Homes in ZIP Code 34239

/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
/43
$3,300 Per Month
- 3 Beds
- 2 Baths
- 1,628 Sq Ft
- House for Rent
3425 Fairview Dr, Sarasota, FL 34239

ANNUAL FURNISHED 3 BEDROOM PLUS DEN POOL HOME AVAILABLE FOR ANNUAL LEASE IN SOUTH GATE! The fully updated home has a beautiful kitchen with granite counters and stainless-steel appliances, modern bathrooms featuring matching granite, a walk-in closet in the primary bedroom, an open floor plan with a spacious great room adjacent to the kitchen, and a bright office overlooking the pool. The

Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

3425 Fairview Dr, Sarasota, FL 34239
/2
$325,000 Sold Jan 23, 2026

2104 S Tuttle Ave, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,121 Sq Ft
- Built 1960
Last Sold Summary
- 32% Below List Price
- $290/SF
- 129 Days On Market
Current Estimated Value $391,644

Last Listing Agent Brett Keyser, Jr RE/MAX ALLIANCE GROUP

2104 S Tuttle Ave, Sarasota, FL 34239

/43
Est $674,640 Not Listed For Sale

2517 Valencia Dr, Sarasota, FL 34239
- 4 Beds
- 3 Baths
- 2,372 Sq Ft
- Built 1956
2517 Valencia Dr, Sarasota, FL 34239

Last Sold Summary
- 5% Above List Price
- $270/SF
- 156 Days On Market
- Last Sold Price $640,000
- Jun 16, 2023
Last Listing Agent Mark Borg LIST WITH 1 REALTY

/86
$1,999,999
- 3 Beds
- 2.5 Baths
- 2,939 Sq Ft
1695 Hyde Park St, Sarasota, FL 34239

Exceptional Living in Sarasota's Premier Southside Village. Discover quality living in one of Sarasota's most sought-after addresses. This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an excellent combination of thoughtful design, premium finishes, and an enviable location just half a block from the vibrant shops and restaurants of Southside Village. The heart of this home is a

Allen Conrad RE/MAX ALLIANCE GROUP

1695 Hyde Park St, Sarasota, FL 34239
/68
$13,000 Per Month
- 5 Beds
- 3.5 Baths
- 3,223 Sq Ft
- House for Rent
1359 Harbor Dr, Sarasota, FL 34239

STUNNING UNFURNISHED SINGLE FAMILY HOME IN THE SOUGHT AFTER COMMUNITY OF HARBOR ACRES IS AVAILABLE TO RENT!!! This is the one you've been looking for! Renovated from top to bottom this home has all the bells and whistles with a contemporary design, spacious floor plan, two stories, split bedrooms and a private second floor primary bedroom. The kitchen is truly the heart of this home with two

C. Alison Hunter JENNETTE PROPERTIES INC

1359 Harbor Dr, Sarasota, FL 34239
/2
$230,000 Sold Oct 28, 2025

3350 S Osprey Ave Unit 211A, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
- Built 1969
Last Sold Summary
- 8% Below List Price
- $205/SF
- 141 Days On Market
Current Estimated Value $232,571

Last Listing Agent John Marabella PREMIER SOTHEBY'S INTERNATIONAL REALTY

3350 S Osprey Ave Unit 211A, Sarasota, FL 34239

/2
Est $528,196 Not Listed For Sale

2136 Clematis Place, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,272 Sq Ft
- Built 1976
2136 Clematis Place, Sarasota, FL 34239

Last Sold Summary
- 8% Below List Price
- $452/SF
- 57 Days On Market
- Last Sold Price $575,000
- Oct 15, 2024
Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S

/50
$2,599,990
- 4 Beds
- 3 Baths
- 3,215 Sq Ft
1885 Clematis St, Sarasota, FL 34239

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 and only minutes to downtown Sarasota

Monica Verinder COLDWELL BANKER REALTY

1885 Clematis St, Sarasota, FL 34239
/5
$5,500 Per Month
- 5 Beds
- 3 Baths
- 1,863 Sq Ft
- House for Rent
2317 Grove St, Sarasota, FL 34239

Welcome to this stunning, fully renovated home located on Grove Street in the heart of Sarasota. This property blends classic Florida charm with modern updates, offering a move-in-ready home designed for today’s lifestyle. Step inside to find a thoughtfully updated interior featuring a bright, open layout, stylish finishes, and quality craftsmanship throughout. The renovation highlights include

James Hogan EXP REALTY LLC

2317 Grove St, Sarasota, FL 34239
/2
$460,000 Sold Dec 30, 2025

2629 Bigelow Dr, Sarasota, FL 34239
- 4 Beds
- 3 Baths
- 2,056 Sq Ft
- Built 1962
Last Sold Summary
- 3% Below List Price
- $224/SF
- 33 Days On Market
Current Estimated Value $455,282

Last Listing Agent Carol Burke WHITE SANDS REALTY GROUP FL

2629 Bigelow Dr, Sarasota, FL 34239

/65
Est $1,812,025 Not Listed For Sale

1964 Datura St, Sarasota, FL 34239
- 4 Beds
- 3.5 Baths
- 3,272 Sq Ft
- Built 2006
1964 Datura St, Sarasota, FL 34239

Last Sold Summary
- 5% Below List Price
- $581/SF
- 345 Days On Market
- Last Sold Price $1,900,000
- Mar 14, 2025
Last Listing Agent Mackenzie Longueuil Michael Saunders

/64
$237,900
- 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
/10
$1,575 Per Month
- 2 Beds
- 2 Baths
- 800 Sq Ft
- Apartment for Rent
2055 Arlington St, Sarasota, FL 34239

Move in with up to $0 deposit! Welcome to your new home in the heart of Sarasota, FL! This 2-bedroom, 2-bathroom apartment offers a perfect blend of comfort and convenience. Located in downtown Sarasota across from SMH, you'll be just steps away from a variety of shopping destinations, dining options, and entertainment venues. The apartment is also conveniently situated near bus lines, making

Lisa Thompsen STOCKTON REALTY ADVISORS LLC

2055 Arlington St, Sarasota, FL 34239
/2
$192,500 Sold Apr 06, 2026

3206 Village Green Dr Unit 1036, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,419 Sq Ft
- Built 1971
Last Sold Summary
- 4% Below List Price
- $136/SF
- 5 Days On Market
Current Estimated Value $239,254

Last Listing Agent Jesse Bauer KW COASTAL LIVING III

3206 Village Green Dr Unit 1036, Sarasota, FL 34239

/44
Est $804,423 Not Listed For Sale

2531 Siesta Dr, Sarasota, FL 34239
- 2 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 1959
2531 Siesta Dr, Sarasota, FL 34239

Last Sold Summary
- 13% Below List Price
- $440/SF
- 188 Days On Market
- Last Sold Price $925,000
- Jun 14, 2024
Last Listing Agent Albert Wooster ALBERT WOOSTER & COMPANY

/82
$2,400,000 Open Sat 12PM - 3PM
- 6 Beds
- 7 Baths
- 3,574 Sq Ft
2124 Clematis Place, Sarasota, FL 34239

Now presenting a stunning new construction residence in Arlington Park, built by Courtyard Modern Development, where modern design, functionality, and Sarasota luxury lifestyle come together seamlessly. This exceptional two-story home offers 6 bedrooms, 7 full bathrooms, and approximately 3,574 sq ft of living space, thoughtfully designed to deliver both elegance and comfort in every detail. The

Alberto Rueda Ramirez MICHAEL SAUNDERS & COMPANY

2124 Clematis Place, Sarasota, FL 34239
/24
$3,000 Per Month
- 3 Beds
- 2.5 Baths
- 2,208 Sq Ft
- House for Rent
2408 Hillview St, Sarasota, FL 34239

Welcome to Hillview Digs! Hillview Digs is a fully furnished two story Farmhouse moved from downtown Sarasota in the mid fifties . Just shy of 2000 square feet and equipped with 3 bedrooms, 2.5 bathrooms, an office area, a family room/den separate from the main living room. For your convenience, the master bedroom is on the first floor with the other 2 bedrooms upstairs. This cozy home features

Deserea Hardy ROSSI & COMPANY INC

2408 Hillview St, Sarasota, FL 34239
/2
$342,000 Sold Dec 04, 2025

2329 Rose St, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,866 Sq Ft
- Built 1952
Last Sold Summary
- 25% Below List Price
- $183/SF
- 12 Days On Market
Current Estimated Value $354,774

Last Listing Agent Sandra Houghton BRIGHT REALTY

2329 Rose St, Sarasota, FL 34239

/2
Est $565,805 Not Listed For Sale

2504 Fruit Tree Dr, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1960
2504 Fruit Tree Dr, Sarasota, FL 34239

Last Sold Summary
- 15% Below List Price
- $554/SF
- 28 Days On Market
- Last Sold Price $665,000
- Jul 23, 2024
Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

/54
$1,525,000
- 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
/73
$6,500 Per Month
- 4 Beds
- 2.5 Baths
- 2,131 Sq Ft
- House for Rent
1738 Siesta Dr, Sarasota, FL 34239

Available June 1st, this newer (2013) “West of Trail” pool home offers an ideal opportunity to get settled ahead of the upcoming school year in the highly regarded Southside Elementary district, just a short bike ride away. Offered at $6,500/month with an annual lease preferred (6-month considered), the home provides flexibility with furnishings — available furnished or unfurnished. Elevated 22

Ryan Adamson COLDWELL BANKER REALTY

1738 Siesta Dr, Sarasota, FL 34239
/2
$3,100,000 Sold Apr 27, 2026

2624 Mulberry Terrace, Sarasota, FL 34239
- 4 Beds
- 5 Baths
- 3,744 Sq Ft
- Built 2021
Last Sold Summary
- 10% Below List Price
- $828/SF
- 104 Days On Market
Current Estimated Value $3,231,231

Last Listing Agent Karen Greco GRECO REAL ESTATE

2624 Mulberry Terrace, Sarasota, FL 34239

/2
Est $682,962 Not Listed For Sale

1905 Jasmine Dr, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,658 Sq Ft
- Built 1952
1905 Jasmine Dr, Sarasota, FL 34239

Last Sold Summary
- 1% Above List Price
- $410/SF
- 2 Days On Market
- Last Sold Price $679,000
- Dec 30, 2024
Last Listing Agent Chet Zoltak COLDWELL BANKER REALTY

/50
$1,495,000
- 4 Beds
- 5 Baths
- 2,881 Sq Ft
1751 Floyd St, Sarasota, FL 34239

In the "heart" of the most popular West of Trail neighborhood, step into a rare piece of Sarasota history just a short stroll to Southside Village restaurants and shops, downtown and 2 blocks to Sarasota Memorial Hospital. Behind a classic white picket fence, this 1926 home welcomes you with a generous yard framed by mature landscaping and colorful gardens. A cozy front porch sets the tone for

Barbara May MICHAEL SAUNDERS & COMPANY

1751 Floyd St, Sarasota, FL 34239
/52
$2,000 Per Month
- 1 Bed
- 1 Bath
- 431 Sq Ft
- House for Rent
2084 Grove St Unit B, Sarasota, FL 34239

This one-bedroom, one-bath furnished rental guest house is recently renovated with private entrance, fenced patio/yard area, your own free- standing HOT TUB and access to the shared POOL in the back yard! There is a stackable PRIVATE LAUNDRY conveniently located in the walk-in closet to the bedroom. The kitchenette boasts a large granite countertop with induction cooktop, refrigerator, small

Kari Klein KW COASTAL LIVING III

2084 Grove St Unit B, Sarasota, FL 34239
/2
$1,000,000 Sold Aug 21, 2025

1746 Stapleton St, Sarasota, FL 34239
- 4 Beds
- 3 Baths
- 2,895 Sq Ft
- Built 2006
Last Sold Summary
- 37% Below List Price
- $345/SF
- 160 Days On Market
Current Estimated Value $1,018,208

Last Listing Agent Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

1746 Stapleton St, Sarasota, FL 34239

/2
Est $2,574,566 Not Listed For Sale

1632 Floyd St, Sarasota, FL 34239
- 4 Beds
- 4.5 Baths
- 4,338 Sq Ft
- Built 1995
1632 Floyd St, Sarasota, FL 34239

Last Sold Summary
- 4% Below List Price
- $617/SF
- 241 Days On Market
- Last Sold Price $2,675,000
- Oct 16, 2024
Last Listing Agent Lisa Rooks Morris Michael Saunders

/66
$1,445,000
- 3 Beds
- 2 Baths
- 1,595 Sq Ft
1780 Spring Creek Dr, Sarasota, FL 34239

Architectural character, curated design, and resort-style outdoor living define this exceptional Sarasota residence at 1780 Spring Creek Drive.Privately positioned behind a gated entry and surrounded by lush tropical landscaping, this distinctive home offers a refined Florida lifestyle with thoughtful upgrades, timeless style, and true peace of mind. Located in one of the the location that

Adnan Dedic COMPASS FLORIDA LLC

1780 Spring Creek Dr, Sarasota, FL 34239
/63
$4,200 Per Month
- 3 Beds
- 2 Baths
- 1,434 Sq Ft
- House for Rent
2572 Jefferson Cir, Sarasota, FL 34239

Welcome to the JefferSun House- a light & bright breath of fresh air & sunshine just minutes from world famous beaches & downtown Sarasota and located within the coveted Southside school district. This turnkey furnished 3 bedroom 2 bathroom heated pool home sleeps 8 & offers a private, fully fenced backyard w/ heated pool & BBQ grill. We are a dog friendly house, walkable to Arlington Park w/ its

Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

2572 Jefferson Cir, Sarasota, FL 34239
/2
$1,150,000 Sold Dec 19, 2025

3716 Camino Real, Sarasota, FL 34239
- 3 Beds
- 2.5 Baths
- 2,023 Sq Ft
- Built 1951
Last Sold Summary
- 16% Below List Price
- $568/SF
- 254 Days On Market
Current Estimated Value $1,122,178

Last Listing Agent Ryan Adamson COLDWELL BANKER REALTY

3716 Camino Real, Sarasota, FL 34239

/28
Est $2,439,514 Not Listed For Sale

1846 Datura St, Sarasota, FL 34239
- 4 Beds
- 4.5 Baths
- 3,332 Sq Ft
- Built 2003
1846 Datura St, Sarasota, FL 34239

Last Sold Summary
- 10% Below List Price
- $810/SF
- 73 Days On Market
- Last Sold Price $2,700,000
- May 31, 2024
Last Listing Agent Brad Brown WHITE SANDS REALTY GROUP FL

/50
$210,000
- 2 Beds
- 2 Baths
- 982 Sq Ft
2232 Bahia Vista St Unit A1, Sarasota, FL 34239

Location truly makes all the difference—and this one delivers. Welcome to Cordova Gardens, a charming and peaceful community surrounded by lush, mature landscaping and ideally situated in the heart of Sarasota. Just minutes from the area’s world-renowned beaches, vibrant downtown, and iconic St. Armands Circle, you’ll have effortless access to boutique shopping, top-rated restaurants, Sarasota

Christian Tateo HORIZONS BY THE SEA, INC

2232 Bahia Vista St Unit A1, Sarasota, FL 34239
/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:Short Term or Long-term starting from May 1, 2026 for $7000 OR **option**SEASONAL RATE from December 2026 through April,2027 is $12,000.Should you wish to rent TWO LUXURY RESIDENCES for a larger gathering of guests (up to 18), consider our alternative property named "Sky Blue

Claudia Dybala DALTON WADE INC

2375 Waldemere St, Sarasota, FL 34239
/2
$535,000 Sold Mar 26, 2026

2115 Grove St, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
- Built 1956
Last Sold Summary
- 11% Below List Price
- $380/SF
- 56 Days On Market
Current Estimated Value $529,522

Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

2115 Grove St, Sarasota, FL 34239
/31
$1,825,000 New Construction
- 3 Beds
- 3.5 Baths
- 2,454 Sq Ft
2069 Hibiscus St, Sarasota, FL 34239

Under Construction. Soon to receive COO APRIL 2026! No expense has been spared in the construction of this luxurious new offering in the highly coveted Arlington Park Neighborhood! Featuring a solid block concrete exterior, aluminum impact windows, spray foam insulation, and a TPO roof to ensure your home LASTS; as well as tall ceilings, luxury vinyl plank and handpicked tile flooring, designer

Thatcher Miner THE REAL ESTATE STORE

2069 Hibiscus St, Sarasota, FL 34239
/35
$2,600 Per Month
- 2 Beds
- 1 Bath
- 1,091 Sq Ft
- House for Rent
1891 Prospect St, Sarasota, FL 34239

Welcome to this charming West of the Trail 2-bedroom, 1-bathroom home! This cozy gem offers a blend of comfort and convenience. Inside, you’ll love the abundance of natural light, updated kitchen with stainless steel appliances, and ceiling fans throughout for added comfort. The home also features air conditioning, central heating, and an inside laundry room complete with a washer and dryer. An

Beth Harris COMPASS FLORIDA LLC

1891 Prospect St, Sarasota, FL 34239
/2
$735,000 Sold Nov 04, 2025

1736 Hawthorne St, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,608 Sq Ft
- Built 1924
Last Sold Summary
- $457/SF
Current Estimated Value $789,045

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

1736 Hawthorne St, Sarasota, FL 34239

/2
Est $420,299 Not Listed For Sale

1318 Loma Linda Ct, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,004 Sq Ft
- Built 1952
1318 Loma Linda Ct, Sarasota, FL 34239

Last Sold Summary
- 3% Below List Price
- $433/SF
- 154 Days On Market
- Last Sold Price $435,000
- Feb 28, 2025
Last Listing Agent Michelle Hennessy PREFERRED SHORE LLC

Showing Results 161 - 200, Page 5 of 18

Florida Sarasota County Sarasota 34239

How to Buy a Home How to Finance a Home How to Sell a Home

Properties in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Homes in ZIP Code 34239

Real Estate & Homes

Properties in Nearby Zip Codes

Properties in Nearby Zip Codes

Properties in Nearby Zip Codes

Properties in Nearby Zip Codes