Southside Homes

/52
$2,799,999 Open Fri 12PM - 4PM
- 4 Beds
- 4 Baths
- 2,935 Sq Ft
1915 Tulip Dr, Sarasota, FL 34239

Welcome to 1915 Tulip Drive – a beautiful Single Story home you will love!This just completed Modern Coastal Single Story home is located West of the Trail in the preferred Zone X (unshaded) with elevated storm protection and easy access to Siesta Key beaches, Southside Village and Downtown Sarasota. Built strong and stylish by Majestik Homes, this 4 bedroom 4 bathroom residence

Alesia Stirp ALESIA DEANNA STIRP

1915 Tulip Dr, Sarasota, FL 34239
/63
$13,500 per month
- 3 Beds
- 4 Baths
- 3,104 Sq Ft
- House for Rent
1720 Spring Creek Dr, Sarasota, FL 34239

Welcome to your tropical paradise retreat at 1720 Spring Creek Drive, nestled minutes away from the #1 beach in America, Siesta Key. This fully furnished enchanting oasis awaits with a captivating blend of charm, elegance, and comfort, promising an unforgettable living experience. Step into your own slice of paradise as you're greeted by lush, tropical landscaping and a picturesque facade that

Adnan Dedic COMPASS FLORIDA LLC

1720 Spring Creek Dr, Sarasota, FL 34239
/2
$1,550,000 Sold Jul 15, 2025
- 2,763 Sq Ft
- $561/SF
- 131 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1946
1954 Datura St, Sarasota, FL 34239

This exceptional single-story home in the highly sought-after West of the Trail neighborhood offers the perfect blend of charm, privacy, and convenience. Ideally located near downtown Sarasota, top-rated schools, and world-renowned beaches, this property is an entertainer’s dream and a tranquil wellness retreat. The home features 3 bedrooms, 2.5 baths, and a dedicated den with serene views of the

Bev Murray BERKSHIRE HATHAWAY HOMESERVICE

1954 Datura St, Sarasota, FL 34239

/44
Est $211,878 Not Listed For Sale
- 1 Bed
- 1 Bath
- 751 Sq Ft
3360 S Osprey Ave Unit 207B, Sarasota, FL 34239

3360 S Osprey Ave Unit 207B, Sarasota, FL 34239

/43
$1,850,000 New Construction
- 5 Beds
- 2.5 Baths
- 3,023 Sq Ft
1647 Siesta Dr, Sarasota, FL 34239

Welcome to this stunning 3-story 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
/17
$1,500 per month
- 2 Beds
- 1 Bath
- 991 Sq Ft
- Condo for Rent
3700 S Osprey Ave Unit 113, Sarasota, FL 34239

Welcome to Plaza Gardens, your gateway to the renowned Siesta Key, ranked as the #1 Beach in the USA. Situated in close proximity to numerous attractions, this exceptional 2-bedroom, 1-bathroom condo offers convenience beyond compare. Enjoy the vibrant energy of downtown Sarasota, and rest assured knowing that Sarasota Memorial Hospital is also conveniently nearby. This inviting condo provides

Vincent Ricaud INVESTUS REALTY LLC

3700 S Osprey Ave Unit 113, Sarasota, FL 34239
/2
$3,800,000 Sold Jul 10, 2025
- 5,660 Sq Ft
- $671/SF
- 5 Days On Market
- 4 Beds
- 7 Baths
- Built 2013
1910 Datura St, Sarasota, FL 34239

West of Trail! Custom Build by Voight Construction. Nestled in one of Sarasota’s most coveted neighborhoods, this exceptional custom estate spans over three expansive lots and boasts craftsmanship that is truly one-of-a-kind. A celebration of fine design, this home features intricate millwork, rich stained oak floors, and soaring ceilings adorned with stunning pecky cypress inlays.Step

Kelly Gettel COLDWELL BANKER REALTY

1910 Datura St, Sarasota, FL 34239

/34
Est $292,887 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
3350 S Osprey Ave Unit 109A, Sarasota, FL 34239

3350 S Osprey Ave Unit 109A, Sarasota, FL 34239

/76
$1,990,000 New Construction
- 4 Beds
- 6 Baths
- 2,847 Sq Ft
3464 Camino Real, Sarasota, FL 34239

Love where you live or rent it out! Now completed ( June 2025) perfect sun drenched vacation home or rental property.This beautiful new construction showcase home by Siesta Kay Properties has it all ! Peace of mind when it comes to hurricane proof estate! Solid masonry built thru two floors, impact windows and doors with heat and sound proof quadruple glass. Elevation 17.4 ft above the sea

Sylvia Nowicki PREFERRED SHORE LLC

3464 Camino Real, Sarasota, FL 34239
/16
$5,000 per month
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
- Condo for Rent
3360 S Osprey Ave Unit 210B, Sarasota, FL 34239

JUST LISTED! 2026 SEASONAL RENTAL - 2 bed/2 bath upstairs condo w/elevator! This well appointed condo is within a 5 minute drive to the world famous Siesta Beach ...yet it is on the mainland! The complex has a nice community heated pool and is VERY close to restaurants and shopping, It's a 10 minute drive to downtown Sarasota where you can enjoy the Opera, Library, farmers market,gourmet shops

Annabelle Newland STOCKTON REALTY ADVISORS LLC

3360 S Osprey Ave Unit 210B, Sarasota, FL 34239
/2
$290,000 Sold Jul 09, 2025
- 1,056 Sq Ft
- $275/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
3745 Almeria Ave Unit 7S, Sarasota, FL 34239

Ground floor end unit with spacious lanai/screened-in porch. West of Tail location minutes to shopping, Publix, restaurants and a short distance to Siesta Key beach. Almeria is tucked away on a tree lined street with great privacy. Light and bright condo with an open floor planand features a large, screened lanai facing west. Enjoy the wonderful canopy of Florida Oak trees. Nice split

Brian Livesey WATERSIDE REALTY LLC

3745 Almeria Ave Unit 7S, Sarasota, FL 34239

/24
Est $287,406 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
3350 S Osprey Ave Unit 103A, Sarasota, FL 34239

3350 S Osprey Ave Unit 103A, Sarasota, FL 34239

/35
$1,990,000 New Construction
- 4 Beds
- 4.5 Baths
- 3,005 Sq Ft
1734 Wisconsin Ln, Sarasota, FL 34239

Don’t miss out on your opportunity to own a rare NEW West of the Trail Modern Beauty. Canvas Sarasota represents your opportunity to own a modern Green Certified Home that is extremely Energy Efficient, Ecologically Conscious & Environmentally Friendly, Termite & Fire Resistant, Safe, Secure and Acoustically Sound. Enjoy the Florida lifestyle at its best in a bright and open floor plan with 9’6”

Oliver McConnell MCCONNELL AND ASSOCIATES

1734 Wisconsin Ln, Sarasota, FL 34239
/23
$2,000 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. More information can be found here Multiple units available

Jason Truluck Williams GRAYSTONE REAL ESTATE

1901 Hyde Park St Unit C, Sarasota, FL 34239
/2
$800,000 Sold Jun 27, 2025
- 1,786 Sq Ft
- $448/SF
- 30 Days On Market
- 3 Beds
- 2 Baths
- Built 1957
1857 Jasmine Dr, Sarasota, FL 34239

BEST LOCATION! ***WEST OF THE TRAIL***Wonderful home, beautifully renovated and ready to move in.*The open floor plan and huge fenced backyard will delight you! Bring your pets and your outdoor grill, gardening skills and enjoy this oasis*. The custom kitchen is equipped with KITCHEN AID stainless steel appliances, huge island and breakfast bar. Plantation shutters. Tile throughout the home.

Livya Hament PREFERRED SHORE LLC

1857 Jasmine Dr, Sarasota, FL 34239

/60
Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,527 Sq Ft
1845 Bougainvillea St, Sarasota, FL 34239

1845 Bougainvillea St, Sarasota, FL 34239

/68
$1,950,000 Pending
- 4 Beds
- 3.5 Baths
- 3,227 Sq Ft
1713 North Dr, Sarasota, FL 34239

Under contract-accepting backup offers. Historic Cherokee Park: This prime, “West of the Trail” property with oak-lined boulevard streets and decorative light posts is located near Southside Village. At 20 feet elevation, this property has NO HISTORY OF FLOODING. There is a low annual HOA and no CDD’s. Situated on a picturesque lot, this home with a guest house boasts privacy and tranquility;

Denise Mei MICHAEL SAUNDERS & COMPANY

1713 North Dr, Sarasota, FL 34239
/12
$1,800 per month
- 1 Bed
- 1 Bath
- 500 Sq Ft
- Apartment for Rent
1901 Hyde Park St Unit G, Sarasota, FL 34239

Enjoy this comfortable & spacious studio 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.

Jason Truluck Williams GRAYSTONE REAL ESTATE

1901 Hyde Park St Unit G, Sarasota, FL 34239
/2
$9,500,000 Sold Jun 09, 2025
- 5,932 Sq Ft
- $1,601/SF
- 373 Days On Market
- 3 Beds
- 5 Baths
- Built 2014
3336 Old Oak Dr, Sarasota, FL 34239

Nestled within the vibrant city of Sarasota, Florida, this exquisite estate offers an unparalleled blend of luxury, privacy, and natural beauty. Situated on a sprawling 2-acre parcel of prime bayfront land, this custom-built residence boasts panoramic views of the shimmering waters, ensuring breathtaking sunsets year-round. As you enter through the gated entrance, you are greeted by meticulously

Thomas Cail RE/MAX ALLIANCE GROUP

3336 Old Oak Dr, Sarasota, FL 34239

/70
Est $7,460,799 Not Listed For Sale
- 5 Beds
- 6.5 Baths
- 5,277 Sq Ft
3740 Tangier Terrace, Sarasota, FL 34239

3740 Tangier Terrace, Sarasota, FL 34239

/5
$1,000,000
- Land
- 0.24 Acre
- $4,166,667 per Acre
3500 Flores Ave, Sarasota, FL 34239

Renderings can be found under attachments. Excellent Development and Investment Opportunity just minutes from Siesta Key Beach in the coveted Granada neighborhood! Refurbish and renovate the existing property, or tear it down and build your dream home on this prime oversized corner lot. All plans and permits have already been city-approved to build a new home on the property. The preliminary

Chad Fonder COLDWELL BANKER REALTY

3500 Flores Ave, Sarasota, FL 34239
/36
$2,800 per month
- 2 Beds
- 1 Bath
- 991 Sq Ft
- Apartment for Rent
3700 S Osprey Ave Unit 214, Sarasota, FL 34239

Plaza Gardens is the perfect place to call home if you are looking for a peaceful retreat with a touch of luxury. The tropical greenery and well-maintained gardens throughout the building give it a boutique feel, making it the perfect place for those who appreciate a tranquil and serene environment. Situated just southeast of Siesta Key's North Bridge and west of the trail, this condo offers easy

Andrea Cohen COLDWELL BANKER REALTY

3700 S Osprey Ave Unit 214, Sarasota, FL 34239
/2
$1,220,000 Sold Jun 06, 2025
- 1,867 Sq Ft
- $653/SF
- 50 Days On Market
- 3 Beds
- 2 Baths
- Built 1955
3414 Old Oak Dr, Sarasota, FL 34239

Close to Siesta Key and Southside Village, yet consistently safe from storm damage. This West-of-Trail, midcentury-coastal ranch offers comfortable living with the security of impact windows and a metal roof while safely positioned above flood zone. Entering the residence through the walled, private courtyard with tropical foliage and a peaceful fountain, the stress of your day will be swept

Christopher Bush PREMIER SOTHEBY'S INTERNATIONAL REALTY

3414 Old Oak Dr, Sarasota, FL 34239

/55
Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,691 Sq Ft
1936 Grove St, Sarasota, FL 34239

1936 Grove St, Sarasota, FL 34239

/2
$895,000
- Land
- 0.2 Acre
- $4,475,000 per Acre
1603 Bay Rd, Sarasota, FL 34239

Newly available west of trail lot. 70x125. This is in the county. Not the city. X zone. Lot is surrounded by beautiful new luxury homes. Survey available.

Paul Defelice HOUSEMAX REALTY LLC

1603 Bay Rd, Sarasota, FL 34239
/29
$10,000 per month
- 4 Beds
- 3 Baths
- 2,252 Sq Ft
- House for Rent
1865 Orchid St, Sarasota, FL 34239

Welcome to Tropical Paradise! This stunning, fully renovated home away from home is in a prime location, West of Trail. Take a dip in the private heated pool, sip cocktails at the tiki bar, and soak up the Florida sun. With spacious bedrooms, a fully equipped kitchen, and cozy living areas, you'll have everything you need for a comfortable stay. Located five minutes to downtown Sarasota and ten

Tina Ellis COMPASS FLORIDA LLC

1865 Orchid St, Sarasota, FL 34239
/2
$4,450,000 Sold Jun 02, 2025
- 5,160 Sq Ft
- $862/SF
- 211 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2006
1502 Siesta Dr, Sarasota, FL 34239

Welcome to this captivating property located in the beautiful San Remo Estates and minutes away from Siesta Key Beaches and downtown Sarasota. This house is located in an incredible location so close in proximity to great schools, restaurants, cultural destinations, and parks. This 5,160 SqFt waterfront property is nestled on a 18,416 SqFt lot behind a private gate. As you enter the front

Samantha Jennen PREFERRED SHORE LLC

1502 Siesta Dr, Sarasota, FL 34239

/28
Est $2,424,603 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,332 Sq Ft
1846 Datura St, Sarasota, FL 34239

1846 Datura St, Sarasota, FL 34239

/33
$1,750,000
- Land
- 0.43 Acre
- $4,069,767 per Acre
2315 Mcclellan Pkwy, Sarasota, FL 34239

Rarely available in McClellan Park, a premier West of the Trail location, the existing home can be remodeled or build new on this almost 1⁄2 acre lot. A GREAT VALUE

Barbara May MICHAEL SAUNDERS & COMPANY

2315 Mcclellan Pkwy, Sarasota, FL 34239
/64
$12,000 per month
- 3 Beds
- 2.5 Baths
- 2,080 Sq Ft
- House for Rent
1905 Tulip Dr, Sarasota, FL 34239

Welcome to the Siesta Stunner! This 1950s pool home has been completely remodeled down to the studs w/ designer finishes & furnishings & high ceilings throughout. A short walk or bike ride will get you onto Siesta Key & the house is walkable to both Publix & the Siesta Key Mall! The space is light and bright thanks to the 10ft ceilings, abundant windows and southern exposure. Upon entering the

Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

1905 Tulip Dr, Sarasota, FL 34239
/2
$1,250,000 Sold May 30, 2025
- 2,162 Sq Ft
- $578/SF
- 416 Days On Market
- 3 Beds
- 3 Baths
- Built 1948
3800 Flores Ave, Sarasota, FL 34239

This location in the Granada neighborhood is perfect for your future home! Rental potential or build your Estate-Sized Sarasota home on this 10,485 sq. ft. lot with room for pool! This West of the Trail property offers a peaceful retreat with its spacious lot and beautiful mature trees with no deed restrictions! It is near newer homes on estate size lot side of Flores (minimum 100' of frontage),

Solveiga Spalvins LPT REALTY LLC

3800 Flores Ave, Sarasota, FL 34239

/51
Est $474,871 Not Listed For Sale
- 3 Beds
- 2 Baths
- 948 Sq Ft
2128 Goldenrod St, Sarasota, FL 34239

2128 Goldenrod St, Sarasota, FL 34239

/25
$475,000
- 1 Bed
- 1 Bath
- 576 Sq Ft
1740 Wisconsin Ln, Sarasota, FL 34239

It is all about location. This is a rarely available property and is situated in the highly desirable West of Osprey Ave. and just south of the Cherokee Park area. The home is a 76 year old Cracker style, one bedroom cottage built in 1949 on 50x104 lot. No question here, this property is being offered for it's tremendous location and potential to build new on this quaint treelined canopy street

Dan Heschmeyers GULF SHORES REALTY

1740 Wisconsin Ln, Sarasota, FL 34239
/2
$1,050,000 Sold May 16, 2025
- 3,121 Sq Ft
- $336/SF
- 49 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2002
1904 Hyde Park St, Sarasota, FL 34239

Move In Ready! This updated West of the Trail home has been recently given a make over with fresh paint, new carpets and more! A charming custom home ideally located just a gentle stroll away from Morton’s Market and the exclusive Southside Village. Beautifully appointed both inside and out with an inviting courtyard and fenced yard. Master Bedroom is located on the ground level, boasts a dream

Lisa Warren OWN SRQ LLC

1904 Hyde Park St, Sarasota, FL 34239

/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

/40
$285,000
- 2 Beds
- 2 Baths
- 976 Sq Ft
3745 Almeria Ave Unit 6S, Sarasota, FL 34239

One or more photo(s) has been virtually staged. Welcome to your peaceful retreat in the heart of Sarasota! This beautifully maintained 2-bedroom, 2-bath condo is perfectly situated on the second floor, offering enhanced privacy, with serene views and filtered natural light throughout this West-facing unit. Enter through a spacious, oversized screened front porch—ideal for enjoying your morning

Jennifer Linehan MICHAEL SAUNDERS & COMPANY

3745 Almeria Ave Unit 6S, Sarasota, FL 34239
/2
$3,300,000 Sold May 16, 2025
- 4,696 Sq Ft
- $703/SF
- 14 Days On Market
- 5 Beds
- 6 Baths
- Built 1936
1744 South Dr, Sarasota, FL 34239

The McKaig House built by Sarasota originals Logan and Currin sits on over half an acre and is one of the few remaining crown jewels of Cherokee Park. The home has been impeccably maintained keeping as much of the 1930s character and materials as possible. Recently, Perrone Construction was used for the primary bedroom renovation and solarium style kitchen/great room addition. The huge entry

Charlotte Hedge PREMIER SOTHEBY'S INTERNATIONAL REALTY

1744 South Dr, Sarasota, FL 34239

/80
Est $3,042,182 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

/50
$2,480,000
- 10 Beds
- 9 Baths
1761 Siesta Dr, Sarasota, FL 34239

Exceptional 6-Unit Income Property – Prime Location Near Siesta Key! Incredible opportunity to own a fully leased, 6+ unit (ability to make it 8-unit) multifamily property just minutes from world-renowned Siesta Key Beach. This rare income-producing property combines two adjacent triplexes offering a versatile mix of units: (1) 2BR/2BA (Front-Pink, Siesta- able to split as 1/1 and 1/1 Efficiency)

Michael Laconca Coldwell Banker Residential RE

1761 Siesta Dr, Sarasota, FL 34239
/2
$1,600,000 Sold May 11, 2025
- 2,642 Sq Ft
- $606/SF
- 1,019 Days On Market
- 3 Beds
- 3 Baths
- Built 2023
3934 Sunshine Ave, Sarasota, FL 34231

**Move-In Ready**Introducing the Nassau by Heritage Builders. Located in Sarasota's West of Trail area, this well-conceived one-story design offers the perfect balance of style and functionality. The home’s clean coastal elevation is accented by elegant bay windows and inviting double entry doors. This 3 Bedroom, 3 Bathroom home features an open design and a private Study. Once inside, the

Leif Schmidt HB REALTY GROUP INC.

3934 Sunshine Ave, Sarasota, FL 34231

Showing Results 41 - 80, Page 2 of 18

Florida Sarasota County Sarasota Southside

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes 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