Homes in ZIP Code 34239

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  /18

  $415,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft

  2342 Sunnyside Place, Sarasota, FL 34239

  Welcome to popular and sought-after Sunnyside Park, ideally positioned between Arlington Park and South Gate in the desirable Southside School District. This solid block home features a fully fenced backyard with ample room for family, pets, and outdoor enjoyment. Recent updates include new AC, ensuring comfort and peace of mind. The interior boasts large neutral tile flooring throughout,

  Maureen Doherty MICHAEL SAUNDERS & COMPANY

  2342 Sunnyside Place, Sarasota, FL 34239
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  /18

  $2,550 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • House for Rent

  2311 Waldemere St Unit B, Sarasota, FL 34239

  This one-bedroom, one-bath furnished rental guest house is recently renovated with full kitchen, a privately fenced patio and yard, one covered parking space and private laundry. There is one shared soundproofed wall. Access to Arlington Park pool, basketball and tennis courts, workout facility and playground. Also close to SMH and Southside Village restaurants and shops. Minutes from Bayfront

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2311 Waldemere St Unit B, Sarasota, FL 34239
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  /2

  $190,000 Sold Apr 10, 2025

  3211 Gifford Ln Unit 408, Sarasota, FL 34239

  • 2 Beds
  • 2 Baths
  • 1,323 Sq Ft
  • Built 1968

  Last Sold Summary

  • 34% Below List Price
  • $144/SF
  • 115 Days On Market

  Current Estimated Value $192,809

  Last Listing Agent Doris Edwards A & D EDWARDS AMERICAN DREAM

  3211 Gifford Ln Unit 408, Sarasota, FL 34239
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  /24

  Est $268,198 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  3289 Fairhaven Ln Unit 112, Sarasota, FL 34239

  3289 Fairhaven Ln Unit 112, Sarasota, FL 34239
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  /4

  $825,000

  • Land
  • 0.2 Acre
  • $4,125,000 per Acre

  2079 Hibiscus St, Sarasota, FL 34239

  Lot for sale! All work and permits have been done, lot is fully demolished and ready to build. The seller has Plans as well as a builder relationship they are willing to provide with an offer. Could start construction within 1 week of closing. Photos are from before Lots were demolished and separated. The seller owns both Lots. The price listed is for 1 Lot, 2079 Hibiscus.

  Thatcher Miner THE REAL ESTATE STORE

  2079 Hibiscus St, Sarasota, FL 34239
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  /32

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,515 Sq Ft
  • House for Rent

  3236 S Lockwood Ridge Rd, Sarasota, FL 34239

  Annual/ Seasonal TURNKEY furnished Wonderfully renovated 3/2 pool home in South Gate! The open floor plan makes this home easy for family time and entertaining. The kitchen features solid wooden cabinetry, slab quartz counters with a breakfast bar, a custom tile backsplash, and is complemented by stainless steel appliances. The dining room is adjacent to the kitchen and living room. The main

  Cody Smith RENT SARASOTA

  3236 S Lockwood Ridge Rd, Sarasota, FL 34239
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  /2

  $1,495,000 Sold Jun 24, 2025

  1610 S Orange Ave, Sarasota, FL 34239

  • 3 Beds
  • 2 Baths
  • 2,193 Sq Ft
  • Built 1969

  Last Sold Summary

  • $682/SF
  • 0 Days On Market

  Current Estimated Value $1,544,985

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  1610 S Orange Ave, Sarasota, FL 34239
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  /43

  Est $719,212 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft

  2235 Datura St, Sarasota, FL 34239

  2235 Datura St, Sarasota, FL 34239
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  /31

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,386 Sq Ft

  2215 River Ridge Dr, Sarasota, FL 34239

  PRICE ADJUSTMENT! $50,000 PRICE REDUCTION. RARE OPPORTUNITY IN SOUTH GATE! One of the largest ranch style homes in the neighborhood is available with four oversized bedrooms, including dual master suites, three bathrooms, extra large family room and a huge INDOOR pool. This home is over 6500 square feet under roof and almost 3400 square feet of air-conditioned space. Please refer to the

  Richard Scott Waid LOKATION

  2215 River Ridge Dr, Sarasota, FL 34239
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  /33

  $4,400 per month

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • House for Rent

  2469 Waldemere St, Sarasota, FL 34239

  Tropical Oasis in the Heart of Sarasota – 4BR/2BA Home with Screened Lanai & Hot TubWelcome to your Sarasota sanctuary! This beautifully updated 4-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and style. With a true open-concept floor plan, the home is filled with natural light, creating a bright and airy living environment.Step into the expansive screened Florida

  Robert Bevington SHOWTIME REALTY

  2469 Waldemere St, Sarasota, FL 34239
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  /2

  $485,000 Sold Jun 13, 2025

  2574 Hawthorne St, Sarasota, FL 34239

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft
  • Built 1952

  Last Sold Summary

  • 9% Below List Price
  • $356/SF
  • 123 Days On Market

  Current Estimated Value $486,380

  Last Listing Agent Justin Benz EXP REALTY LLC

  2574 Hawthorne St, Sarasota, FL 34239
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  /46

  Est $452,100 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,272 Sq Ft

  1329 S Brink Ave, Sarasota, FL 34239

  1329 S Brink Ave, Sarasota, FL 34239
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  /70

  $2,199,000

  • 3 Beds
  • 4 Baths
  • 2,745 Sq Ft

  1760 Arlington St, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. Ideally positioned in Sarasota’s desired West of Trail, this 2012 custom-built three-bedroom, four-bath home blends timeless architecture with modern comfort—just a short stroll to Southside Village’s boutiques and cafes, Selby Gardens, the bay front, and Sarasota Memorial Hospital. Set on a fully fenced, 1/3-acre lot in the sought-after Southside

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1760 Arlington St, Sarasota, FL 34239
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  /51

  $3,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • House for Rent

  2144 Webber St, Sarasota, FL 34239

  AVAILABLE NOW - Welcome to luxury living at 2144 Webber Street in Sarasota, FL. This modern 3-bedroom, 2.5-bathroom sanctuary offers 1,650 square feet of meticulously designed living space, seamlessly integrating sleek, contemporary features with cutting-edge smart home technologies. Every corner of this home is crafted for comfort and style, inviting you to enjoy a light and airy

  Beth Harris COMPASS FLORIDA LLC

  2144 Webber St, Sarasota, FL 34239
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  /2

  $360,000 Sold Aug 08, 2025

  2727 Waldemere St, Sarasota, FL 34239

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1958

  Last Sold Summary

  • 20% Below List Price
  • $304/SF
  • 115 Days On Market

  Current Estimated Value $385,448

  Last Listing Agent Dave Beachy BEACHY PROPERTIES

  2727 Waldemere St, Sarasota, FL 34239
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  /2

  Est $204,735 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 982 Sq Ft

  2228 Bahia Vista St Unit C1, Sarasota, FL 34239

  2228 Bahia Vista St Unit C1, Sarasota, FL 34239
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  /67

  $839,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  1702 Hillview St, Sarasota, FL 34239

  Step into this West of the Trail Charmer, Sarasota’s most sought-after neighborhood... where the canopy of mature trees, coastal breezes, and timeless architecture set the stage for an unparalleled lifestyle. Perfectly positioned just steps from Southside Village’s restaurants and boutiques, and only a short drive to Downtown Sarasota, the Bayfront, and the powdery sands of Siesta Key, this

  Melissa Perrigoue COLDWELL BANKER REALTY

  1702 Hillview St, Sarasota, FL 34239
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  /9

  $1,750 per month

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

  3101 Bee Ridge Rd Unit 214, Sarasota, FL 34239

  Move-in ready, this clean and well-maintained 1-bedroom, 1-bathroom second-floor unit offers comfort, convenience, and a fantastic central location. Enjoy the ease of an assigned parking space, with additional guest parking available for visitors. The community features great amenities, including a heated pool, on-site laundry facilities, and extra storage space for your

  Anita Darvai Seaton OFFERMATE REAL ESTATE

  3101 Bee Ridge Rd Unit 214, Sarasota, FL 34239
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  /2

  $4,450,000 Sold Jan 02, 2025

  1623 North Dr, Sarasota, FL 34239

  • 4 Beds
  • 4.5 Baths
  • 4,215 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $1,056/SF
  • 5 Days On Market

  Current Estimated Value $4,234,489

  Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

  1623 North Dr, Sarasota, FL 34239
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  /99

  Est $12,189,696 Not Listed For Sale

  • 8 Beds
  • 12 Baths
  • 11,275 Sq Ft

  1233 Hillview Dr, Sarasota, FL 34239

  1233 Hillview Dr, Sarasota, FL 34239
• 

  

  /25

  $1,750,000

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  1389 Harbor Dr, Sarasota, FL 34239

  BUILD YOUR DREAM HOME IN HARBOR ACRES! Welcome to HARBOR ACRES Sarasota's most coveted neighborhood! This beautiful neighborhood is nestled close to St. Armand's Circle, Southside Village, and the vibrant pulse of downtown Sarasota. Here, coastal living seamlessly mingles with cosmopolitan delights—you’re just moments away from sun-kissed beaches, boutique shopping, exquisite dining, and

  Colby Lengel COMPASS FLORIDA LLC

  1389 Harbor Dr, Sarasota, FL 34239
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  /23

  $7,500 per month

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

  1638 South Dr, Sarasota, FL 34239

  FULLY REMODELED - UNFURNISHED 4 BEDROOM - VERY ATTRACTIVE MODERN - GREAT FAMILY HOME. EXTENDED WIDE-OPEN BACKYARD FULLY FENCED. A MUST SEE IF YOU LIKE RANCH STYLE. THE ENTIRE HOME WAS REMODELED IN 2025, NOTHING LEFT TO DO JUST MOVE IN. ALL NEW - HVAC - ELECTRIC - WINDOWS – DOORS- KITCHEN - BATHS - ROOF - GARAGE DOOR. NOTHING MISSED ON THIS VERY ATTRACTIVE HOME IN CHEROKEE PARK, SOUTH SIDE SCHOOL

  Ryan Ackerman COLDWELL BANKER REALTY

  1638 South Dr, Sarasota, FL 34239
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  /2

  $3,800,000 Sold Jul 10, 2025

  1910 Datura St, Sarasota, FL 34239

  • 4 Beds
  • 7 Baths
  • 5,660 Sq Ft
  • Built 2013

  Last Sold Summary

  • $671/SF
  • 5 Days On Market

  Current Estimated Value $3,767,936

  Last Listing Agent Kelly Gettel COLDWELL BANKER REALTY

  1910 Datura St, Sarasota, FL 34239
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  /40

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,330 Sq Ft

  1864 Clematis St, Sarasota, FL 34239

  1864 Clematis St, Sarasota, FL 34239
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  /81

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  2355 Bahia Vista St, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. UNRIVALED LUXURY LIVING IN PRIME SARASOTA LOCATION! Experience the epitome of luxury with this stunning custom 4 bed 2 and a half bath residential masterpiece! This immaculate two-story traditional home boasts unrivaled craftsmanship and top-tier amenities throughout. Every detail exudes sophistication, from the soaring 9’4” ceilings and elegant

  Rory McDonald PREFERRED SHORE LLC

  2355 Bahia Vista St, Sarasota, FL 34239
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  /34

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • House for Rent

  2141 Hyde Park St, Sarasota, FL 34239

  Sunshine, palm trees, majestic oaks, and your own private pool—this beautiful turnkey furnished downtown Sarasota home is ready for your next getaway, available for monthly rental year-round with a 30-day minimum stay—just bring your sunscreen and flip flops! Step inside to an open and inviting living area filled with natural light, flowing seamlessly into the dining space and a well-equipped

  Scott Nold TNG PROPERTY MANAGEMENT

  2141 Hyde Park St, Sarasota, FL 34239
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  /2

  $2,650,000 Sold Mar 27, 2025

  1805 Datura St, Sarasota, FL 34239

  • 4 Beds
  • 4.5 Baths
  • 3,318 Sq Ft
  • Built 2012

  Last Sold Summary

  • 12% Below List Price
  • $799/SF
  • 68 Days On Market

  Current Estimated Value $2,509,545

  Last Listing Agent Barbara May MICHAEL SAUNDERS & COMPANY

  1805 Datura St, Sarasota, FL 34239
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  /80

  Est $3,038,955 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,358 Sq Ft

  2131 Mcclellan Pkwy, Sarasota, FL 34239

  2131 Mcclellan Pkwy, Sarasota, FL 34239
• 

  

  /97

  $5,999,995

  • 4 Beds
  • 4.5 Baths
  • 6,091 Sq Ft

  3576 San Remo Terrace, Sarasota, FL 34239

  One or more photo(s) has been virtually staged. 3576 San Remo Terrace – A Waterfront Masterpiece in SarasotaDiscover the pinnacle of coastal luxury at this exquisite estate, nestled in the highly sought after San Remo Estates. Offering the best views over Roberts Bay, this 6,091-square-foot residence seamlessly blends timeless elegance, modern sophistication, and unparalleled waterfront

  Nazare Edelson COMPASS FLORIDA LLC

  3576 San Remo Terrace, 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

  $2,500,000 Sold Jan 15, 2025

  2116 Hyde Park St, Sarasota, FL 34239

  • 5 Beds
  • 5 Baths
  • 4,284 Sq Ft
  • Built 2024

  Last Sold Summary

  • 11% Below List Price
  • $584/SF
  • 40 Days On Market

  Current Estimated Value $2,424,500

  Last Listing Agent Vladislav Konatar KONA REALTY

  2116 Hyde Park St, Sarasota, FL 34239
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  /90

  Est $7,354,345 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,040 Sq Ft

  1447 Tangier Way, Sarasota, FL 34239

  1447 Tangier Way, Sarasota, FL 34239
• 

  

  /79

  $1,650,000

  • 3 Beds
  • 2 Baths
  • 2,282 Sq Ft

  2711 Blossom Dr, Sarasota, FL 34239

  SMART, SOPHISTICATED, STUNNING ~ YOUR CUSTOM SARASOTA OASIS AWAITS! Experience modern elegance and luxury living in this exceptional custom-built home with a resort-style pool in one of Sarasota’s most sought-after neighborhoods near Southside Elementary. Designed with impeccable attention to detail, this stunning residence showcases high-end finishes, luxury, technology, and thoughtful design

  Mary Elizabeth Mock COLDWELL BANKER REALTY

  2711 Blossom Dr, Sarasota, FL 34239
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  /38

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  2365 Waldemere St, Sarasota, FL 34239

  Please contact the Listing Agent to obtain details about the WEEKLY and MONTHLY rates. Available Dates in 2025:From November 25 to December 10, 2025;From December 30, 2025, to January 10, 2026;Available Dates in 2026:From April 20,2026OR Long-term starting May 1, 2026Should you wish to rent TWO LUXURY RESIDENCES for a larger gathering of guests (up to 18), consider our

  Claudia Dybala DALTON WADE INC

  2365 Waldemere St, Sarasota, FL 34239
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  /2

  $800,000 Sold Feb 28, 2025

  2127 S Jefferson Ave, Sarasota, FL 34239

  • 5 Beds
  • 2 Baths
  • 2,825 Sq Ft
  • Built 1949

  Last Sold Summary

  • 6% Below List Price
  • $283/SF
  • 68 Days On Market

  Current Estimated Value $765,118

  Last Listing Agent Peter G. Laughlin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2127 S Jefferson Ave, Sarasota, FL 34239
• 

  /2

  Est $110,038 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 369 Sq Ft

  3700 S Osprey Ave Unit 112, Sarasota, FL 34239

  3700 S Osprey Ave Unit 112, Sarasota, FL 34239
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  /57

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,121 Sq Ft

  2104 S Tuttle Ave, Sarasota, FL 34239

  Multiple offers received. Please submit your highest and best offer by Monday 12/22. Pool Home on a Spacious Corner Lot – Sarasota Living at Its Best Welcome to 2104 S Tuttle Avenue, where everyday life feels like a getaway. This move-in ready 2-bedroom, 2-bath home sits on a huge corner lot in flood zone X—the lowest risk—giving you peace of mind and freedom to simply enjoy the Sarasota

  Brett Keyser, Jr RE/MAX ALLIANCE GROUP

  2104 S Tuttle Ave, Sarasota, FL 34239
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  /36

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  2375 Waldemere St, Sarasota, FL 34239

  Please contact the Listing Agent to obtain details about the WEEKLY and MONTHLY rates. Available Dates in 2026:January 20-31, 2026;March 30 to April 22, 2026;OR Long-term starting from May 1, 2026.Should you wish to rent TWO LUXURY RESIDENCES for a larger gathering of guests (up to 18), consider our alternative property named "Sky Blue Sarasota" (2365 Waldemere St, Sarasota),

  Claudia Dybala DALTON WADE INC

  2375 Waldemere St, Sarasota, FL 34239
• 

  /2

  $1,670,000 Sold Sep 18, 2025

  2554 Arlington St, Sarasota, FL 34239

  • 4 Beds
  • 3.5 Baths
  • 2,915 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Below List Price
  • $573/SF
  • 105 Days On Market

  Current Estimated Value $1,623,157

  Last Listing Agent Alesia Stirp ALESIA DEANNA STIRP

  2554 Arlington St, Sarasota, FL 34239
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  /63

  Est $489,089 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,001 Sq Ft

  2106 Temple St, Sarasota, FL 34239

  2106 Temple St, Sarasota, FL 34239

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