Southside Homes for Sale

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  /76

  $2,150,000

  Open Sun 1PM - 4PM

  • 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

  

  Michael James

  MICHAEL SAUNDERS & COMPANY

  2631 Puritan Terrace, Sarasota, FL 34239
• Explore Southside

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  /52

  $1,039,000

  Open Sun 3PM - 5PM

  • 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

  

  Lise Wosick

  EXP REALTY LLC

  3424 Old Oak Dr, Sarasota, FL 34239
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  /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

  

  Ryan Carson

  RE/MAX ALLIANCE GROUP

  1824 Webber St Unit 18, Sarasota, FL 34239
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  /100

  $4,295,000

  New Construction Open Sun 12PM - 5PM $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

  

  Joshua Freed

  PREFERRED SHORE LLC

  3800 Flores Ave, Sarasota, FL 34239
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  /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
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  /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
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  /54

  $1,475,000

  Open Sun 2PM - 4PM $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
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  /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
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  /58

  $6,500,000

  New Construction $1M PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 3,294 Sq Ft

  1406 Tangier Way, Sarasota, FL 34239

  Welcome to 1406 Tangier Way, a breathtaking expression of coastal contemporary luxury in San Remo Estates in Sarasota, where architectural excellence meets waterfront serenity. This 3,294 sq. ft. home is a seamless blend of sophistication, innovation, and artisanal craftsmanship, offering four bedrooms, three full baths, and unparalleled views of Sarasota Bay.Every detail has been

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1406 Tangier Way, Sarasota, FL 34239
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  /46

  $3,150,000

  New Construction Open Wed 12PM - 4PM

  • 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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  /54

  $2,100,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,784 Sq Ft

  2045 Goldenrod St, Sarasota, FL 34239

  Virtually Staged. Experience elevated coastal living in this nearly new Coastal Modern Farmhouse, thoughtfully built in 2025 by WG Homes with exceptional quality and craftsmanship. Constructed with solid block all the way up and topped with a standing-seam metal roof, this two-story residence offers five bedrooms, four-and-a-half baths, and a spacious, well-designed layout ideal for both everyday

  Victoria Turner MICHAEL SAUNDERS & COMPANY

  2045 Goldenrod St, Sarasota, FL 34239
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  /78

  $4,490,000

  New Construction

  • 4 Beds
  • 6 Baths
  • 3,262 Sq Ft

  1800 Webber St, Sarasota, FL 34239

  Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 bedrooms, 4 full bathrooms, and 2 half baths, all thoughtfully designed for both comfort and functionality. Set on an expansive 15,930-square-foot lot, the residence offers tranquility just moments from the shops and dining of

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1800 Webber St, Sarasota, FL 34239
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  /30

  $159,000

  $60K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft

  3700 S Osprey Ave Unit 115, Sarasota, FL 34239

  West of the Trail location with convenient access to downtown Sarasota and Siesta Key. Ground floor condo featuring a newly updated kitchen with new appliances and new carpet in the bedrooms. The enclosed lanai with vinyl windows opens directly to the parking area for easy access. Unit includes in-home washer and dryer and a Jack-and-Jill bathroom layout. Assigned parking space #56 located just

  Robin De Busk STRINGER MANAGEMENT INC

  3700 S Osprey Ave Unit 115, Sarasota, FL 34239
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  /41

  $2,997,000

  Open Sun 1PM - 4PM $98K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,377 Sq Ft

  1794 Cunliff Ln, Sarasota, FL 34239

  Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed

  Jill Berg MICHAEL SAUNDERS & COMPANY

  1794 Cunliff Ln, Sarasota, FL 34239
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  /73

  $3,790,000

  New Construction

  • 5 Beds
  • 5 Baths
  • 3,640 Sq Ft

  1805 Goldenrod St, Sarasota, FL 34239

  Welcome to this exceptional new construction, upgraded residence located West of Trail, featuring 5 bedrooms, 5 full bathrooms, and 3,640 square feet of thoughtfully curated living space. Designed with a refined modern aesthetic, the home blends clean architectural lines with elevated finishes and seamless indoor-outdoor living. Upon entry, soaring 20-foot ceilings, warm designer lighting, and an

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1805 Goldenrod St, Sarasota, FL 34239
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  /29

  $2,500,000

  • 2 Beds
  • 1 Bath
  • 1,091 Sq Ft

  1891 Prospect St, Sarasota, FL 34239

  Discover this UNIQUELY RARE OPPORTUNITY in the Coveted West of the Trail Neighborhood, amongst other very beautiful multi-million-dollar homes (two back-to-back lots, 1891 Prospect with frontage of 88’ and 1894 Loma Linda with frontage of 78’ and with depth of 296’ for a total of both properties). The property on Loma Linda side is located on a quiet cul de sac at the end of the street. The two

  Beth Harris COMPASS FLORIDA LLC

  1891 Prospect St, Sarasota, FL 34239
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  /43

  $1,690,000

  New Construction

  • 5 Beds
  • 2.5 Baths
  • 3,032 Sq Ft

  1647 Siesta Dr, Sarasota, FL 34239

  Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings,

  Faith Stutzman THE STUTZMAN REALTY GROUP, LLC

  1647 Siesta Dr, Sarasota, FL 34239
• 

  

  /96

  $3,075,000

  $125K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,161 Sq Ft

  1915 Clematis St, Sarasota, FL 34239

  A timeless statement of modern luxury, this impeccably reimagined West of Trail residence exudes sophistication, serenity and refined coastal elegance. Completely remodeled, professionally designed and expertly curated, this extraordinary Sarasota home showcases one-of-a-kind craftsmanship, elevated design and exceptional finishes throughout, creating an unparalleled luxury living experience in

  Moriah Taliaferro PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1915 Clematis St, Sarasota, FL 34239
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  /23

  $16,000,000

  New Construction

  • 4 Beds
  • 6 Baths
  • 4,865 Sq Ft

  1386 Tangier Way, Sarasota, FL 34239

  Pre-Construction. To be built. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new construction home, designed and built by Pham Development, represents the pinnacle of luxury living in one of the city's most sought-after locations. Perfectly positioned West of the Trail, just before the North Siesta Key Bridge, the home provides effortless

  Faith Stutzman PHAM REALTY GROUP LLC

  1386 Tangier Way, Sarasota, FL 34239
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  /36

  $225,000

  $12K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 991 Sq Ft

  3700 S Osprey Ave Unit 205, Sarasota, FL 34239

  This fully renovated West-of-the-Trail condominium offers a rare opportunity to enjoy one of Sarasota’s most desirable locations at an approachable price point. Thoughtfully updated with custom imported Italian cabinetry and modern finishes, the residence features generous, well-proportioned living spaces that provide a level of comfort and openness not typically found in this price range. The

  Roman Donato Ruiz LPT REALTY, LLC

  3700 S Osprey Ave Unit 205, Sarasota, FL 34239
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  /6

  $460,000

  • Land
  • 9,147 Sq Ft
  • $2,190,476 per Acre

  2101 Rose St, Sarasota, FL 34239

  Cleared, Shovel-Ready Homesite Near Arlington Park. 9,016 SF Buildable Lot. Approx. 63' of frontage by 144' deep - efficient footprint for a new home in one of Sarasota's best inland neighborhoods. The 1950s home that once stood here has been fully removed, leaving a clean, level, buildable lot in the sought-after 34239 corridor near Arlington Park. No demolition, no teardown hassle - just bring

  Steven Koleno BEYCOME OF FLORIDA LLC

  2101 Rose St, Sarasota, FL 34239
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  /50

  $2,299,000

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

  3606 Palonia Ct, Sarasota, FL 34239

  Completely rebuilt from the ground up, this is a rare opportunity to own essentially new construction on one of the largest usable lots in Granada, one of Sarasota's most sought-after West of the Trail neighborhoods. The home was taken down and rebuilt with all-new major systems, including electrical, plumbing, HVAC, insulation, windows, doors, finishes and interior construction, creating the

  Daria Fairchild COLDWELL BANKER REALTY

  3606 Palonia Ct, Sarasota, FL 34239
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  /45

  $1,549,000

  New Construction $101K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,910 Sq Ft

  1734 Wisconsin Ln, Sarasota, FL 34239

  Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibility, and an exceptional West of the Trail location. Built in 2024, this contemporary residence offers approximately 2,900 square feet with 4 bedrooms+ den and 4.5 baths, featuring open-concept living spaces, clean modern design,

  Keith Kleppinger COLDWELL BANKER REALTY

  1734 Wisconsin Ln, Sarasota, FL 34239
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  /55

  $1,495,000

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  1907 Magnolia St, Sarasota, FL 34239

  Classic Sarasota charm takes on a fresh, sophisticated spirit in this beautifully updated residence, where relaxed interiors, thoughtful details and lush outdoor spaces create an inviting retreat designed for modern Florida living. At the heart of the home, an open and inviting floor plan creates an easy flow for everyday living and entertaining alike. The spacious great room transitions

  Kelly Quigley MICHAEL SAUNDERS & COMPANY

  1907 Magnolia St, Sarasota, FL 34239
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  /68

  $2,695,000

  New Construction $165K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 4,165 Sq Ft

  1870 Jasmine Dr, Sarasota, FL 34239

  Experience modern luxury in this stunning new construction home located in Sarasota's highly sought-after West of Trail area. Offering 5 bedrooms, 5.5 bathrooms, and 4,165 square feet under air (5,614 total square feet), this exceptional residence combines custom design with everyday functionality.A grand entry welcomes you with soaring 12-foot ceilings, a spacious foyer, and a striking

  Samantha Jennen PREFERRED SHORE LLC

  1870 Jasmine Dr, Sarasota, FL 34239
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  /82

  $3,790,000

  New Construction $100K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 4,755 Sq Ft

  1850 Webber St, Sarasota, FL 34239

  Virtually Staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes.This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired

  Kelly Gettel COLDWELL BANKER REALTY

  1850 Webber St, Sarasota, FL 34239
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  /47

  $6,950,000

  $40K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,450 Sq Ft

  1504 S Lodge Dr, Sarasota, FL 34239

  Dreaming of breathtaking sunsets? This property is for you! A one of a kind bayfront lot located in highly sought-after Cherokee Park, West of Trail. Located in "X" flood zone this property offers unobstructed panoramic views of Sarasota Bay. The stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a

  Melody Davis COLDWELL BANKER REALTY

  1504 S Lodge Dr, Sarasota, FL 34239
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  /46

  $1,695,000

  Open Sun 1PM - 4PM $55K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  1905 Tulip Dr, Sarasota, FL 34239

  **This is the One!** Welcome to a beautifully renovated 3-bedroom, 2.5-bath pool home blending modern luxury with Sarasota charm in one of the area's most desirable locations. Completely remodeled, the home features soaring 10-foot ceilings, an open-concept floor plan, abundant natural light, designer finishes, and stylish furnishings throughout that are included with the sale.The

  Ryan Miller HARRY ROBBINS ASSOC INC

  1905 Tulip Dr, Sarasota, FL 34239
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  /56

  $1,395,000

  $80K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,435 Sq Ft

  1704 Fortuna St, Sarasota, FL 34239

  Virtually Staged. Nestled on one of the most picturesque oak-lined streets in Sarasota's highly sought-after Granada neighborhood, this beautifully updated residence offers the perfect blend of elegance, privacy, and effortless Florida living. Surrounded by lush tropical landscaping and a fully fenced yard, the home lives like a maintenance-free property while providing the space, comfort, and

  Kelly Baldwin COLDWELL BANKER REALTY

  1704 Fortuna St, Sarasota, FL 34239
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  /34

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  3360 S Osprey Ave Unit 104B, Sarasota, FL 34239

  Move-in ready 2-bedroom, 2-bath tastefully decorated ground floor condo located in the desirable Oasis of Osprey, West of the Trail. This well-maintained unit features an upgraded kitchen with granite countertops and stainless steel appliances, along with updated bathrooms. Enjoy indoor-outdoor living with a screened lanai and brick paver patio, plus the added convenience of a private 6x6 storage

  Marlin Yoder HARRY ROBBINS ASSOC INC

  3360 S Osprey Ave Unit 104B, Sarasota, FL 34239
• 

  

  /14

  $2,490,000

  • 4 Beds
  • 3 Baths
  • 2,696 Sq Ft

  3727 Tangier Terrace, Sarasota, FL 34239

  Welcome to a rare opportunity to own a spacious residence in the highly sought-after San Remo Estates, one of Sarasota's most desirable West of the Trail neighborhoods, ideally positioned just before the North Siesta Key Bridge. Set on a generous 0.28-acre homesite, this property presents an exceptional opportunity to enjoy one of the area's premier locations. The 4-bedroom, 3-bath home

  Faith Stutzman PHAM REALTY GROUP LLC

  3727 Tangier Terrace, Sarasota, FL 34239
• 

  /2

  $2,000,000

  • Land
  • 20,037 Sq Ft
  • $4,347,826 per Acre

  1749 Cherokee Dr, Sarasota, FL 34239

  This exceptional 100X200 lot in historic Cherokee Park awaits your dream home, with Fergeson Brothers as the designated design and construction company;this west-of-the-trail neighborhood is located on Sarasota Bay in the City of Sarasota; The adjoining lot is also available.

  Rogers Moore COLDWELL BANKER REALTY

  1749 Cherokee Dr, Sarasota, FL 34239
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  /92

  $12,750,000

  Open Sun 1PM - 4PM $500K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 8,125 Sq Ft

  3000 Southwest Dr, Sarasota, FL 34239

  One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  3000 Southwest Dr, Sarasota, FL 34239
• 

  

  /59

  $1,099,900

  $350K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,362 Sq Ft

  1958 Morris St, Sarasota, FL 34239

  Virtually Staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility, and prime Sarasota location. Featuring 4 bedrooms and 3 full bathrooms, this residence is thoughtfully designed to accommodate a variety of living arrangements, including two primary suites, each with its own en suite

  Jon Patella WAGNER REALTY

  1958 Morris St, Sarasota, FL 34239
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  /62

  $2,095,000

  Open Sun 1PM - 3PM $150K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,105 Sq Ft

  1714 South Dr, Sarasota, FL 34239

  Virtually Staged. Tucked beneath a canopy of mature trees in one of Sarasota’s most coveted neighborhoods, 1714 South Drive presents a rare opportunity to secure a prime homesite in Cherokee Park, West of the Trail and moments from the very best of Sarasota living. Set on a beautifully established lot with lush, mature landscaping, a paver driveway, and a combination of garage and carport

  Joel Schemmel DOUGLAS ELLIMAN

  1714 South Dr, Sarasota, FL 34239
• 

  

  /69

  $2,100,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 4 Baths
  • 3,148 Sq Ft

  1850 Magnolia St, Sarasota, FL 34239

  Virtually Staged. In the heart of Southside Village, this exceptional home offers one of Sarasota’s sought-after lifestyles. Just west of Tamiami Trail in Poinsettia Park’s charming Flower Streets, the neighborhood is known for its tree-lined streets, diverse architectural character, and proximity to restaurants, boutiques, gourmet markets, Sarasota Memorial Hospital, Southside Elementary,

  CARMEN BASKIND PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1850 Magnolia St, Sarasota, FL 34239
• 

  

  /74

  $8,750,000

  $1M PRICE DROP

  • 5 Beds
  • 5 Baths
  • 4,031 Sq Ft

  1500 Bayview Dr, Sarasota, FL 34239

  Nestled in the heart of Sarasota, Florida, "The Seathrough House" stands as a testament to timeless elegance and modern sophistication. Designed by the acclaimed architectural firm Sweet Sparkman and meticulously crafted by builder Josh Wynne, this mid-century marvel redefines luxury living. From the moment you step inside, the panoramic bay views captivate the senses, seamlessly blending the

  Thomas Cail RE/MAX ALLIANCE GROUP

  1500 Bayview Dr, Sarasota, FL 34239
• 

  

  /84

  $3,295,000

  • 4 Beds
  • 3 Baths
  • 3,230 Sq Ft

  1838 Oleander St, Sarasota, FL 34239

  Poised on one of the prettiest tree-lined West of Trail streets, this modern coastal residence offers the ideal blend of casual elegance, thoughtful design, and everyday livability. In like-new condition and custom built in 2020 by award-winning Allegra Homes—recognized by the Building Industry Association for outstanding craftsmanship and innovative home design—this 3,220-square-foot residence

  Karen Greco GRECO REAL ESTATE

  1838 Oleander St, Sarasota, FL 34239
• 

  

  /5

  $749,999

  • Land
  • 8,276 Sq Ft
  • $3,947,363 per Acre

  1871 Siesta Dr, Sarasota, FL 34239

  Excellent opportunity to own an 8,158 sq. ft. vacant lot in a prime Sarasota location, less than 2 miles from Siesta Key and Downtown Sarasota. This south-facing lot offers a convenient setting for a new home with quick access to the beach, restaurants, shopping, boating, arts, museums, theaters, festivals, and everything Sarasota has to offer. Much of the upfront utility work has already been

  Zach Hilferding NEW ALLIANCE GROUP REALTY

  1871 Siesta Dr, Sarasota, FL 34239
• 

  

  /55

  $489,500

  • 3 Beds
  • 1 Bath
  • 1,382 Sq Ft

  2065 Goldenrod St, Sarasota, FL 34239

  Nestled in the heart of Sarasota within the top A-rated school district, this charming 3-bedroom, 1-bath home offers a prime position near various amenities. Located close to Siesta and Lido Key Beaches, the inviting shops and restaurants of Southside Village, the cultural richness of Downtown Sarasota, the upscale allure of St. Armands Circle, and the convenient Sarasota Memorial Hospital, this

  Patrick Brogley KELLER WILLIAMS ON THE WATER S

  2065 Goldenrod St, Sarasota, FL 34239

Showing Results 1 - 40, Page 1 of 2

Why Live in Southside

Sarasota's Southside is an architecturally diverse neighborhood that sits between Sarasota Bay and the Tamiami Trail corridor. The area is anchored by Southside Village, a walkable commercial district that features popular eateries like Libby’s Neighborhood Brasserie and Veronica Fish and Oyster, as well as boutique shops like Marmalade Salon and Beautiful You. The neighborhood's housing includes a mix of large Spanish Mediterranean homes, smaller Spanish Mission-style dwellings, modern-style properties, Colonial Revivals, traditional Florida ranch-style homes and colorful shotgun-style houses. There are also multi-family condominiums available. Southside Elementary School is one of the highly rated schools serving the area, along with Brookside Middle and Sarasota High. Notable community buildings include Sarasota Memorial Hospital and the Sarasota Art Museum. Residents can enjoy fishing and boating on Sarasota Bay, and they have easy access to Siesta Key via Siesta Drive. Parks like Nora Patterson Bay Island Park and Bonita Park offer green spaces with public art. Tamiami Trail provides easy access to Venice and Bradenton, both about 15 miles away, and public transportation options like buses are available.

Learn more about living in Southside

Southside Home Prices vs. Nearby Sarasota, FL Neighborhoods

	Southside	Hudson Bayou	Lido Key
Median Home Price	$2,125,000	$2,500,000	$1,622,500
Median Sale Price	$1,787,500 +12% YoY	$1,600,000 -18% YoY	$1,345,000 -6% YoY
Median Single Family Price	$2,095,000	$2,350,000	$3,695,000
Median Townhouse Price	$650,000	--	$3,750,000
Median Condo Price	$225,000	$329,000	$1,020,000
Total Active Listings	39 listings	18 listings	69 listings
Market Conditions	6 Months of Supply Balanced Market	8 Months of Supply Buyer's Market	9 Months of Supply Buyer's Market

Frequently Asked Questions

Is Southside a good place to live?

Southside is a good place to live. Southside is considered somewhat walkable and bikeable with minimal transit options. Southside has 6 parks for recreational activities. It is fairly sparse in population with 5.0 people per acre and a median age of 51. The average household income is $137,412 which is above the national average. College graduates make up 59.8% of residents. A majority of residents in Southside are home owners, with 22% of residents renting and 78% of residents owning their home. A local real estate agent serving Southside can help you decide if this neighborhood is the right one for you. Learn more on our Southside neighborhood guide.

Is Southside, FL a safe neighborhood?

Southside, FL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.

How much do you need to make to afford a house in Southside?

The median home price in Southside is $2,125,000. If you put a 20% down payment of $425,000 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $10,910 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $468K a year to afford the median home price in Southside. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Southside is $137K.

What are the best public schools in Southside?

The best public schools that serve Southside are:

• Phillippi Shores Elementary School has an A Niche grade, a student teacher ratio of 16:1 and an average review score of 4.8.
• Riverview High School has an A Niche grade, a student teacher ratio of 20:1 and an average review score of 3.9.
• Southside Elementary School has an A Niche grade, a student teacher ratio of 15:1 and an average review score of 3.6.

What are the best private schools in Southside?

The best private schools that serve Southside are:

• Out-Of-Door Academy has an A+ Niche grade, a student teacher ratio of 7:1 and an average review score of 4.6.
• Incarnation Catholic School has an A Niche grade, a student teacher ratio of 11:1 and an average review score of 4.3.
• Agape Christian School Of Sarasota has a student teacher ratio of 8:1.

What are the most popular zip codes in Southside, Sarasota, FL?

The most popular zip codes in Southside, Sarasota, FL include 34239, 34231, 34242, 34236 and 34237.

What are the most popular neighborhoods near Southside, Sarasota, FL?

The most popular neighborhoods near Southside, Sarasota, FL are Southgate, Arlington Park, Hudson Bayou, South Sarasota and Downtown Sarasota.

Are home prices dropping in Southside?

Yes, home prices in Southside are down 1% in the last 12 months.