Homes in ZIP Code 34239

/48
$1,895,000
- 4 Beds
- 3 Baths
- 2,252 Sq Ft
1865 Orchid St, Sarasota, FL 34239

Welcome to your dream home in Sarasota’s coveted West of Trail neighborhood—one of the area’s most sought-after locations, known for its quiet, tree-lined streets, upscale homes, and unbeatable proximity to the water. This beautifully designed 4-bedroom, 3-bathroom residence offers the perfect blend of comfort, style, and income potential, complete with a spacious garage for added convenience.

Tina Ellis COMPASS FLORIDA LLC

1865 Orchid St, Sarasota, FL 34239
/26
$3,500 Per Month
- 2 Beds
- 2 Baths
- 1,178 Sq Ft
- House for Rent
2266 Clematis St, Sarasota, FL 34239

Adorable turnkey furnished vacation rental on oversized lot and walkable to Arlington Park and Sarasota Memorial. Available for weekly, monthly and annual rental.

Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

2266 Clematis 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 $1,573,233

Last Listing Agent Alesia Stirp ALESIA DEANNA STIRP

2554 Arlington St, Sarasota, FL 34239

/2
Est $2,660,963 Not Listed For Sale

2004 S Osprey Ave, Sarasota, FL 34239
- 4 Beds
- 2.5 Baths
- 2,670 Sq Ft
- Built 2014
2004 S Osprey Ave, Sarasota, FL 34239

Last Sold Summary
- 10% Below List Price
- $1,105/SF
- 14 Days On Market
- Last Sold Price $2,950,000
- Jan 31, 2025
Last Listing Agent Nora Johnson Michael Saunders

/65
$1,950,000
- 4 Beds
- 3.5 Baths
- 2,483 Sq Ft
3331 Old Oak Dr, Sarasota, FL 34239

A private, gated masterpiece where Old Florida romance meets modern coastal luxury.Tucked within the coveted West of the Trail enclave, this exquisitely reimagined estate delivers a rare blend of architectural heritage, refined craftsmanship, and elevated contemporary living. Beyond the stately motorized wrought-iron gate, a sweeping brick-paver drive meanders beneath towering live oaks,

Adnan Dedic COMPASS FLORIDA LLC

3331 Old Oak Dr, Sarasota, FL 34239
/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
/2
$208,000 Sold Dec 29, 2025

3140 Village Green Dr Unit 1119, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,323 Sq Ft
- Built 1970
Last Sold Summary
- 3% Below List Price
- $157/SF
- 6 Days On Market
Current Estimated Value $208,814

Last Listing Agent Cody Craig EXIT KING REALTY

3140 Village Green Dr Unit 1119, Sarasota, FL 34239

/90
Est $7,215,891 Not Listed For Sale

1447 Tangier Way, Sarasota, FL 34239
- 4 Beds
- 4.5 Baths
- 5,040 Sq Ft
- Built 2008
1447 Tangier Way, Sarasota, FL 34239

Last Sold Summary
- 15% Below List Price
- $1,677/SF
- 29 Days On Market
- Last Sold Price $8,450,000
- Jun 07, 2023
Last Listing Agent Lisa Rooks Morris Michael Saunders

/16
$1,375,000
- 2 Beds
- 1 Bath
- 991 Sq Ft
1702 Waldemere St, Sarasota, FL 34239

Wonderful opportunity to build your dream home in the heart of Sarasota. Found in the desired West of Trail area, this quarter acre lot is 75' wide and offers endless possibilities. Located only one block from Sarasota Memorial Hospital, three blocks to Southside Village with tons of wonderful restaurants and shops, along with Morton's Market, and less than 1.5 miles to Main St in Downtown

Victoria Beckham MICHAEL SAUNDERS & COMPANY

1702 Waldemere St, Sarasota, FL 34239
/43
$5,500 Per Month
- 3 Beds
- 3.5 Baths
- 1,867 Sq Ft
- House for Rent
1894 Loma Linda St, Sarasota, FL 34239

AVAILABLE MAY 1ST - Unfurnished and annual rental only, is this contemporary gem located West of the Trail in vibrant Sarasota, FL. This spacious home offers a seamless blend of modern design and cozy charm, featuring an open floor plan that is perfect for both entertaining and everyday living. Step inside to discover a beautifully appointed chef's kitchen, complete with solid wood cabinets,

Beth Harris COMPASS FLORIDA LLC

1894 Loma Linda St, Sarasota, FL 34239
/2
$1,320,000 Sold Mar 04, 2026

1355 Harbor Dr, Sarasota, FL 34239
- Land
- 13,939 Sq Ft
- $4,125,000 per Acre
Last Sold Summary
Current Estimated Value $1,581,543

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

1355 Harbor Dr, Sarasota, FL 34239

/2
Est $567,625 Not Listed For Sale

1742 Wisconsin Ln, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,468 Sq Ft
- Built 1989
1742 Wisconsin Ln, Sarasota, FL 34239

Last Sold Summary
- 10% Above List Price
- $353/SF
- 47 Days On Market
- Last Sold Price $518,000
- Dec 31, 2024
Last Listing Agent Roberta Tengerdy, PA PREMIER SOTHEBY'S INTERNATIONAL REALTY

/35
$599,000
- 3 Beds
- 2 Baths
- 1,126 Sq Ft
2374 Arlington St, Sarasota, FL 34239

One or more photo(s) has been virtually staged. Located in Sarasota’s highly sought-after Arlington Park neighborhood, this thoughtfully updated residence delivers a compelling combination of comfort, functionality, and proximity to the city’s most popular destinations. With a renovated three-bedroom layout, the home is move-in ready and ideally positioned just minutes from downtown Sarasota and

Roger Pettingell COLDWELL BANKER REALTY

2374 Arlington St, Sarasota, FL 34239
/54
$3,200 Per Month
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
- House for Rent
3507 Pinecrest St, Sarasota, FL 34239

Available August 2026. Vacation or Long-Term rental! 3 month minimum. Sarasota Village Green Golf Course 3/2 home on a beautifully landscaped corner lot. The back yard is fully fenced and the home has a spacious lanai and swimming pool (not heated). The open floor plan lends itself to views of the back yard from the family room and kitchen.Modern upgrades throughout and new LVP flooring in

Margaret Young JENNETTE PROPERTIES, INC.

3507 Pinecrest St, Sarasota, FL 34239
/2
$1,750,000 Sold Mar 27, 2026

1504 S Orange Ave, Sarasota, FL 34239
- 3 Beds
- 3 Baths
- 3,238 Sq Ft
- Built 1954
Last Sold Summary
- 3% Above List Price
- $540/SF
- 3 Days On Market
Current Estimated Value $1,751,464

Last Listing Agent Barbara May MICHAEL SAUNDERS & COMPANY

1504 S Orange Ave, Sarasota, FL 34239

/45
Est $376,144 Not Listed For Sale

2343 Loma Linda St, Sarasota, FL 34239
- 2 Beds
- 1 Bath
- 724 Sq Ft
- Built 1952
2343 Loma Linda St, Sarasota, FL 34239

Last Sold Summary
- 1% Below List Price
- $525/SF
- 5 Days On Market
- Last Sold Price $380,000
- Jun 27, 2023
Last Listing Agent Dave Beachy BEACHY PROPERTIES

/30
$349,900 Pre-Foreclosure
- 3 Beds
- 2 Baths
- 1,267 Sq Ft
2916 Hawthorne St, Sarasota, FL 34239

Live the Sarasota lifestyle in Rio Vista. This 3-bedroom, 2-bath home delivers the convenience of single-story living in a neighborhood people wait to get into. Enjoy a practical floor plan, bright interior spaces, and a generous yard that’s ready for entertaining, pets, or your future outdoor vision. You’re close to downtown Sarasota, bayfront parks, restaurants, shopping, and quick drives to

Patrizia Tornatore Brokernation Real Estate Doral

2916 Hawthorne St, Sarasota, FL 34239
/15
$2,400 Per Month
- 2 Beds
- 2 Baths
- 1,480 Sq Ft
- House for Rent
2624 Sunnybrook Dr, Sarasota, FL 34239

Located on a quiet meandering street in the centrally located community of South Gate, this 2 bedroom 2 bath 2 car garage home is available for rent immediately. The open floor plan home features a newly renovated kitchen with new cabinets, countertops, and stainless steel appliances. You will find easy care vinyl flooring throughout the home and both bathrooms are on point with new ceramic tile

Wade Ongstad PREFERRED SHORE LLC

2624 Sunnybrook Dr, Sarasota, FL 34239
/2
$435,000 Sold Dec 02, 2025

3072 Meyer Dr, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,868 Sq Ft
- Built 1959
Last Sold Summary
- 5% Below List Price
- $233/SF
- 55 Days On Market
Current Estimated Value $434,823

Last Listing Agent Laurie Minear MICHAEL SAUNDERS & COMPANY

3072 Meyer Dr, Sarasota, FL 34239

/31
Est $202,097 Not Listed For Sale

2224 Bahia Vista St Unit E8, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 982 Sq Ft
- Built 1979
2224 Bahia Vista St Unit E8, Sarasota, FL 34239

Last Sold Summary
- 10% Below List Price
- $229/SF
- 29 Days On Market
- Last Sold Price $225,000
- Jan 31, 2024
Last Listing Agent Raffilena Hamilton GOOD LIFE REALTY LLC

/35
$625,000 Pending
- 2 Beds
- 2 Baths
- 1,519 Sq Ft
2527 Sheridan Dr, Sarasota, FL 34239

Under contract-accepting backup offers. Southgate living at its best. This 2/2 with an office is the perfect size home with large living and outdoor areas. The most important feature is that it is move-in ready. Since the owners purchased the home in 2014, they've lovingly updated just about everything. Most recently a new roof was installed in 2022, a gorgeous new heated pool with spa and cage

Mary Jo Violett MICHAEL SAUNDERS & COMPANY

2527 Sheridan Dr, Sarasota, FL 34239
/24
$1,450 Per Month
- 2 Beds
- 1 Bath
- 675 Sq Ft
- Condo for Rent
3001 Bee Ridge Rd Unit 201, Sarasota, FL 34239

One or more photo(s) has been virtually staged. Move-in Specials: Only $700 Security Deposit! Apply before May 8th and get half off on your Application Fee. Step on in to this stunning 2-bedroom, 1-bathroom apartment off of Bee Ridge Road! This light and bright second floor, end unit features tile flooring, neutral paint, and an open concept floorplan perfect for entertaining! The kitchen

MJ LoParco PMI SOUTHWEST FLORIDA

3001 Bee Ridge Rd Unit 201, Sarasota, FL 34239
/2
$1,550,000 Sold Jul 15, 2025

1954 Datura St, Sarasota, FL 34239
- 3 Beds
- 2.5 Baths
- 2,763 Sq Ft
- Built 1946
Last Sold Summary
- 14% Below List Price
- $561/SF
- 131 Days On Market
Current Estimated Value $1,533,780

Last Listing Agent Bev Murray BERKSHIRE HATHAWAY HOMESERVICE

1954 Datura St, Sarasota, FL 34239

/28
Est $207,421 Not Listed For Sale

2232 Bahia Vista St Unit A3, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 982 Sq Ft
- Built 1979
2232 Bahia Vista St Unit A3, Sarasota, FL 34239

Last Sold Summary
- 13% Below List Price
- $243/SF
- 302 Days On Market
- Last Sold Price $239,000
- May 31, 2023
Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP

/80
$855,000 New Construction
- 4 Beds
- 2.5 Baths
- 2,141 Sq Ft
2369 Bahia Vista St, Sarasota, FL 34239

Discover the ultimate in luxury living just a short drive from downtown Sarasota, St. Armands Circle, and Lido Beach! Designed by Arrow Homes, this inviting custom-built 2 story residence offers 4 bedrooms and 21/2 baths. Don’t miss the elegant traditional design and exceptional craftsmanship. Enjoy impressive 9’-4” ceilings, spacious owners suite, bonus loft area, custom PGT Florida Impact Rated

Rory McDonald PREFERRED SHORE LLC

2369 Bahia Vista St, Sarasota, FL 34239
/23
$1,950 Per Month
- 1 Bed
- 1 Bath
- 750 Sq Ft
- Apartment for Rent
1901 Hyde Park St Unit C, Sarasota, FL 34239

Enjoy this comfortable & spacious one bedroom apartment located in wonderful Southside Village, recently renovated, 1 block to Sarasota Memorial Hospital. Brand new pool with large deck to enjoy the summer heat. Easy walk to so many wonderful restaurants and cute boutique stores. Siesta Key and Lido Key beaches 10 minutes away. Multiple units available

Jason Truluck Williams GRAYSTONE REAL ESTATE

1901 Hyde Park St Unit C, Sarasota, FL 34239
/2
$2,224,500 Sold Jul 18, 2025

1813 Boyce St, Sarasota, FL 34239
- 4 Beds
- 3.5 Baths
- 3,584 Sq Ft
- Built 2013
Last Sold Summary
- 11% Below List Price
- $621/SF
- 28 Days On Market
Current Estimated Value $2,208,213

Last Listing Agent Lindsey Nussbaum COLDWELL BANKER REALTY

1813 Boyce St, Sarasota, FL 34239

/38
Est $227,986 Not Listed For Sale

2200 Bahia Vista St Unit B2, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
- Built 1980
2200 Bahia Vista St Unit B2, Sarasota, FL 34239

Last Sold Summary
- 13% Below List Price
- $256/SF
- 19 Days On Market
- Last Sold Price $262,250
- May 31, 2024
Last Listing Agent Marci McFarland Michael Saunders

/31
$625,000
- 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
/70
$12,000 Per Month
- 3 Beds
- 2 Baths
- 1,934 Sq Ft
- House for Rent
2641 Hyde Park St, Sarasota, FL 34239

Welcome to Palm & Oak, an expertly curated turnkey rental unlike any other in Sarasota w/ direct access on 2 sides to the coveted Arlington Park. This fully renovated Coastal Pool & Spa home offers nearly 2000 sq ft of living space on a huge 1/3 acre lot w/ vast park views & direct park access from your private fenced backyard. Just minutes from Siesta Key Beach & Downtown Sarasota, this property

Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

2641 Hyde Park St, Sarasota, FL 34239
/2
$512,500 Sold Feb 19, 2026

2238 Rose St, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 1,781 Sq Ft
- Built 1956
Last Sold Summary
- 11% Below List Price
- $288/SF
- 103 Days On Market
Current Estimated Value $505,372

Last Listing Agent Janice Politz COLDWELL BANKER REALTY

2238 Rose St, Sarasota, FL 34239

/2
Est $1,757,828 Not Listed For Sale

1827 Grove St, Sarasota, FL 34239
- 3 Beds
- 2 Baths
- 2,479 Sq Ft
- Built 2001
1827 Grove St, Sarasota, FL 34239

Last Sold Summary
- 8% Below List Price
- $772/SF
- 1 Day On Market
- Last Sold Price $1,915,000
- Oct 23, 2024
Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

/40
$639,999 Pending
- 3 Beds
- 2 Baths
- 1,387 Sq Ft
2540 Sunnyside St, Sarasota, FL 34239

Under contract-accepting backup offers. Beautifully renovated pool home in South Gate on a double lot! As you enter through the front door you notice the open layout featuring freshly polished terrazzo flooring, decorative beams, and a fresh beachy look! Every chef will take delight in the remodeled kitchen (2020) featuring a plethora of cabinets, granite countertops, and New stainless-steel

Kendall Williams HOUSE MATCH

2540 Sunnyside St, Sarasota, FL 34239
/30
$3,450 Per Month
- 1 Bed
- 1 Bath
- 751 Sq Ft
- Condo for Rent
3360 S Osprey Ave Unit 205B, Sarasota, FL 34239

Are you ready to enjoy all that Sarasota and the Gulf beaches have to offer? The location of this 1 bedroom, 1 bath is fantastic! So close to Siesta Key, Southside Village and Downtown Sarasota. Asking $3,450/month.

Philip Pisano, III MICHAEL SAUNDERS & COMPANY

3360 S Osprey Ave Unit 205B, Sarasota, FL 34239
/2
$190,000 Sold Jul 03, 2025

3259 Fairhaven Ln Unit 211, Sarasota, FL 34239
- 2 Beds
- 2 Baths
- 1,323 Sq Ft
- Built 1968
Last Sold Summary
- 10% Below List Price
- $144/SF
- 37 Days On Market
Current Estimated Value $189,481

Last Listing Agent Steve Slocum COLDWELL BANKER REALTY

3259 Fairhaven Ln Unit 211, Sarasota, FL 34239

/96
Est $2,044,453 Not Listed For Sale

2627 Pleasant Place, Sarasota, FL 34239
- 4 Beds
- 3.5 Baths
- 3,782 Sq Ft
- Built 1988
2627 Pleasant Place, Sarasota, FL 34239

Last Sold Summary
- 5% Above List Price
- $516/SF
- 70 Days On Market
- Last Sold Price $1,950,000
- Mar 01, 2024
Last Listing Agent Sandra Appignani PREMIER SOTHEBY'S INTERNATIONAL REALTY

/16
$225,000
- Land
- 6,098 Sq Ft
- $1,607,143 per Acre
2445 Webber St, Sarasota, FL 34239

Lot is 48.5' X 117'. Located approximately 5 miles to Siesta key Beach, 2 miles to hospital, shopping, and schools. Home is a tear down although owner occupied. Public Water, Public sewage, and electric are connected.The property is zoned RSF and would allow for a single family structure or a modular home on a permanent foundation. Please see attached RSF code for additional uses and development

Kathy Wilkes SARASOTA'S WEST COAST REALTY

2445 Webber St, Sarasota, FL 34239
/18
$1,800 Per Month
- 2 Beds
- 1 Bath
- 991 Sq Ft
- Condo for Rent
3700 S Osprey Ave Unit 216, Sarasota, FL 34239

WEST OF THE TRAIL...this charming 2nd floor condo offers 2 bedrooms and 1 bathroom. The balcony is enclosed with screens and windows. Excellent location, convenience is key with this property. Situated just around the corner from the north bridge and minutes away from the world renowned SIESTA KEY BEACH. Live the best of both worlds in a peaceful, quiet area and easy access to coastal living.

Teresa Ribaudo JENNETTE PROPERTIES INC

3700 S Osprey Ave Unit 216, Sarasota, FL 34239
/2
$3,495,000 Sold May 01, 2026

2323 Okobee Dr, Sarasota, FL 34239
- 4 Beds
- 4.5 Baths
- 3,497 Sq Ft
- Built 2026
Last Sold Summary
- 3% Below List Price
- $999/SF
- 0 Days On Market
Current Estimated Value $2,535,508

Last Listing Agent Ryan Carson RE/MAX ALLIANCE GROUP

2323 Okobee Dr, Sarasota, FL 34239

/2
Est $685,248 Not Listed For Sale

2575 Hyde Park St, Sarasota, FL 34239
- 3 Beds
- 3 Baths
- 1,881 Sq Ft
- Built 1957
2575 Hyde Park St, Sarasota, FL 34239

Last Sold Summary
- 12% Below List Price
- $412/SF
- 10 Days On Market
- Last Sold Price $775,000
- Oct 30, 2024
Last Listing Agent Tina Ellis COMPASS FLORIDA LLC

Showing Results 241 - 280, Page 7 of 18

Florida Sarasota County Sarasota 34239

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