downtown Sarasota, Longboat Key, Lido Key, and St. Armands than The DiPinto Group. Their enthusiasm and positive attitude towards finding the perfect home in these idyllic locations are palpable and infectious. People trust them with their single largest asset when exploring the vibrant real estate landscape of Sarasota. It is a responsibility they shoulder with utmost seriousness. They understand that their success is a direct reflection of their clients' success in securing their dream abode in these picturesque locales. The Group's dedication is evident as they navigates the real estate market of Sarasota, Longboat Key, Lido Key, and St. Armands, ensuring a seamless and rewarding property acquisition experience for their clients.

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Contact Details

The DiPinto Group 

(941) 388-2021

[email protected]



53 S Palm Ave

Sarasota, Fl 34236