Siesta Key, FL Homes

/37
$687,000
- 2 Beds
- 2 Baths
- 975 Sq Ft
1130 W Peppertree Ln Unit 118, Sarasota, FL 34242

This delightful unit is just a short stroll from the tennis/pickelball courts, pool and siesta key private access beach, nestled in a quiet Gulf-side location. This 2 bedroom 2 bath condo is positioned upstairs on the 2nd floor, it offers serene views of one of the picturesque pond within the Peppertree complex. The unit has consistently generated rental income during peak season, or you could

Cheryl Santelli PEPPERTREE BAY REALTY INC

1130 W Peppertree Ln Unit 118, Sarasota, FL 34242
/30
$7,000 per month
- 2 Beds
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1360 Siesta Bayside Dr, Sarasota, FL 34242

This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world- renowned white sandy beach on the

Andy Moore GULF COAST REALTY & MANAGEMENT

1360 Siesta Bayside Dr, Sarasota, FL 34242
/2
$2,100,000 Sold Apr 14, 2025

3927 Somerset Dr, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 2,758 Sq Ft
- Built 1990
Last Sold Summary
- 10% Below List Price
- $761/SF
- 64 Days On Market
Current Estimated Value $1,872,245

Last Listing Agent Patrick Dipinto, III OCEAN REAL ESTATE LLC

3927 Somerset Dr, Sarasota, FL 34242

/2
Est $976,070 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,212 Sq Ft
6145 Midnight Pass Rd Unit F6, Sarasota, FL 34242

6145 Midnight Pass Rd Unit F6, Sarasota, FL 34242

/67
$5,290,000 New Construction
- 8 Beds
- 8.5 Baths
- 4,380 Sq Ft
135 Avenida Veneccia, Sarasota, FL 34242

Experience elevated coastal living just moments from the powdery sands of Siesta Key Beach and the heart of Siesta Village. This newly built island escape offers eight bedrooms and eight and a half baths, thoughtfully designed for style, comfort, and effortless group living.Step into your own resort-inspired backyard with a shimmering pool, relaxing spa, and a waterslide wrapped in tropical

Curtis Ware KW COASTAL LIVING III

135 Avenida Veneccia, Sarasota, FL 34242
/31
$9,300 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242

Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment you arrive at Gulf & Bay Club Bayside, you’ll appreciate the beauty, serenity, and charm of this "Key West” style village. Located on the bay across the street from world-famous Siesta

Andy Moore GULF COAST REALTY & MANAGEMENT

1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
/2
$20,000 Sold Apr 25, 2025

915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 1,900 Sq Ft
- Built 2009
Last Sold Summary
- 74% Below List Price
- $11/SF
- 175 Days On Market
Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242

/63
Est $687,822 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
6145 Midnight Pass Rd Unit F3, Sarasota, FL 34242

6145 Midnight Pass Rd Unit F3, Sarasota, FL 34242

/77
$889,999
- 2 Beds
- 2 Baths
- 1,475 Sq Ft
6263 Midnight Pass Rd Unit 403, Sarasota, FL 34242

Discover this one-of-a-kind unit in Excelsior, featuring two spacious bedrooms and two bathrooms, complemented by an added staircase leading to a spacious second-story loft. A structural beam has been expertly installed to support the loft, and all ceilings have been raised, enhanced with foam insulation throughout the attic for improved energy efficiency. The kitchen boasts custom solid wood

Brian Ward WATERSIDE REALTY LLC

6263 Midnight Pass Rd Unit 403, Sarasota, FL 34242
/26
$9,300 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court view from the lanai. A few of your amenities include your own private garage, a washer and dryer IN THE CONDO, and a fully-equipped kitchen The community offers BBQ grills (6), two tennis courts,

Andy Moore GULF COAST REALTY & MANAGEMENT

1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
/2
$890,000 Sold Apr 01, 2025

5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1981
Last Sold Summary
- 9% Below List Price
- $654/SF
- 124 Days On Market
Current Estimated Value $876,034

Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242

/60
Est $1,298,801 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,110 Sq Ft
1660 Summerhouse Ln Unit 302, Sarasota, FL 34242

1660 Summerhouse Ln Unit 302, Sarasota, FL 34242

/18
$799,900 Pending
- Land
- 0.18 Acre
- $4,443,889 per Acre
0 Avenida Leona, Siesta Key, FL 34242

Under contract-accepting backup offers. 20% Down Seller Financing Offered. Design Your Legacy on Siesta Key – Premier Waterfront Lot in Siesta ManorWelcome to Lot 17 on Avenida Leona—an extraordinary opportunity to create your own masterpiece in one of Florida’s most coveted coastal enclaves. Nestled along a private, tree-lined lane in Siesta Manor, this canal-front parcel offers the rare

Ron Pepka KW SUNCOAST

0 Avenida Leona, Siesta Key, FL 34242
/38
$9,350 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
Unlisted Address

Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and

Andy Moore GULF COAST REALTY & MANAGEMENT

Unlisted Address
/2
$450,000 Sold Dec 19, 2025

1350 N Portofino Dr Unit 208, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Built 1969
Last Sold Summary
- 18% Below List Price
- $484/SF
- 188 Days On Market
Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

1350 N Portofino Dr Unit 208, Sarasota, FL 34242

/48
Est $1,652,683 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,490 Sq Ft
1660 Summerhouse Ln Unit 201, Sarasota, FL 34242

1660 Summerhouse Ln Unit 201, Sarasota, FL 34242

/99
$645,000 Pending
- 2 Beds
- 2 Baths
- 939 Sq Ft
6150 Midnight Pass Rd Unit 12, Sarasota, FL 34242

Under contract-accepting backup offers. This is the one * WELCOME TO THIS STUNNING WATERFRONT SIESTA KEY VILLA IN MUCH SOUGHT AFTER ISLAND HOUSE BEACH RESORT *The LOWEST PRICED VILLA and the BEST VALUE in ISLAND HOUSE * The current homeowner painstakingly oversaw every step of the renovations from the NEW KITCHEN to the NEW BATHROOMS, NEW FLOORING & NEW LIGHTING * 1 Car Carport with Utility Room

Glenn Brown RE/MAX ALLIANCE GROUP

6150 Midnight Pass Rd Unit 12, Sarasota, FL 34242
/27
$6,900 per month
- 1 Bed
- 1 Bath
- 845 Sq Ft
- Condo for Rent
1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.

Andy Moore GULF COAST REALTY & MANAGEMENT

1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
/2
$865,000 Sold Feb 14, 2025

5780 Midnight Pass Rd Unit 402, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1979
Last Sold Summary
- 35% Below List Price
- $636/SF
- 581 Days On Market
Current Estimated Value $835,329

Last Listing Agent Stephanie Kitsemble COLDWELL BANKER REALTY

5780 Midnight Pass Rd Unit 402, Sarasota, FL 34242

/57
Est $1,742,316 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,490 Sq Ft
1660 Summerhouse Ln Unit 104, Sarasota, FL 34242

1660 Summerhouse Ln Unit 104, Sarasota, FL 34242

/39
$705,000
- 2 Beds
- 2 Baths
- 1,550 Sq Ft
6263 Midnight Pass Rd Unit 105, Sarasota, FL 34242

Huge Price Reduction!! Stunning Beach-to-Bay Condo on Siesta Key – 2 Bed, 2 Bath Excelsior Beach to Bay Condo Discover your perfect slice of paradise at this beautifully appointed 2-bedroom, 2-bathroom condo located in the coveted Excelsior Beach to Bay community on Siesta Key. This light-filled retreat offers the ultimate Florida lifestyle, with private beach access to the powdery white sands of

Randy Owens COLDWELL BANKER REALTY

6263 Midnight Pass Rd Unit 105, Sarasota, FL 34242
/60
$15,000 per month
- 3 Beds
- 2 Baths
- 2,259 Sq Ft
- House for Rent
5516 Avenida Del Mare, Sarasota, FL 34242

This is a short term rental. Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living

Beth Dilley ASCENDIA REAL ESTATE

5516 Avenida Del Mare, Sarasota, FL 34242
/2
$2,200,000 Sold Apr 02, 2025

447 Canal Rd Unit 447, Sarasota, FL 34242
- 3 Beds
- 4 Baths
- 2,635 Sq Ft
- Built 2003
Last Sold Summary
- 12% Below List Price
- $835/SF
- 81 Days On Market
Current Estimated Value $2,044,424

Last Listing Agent Joseph Kesslak COLDWELL BANKER REALTY

447 Canal Rd Unit 447, Sarasota, FL 34242

/2
Est $370,042 Not Listed For Sale
- 1 Bed
- 1 Bath
- 435 Sq Ft
6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242

6006 Midnight Pass Rd Unit 10, 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
/59
$2,800 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1350 N Portofino Dr Unit 108, Sarasota, FL 34242

Gorgeous Canal View Condo now available on Siesta Key as an annual rental. Rent March 31, 2026 through the Winter Season in 2027, fully furnished! Work from home, walk out to the Pier from your first floor lanai, directly on the Intracoastal Waterway. Incredible View of the ICW, Beautiful two bedroom, two bath spacious first floor walk-out with lots of natural light. Completely remodeled and

Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

1350 N Portofino Dr Unit 108, Sarasota, FL 34242
/2
$810,000 Sold Nov 21, 2025

1080 W Peppertree Ln Unit 506A, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Built 1974
Last Sold Summary
- 25% Below List Price
- $696/SF
- 264 Days On Market
Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

1080 W Peppertree Ln Unit 506A, Sarasota, FL 34242

/64
Est $609,697 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 975 Sq Ft
1041 W Peppertree Dr Unit 1113, Sarasota, FL 34242

1041 W Peppertree Dr Unit 1113, Sarasota, FL 34242

/90
$1,365,000
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
445 Reid St, Sarasota, FL 34242

Coastal Chic meets Contemporary Classic on Siesta Key. This 3-bed, 2-bath oasis with saltwater pool boasts 1,750 square feet under air, $100,000 in upgrades and $50,000+ in brand new designer furnishings from Crate & Barrel. In 2025, the owners installed new tile flooring throughout the home, all new appliances, new washer & dryer, new doors (except the front door), new water heater and pool

Robin Leonardi MICHAEL SAUNDERS & COMPANY

445 Reid St, Sarasota, FL 34242
/65
$8,700 per month
- 2 Beds
- 2 Baths
- 1,256 Sq Ft
- Condo for Rent
5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242

Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,

Beth Dilley ASCENDIA REAL ESTATE

5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
/2
$900,000 Sold Aug 29, 2025

5108 Saint Albans Ave, Sarasota, FL 34242
- 3 Beds
- 3.5 Baths
- 1,767 Sq Ft
- Built 1968
Last Sold Summary
- 20% Below List Price
- $509/SF
- 57 Days On Market
Current Estimated Value $904,680

Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

5108 Saint Albans Ave, Sarasota, FL 34242

/14
Est $949,513 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,319 Sq Ft
6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

/51
$1,395,000
- 3 Beds
- 3 Baths
- 2,200 Sq Ft
1260 Dolphin Bay Way Unit 404, Sarasota, FL 34242

ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a

Mina Johnson MICHAEL SAUNDERS & COMPANY

1260 Dolphin Bay Way Unit 404, Sarasota, FL 34242
/98
$18,000 per month
- 3 Beds
- 2 Baths
- 1,617 Sq Ft
- House for Rent
345 Avenida Leona, Sarasota, FL 34242

Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a

Beth Dilley ASCENDIA REAL ESTATE

345 Avenida Leona, Sarasota, FL 34242
/2
$925,000 Sold Dec 08, 2025

396 Avenida Madera, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 1,964 Sq Ft
- Built 1958
Last Sold Summary
- 20% Below List Price
- $471/SF
- 148 Days On Market
Last Listing Agent Michael Nogueira LUXURY & BEACH REALTY INC

396 Avenida Madera, Sarasota, FL 34242

/43
Est $687,735 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,365 Sq Ft
1080 W Peppertree Ln Unit 303A, Sarasota, FL 34242

1080 W Peppertree Ln Unit 303A, Sarasota, FL 34242

/46
$1,795,000
- 3 Beds
- 3 Baths
- 2,200 Sq Ft
1260 Dolphin Bay Way Unit 301, Sarasota, FL 34242

Discover this truly exceptional 3-bedroom, 3-bathroom condominium offering mesmerizing views of the Intracoastal Waterway. Redesigned with modern elegance, this home features a spacious chef's kitchen equipped with Sub Zero, Monogram, and Viking appliances, along with an impressive six-foot-tall built-in double-door wine cellar. This stunning residence boasts 9-foot ceilings, copious custom

Mina Johnson MICHAEL SAUNDERS & COMPANY

1260 Dolphin Bay Way Unit 301, Sarasota, FL 34242
/46
$12,000 per month
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Condo for Rent
20 Whispering Sands Dr Unit 903, Sarasota, FL 34242

Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of

Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
/2
$3,990,000 Sold Aug 12, 2025

4815 Featherbed Ln, Sarasota, FL 34242
- 5 Beds
- 4 Baths
- 3,329 Sq Ft
- Built 2024
Last Sold Summary
- 7% Below List Price
- $1,199/SF
- 178 Days On Market
Current Estimated Value $3,875,768

Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

4815 Featherbed Ln, Sarasota, FL 34242

/41
Est $1,333,536 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,976 Sq Ft
6150 Midnight Pass Rd Unit 40, Sarasota, FL 34242

6150 Midnight Pass Rd Unit 40, Sarasota, FL 34242

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