Southside Homes

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  /67

  $3,449,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 3.5 Baths
  • 3,136 Sq Ft

  1547 Sandpiper Ln, Sarasota, FL 34239

  This one-of-a-kind, fully renovated residence is nestled in the heart of Sarasota’s historic McClellan Park—just steps from the bayfront, downtown, and Southside Village. Set on an elevated lot, the home experienced no flooding or storm damage during last year’s storms. Originally built by a builder as his personal home and reimagined in 2022 by the previous owner, an interior designer, the

  Marlin Yoder HARRY ROBBINS ASSOC INC

  1547 Sandpiper Ln, Sarasota, FL 34239
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  Explore Southside

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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

  Luxurious Fully Furnished, 3-Bedroom Home with Elevator in Gated Sarasota Community – Now Available for Rent! Short Term and Long Term rental options. AVAILABLE 10/1/25Discover 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

  $615,000 Sold Sep 17, 2025

  • 1,334 Sq Ft
  • $461/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1952

  1857 Siesta Dr, Sarasota, FL 34239

  Opportunity knocks in one of Sarasota’s most desirable locations! Situated just over the North Bridge and only one mile to the world-famous Siesta Key Beach, this charming 2-bedroom home sits on just under a 1/4 acre lot with NO HOA or deed restrictions. Whether you’re a first-time buyer wanting that coastal lifestyle, or an investor seeking your next high-potential property, this checks off all

  Noah Ward EXP REALTY LLC

  1857 Siesta Dr, Sarasota, FL 34239
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  /36

  Est $1,677,940 Not Listed For Sale

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

  1744 Fortuna St, Sarasota, FL 34239

  1744 Fortuna St, Sarasota, FL 34239
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  /28

  $574,900

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft

  2110 Goldenrod St, Sarasota, FL 34239

  **** $15,000 PRICE REDUCTION ****Right Where You Want to Be—With a Pool That’s Ready to Dive Into! Att:Investors - ARBNB Income is $75,000This well-cared-for gem is all about location and lifestyle. New Roof in 2025 and New Pool Heater in 2024. Tucked into the private, dead-end street but just minutes to Siesta Key Beach, the Village, Sarasota Memorial, and loads of great local

  Steven Weiss REDFIN CORPORATION

  2110 Goldenrod St, Sarasota, FL 34239
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  /19

  $4,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • House for Rent

  3521 Almeria Ave, Sarasota, FL 34239

  Great condition, Great location 1 mile to beach, Great school district,Fully Furnished

  3521 Almeria Ave, Sarasota, FL 34239
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  /2

  $2,550,000 Sold Aug 31, 2025

  • 3,237 Sq Ft
  • $788/SF
  • 97 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  1559 Bay Rd, Sarasota, FL 34239

  New Construction by Majestik HomesMove-In Ready | Easy to ShowWelcome to 1559 Bay Road, a new home by Majestik Homes, ideally located West of the Trail in Sarasota’s coveted Granada neighborhood. Just 4.6 miles from Siesta Beach, 6.0 miles from Lido Beach, and only 1.9 miles from Sarasota Memorial Hospital, this prime address places you near upscale restaurants, artisan deli

  Alesia Stirp ALESIA DEANNA STIRP

  1559 Bay Rd, Sarasota, FL 34239
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  /100

  Not Listed For Sale

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

  1705 Wisconsin Ln, Sarasota, FL 34239

  1705 Wisconsin Ln, Sarasota, FL 34239
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  /71

  $4,650,000

  • 5 Beds
  • 7 Baths
  • 6,128 Sq Ft

  1686 North Dr, Sarasota, FL 34239

  Welcome to this stunning 2021-built home in one of Sarasota’s most iconic and picturesque historic neighborhoods, Cherokee Park. Offering luxurious living with thoughtful design, this spacious residence of over 6000 square feet features a desirable first-floor primary suite with a decadent bathroom with soaking tub, oversized marble shower, and access to the covered porch for your morning coffee.

  Samantha Callaway RE/MAX ALLIANCE GROUP

  1686 North Dr, Sarasota, FL 34239
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  /11

  $1,800 per month

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

  3360 S Osprey Ave Unit 201B, Sarasota, FL 34239

  Annual rental - unfurnished. One step away from Siesta Key, Sarasota Memorial and Hillview. West of the trail. Beautiful condo in Oasis on Osprey. 2 bedrooms, 2 bathrooms. All tiled for easy maintenance. Granite countertop in kitchen. Vacant and move-in ready. Sorry no pets. Application fee $75 + HOA application fee $100

  Vincent Ricaud INVESTUS REALTY LLC

  3360 S Osprey Ave Unit 201B, Sarasota, FL 34239
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  /2

  $900,000 Sold Aug 29, 2025

  • 2,013 Sq Ft
  • $447/SF
  • 9 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1948

  1926 Morris St, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. Rare West of the Trail home! Discover the perfect blend of vintage charm and modern convenience in this delightful home with an attached garage on a double lot. Known for its prime location, this home is ideally positioned between the world renowned Siesta Key beaches and minutes to the vibrant cultural hub of Downtown Sarasota, offering you the

  Tracy Seider RE/MAX ALLIANCE GROUP

  1926 Morris St, Sarasota, FL 34239
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  /10

  Est $3,604,366 Not Listed For Sale

  1615 N Lodge Dr, Sarasota, FL 34239

  1615 N Lodge Dr, Sarasota, FL 34239
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  /97

  $4,750,000

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

  1873 Rose St, Sarasota, FL 34239

  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, soaring ceilings and a flawless Stage 5

  Brian Partie ENGEL + VOELKERS SARASOTA

  1873 Rose St, Sarasota, FL 34239
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  /22

  $3,500 per month

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

  3700 S Osprey Ave Unit 315, Sarasota, FL 34239

  ***AVAILABLE December 2025 through April 2026*** ($3,500/month with 3-month minimum) WEST OF TAMIAMI TRAIL! Less than 1 mile from North Bridge entrance to Siesta Key. 3-story unit with the elevator in the center of courtyard. Two-bedroom condo with beautiful kitchen. Second bedroom used as an office and has a pull-out bed. Living room has pull out couch. Washer/dryer in bathroom and the condo has

  Anthony DeLuca AUDREY RAIN RENTALS, INC

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

  $3,200,000 Sold Aug 22, 2025

  • 3,613 Sq Ft
  • $886/SF
  • 387 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 2024

  1783 Bayview Dr, Sarasota, FL 34239

  Welcome to an exquisite 3,613 sqft New Construction home nestled near a highly coveted and sought after location in Sarasota. Built by M&J Pham Development, this residence offers unparalleled combination of complete sophistication and designed for livable luxury. The warm and inviting palette is both trend-forward and timeless. As you enter, you will be greeted by a soaring 2 story great room

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1783 Bayview Dr, Sarasota, FL 34239
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  /3

  Est $1,573,977 Not Listed For Sale

  • 3 Beds

  1700 Seminole Dr, Sarasota, FL 34239

  1700 Seminole Dr, Sarasota, FL 34239
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  /55

  $2,171,000

  • 4 Beds
  • 4.5 Baths
  • 3,554 Sq Ft

  3319 S Osprey Ave, Sarasota, FL 34239

  Welcome to 3319 S Osprey Avenue, a glourious 2023 newly built home offering 4 bedrooms, 4.5 bathrooms, and over 3,500 sq. ft. of refined living. Blending elegance and functionality, the home features a gourmet chef’s kitchen with quartz countertops, custom cabinetry, and premium Fulgor Milano appliances, an inviting first floor primary suite with spa-like bath and walk-in California Closet, and

  Austin Morris PLATINUM PALM PROPERTIES

  3319 S Osprey Ave, Sarasota, FL 34239
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  /10

  $1,900 per month

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

  3835 Almeria Ave Unit C3, Sarasota, FL 34239

  Near the north Siesta Key Bridge and Bay. Amazing location. Unfurnished.Minutes to Siesta Key, minutes to SMH. Minutes to Hillview district. Southside Elementary school district. Dead end street. Walk to restaurants and shopping. top floor of a 2 story building with a big relaxing Lanai. Covered Parking. In unit laundry Quiet location. Cats allowed

  Richard Dear SUNCOAST LUXURY PROPERTIES

  3835 Almeria Ave Unit C3, Sarasota, FL 34239
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  /2

  $1,000,000 Sold Aug 21, 2025

  • 2,895 Sq Ft
  • $345/SF
  • 160 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2006

  1746 Stapleton St, Sarasota, FL 34239

  Luxury Living in Granada Park – A Fully Renovated Gem! Step into luxury, style, and modern convenience with this stunning, fully renovated home in the sought-after gated community of Granada Park. Designed for effortless living, this 4-bedroom, 3-bathroom home with a bonus room offers the perfect balance of elegance and functionality, ideal for families and entertainers alike. Exceptional

  Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

  1746 Stapleton St, Sarasota, FL 34239
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  /4

  Est $4,549,505 Not Listed For Sale

  2100 McClellen Pkwy, Sarasota, FL 34239

  2100 McClellen Pkwy, Sarasota, FL 34239
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  /60

  $2,450,000

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft

  1857 Tulip Dr, Sarasota, FL 34239

  Modern luxury meets Florida beach house style in this impeccably renovated residence, located in the highly sought-after “West of the Trail” enclave — just minutes from Siesta Key’s world-renowned beaches and Downtown Sarasota’s cultural district.This designer 3-bedroom, 2-bath home offers nearly 1,900 square feet of refined interior space, thoughtfully reimagined for both elegant living

  Ralf Michael Guensch EXP REALTY LLC

  1857 Tulip Dr, Sarasota, FL 34239
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  /9

  $1,700 per month

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

  3700 S Osprey Ave Unit 219, Sarasota, FL 34239

  LOCATION, LOCATION! Minutes to Siesta Key, Publix, shopping, restaurants and more across the street. 2 bedroom, 1 bath, double sinks, walk-in closet, no carpet, on-site washer & dryer. Building has an elevator. No pets. Turn-Key Furnished. One covered parking spot, guest parking. Available September through December 2025.

  Kelly Anderson RE/MAX ALLIANCE GROUP

  3700 S Osprey Ave Unit 219, Sarasota, FL 34239
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  /2

  $1,050,000 Sold Aug 15, 2025

  • 1,742 Sq Ft
  • $603/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1949

  1934 Bougainvillea St, Sarasota, FL 34239

  Rare West of Trail home, set in Sarasota’s highly sought after Poinsettia Park neighborhood, just minutes from Sarasota Memorial Hospital, Southside Village and Siesta Key, is a beautifully redesigned, 100% move-in ready 3BR/2BA home (with the 3rd bedroom currently used as a home office), with an effective year built of 2003, when it was newly constructed minus the original slab foundation and

  Ryan Ackerman COLDWELL BANKER REALTY

  1934 Bougainvillea St, Sarasota, FL 34239
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  /15

  Est $1,856,792 Not Listed For Sale

  • 4 Beds

  0 Jacinto Ct, Sarasota, FL 34239

  0 Jacinto Ct, Sarasota, FL 34239
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  /81

  $2,895,000

  • 4 Beds
  • 4.5 Baths
  • 4,867 Sq Ft

  1671 South Dr, Sarasota, FL 34239

  Nestled on one of Sarasota's most sought-after streets, this classic brick residence on South Drive presents a rare opportunity to own a truly special property in the heart of Cherokee Park. Lovingly maintained by its original owner, the home rests on an exceptional, oversized lot - enhanced by deeded access from South Lodge Drive, adding a unique level of privacy and convenience. The timeless

  Kelly Quigley MICHAEL SAUNDERS & COMPANY

  1671 South Dr, Sarasota, FL 34239
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  /27

  $5,900 per month

  • 3 Beds
  • 2 Baths
  • 2,259 Sq Ft
  • House for Rent

  1763 South Dr, Sarasota, FL 34239

  Location, location, in the Southside Village neighborhood! This distinctive home is set on a fully fenced 15,000 SF (100 ft X 150 ft) homesite located West of Trail in picturesque Cherokee Park. Upon entering you will be amazed at how light and bright each room feels. This three-bedroom, two-bathroom, two-car detached garage home features a wood burning fireplace, separate dining room, family

  Ryan Ackerman COLDWELL BANKER REALTY

  1763 South Dr, Sarasota, FL 34239
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  /2

  $610,000 Sold Aug 11, 2025

  • 1,082 Sq Ft
  • $564/SF
  • 121 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  1870 Jasmine Dr, Sarasota, FL 34239

  Welcome to 1870 Jasmine Drive, a rare opportunity in one of the sought-after West of Trail neighborhoods. On a spacious .21-acre lot, this charming two-bedroom, one-bath home with a sunroom offers exceptional potential whether as a full-time residence, a short-term rental or the ideal site for your dream home. The south-facing backyard provides abundant natural light, creating a warm and inviting

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1870 Jasmine Dr, Sarasota, FL 34239
• 

  

  /11

  Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 6,428 Sq Ft

  3300 Old Oak Dr, Sarasota, FL 34239

  3300 Old Oak Dr, Sarasota, FL 34239
• 

  /2

  $1,899,000

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft

  1719 Shoreland Dr, Sarasota, FL 34239

  This newly remodeled West of the Trail home sits on a rare spring-fed lake on a private street. The home has been tastefully updated and offers 2 en-suite guest bedrooms with a split-plan master bedroom. The home is complete with high ceilings, an open floor plan, new paint, new luxury plank flooring, contemporary fixtures, some new vanities, and other new features. Beautiful sliding doors and

  Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1719 Shoreland Dr, Sarasota, FL 34239
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  /54

  $13,000 per month

  • 4 Beds
  • 4 Baths
  • 3,176 Sq Ft
  • House for Rent

  1905 Goldenrod St, Sarasota, FL 34239

  LOCATION, LOCATION, LOCATION. Stunning turnkey furnished single family home available to rent in the sought after community of Poinsettia Park of Sarasota. This West of the Trail, 2020 build, Classic Homes by Clayton Inc., property is energy-efficient, elegant, beautifully furnished, and well appointed. Pulling up to the home you immediately notice the professional landscaping and lighting with

  C. Alison Hunter JENNETTE PROPERTIES INC

  1905 Goldenrod St, Sarasota, FL 34239
• 

  /2

  $2,600,000 Sold Aug 07, 2025

  • 3,678 Sq Ft
  • $707/SF
  • 25 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2023

  1954 Goldenrod St, Sarasota, FL 34239

  Welcome to 1954 Goldenrod Street, a stunning newly constructed residence located in the highly coveted West of Trail neighborhood. Thoughtfully upgraded and meticulously redesigned, this home embodies modern luxury and comfort at every turn. Behind a newly added front gate, you'll find a residence that now features an elevator system, custom closets, lush landscaping, and a completely reimagined

  Matthew Voss PREFERRED SHORE LLC

  1954 Goldenrod St, Sarasota, FL 34239
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  /56

  Est $2,123,468 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,576 Sq Ft

  1715 Bonita Ct, Sarasota, FL 34239

  1715 Bonita Ct, Sarasota, FL 34239
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  /52

  $2,799,999 Open Sat 12PM - 4PM

  • 4 Beds
  • 4 Baths
  • 2,935 Sq Ft

  1915 Tulip Dr, Sarasota, FL 34239

  Welcome to 1915 Tulip Drive – a beautiful Single Story home you will love!This just completed Modern Coastal Single Story home is located West of the Trail in the preferred Zone X (unshaded) with elevated storm protection and easy access to Siesta Key beaches, Southside Village and Downtown Sarasota. Built strong and stylish by Majestik Homes, this 4 bedroom 4 bathroom residence

  Alesia Stirp ALESIA DEANNA STIRP

  1915 Tulip Dr, Sarasota, FL 34239
• 

  

  /23

  $7,800 per month

  • 4 Beds
  • 3.5 Baths
  • 2,539 Sq Ft
  • House for Rent

  1638 South Dr, Sarasota, FL 34239

  FULLY REMODELED 4 BEDROOM GREAT FAMILY HOME. NO POOL LESS EXPENSES. NO SHORT TERM RENTAL. A MUST SEE IF YOU LIKE RANCH STYLE. ALL NEW - HVAC - ELECTRIC - WINDOWS - KITCHEN - BATHS - ROOF. NOTHING MISSED ON THIS VERY ATTRACTIVE HOME IN CHEROKEE PARK, SOUTH SIDE SCHOOL AND THE HOSPITAL CORE.

  Ryan Ackerman COLDWELL BANKER REALTY

  1638 South Dr, Sarasota, FL 34239
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  /2

  $3,530,000 Sold Jul 28, 2025

  • 3,262 Sq Ft
  • $1,082/SF
  • 356 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  1800 Webber St, Sarasota, FL 34239

  Pre-Construction. To be built. Nestled within the heart of West of the Trail lies a world-class estate proudly standing as the pinnacle of future luxury homes. Collectively envisioned by the esteemed team of M&J Pham Development, the residence is a masterwork of inspiring design and immaculate execution. Situated on a majestic parcel of approximately 15,930 sqft, the home promises an unrivaled

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1800 Webber St, Sarasota, FL 34239
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  /37

  Est $4,241,458 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,538 Sq Ft

  1739 Cherokee Dr, Sarasota, FL 34239

  1739 Cherokee Dr, Sarasota, FL 34239
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  /76

  $1,990,000 New Construction

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

  3464 Camino Real, Sarasota, FL 34239

  Love where you live or rent it out! Now completed ( June 2025) perfect sun drenched vacation home or rental property.This beautiful new construction showcase home by Siesta Kay Properties has it all ! Peace of mind when it comes to hurricane proof estate! Solid masonry built thru two floors, impact windows and doors with heat and sound proof quadruple glass. Elevation 17.4 ft above the sea

  Sylvia Nowicki PREFERRED SHORE LLC

  3464 Camino Real, Sarasota, FL 34239
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  /17

  $1,900 per month

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

  3700 S Osprey Ave Unit 216, Sarasota, FL 34239

  WEST OF THE TRAIL...this charming 2nd floor condo offers 2 bedrooms and 1 bathroom. The balcony is enclosed with screens and windows. Excellent location, convenience is key with this property. Situated just around the corner from the north bridge and minutes away from the world renowned SIESTA KEY BEACH. Live the best of both worlds in a peaceful, quiet area and easy access to coastal living.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3700 S Osprey Ave Unit 216, Sarasota, FL 34239
• 

  /2

  $900,000 Sold Jul 24, 2025

  • 2,529 Sq Ft
  • $356/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1956

  3705 Tangier Terrace, Sarasota, FL 34239

  **Mid-Century Modern Charm in San Remo – Prime Location & Endless Potential**Discover this **mid-century modern 3-bedroom, 2.5-bath ranch** in the sought-after **San Remo Estates**. Set on a lush **1/3-acre lot West of the Trail**, this home is just minutes from **Siesta Key Beach, Morton’s Market, CineBistro, the Farmers Market, and Downtown Sarasota’s dining, shopping, and cultural

  Grace Bonaccorso FINE PROPERTIES

  3705 Tangier Terrace, Sarasota, FL 34239
• 

  

  /90

  Est $2,794,500 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,763 Sq Ft

  1874 Oleander St, Sarasota, FL 34239

  1874 Oleander St, Sarasota, FL 34239

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