1,545

Southside Homes

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  • /100

    $4,495,000

    New Construction Open Wed 1PM - 3PM
    • 4 Beds
    • 6 Baths
    • 4,106 Sq Ft

    3800 Flores Ave, Sarasota, FL 34239

    NEW CONSTRUCTION - Experience the pinnacle of Sarasota luxury in this newly completed, move-in-ready residence, ideally located within the City of Sarasota and attractively priced for today's market. Offering 4 bedrooms, a private den, 4.5 baths, and 4,106 square feet of thoughtfully designed living space, this exceptional home seamlessly blends contemporary elegance with relaxed coastal living.

    Agent Photo

    Joshua Freed

    PREFERRED SHORE LLC

    3800 Flores Ave, Sarasota, FL 34239
  • /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

    Agent Photo

    Anthony DeLuca

    AUDREY RAIN RENTALS, INC

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

    $1,750,000

    Sold Mar 19, 2026

    1834 Bougainvillea St, Sarasota, FL 34239

    • 3 Beds
    • 3 Baths
    • 1,850 Sq Ft
    • Built 1966

    Last Sold Summary

    • 3% Below List Price
    • $946/SF
    • 8 Days On Market

    Current Estimated Value $1,691,672

    Last Listing Agent Victoria Turner MICHAEL SAUNDERS & COMPANY

    1834 Bougainvillea St, Sarasota, FL 34239
    • /2

      Est $783,242

      Not Listed For Sale

      1857 Jasmine Dr, Sarasota, FL 34239

      • 3 Beds
      • 2 Baths
      • 1,786 Sq Ft
      • Built 1957
      1857 Jasmine Dr, Sarasota, FL 34239

      Last Sold Summary

      • 30 Days On Market

  • /77

    $5,985,000

    $265K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,310 Sq Ft

    1389 Tangier Way, Sarasota, FL 34239

    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 functionality—perfect for buyers

    Joel Schemmel DOUGLAS ELLIMAN

    1389 Tangier Way, Sarasota, FL 34239
  • /19

    $4,900

    Total Monthly Price

    • 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
  • /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 $2,248,052

    Last Listing Agent Nick Gard COLDWELL BANKER REALTY

    1585 South Dr, Sarasota, FL 34239
    • /36

      Est $1,610,818

      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

      • 74 Days On Market

  • /76

    $7,995,000

    $800K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,705 Sq Ft

    3631 San Remo Terrace, Sarasota, FL 34239

    Anchored in one of Sarasota’s most coveted deep water waterfront communities, 3631 San Remo Terrace presents a rare opportunity to own a modern luxury home with direct boating access in San Remo Estates, just moments from Siesta Key, Downtown Sarasota, and Southside Village. Completed in 2021 by award-winning designer Stephen Chung and enhanced with thoughtful 2025 upgrades, this coastal

    Joel Schemmel DOUGLAS ELLIMAN

    3631 San Remo Terrace, Sarasota, FL 34239
  • /15

    Starting at $1,750 Per Month

    • 1 Bed

    1887 Hyde Park St, Sarasota, FL 34239

    Bluebird Apartments are located West of the Trail in the sought-after neighborhood of Southside Village, just one block from Sarasota Memorial Hospital, Morton's Gourmet Market and many fine restaurants, pubs and professional services, all within walking distance. The are 6 apartments in two buildings separated by a fenced-in courtyard with a magnificent, mature Mango tree (all you can eat Mangos

    Hyde Park Apartments

    1887 Hyde Park St, Sarasota, FL 34239
  • /2

    $3,150,000

    Sold Apr 09, 2026

    1386 Tangier Way, Sarasota, FL 34239

    • 4 Beds
    • 3.5 Baths
    • 2,349 Sq Ft
    • Built 1957

    Last Sold Summary

    • 10% Below List Price
    • $1,341/SF
    • 98 Days On Market

    Current Estimated Value $3,212,688

    Last Listing Agent Julie Larson WHITE SANDS REALTY GROUP FL

    1386 Tangier Way, Sarasota, FL 34239
    • /2

      Est $1,419,211

      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

      • 59 Days On Market

  • /57

    $1,950,000

    $45K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,554 Sq Ft

    3319 S Osprey Ave, Sarasota, FL 34239

    A rare fusion of modern luxury, designer finishes, and an unbeatable Sarasota location, this stunning 2023-built residence at 3319 S Osprey Ave delivers the ultimate move-in-ready lifestyle just moments from Siesta Key Beach and Downtown Sarasota. Tucked within the highly sought-after Southside School District, this exceptional home by M&J Pham Development showcases impeccable craftsmanship,

    Adnan Dedic COMPASS FLORIDA LLC

    3319 S Osprey Ave, Sarasota, FL 34239
  • /20

    $2,500 Per Month

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

    2164 Bougainvillea St, Sarasota, FL 34239

    Property Id: 2609014Updated classic Florida bungalow-style home with a brand new kitchen, Mexican tiles, beautiful archways, full of natural lighting, a full-length mirrored wall and washer/dryer included -- now available for rent in the coveted Southgate community, with several million dollar properties on the block. Just a couple minutes from the North Siesta Key Bridge, enjoy modern

    2164 Bougainvillea St, Sarasota, FL 34239
  • /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 $2,070,895

    Last Listing Agent Elizabeth Snyder PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1815 Grove St, Sarasota, FL 34239
    • /2

      Est $1,823,012

      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

      • 123 Days On Market

  • /79

    $5,900,000

    • 5 Beds
    • 9 Baths
    • 6,355 Sq Ft

    1655 South Dr, Sarasota, FL 34239

    One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the

    Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1655 South Dr, Sarasota, FL 34239
  • /20

    $2,200 Per Month

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

    3360 S Osprey Ave Unit 212B, Sarasota, FL 34239

    Property Id: 25100722 bedroom, 2 bathroom open floor plan condo. Easy access to the community pool, designated parking and a fitness room. Fully furnished in coastal decor and minutes to Southside Village, Sarasota Memorial Hospital, Siesta Key Beach and Siesta Key Village.

    3360 S Osprey Ave Unit 212B, Sarasota, FL 34239
  • /2

    $3,775,000

    Sold Mar 27, 2026

    1873 Rose St, Sarasota, FL 34239

    • 5 Beds
    • 4.5 Baths
    • 4,550 Sq Ft
    • Built 2023

    Last Sold Summary

    • 21% Below List Price
    • $830/SF
    • 151 Days On Market

    Current Estimated Value $3,850,044

    Last Listing Agent Brian Partie ENGEL + VOELKERS SARASOTA

    1873 Rose St, Sarasota, FL 34239
    • /10

      Est $2,941,972

      Not Listed For Sale

      1615 N Lodge Dr, Sarasota, FL 34239

      1615 N Lodge Dr, Sarasota, FL 34239

      Last Sold Summary

      • 10 Days On Market

  • /50

    $2,499,990

    $100K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 3,215 Sq Ft

    1885 Clematis St, Sarasota, FL 34239

    Under contract-accepting backup offers. Perfectly positioned on one of Sarasota's most coveted West of Trail locations - the "Flower" streets - this custom built residence delivers a lifestyle that's walkable, central and effortlessly connected to everything Sarasota. Just three blocks to Hillview's shopping, dining and Sarasota Memorial Hospital, a short stroll to top-rated Southside Elementary

    Monica Verinder COLDWELL BANKER REALTY

    1885 Clematis St, Sarasota, FL 34239
  • /10

    $1,800 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. Walk to see sunset over Sarasota Bay. Unfurnished. 1 car covered parking. Minutes to Siesta Key Beach. Minutes to Hillview and Southside. Part of 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

    Richard Dear SUNCOAST LUXURY PROPERTIES

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

    $4,090,000

    Sold Apr 28, 2026

    1686 North Dr, Sarasota, FL 34239

    • 5 Beds
    • 7 Baths
    • 6,128 Sq Ft
    • Built 2021

    Last Sold Summary

    • 4% Below List Price
    • $667/SF
    • 12 Days On Market

    Current Estimated Value $4,029,065

    Last Listing Agent Samantha Callaway RE/MAX ALLIANCE GROUP

    1686 North Dr, Sarasota, FL 34239
    • /3

      Est $1,456,679

      Not Listed For Sale

      1700 Seminole Dr, Sarasota, FL 34239

      • 3 Beds
      • Built 1916
      1700 Seminole Dr, Sarasota, FL 34239

      Last Sold Summary

      • 0 Days On Market

  • /64

    $232,900

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 991 Sq Ft

    3700 S Osprey Ave Unit 118, Sarasota, FL 34239

    Welcome to your slice of Sarasota paradise! This vibrant, first-floor condo is the ultimate tropical retreat, located just four miles from the world-renowned sands of Siesta Key Beach and a mile from Southside Village. Whether you are searching for a savvy investment, a seasonal vacation getaway, or a low-maintenance primary residence, this home is perfectly positioned for the Florida lifestyle.

    Rory McDonald PREFERRED SHORE LLC

    3700 S Osprey Ave Unit 118, Sarasota, FL 34239
  • /68

    $3,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,122 Sq Ft
    • Charming 2/2 Seasonal Rental in Sarasota – Minutes from the Beach! Private Courtyard Included!!

    3350 S Osprey Ave Unit 103A, Sarasota, FL 34239

    AVAILABLE FOR A MINIMUM 30-DAY RENTAL @ $3300 PER MONTH PLUS TAX - April - May 2026!! Welcome to your perfect seasonal retreat in sunny Sarasota! This beautifully furnished 2-bedroom, 2-bathroom gem offers a blend of comfort, convenience, and coastal charm. Located just minutes from the pristine sands of Siesta Key and Sarasota Beaches this rental provides the ideal escape for those looking to

    3350 S Osprey Ave Unit 103A, Sarasota, FL 34239
  • /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 $997,347

    Last Listing Agent Derek Patti NEXTHOME EXCELLENCE

    1735 Shoreland Dr, Sarasota, FL 34239
    • /4

      Est $5,015,353

      Not Listed For Sale

      2100 McClellen Pkwy, Sarasota, FL 34239

      • Built 1941
      2100 McClellen Pkwy, Sarasota, FL 34239

      Last Sold Summary

      • 119 Days On Market

  • /100

    $8,250,000

    • 5 Beds
    • 5.5 Baths
    • 5,664 Sq Ft

    1525 Mallard Ln, Sarasota, FL 34239

    A true masterpiece of modern coastal design, this custom-built 2021 waterfront estate is a stunning showcase of luxury, craftsmanship, and breathtaking views. Nestled in the highly coveted West of Trail Paradise Shores community, this 5,664 sq. ft. architectural beauty offers five bedrooms, five and a half baths, and state-of-the-art amenities designed for the discerning buyer. Step through the

    Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

    1525 Mallard Ln, Sarasota, FL 34239
  • /30

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,559 Sq Ft
    • House for Rent

    1828 Grove St, Sarasota, FL 34239

    Great West of Trail home that has been updated with modern conveniences while retaining the original charm of the classic Florida bungalow. The primary suite addition has a huge walk-in closet and large spa like bath with double sinks and walk in stepless oversized shower. The split bedroom plan has the second bedroom and bath off the living room. The updated kitchen is open to the living area

    Barbara May MICHAEL SAUNDERS & COMPANY

    1828 Grove St, Sarasota, FL 34239
  • /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 $7,471,567

    Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

    3638 San Remo Terrace, Sarasota, FL 34239
    • /2

      Est $298,163

      Not Listed For Sale

      3745 Almeria Ave Unit 3-S, Sarasota, FL 34239

      • 2 Beds
      • 2 Baths
      • 976 Sq Ft
      • Built 1979
      3745 Almeria Ave Unit 3-S, Sarasota, FL 34239

      Last Sold Summary

      • 62 Days On Market

  • /54

    $1,499,000

    $96K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,853 Sq Ft

    1775 Stapleton St, Sarasota, FL 34239

    Between North Siesta Key and Oyster Bay, this coastal craftsman contemporary residence offers the leisure of a maintenance-free lifestyle in a desirable location. Visit nearby shopping and dining, or just a quick drive to Siesta Key Beach or downtown Sarasota. Positioned across from the community pool, the home offers easy-care landscaping complemented by a charming herb garden. Built of solid

    Andrew Tanner PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1775 Stapleton St, Sarasota, FL 34239
  • /9

    $1,595 Per Month

    • 2 Beds
    • 2 Baths
    • 1,053 Sq Ft
    • Townhouse for Rent

    3700 S Osprey Ave, Sarasota, FL 34239

    Ideally situated close to downtown Sarasota and Sarasota Memorial Hospital. This non-street facing, second-floor end unit, providing extra privacy has 2 bedrooms and 2 baths, private screened lanai and assigned parking. The building is equipped with a convenient elevator for easy access to your unit. Publix grocery store is just across the street and Siesta Key beach is over the bridge 5 minutes

    3700 S Osprey Ave, Sarasota, FL 34239
  • /2

    $2,350,000

    Sold Jan 30, 2026

    1536 Sandpiper Ln, Sarasota, FL 34239

    • Land
    • 13,939 Sq Ft
    • $7,343,750 per Acre

    Last Sold Summary

    • 22% Below List Price
    • 211 Days On Market

    Current Estimated Value $2,366,469

    Last Listing Agent Fred Sassen MICHAEL SAUNDERS & COMPANY

    1536 Sandpiper Ln, Sarasota, FL 34239
    • /47

      Est $1,575,533

      Not Listed For Sale

      1716 Stapleton St, Sarasota, FL 34239

      • 3 Beds
      • 5 Baths
      • 3,073 Sq Ft
      • Built 2016
      1716 Stapleton St, Sarasota, FL 34239

      Last Sold Summary

      • 9 Days On Market

  • /31

    $625,000

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    1704 Wisconsin Ln, Sarasota, FL 34239

    Welcome to your perfect coastal escape—an inviting cottage offering charm, comfort, and an ideal location away from the hustle and bustle of city life. Just a few miles from Siesta Key Beach, you’re only a short bike or golf cart ride from the world-famous quartz sand shores.This beautifully renovated two-bedroom, one-bath home has been thoughtfully updated from top to bottom. Inside, you’ll

    Oliver McConnell MCCONNELL AND ASSOCIATES

    1704 Wisconsin Ln, Sarasota, FL 34239
  • /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
  • /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 $1,906,291

    Last Listing Agent Sylvia Nowicki PREFERRED SHORE LLC

    3464 Camino Real, Sarasota, FL 34239
    • /11

      Not Listed For Sale

      3300 Old Oak Dr, Sarasota, FL 34239

      • 4 Beds
      • 7 Baths
      • 6,428 Sq Ft
      • Built 2023
      3300 Old Oak Dr, Sarasota, FL 34239

      Last Sold Summary

      • 360 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,750,000
Median Single Family Sale Price
$2,097,500
Median Townhouse Sale Price
$650,000
Median 2 Bedroom Sale Price
$299,000
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$728
Number of Homes for Sale
51
Last 12 months Home Sales
81
Months of Supply
7.60
Median List Price
$1,999,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
9%
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