1,551

Southside Homes

Section Image Section Image
  • /77

    $2,150,000

    • 4 Beds
    • 4 Baths
    • 3,675 Sq Ft

    2631 Puritan Terrace, Sarasota, FL 34239

    Welcome to this 3,675-square-foot, single story residence on an expansive 15,625-square-foot lot in Sarasota's sought-after West of Trail neighborhood of Bay View Heights. The refreshed open floor plan features new custom kitchen cabinetry, Thermador appliances, Mexican tile and Wood flooring throughout the main living areas, and PGT impact windows and doors throughout the home. The spacious

    Agent Photo

    Michael James

    MICHAEL SAUNDERS & COMPANY

    2631 Puritan Terrace, 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 $1,651,814

    Last Listing Agent Victoria Turner MICHAEL SAUNDERS & COMPANY

    1834 Bougainvillea St, Sarasota, FL 34239
    • /2

      Est $1,401,039

      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

      Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  • /52

    $1,039,000

    Open Sun 10AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    3424 Old Oak Dr, Sarasota, FL 34239

    A private garden retreat in one of Sarasota’s most coveted West of Trail locations.** Nestled among lush tropical gardens and mature landscaping, 3424 Old Oak Drive is a captivating Sarasota bungalow where privacy, character, and effortless coastal living come together.From the moment you arrive, the home unfolds through a collection of intimate, inviting spaces. A charming front patio

    Agent Photo

    Lise Wosick

    EXP REALTY LLC

    3424 Old Oak Dr, 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

    $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 $2,269,758

    Last Listing Agent Nick Gard COLDWELL BANKER REALTY

    1585 South Dr, Sarasota, FL 34239
    • /2

      Est $2,172,727

      Not Listed For Sale

      1813 Boyce St, Sarasota, FL 34239

      • 4 Beds
      • 3.5 Baths
      • 3,584 Sq Ft
      • Built 2013
      1813 Boyce St, Sarasota, FL 34239

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Lindsey Nussbaum COLDWELL BANKER REALTY

  • /17

    $650,000

    • 4 Beds
    • 4 Baths
    • 1,680 Sq Ft

    1824 Webber St Unit 18, Sarasota, FL 34239

    Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside Elementary School, this property offers incredible potential for redevelopment.The existing structure is a grandfathered duplex that is in very poor condition and best suited for teardown. The true value lies in the land — a

    Agent Photo

    Ryan Carson

    RE/MAX ALLIANCE GROUP

    1824 Webber St Unit 18, Sarasota, FL 34239
  • /20

    $2,500 Per Month

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

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

    Property Id: 2510072 2 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

    $575,000

    Sold Aug 11, 2026

    3625 Jacinto Ct, Sarasota, FL 34239

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1957

    Last Sold Summary

    • 12% Below List Price
    • $570/SF
    • 126 Days On Market

    Current Estimated Value $574,300

    Last Listing Agent Marc Rasmussen CORCORAN DWELLINGS REALTY

    3625 Jacinto Ct, Sarasota, FL 34239
    • /2

      Est $1,813,242

      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

      Last Listing Agent Paul Defelice HOUSEMAX REALTY LLC

  • /100

    $4,295,000

    New Construction Open Sat 11AM - 2PM $200K PRICE DROP
    • 6 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 5 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

    Agent Photo

    Joshua Freed

    PREFERRED SHORE LLC

    3800 Flores Ave, Sarasota, FL 34239
  • /20

    $2,500 Per Month

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

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

    Property Id: 2510072 2 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

    $2,400,000

    Sold Jul 28, 2026

    1885 Clematis St, Sarasota, FL 34239

    • 4 Beds
    • 3 Baths
    • 3,215 Sq Ft
    • Built 2011

    Last Sold Summary

    • 8% Below List Price
    • $747/SF
    • 45 Days On Market

    Current Estimated Value $2,467,387

    Last Listing Agent Monica Verinder COLDWELL BANKER REALTY

    1885 Clematis St, Sarasota, FL 34239
    • /10

      Est $3,156,586

      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

      Last Listing Agent Kelly Gettel COLDWELL BANKER REALTY

  • /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
  • /20

    $7,371

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,098 Sq Ft
    • Condo for Rent

    1919 Siesta Dr Unit SI ID1591372P, Sarasota, FL 34239

    The advertised rate of $7,371/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 27, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1919 Siesta Dr Unit SI ID1591372P, 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 $2,060,603

    Last Listing Agent Elizabeth Snyder PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1815 Grove St, Sarasota, FL 34239
    • /2

      Est $3,188,576

      Not Listed For Sale

      1783 Bayview Dr, Sarasota, FL 34239

      • 4 Beds
      • 6 Baths
      • 3,613 Sq Ft
      • Built 2024
      1783 Bayview Dr, Sarasota, FL 34239

      Last Sold Summary

      • 387 Days On Market

      Last Listing Agent Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  • /76

    $7,995,000

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

    3631 San Remo Terrace, Sarasota, FL 34239

    Under contract-accepting backup offers. 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

    Joel Schemmel DOUGLAS ELLIMAN

    3631 San Remo Terrace, Sarasota, FL 34239
  • /20

    $7,371

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,098 Sq Ft
    • Condo for Rent

    1919 Siesta Dr Unit SI ID1591372P, Sarasota, FL 34239

    The advertised rate of $7,371/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 27, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1919 Siesta Dr Unit SI ID1591372P, 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 $3,828,957

    Last Listing Agent Brian Partie DOUGLAS ELLIMAN

    1873 Rose St, Sarasota, FL 34239
    • /3

      Est $1,419,866

      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

      Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  • /57

    $1,890,000

    $105K PRICE DROP Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,554 Sq Ft

    3319 S Osprey Ave, Sarasota, FL 34239

    Under contract-accepting backup offers. 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

    Adnan Dedic COMPASS FLORIDA LLC

    3319 S Osprey Ave, 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 $4,046,371

    Last Listing Agent Samantha Callaway RE/MAX ALLIANCE GROUP

    1686 North Dr, Sarasota, FL 34239
    • /4

      Est $5,004,954

      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

      Last Listing Agent Donna Spencer EXIT KING REALTY

  • /64

    $220,000

    $18K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 991 Sq Ft

    3700 S Osprey Ave Unit 118, Sarasota, FL 34239

    great price reduction and motivated sellers !!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

    Rory McDonald PREFERRED SHORE LLC

    3700 S Osprey Ave Unit 118, Sarasota, FL 34239
  • /20

    $8,970

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,614 Sq Ft
    • Condo for Rent

    1750 Bayview Dr Unit SI FL1-ID1590855P, Sarasota, FL 34239

    The advertised rate of $8,970/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1750 Bayview Dr Unit SI FL1-ID1590855P, 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 $995,955

    Last Listing Agent Derek Patti NEXTHOME EXCELLENCE

    1735 Shoreland Dr, Sarasota, FL 34239
    • /2

      Est $294,569

      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

      Last Listing Agent Alex Chau COLDWELL BANKER REALTY

  • /54

    $1,475,000

    $120K 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
  • /7

    $1,195 Per Month

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

    3700 S Osprey Ave Unit 212, Sarasota, FL 34239

    UNFURNISHED ANNUAL RENTAL, 1/1 with an enclosed lanai that can be used as a den. Great room floor plan, no carpets, tub/shower in bathroom, walk in closet. A cat would be permitted with a pet fee.

    Robin De Busk STRINGER MANAGEMENT INC

    3700 S Osprey Ave Unit 212, 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 $7,390,288

    Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

    3638 San Remo Terrace, Sarasota, FL 34239
    • /47

      Est $1,541,167

      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

      Last Listing Agent Rory McDonald PREFERRED SHORE LLC

  • /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
  • /29

    $4,617

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft
    • Condo for Rent

    1875 Oleander St Unit SI FL1-ID1590876P, Sarasota, FL 34239

    The advertised rate of $4,617/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1875 Oleander St Unit SI FL1-ID1590876P, 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 $2,401,553

    Last Listing Agent Fred Sassen MICHAEL SAUNDERS & COMPANY

    1536 Sandpiper Ln, 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

      Last Listing Agent Barbara May MICHAEL SAUNDERS & COMPANY

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,787,500
Median Single Family Sale Price
$2,097,500
Median Townhouse Sale Price
$650,000
Median 2 Bedroom Sale Price
$575,000
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$770
Number of Homes for Sale
40
Last 12 months Home Sales
78
Months of Supply
6.20
Median List Price
$2,150,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
12%
How to Buy a Home How to Finance a Home How to Sell a Home