Sarasota, FL Homes in ZIP Code 34242

/45
$1,250,000
- 3 Beds
- 3 Baths
- 2,222 Sq Ft
4859 Commonwealth Dr, Sarasota, FL 34242

INCOME-GENERATING TRIPLEX JUST MINUTES FROM WORLD-FAMOUS SIESTA KEY BEACH!Located in the desirable Siesta Beach neighborhood on Siesta Key, this opportunity to own Tangerine Dream offers incredible potential for investors, vacation rental owners, or anyone seeking a coastal lifestyle with income potential.This well-maintained triplex features three individual 1-bedroom, 1-bath units,

Isaiah Miller HARRY ROBBINS ASSOC INC

4859 Commonwealth Dr, Sarasota, FL 34242
/40
$11,000 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242

Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach

Andy Moore GULF COAST REALTY & MANAGEMENT

1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
/2
$630,000 Sold May 30, 2025
- 1,115 Sq Ft
- $565/SF
- 49 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
8635 Midnight Pass Rd Unit 206C, Sarasota, FL 34242

Look no further - you've just found your perfect beach retreat in Bay Tree Club, a very special Gulf to Bay community with deeded Beach and Bay Access. Enjoy the amazing water and garden views from your spacious lanai and watch the boats on the Intracoastal waterway or bask in the tranquility of the majestic oaks. This 2 Bedroom 2 Bath condo is partially furnished and beautifully updated with an

Anna Rees FINE PROPERTIES

8635 Midnight Pass Rd Unit 206C, Sarasota, FL 34242

/46
Est $662,922 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
141 Avenida Messina Unit 1, Sarasota, FL 34242

141 Avenida Messina Unit 1, Sarasota, FL 34242

/100
$538,000
- 2 Beds
- 2 Baths
- 1,233 Sq Ft
8897 Midnight Pass Rd Unit 105, Sarasota, FL 34242

Siesta Key! Sunrise Cove has beautifully maintained grounds. Pool and Bay views. Two bedroom, two bath! Kitchen with all appliances and Island. Carport and extra storage. Amenities include two pools, tennis and pickleball, fitness center, boat slips, kayak and bike storage, Located across from Turtle Beach and Park. Close to two of Siesta Keys favorite Restaurants. (Turtle and Ophelia’s). Free

Marlene Marshall MICHAEL SAUNDERS & COMPANY

8897 Midnight Pass Rd Unit 105, Sarasota, FL 34242
/80
$8,500 per month
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- House for Rent
5216 Calle de Costa Rica, Sarasota, FL 34242

Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely

Beth Dilley ASCENDIA REAL ESTATE

5216 Calle de Costa Rica, Sarasota, FL 34242
/2
$425,000 Sold May 30, 2025
- 1,163 Sq Ft
- $365/SF
- 88 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
1255 E Peppertree Dr Unit 402, Sarasota, FL 34242

Your Slice of Paradise Awaits at Siesta Key!Live the dream on the #1 beach in the USA with this adorable 4th-floor condo. This 2-bedroom, 2-bath gem offers a serene pool view and direct beach access, making it the perfect place to unwind. Move right in – it’s fully furnished and features luxurious vinyl flooring, new carpet, and fresh paint throughout.Relax on your enclosed lanai, where you can

Cheryl Santelli PEPPERTREE BAY REALTY INC

1255 E Peppertree Dr Unit 402, Sarasota, FL 34242

/62
Est $716,987 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,212 Sq Ft
6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

/26
$3,750,000
- Land
- 0.59 Acre
- $6,355,932 per Acre
7233 Midnight Pass Rd, Sarasota, FL 34242

LIVE, BOAT, PARK while you build your waterfront dream home. Premiere waterfront lot opportunity in Sanderling Neighborhood. A rare chance to own one of the most sought-after lots in Sanderling. This private, fenced, waterfront retreat is located directly across from the neighborhood’s gated entrance, nestled in a serene basin leading to the Intracoastal Waterway. Extensive upgrades allow the

Kiki Bowers COLDWELL BANKER REALTY

7233 Midnight Pass Rd, Sarasota, FL 34242
/48
$13,200 per month
- 3 Beds
- 2.5 Baths
- 2,041 Sq Ft
- Condo for Rent
306 Beach Rd Unit 306, Sarasota, FL 34242

Take some time to get away from it all.. we have the perfect place for you and your family to stay! This Spanish style tri-level home is in one of the greatest locations on Siesta Key Beach, Florida. Walk up the windowed staircase to the second floor where you’ll enjoy cooking and hanging out with the family! Enjoy your morning coffee or dinner on the balcony. Time for some fun in the sun! Walk,

Beth Dilley ASCENDIA REAL ESTATE

306 Beach Rd Unit 306, Sarasota, FL 34242
/2
$670,000 Sold May 28, 2025
- 1,352 Sq Ft
- $496/SF
- 23 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
1113 Lake House Cir Unit C110, Sarasota, FL 34242

Rarely available, this recently fully-renovated lake-front townhome is steps away from the crystal sands of Siesta Key Beach! Beautifully updated with a Coastal Chic interior, this end unit townhouse lives large. Light & bright with high ceilings, an open floor plan & four sets of glass sliders inviting the Gulf breezes inside makes each new day a delight. This 2-bedroom, 2-full bathroom home

Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

1113 Lake House Cir Unit C110, Sarasota, FL 34242

/2
Est $4,158,515 Not Listed For Sale
- 5 Beds
- 8 Baths
- 3,759 Sq Ft
5310 Avenida Del Mare, Siesta Key, FL 34242

5310 Avenida Del Mare, Siesta Key, FL 34242

/61
$449,000
- 1 Bed
- 1 Bath
- 522 Sq Ft
5955 Midnight Pass Rd Unit 4E, Sarasota, FL 34242

***Seller Financing Available*** Discover a rare investment opportunity at Sea Club II, one of the few Siesta Key communities that allows nightly rentals—making it a standout choice for short-term vacation income. This turnkey furnished, ground-floor one-bedroom, one-bath unit sustained no flood damage and boasts a strong rental history. Fully equipped for a seamless guest experience, it’s ready

Taylor Thompson WILLIAM RAVEIS REAL ESTATE

5955 Midnight Pass Rd Unit 4E, Sarasota, FL 34242
/58
$8,000 per month
- 3 Beds
- 2 Baths
- 2,002 Sq Ft
- House for Rent
5640 Cape Leyte Dr, Sarasota, FL 34242

It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

Beth Dilley ASCENDIA REAL ESTATE

5640 Cape Leyte Dr, Sarasota, FL 34242
/2
$550,000 Sold May 27, 2025
- 748 Sq Ft
- $735/SF
- 1 Day On Market
- 1 Bed
- 1 Bath
- Built 1967
6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242

SIESTA KEY INTERCOASTAL WATERFRONT, WATERVIEW...Welcome to Paradise in PROVINCIAL GARDENS, a small 26 unit enclave. You will love the MILLION DOLLAR VIEW from this quaint, Mid-Century Modern one bedroom, one bath first floor condo with Florida room addition overlooking the community park, NEW fishing pier with new sea wall and the Intercoastal channel. Deeded beach access and Olympic pool use

Scotty Ledford VUE REALTY, LLC

6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242

/46
Est $4,153,888 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,242 Sq Ft
1035 Seaside Dr Unit 506, Sarasota, FL 34242

1035 Seaside Dr Unit 506, Sarasota, FL 34242

/62
$1,785,000
- 3 Beds
- 2 Baths
- 1,972 Sq Ft
5164 Windward Ave, Sarasota, FL 34242

***SELLER FINANCING AVAILABLE*** Tucked away on a quiet dead-end street, this exceptional waterfront estate on Siesta Key offers the perfect balance of seclusion and accessibility. Situated on an oversized 0.40-acre corner lot with 260 feet of water frontage and coveted western exposure, the property provides direct access to the Intracoastal Waterway—ideal for boating enthusiasts and water

Taylor Thompson WILLIAM RAVEIS REAL ESTATE

5164 Windward Ave, Sarasota, FL 34242
/41
$5,000 per month
- 2 Beds
- 2 Baths
- 1,424 Sq Ft
- House for Rent
5577 Contento Dr, Sarasota, FL 34242

Check out this COMPLETELY REMODELED canal-front pool home on Siesta Key! Picture this: you roll out of bed and grab your coffee, take two steps out of the sliding glass doors, and enjoy it by the saltwater pool. After your coffee, take your morning swim. Then take another 10 steps, or so, and catch some significant fish in the canal which happens to be in your backyard. Chances are that an

Beth Dilley ASCENDIA REAL ESTATE

5577 Contento Dr, Sarasota, FL 34242
/2
$1,185,000 Sold May 23, 2025
- 1,288 Sq Ft
- $920/SF
- 90 Days On Market
- 2 Beds
- 2 Baths
- Built 1962
615 Avenida Del Norte, Sarasota, FL 34242

WOW!...Move in NOW!***Updated & VERY DESIRABLE VILLAGE Area Location w/ Private Boat Dock on the Grand Canal*** Modern Beach Cottage with Extensive Indoor/Outdoor Living Spaces---Providing the ULTIMATE in Island Lifestyle Living: Over-sized Screened Lanai with Salt Water Pool & Spa; Outdoor Kitchen & MULTIPLE Entertaining and Lounge Areas. BRIGHT OPEN SPACIOUS Interior Living that Seamlessly

Michael A Martino KELLER WILLIAMS ON THE WATER S

615 Avenida Del Norte, Sarasota, FL 34242

/58
Est $708,908 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,357 Sq Ft
8735 Midnight Pass Rd Unit 406B, Sarasota, FL 34242

8735 Midnight Pass Rd Unit 406B, Sarasota, FL 34242

/39
$679,000
- 4 Beds
- 3 Baths
- 2,064 Sq Ft
643 Calle de Peru, Sarasota, FL 34242

Prime Opportunity less than a mile to the #1 Rated Beach in the Nation- Siesta Beach! Enjoy days with your toes in the cool, white, powder sand, take in a yoga class, or take a swim in The Gulf! Then stroll to the vibrant Siesta Key Village for dining, live music, shops, farmers market, and festivals! Do you dream of building a new island home? Plans and competitive pricing for new construction

Rachelle Tirey PREFERRED SHORE LLC

643 Calle de Peru, Sarasota, FL 34242
/66
$7,500 per month
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Condo for Rent
116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242

An Ascendia Property! **Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Welcome to your BOHO CHIC beach retreat located near the famous Crescent Beach on Siesta Key! You'll feel right at home when you stay in this 2 bedroom, 2 bathroom (sleeps 5) condo. Spend time cooking your favorite meals in the fully stocked kitchen... Cozy up

Beth Dilley ASCENDIA REAL ESTATE

116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242
/2
$1,735,000 Sold May 23, 2025
- 1,380 Sq Ft
- $1257/SF
- 32 Days On Market
- 2 Beds
- 2 Baths
- Built 1947
303 Beach Rd, Sarasota, FL 34242

Location is Everything with this Fantastic Property. Only a few short steps to having your feet in the Crystal Sands of Siesta Beach and a short leisurely walk to Siesta Village. Zoned Multi-Family with NO HOA. You can rebuild one of the 1940's bungalows and repair the other two or start all over with a fresh new look. This has been a huge income producing property over the years for the

Michelle Shiver KELLER WILLIAMS ON THE WATER S

303 Beach Rd, Sarasota, FL 34242

/83
Est $641,661 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
101 Whispering Sands Dr Unit 203, Sarasota, FL 34242

101 Whispering Sands Dr Unit 203, Sarasota, FL 34242

/93
$7,390,000
- 4 Beds
- 7 Baths
- 5,727 Sq Ft
8585 Midnight Pass Rd, Sarasota, FL 34242

A private legacy estate on Siesta Key. Behind a private gate and walled perimeter on one of Siesta Key’s largest residential parcels, this majestic waterfront estate offers a rare opportunity to own a generational property of striking character, scale, and serenity. Set on 1.6 lushly landscaped acres with 132 feet of direct frontage on Little Sarasota Bay, the residence is introduced by a long,

Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

8585 Midnight Pass Rd, Sarasota, FL 34242
/52
$6,500 per month
- 2 Beds
- 1 Bath
- 680 Sq Ft
- Condo for Rent
446 Canal Rd Unit 5, Sarasota, FL 34242

You will be charmed by how vibrant and quaint this midcentury ground floor condo is... from the lime green exterior, to the pink hibiscus bushes blooming around the turquoise pool, which is nestled behind the privacy of a fence and garden surrounding the property! THE BEST PART ABOUT THIS UNIT... the Keylime Retreat is a 5 minute walk to the pure white sands of Siesta Beach, and an 8 minute walk

Beth Dilley ASCENDIA REAL ESTATE

446 Canal Rd Unit 5, Sarasota, FL 34242
/2
$2,100,000 Sold May 23, 2025
- 2,692 Sq Ft
- $780/SF
- 122 Days On Market
- 3 Beds
- 4 Baths
- Built 1996
5159 Oxford Dr, Sarasota, FL 34242

The best value for amenities offered anywhere on Siesta Key - elevated, hurricane-safe, and with a pool and boat lift! Welcome to your dream waterfront oasis, nestled in the heart of Siesta Key, FL. This exquisite home, featuring 3 bedrooms and 4 baths across 2,692 square feet of elegantly remodeled living space, is a true testament to luxury and comfort. Ideal floor plan for AIRBNB with 3

Andrew Foltz PREFERRED SHORE LLC

5159 Oxford Dr, Sarasota, FL 34242

/68
Est $1,710,395 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,747 Sq Ft
1035 Seaside Dr Unit 310, Sarasota, FL 34242

1035 Seaside Dr Unit 310, Sarasota, FL 34242

/49
$750,000
- 2 Beds
- 2 Baths
- 1,184 Sq Ft
5302 La Rosas, Sarasota, FL 34242

Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build

Dan Miller PREFERRED SHORE LLC

5302 La Rosas, Sarasota, FL 34242
/25
$6,500 per month
- 1 Bed
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242

Heaven on Siesta Key, in perfect condition, up to date, and simply beautiful. This spacious, first floor one bedroom with a bay/harbor water view from your lanai is immaculate, beautifully decorated and offers every comfort for your favorite vacation stay. The modern kitchen shines with new cabinets, lighting, paint, and kitchen work desk. Elegant bathroom with new walk in shower featuring

Andy Moore GULF COAST REALTY & MANAGEMENT

1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
/2
$475,000 Sold May 22, 2025
- 1,264 Sq Ft
- $376/SF
- 52 Days On Market
- 2 Beds
- 2 Baths
- Built 1968
147 Whispering Sands Dr Unit V-29, Sarasota, FL 34242

GREAT GULF FRONT OPPORTUNITY! This incredibly well priced 2 bed/2 bath villa represents an exceptional opportunity to start fresh with almost new construction in the idyllic GULF FRONT property of Whispering Sands on Siesta Key. This lovely unit experienced flooding last fall and is now being sold post remediation and pre rebuild – providing the next owner with the wonderful opportunity to

Harriet Stopher COLDWELL BANKER REALTY

147 Whispering Sands Dr Unit V-29, Sarasota, FL 34242

/37
Est $616,198 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1300 Cove II Place Unit 731, Sarasota, FL 34242

1300 Cove II Place Unit 731, Sarasota, FL 34242

/52
$549,000
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
6157 Midnight Pass Rd Unit G22, Sarasota, FL 34242

Don’t miss this beautifully updated and spacious condominium in Bay Oaks, a charming bayfront community nestled on world-renowned Siesta Key. Ideally located just a short distance to beach access points, with free trolley service to Siesta Key Village and the #1 beach in the country on the Gulf of Mexico. This well-designed unit features two large master suites with walk-in closets and private

Stephen Clementi COLDWELL BANKER REALTY

6157 Midnight Pass Rd Unit G22, Sarasota, FL 34242
/12
$2,795 per month
- 2 Beds
- 2 Baths
- 1,029 Sq Ft
- Condo for Rent
9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242

Beautifully decorated 2 bedroom 2 bath condo located at The Pointe on Midnight Pass Road. Large lanai accessible from master bedroom and living room features views of the Intracoastal. Look out your kitchen window and guest bedroom for a view of the beautiful Gulf. Beautiful furnishings, full size washer/dryer. Complex amenities include heated pool, whirlpool, sauna, fitness room, tennis court &

Pamala Casey CASEY REALTY CORPORATION

9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242
/2
$1,225,000 Sold May 22, 2025
- 2,732 Sq Ft
- $448/SF
- 78 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
716 Tropical Cir, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Luxurious Serenity with Breathtaking Bayou and Nature Preserve Views. This exceptional two-story home, nestled on a sprawling oversized lot, offers a rare blend of natural beauty and sophisticated design, providing an unparalleled living experience. Set back from the road and framed by majestic oaks, this home offers panoramic views of a tranquil

Stacey King MICHAEL SAUNDERS & COMPANY

716 Tropical Cir, Sarasota, FL 34242

/48
Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,625 Sq Ft
915 Seaside Dr Unit 511, Weeks 4-7, Sarasota, FL 34242

915 Seaside Dr Unit 511, Weeks 4-7, Sarasota, FL 34242

/48
$569,900
- 2 Beds
- 2 Baths
- 1,137 Sq Ft
5222 Winding Way, Sarasota, FL 34242

Opportunity knocking loudly! Here it is the least expensive pool home on Siesta Key. You will approach under a charming, canopy lined street. This 2BR/2BA is ready for someone to put their finishing touches on it after hurricane damage. Walls have been removed from 4 ft down, kitchen cabinets and counter removed. Nice Crown molding. Electrical was rewired and raised. Replumbed in 2020. Tankless

Robert Moffatt MICHAEL SAUNDERS & COMPANY

5222 Winding Way, Sarasota, FL 34242
/63
$6,500 per month
- 2 Beds
- 2 Baths
- 1,029 Sq Ft
- Condo for Rent
9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242

OPEN FOR SEASON 2025! Siesta Key Resort Style Vacation Rental, you will love the fabulous renovation these owners have done, everything is brand new and the aboslute best! The kitchen has been updated with gorgeous cabinets, a stunning Quartz waterfall countertop, there is a breakfast bar as well as dining table, and stainless appliances. All new furniture throughout and amazing views of the

Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242
/2
$2,750,000 Sold May 20, 2025
- 3,070 Sq Ft
- $896/SF
- 218 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1998
3920 Roberts Point Rd, Sarasota, FL 34242

One or more photo(s) has been virtually staged. CERTAIN CRYPTOCURRENCIES ACCEPTED. An exquisite waterfront retreat in SIESTA KEY, SARASOTA, FL – a sanctuary of COASTAL LUXURY. Enter the fully REMODELED CONTEMPORARY residence with CUSTOM WOOD CABINETRY, DELUXE APPLIANCES, and STONE COUNTERTOPS. The great room with 11-FOOT CEILINGS and SLIDING DOORS flows to a 50-FOOT PORCH overlooking the water.

Melissa Gissinger MICHAEL SAUNDERS & COMPANY

3920 Roberts Point Rd, Sarasota, FL 34242

/27
Est $602,797 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1600 Cove II Place Unit 414, Sarasota, FL 34242

1600 Cove II Place Unit 414, Sarasota, FL 34242

Showing Results 281 - 320, Page 8 of 18

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