Southside Homes

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  /98

  $2,150,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,270 Sq Ft

  1826 Boyce St, Sarasota, FL 34239

  Under contract-accepting backup offers. Welcome to this stunning 5-bedroom, 5-bathroom home ideally located near the Hillview District, downtown Sarasota, and just minutes from to Southside Elementary School. Enjoy the best of “West of the Trail” living in this beautifully updated residence that blends timeless architectural charm with modern luxury. The home features a brand-new gourmet kitchen

  

  Mirvate Thrower

  EXP REALTY LLC

  (941) 531-9471

  1826 Boyce St, Sarasota, FL 34239
• Explore Southside

• 

  

  

  /19

  $3,500 per month

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft
  • Condo for Rent

  3700 S Osprey Ave Unit 315, Sarasota, FL 34239

  ***AVAILABLE Jan through April 30 2027***(3 month minimum) WEST OF TAMIAMI TRAIL! Less than 1 mile from North bridge entrance to Siesta Key. 3-stry unit with the elevator in the center of courtyard. The unit is fully furnished. Two bedroom condo with beautiful kitchen. Second bedroom presently office, has pull out bed. Living room has pull out couch. Washer/Dryer in bathroom, and the condo has a

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  (941) 335-9368

  3700 S Osprey Ave Unit 315, Sarasota, FL 34239
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  /2

  $2,300,000 Sold Dec 02, 2025

  1585 South Dr, Sarasota, FL 34239

  • 3 Beds
  • 3.5 Baths
  • 2,764 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $832/SF
  • 22 Days On Market

  Current Estimated Value $2,191,741

  Last Listing Agent Nick Gard COLDWELL BANKER REALTY

  1585 South Dr, Sarasota, FL 34239
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  /65

  Est $1,805,140 Not Listed For Sale

  1964 Datura St, Sarasota, FL 34239

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft
  • Built 2006

  1964 Datura St, Sarasota, FL 34239

  Last Sold Summary

  • 5% Below List Price
  • $581/SF
  • 345 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Mackenzie Longueuil Michael Saunders
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  /26

  $3,500,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,349 Sq Ft

  1386 Tangier Way, Sarasota, FL 34239

  Under contract-accepting backup offers. SAN REMO ESTATES WATERFRONT LOT FOR SALE – Here’s your opportunity to bring your favorite architect and builder of choice and start designing your dream home directly on Roberts Bay in one of Sarasota’s most exclusive waterfront communities. On ONE-THIRD PLUS ACRE with 99 FEET OF WATER FRONTAGE and the perfect southwestern backyard exposure, you’ll enjoy

  

  Julie Larson

  WHITE SANDS REALTY GROUP FL

  (941) 326-5952

  1386 Tangier Way, Sarasota, FL 34239
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  /33

  $10,000 per month

  • 3 Beds
  • 5 Baths
  • 3,073 Sq Ft
  • House for Rent

  1716 Stapleton St, Sarasota, FL 34239

  AVAILABLE 6/1/26 Luxurious Fully Furnished, 3-Bedroom Home with Elevator in Gated Sarasota Community – Now Available for Rent! Short Term and Long Term rental options. Discover your sanctuary in one of Sarasota’s most desirable enclaves—West of the Trail—where homes are rarely available. Nestled in the exclusive, gated community of Granada Park, this stunning 3-bedroom, 3 full-bath, and 2

  

  Tracy Srodes

  FINE PROPERTIES

  (941) 393-0480

  1716 Stapleton St, Sarasota, FL 34239
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  /2

  $2,070,000 Sold Nov 21, 2025

  1815 Grove St, Sarasota, FL 34239

  • 4 Beds
  • 5 Baths
  • 2,617 Sq Ft
  • Built 2013

  Last Sold Summary

  • 8% Below List Price
  • $791/SF
  • 28 Days On Market

  Current Estimated Value $2,013,863

  Last Listing Agent Elizabeth Snyder PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1815 Grove St, Sarasota, FL 34239
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  /75

  Est $2,818,557 Not Listed For Sale

  1810 Wisteria St, Sarasota, FL 34239

  • 4 Beds
  • 3 Baths
  • 3,582 Sq Ft
  • Built 2014

  1810 Wisteria St, Sarasota, FL 34239

  Last Sold Summary

  • 8% Below List Price
  • $851/SF
  • 24 Days On Market

  Last Sold Price $3,050,000

  Last Listing Agent Mackenzie Longueuil Michael Saunders
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  /50

  $2,695,000

  • 3 Beds
  • 3.5 Baths
  • 2,714 Sq Ft

  1732 Cunliff Ln, Sarasota, FL 34239

  Located West of the Trail and close to downtown, this warm and welcoming home sits on an oversized corner lot along a quiet, tree-lined street just a short walk to Morton’s Gourmet Market and the dining and shopping of Southside Village. It’s also an easy stroll to Southside Elementary School, making school drop-offs simple and convenient. This custom-built residence showcases exceptional

  

  Georgia Salaverri

  COMPASS FLORIDA LLC

  (941) 214-7156

  1732 Cunliff Ln, Sarasota, FL 34239
• 

  

  /30

  $3,450 per month

  • 1 Bed
  • 1 Bath
  • 751 Sq Ft
  • Condo for Rent

  3360 S Osprey Ave Unit 205B, Sarasota, FL 34239

  Are you ready to enjoy all that Sarasota and the Gulf beaches have to offer? The location of this 1 bedroom, 1 bath is fantastic! So close to Siesta Key, Southside Village and Downtown Sarasota. Asking $3,450/month.

  Philip Pisano, III MICHAEL SAUNDERS & COMPANY

  3360 S Osprey Ave Unit 205B, Sarasota, FL 34239
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  /2

  $970,000 Sold Oct 27, 2025

  1735 Shoreland Dr, Sarasota, FL 34239

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $448/SF
  • 53 Days On Market

  Current Estimated Value $953,099

  Last Listing Agent Derek Patti NEXTHOME EXCELLENCE

  1735 Shoreland Dr, Sarasota, FL 34239
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  /36

  Est $1,590,605 Not Listed For Sale

  1744 Fortuna St, Sarasota, FL 34239

  • 4 Beds
  • 3.5 Baths
  • 2,841 Sq Ft
  • Built 2014

  1744 Fortuna St, Sarasota, FL 34239

  Last Sold Summary

  • 4% Below List Price
  • $581/SF
  • 74 Days On Market

  Last Sold Price $1,650,000

  Last Listing Agent Monica Verinder COLDWELL BANKER REALTY
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  /68

  $6,250,000

  • 4 Beds
  • 4.5 Baths
  • 5,310 Sq Ft

  1389 Tangier Way, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. Step into a private, gated waterfront estate in Sarasota offering deep-water boating access, refined coastal architecture, and an unsurpassed location just minutes to Siesta Key Beach, Southside Village, and downtown Sarasota. Located in the coveted San Remo Estates community, this exceptional residence blends timeless elegance with modern

  Joel Schemmel DOUGLAS ELLIMAN

  1389 Tangier Way, Sarasota, FL 34239
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  /29

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Condo for Rent

  3350 S Osprey Ave Unit 211A, Sarasota, FL 34239

  Updated and unfurnished condo just about 5 min to Siesta Key Beach Access (Shell Rd) and 8 min to Siesta Key Village in well established Oasis at Osprey in the . Located on the second floor with elevator access, this welcoming space truly feels like your home away from home during your Sarasota stay. The condo offers 2 comfortable bedrooms, 2 full bathrooms, a fully kitchen, spacious living and

  Alberto Garcia BRIGHT REALTY

  3350 S Osprey Ave Unit 211A, Sarasota, FL 34239
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  /2

  $7,500,000 Sold Jan 30, 2026

  3638 San Remo Terrace, Sarasota, FL 34239

  • 4 Beds
  • 4.5 Baths
  • 4,559 Sq Ft
  • Built 2016

  Last Sold Summary

  • 5% Below List Price
  • $1,645/SF
  • 47 Days On Market

  Current Estimated Value $7,563,856

  Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

  3638 San Remo Terrace, Sarasota, FL 34239
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  /2

  Est $1,382,535 Not Listed For Sale

  1756 Stapleton St, Sarasota, FL 34239

  • 3 Beds
  • 3.5 Baths
  • 2,304 Sq Ft
  • Built 2015

  1756 Stapleton St, Sarasota, FL 34239

  Last Sold Summary

  • 9% Below List Price
  • $662/SF
  • 59 Days On Market

  Last Sold Price $1,525,000

  Last Listing Agent Kim Ogilvie Michael Saunders
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  /83

  $8,245,000

  • 4 Beds
  • 3.5 Baths
  • 4,705 Sq Ft

  3631 San Remo Terrace, Sarasota, FL 34239

  Anchored in one of Sarasota’s most sought-after deepwater settings, 3631 San Remo Terrace is a modern sanctuary where clean lines meet the warmth of natural textures, creating a home that feels both timeless and alive. Completed in 2021 by award-winning designer Stephen Chung and thoughtfully refined by the current owner, the residence reflects resilience and intention, standing strong through

  Joel Schemmel DOUGLAS ELLIMAN

  3631 San Remo Terrace, Sarasota, FL 34239
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  /12

  $1,995 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  1957 Magnolia St, Sarasota, FL 34239

  Available March 15th, 2026. Just two blocks to Siesta Drive and a few more to the bridge leading to Siesta Key! This immaculate mid-century Florida style home has wood flooring, an updated kitchen, 2 bedrooms, and a den. The large back yard is fenced for privacy and makes for a peaceful retreat. Located in Poinsettia Park, one of Sarasota's most desirable neighborhoods. Shopping, dining, beaches,

  Timothy Bloch QUEST PROPERTIES INC

  1957 Magnolia St, Sarasota, FL 34239
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  /2

  $2,350,000 Sold Jan 30, 2026

  1536 Sandpiper Ln, Sarasota, FL 34239

  • Land
  • 0.32 Acre
  • $7,343,750 per Acre

  Last Sold Summary

  • 22% Below List Price
  • 211 Days On Market

  Current Estimated Value $2,588,174

  Last Listing Agent Fred Sassen MICHAEL SAUNDERS & COMPANY

  1536 Sandpiper Ln, Sarasota, FL 34239
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  /45

  Est $2,069,934 Not Listed For Sale

  3319 S Osprey Ave, Sarasota, FL 34239

  • 4 Beds
  • 4.5 Baths
  • 3,423 Sq Ft
  • Built 2023

  3319 S Osprey Ave, Sarasota, FL 34239

  Last Sold Summary

  • 8% Below List Price
  • $657/SF
  • 0 Days On Market

  Last Sold Price $2,250,000

  Last Listing Agent Faith Stutzman THE STUTZMAN REALTY GROUP, LLC
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  /73

  $2,595,000

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  3606 Palonia Ct, Sarasota, FL 34239

  A rare and extraordinary offering, this is the home everyone has been waiting for. Rebuilt from the ground up between 2021–2024, this stunning farmhouse-coastal estate blends timeless charm with modern luxury on a beautifully landscaped .45-acre lot, providing one of the largest under grass rear yards west of trail in the exclusive Granada neighborhood, ideal for a entertaining and added privacy.

  Daria Fairchild COLDWELL BANKER REALTY

  3606 Palonia Ct, Sarasota, FL 34239
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  /17

  $4,800 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • House for Rent

  3932 Sunshine Ave, Sarasota, FL 34231

  Seasonal/ short term rental Beautifully remodeled private and tranquil home on large fenced lot in Sarasota very close to the north end of Siesta Key. This home is flooded with natural sunlight from abundant windows through this open floor plan. The kitchen is spacious with solid wooden cabinetry topped with slab granite counters with breakfast bar, custom tile backsplash and stainless steel

  Henry Rossi RENT SARASOTA

  3932 Sunshine Ave, Sarasota, FL 34231
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  /2

  $1,900,000 Sold Dec 15, 2025

  3464 Camino Real, Sarasota, FL 34239

  • 4 Beds
  • 6 Baths
  • 2,847 Sq Ft
  • Built 2025

  Last Sold Summary

  • 22% Below List Price
  • $667/SF
  • 416 Days On Market

  Current Estimated Value $1,871,059

  Last Listing Agent Sylvia Nowicki PREFERRED SHORE LLC

  3464 Camino Real, Sarasota, FL 34239
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  /100

  Not Listed For Sale

  1705 Wisconsin Ln, Sarasota, FL 34239

  • 5 Beds
  • 7 Baths
  • 4,871 Sq Ft
  • Built 2016

  1705 Wisconsin Ln, Sarasota, FL 34239

  Last Sold Summary

  • $749/SF
  • 98 Days On Market

  Last Sold Price $3,650,000

  Last Listing Agent Moriah Taliaferro PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /97

  $4,311,400 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,550 Sq Ft

  1873 Rose St, Sarasota, FL 34239

  Under contract-accepting backup offers. Introducing a rare opportunity in Poinsettia Park II, one of the most desirable enclaves within Sarasota’s coveted West of Trail community. Built in 2023 by Voigt Brothers, this single-level custom residence offers 4,550 square feet of elevated living on an oversized .38-acre lot, where timeless design meets modern innovation. From the moment you enter,

  Brian Partie ENGEL + VOELKERS SARASOTA

  1873 Rose St, Sarasota, FL 34239
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  /57

  $15,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,519 Sq Ft
  • House for Rent

  1725 Bonita Ct, Sarasota, FL 34239

  This MAGNIFICENT home is nestled away in the Historic Granada private neighborhood with easy access to all amenities. 4 Bedrooms 3.5 Baths and over 3500+ square feet of elegantly finished living areas. Authentic travertine tile and maple hardwood floors, volume ceilings, solid-wood cabinetry, two-sided fireplace, chef’s kitchen, three-car garage (owner uses one bay) and cypress wood exterior

  Teresa Ribaudo JENNETTE PROPERTIES INC

  1725 Bonita Ct, Sarasota, FL 34239
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  /2

  $1,000,000 Sold Aug 21, 2025

  1746 Stapleton St, Sarasota, FL 34239

  • 4 Beds
  • 3 Baths
  • 2,895 Sq Ft
  • Built 2006

  Last Sold Summary

  • 37% Below List Price
  • $345/SF
  • 160 Days On Market

  Current Estimated Value $1,011,547

  Last Listing Agent Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

  1746 Stapleton St, Sarasota, FL 34239
• 

  /2

  Est $1,713,367 Not Listed For Sale

  3523 Jacinto Ct, Sarasota, FL 34239

  • 4 Beds
  • 4.5 Baths
  • 2,956 Sq Ft
  • Built 2024

  3523 Jacinto Ct, Sarasota, FL 34239

  Last Sold Summary

  • 8% Below List Price
  • $633/SF
  • 123 Days On Market

  Last Sold Price $1,872,000

  Last Listing Agent Paul Defelice HOUSEMAX REALTY LLC
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  /46

  $3,150,000 New Construction

  • 3 Beds
  • 4 Baths
  • 2,844 Sq Ft

  1959 Wisteria St, Sarasota, FL 34239

  Welcome to 1959 Wisteria Street – a beautiful New Construction Single Story home, West of the Trail, that your clients will love!This just-completed modern coastal single story home is located West of the Trail in preferred Flood Zone X, offering elevated storm protection and convenient access to Southside Village, Downtown Sarasota and Siesta Key beaches.Designed and built with Majestik

  Michael Hankin MAJESTIK REALTY, INC

  1959 Wisteria St, Sarasota, FL 34239
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  /63

  $13,500 per month

  • 3 Beds
  • 4 Baths
  • 3,104 Sq Ft
  • House for Rent

  1720 Spring Creek Dr, Sarasota, FL 34239

  Welcome to your tropical paradise retreat at 1720 Spring Creek Drive, nestled minutes away from the #1 beach in America, Siesta Key. This fully furnished enchanting oasis awaits with a captivating blend of charm, elegance, and comfort, promising an unforgettable living experience. Step into your own slice of paradise as you're greeted by lush, tropical landscaping and a picturesque facade that

  Adnan Dedic COMPASS FLORIDA LLC

  1720 Spring Creek Dr, Sarasota, FL 34239
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  /2

  $1,150,000 Sold Dec 19, 2025

  3716 Camino Real, Sarasota, FL 34239

  • 3 Beds
  • 2.5 Baths
  • 2,023 Sq Ft
  • Built 1951

  Last Sold Summary

  • 16% Below List Price
  • $568/SF
  • 254 Days On Market

  Current Estimated Value $1,119,445

  Last Listing Agent Ryan Adamson COLDWELL BANKER REALTY

  3716 Camino Real, Sarasota, FL 34239
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  /10

  Est $2,740,352 Not Listed For Sale

  1615 N Lodge Dr, Sarasota, FL 34239

  1615 N Lodge Dr, Sarasota, FL 34239

  Last Sold Summary

  • 14% Below List Price
  • 10 Days On Market

  Last Sold Price $3,200,000

  Last Listing Agent Kelly Gettel COLDWELL BANKER REALTY
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  /54

  $2,795,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,810 Sq Ft

  3512 Camino Real, Sarasota, FL 34239

  3512 Camino Real represents a rare opportunity to acquire a newly constructed luxury residence strategically positioned for high-performing short-term rental income in one of Sarasota’s most supply-constrained residential corridors. Located inside the City of Sarasota and approximately 10 minutes to Siesta Key Beach, Siesta Key Village, and Downtown Sarasota, this property is purpose-built to

  Mark Coppens EXP REALTY LLC

  3512 Camino Real, Sarasota, FL 34239
• 

  

  /23

  $1,950 per month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  1901 Hyde Park St Unit C, Sarasota, FL 34239

  Enjoy this comfortable & spacious one bedroom apartment located in wonderful Southside Village, recently renovated, 1 block to Sarasota Memorial Hospital. Brand new pool with large deck to enjoy the summer heat. Easy walk to so many wonderful restaurants and cute boutique stores. Siesta Key and Lido Key beaches 10 minutes away. Multiple units available

  Jason Truluck Williams GRAYSTONE REAL ESTATE

  1901 Hyde Park St Unit C, Sarasota, FL 34239
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  /2

  $730,000 Sold Mar 13, 2026

  3530 Flores Ave, Sarasota, FL 34239

  • 3 Beds
  • 3 Baths
  • 1,960 Sq Ft
  • Built 1969

  Last Sold Summary

  • 9% Below List Price
  • $372/SF
  • 88 Days On Market

  Current Estimated Value $780,971

  Last Listing Agent Karen Chandler MICHAEL SAUNDERS & COMPANY

  3530 Flores Ave, Sarasota, FL 34239
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  /3

  Est $1,478,629 Not Listed For Sale

  1700 Seminole Dr, Sarasota, FL 34239

  • 3 Beds
  • Built 1916

  1700 Seminole Dr, Sarasota, FL 34239

  Last Sold Summary

  • 8% Below List Price
  • $362/SF
  • 0 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  /52

  $4,150,000

  • 4 Beds
  • 4.5 Baths
  • 4,353 Sq Ft

  1729 Cherokee Dr, Sarasota, FL 34239

  Priced to sell. Recipient of eleven awards, including Residential Design and Build Design Excellence and Home of the Year by SRQ Magazine, this exceptional residence is the result of a thoughtful collaboration between Jonathan Parks Architect and Michael A. Gilkey Inc landscape designer. Located in one of Sarasota’s oldest and most established neighborhoods, the home seamlessly blends a

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1729 Cherokee Dr, Sarasota, FL 34239
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  /12

  $1,750 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Apartment for Rent

  1901 Hyde Park St Unit G, Sarasota, FL 34239

  Enjoy this comfortable & spacious studio apartment located in wonderful Southside Village, recently renovated, 1 block to Sarasota Memorial Hospital. Brand new pool with large deck to enjoy the summer heat. Easy walk to so many wonderful restaurants and cute boutique stores. Siesta Key and Lido Key beaches 10 minutes away.

  Jason Truluck Williams GRAYSTONE REAL ESTATE

  1901 Hyde Park St Unit G, Sarasota, FL 34239
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  /2

  $6,900,000 Sold Dec 26, 2025

  3544 San Remo Terrace, Sarasota, FL 34239

  • 5 Beds
  • 7 Baths
  • 6,710 Sq Ft
  • Built 2009

  Last Sold Summary

  • 54% Below List Price
  • $1,028/SF
  • 494 Days On Market

  Current Estimated Value $7,461,733

  Last Listing Agent Charles & Gabe Buky COLDWELL BANKER REALTY

  3544 San Remo Terrace, Sarasota, FL 34239
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  /4

  Est $5,466,183 Not Listed For Sale

  2100 McClellen Pkwy, Sarasota, FL 34239

  • Built 1941

  2100 McClellen Pkwy, Sarasota, FL 34239

  Last Sold Summary

  • 320% Above List Price
  • $563/SF
  • 119 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Donna Spencer EXIT KING REALTY

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