Siesta Key, FL Homes

/59
$675,000
- 2 Beds
- 1 Bath
- 1,373 Sq Ft
5019 Commonwealth Dr, Sarasota, FL 34242

PRICED to Sell! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision whether you’re

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 842-0059

5019 Commonwealth Dr, Sarasota, FL 34242
/29
$10,700 per month
- 2 Beds
- 2 Baths
- 1,180 Sq Ft
- House for Rent
6018 W Peppertree Way Unit 231B, Sarasota, FL 34242

Paradise awaits you at Siesta Key! Experience the beauty of the #1 Beach in the USA with this gorgeous 2 bedroom 2 bath stunning beach view condo overlooking the pool. This beautiful condo is just steps from the pool and Direct Beach Access. Amenities for the complex include: 2 fitness centers, 2 heated pools, a fishing pier, 2 clubhouses, pickle-ball and tennis courts. You will enjoy hopping on

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6018 W Peppertree Way Unit 231B, Sarasota, FL 34242
/2
$400,000 Sold Aug 20, 2025

6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
- Built 1974
Last Sold Summary
- 26% Below List Price
- $300/SF
- 86 Days On Market
Current Estimated Value $418,664

Last Listing Agent Julia Montei COLDWELL BANKER REALTY

6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

/27
Est $710,427 Not Listed For Sale

5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,043 Sq Ft
- Built 1975
5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

Last Sold Summary
- 11% Below List Price
- $762/SF
- 0 Days On Market
Last Sold Price $795,000

Last Listing Agent Linda Stowe Michael Saunders

/85
$1,500,000
- 4 Beds
- 3 Baths
- 2,185 Sq Ft
746 Plymouth St, Sarasota, FL 34242

Nestled in the heart of Siesta Key, this home offers the perfect blend of relaxation and opportunity. Whether you're seeking a serene beach getaway, a vacation rental, or a full-time residence, this property checks all the boxes. The home’s unique floor plan is flooded with natural light, creating a bright, inviting atmosphere throughout. A rare find, both the home and the garage are elevated,

Carla Rayman Kidd

COLDWELL BANKER REALTY

(941) 239-2641

746 Plymouth St, Sarasota, FL 34242
/21
$7,800 per month
- 2 Beds
- 2 Baths
- 1,180 Sq Ft
- House for Rent
6039 E Peppertree Way Unit 222, Sarasota, FL 34242

This property is a 30 night minimum.This 2 bedroom, 2 bath is a first floor garden condo on the bay side of Midnight Pass.The master bedroom has a King bed, a ceiling fan, a 32 inch smart TV, and windows for natural light. The master bathroom has updated granite counters and a walk-in shower with a sliding glass door and a removable shower head.The guest bedroom has a king bed, a

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6039 E Peppertree Way Unit 222, Sarasota, FL 34242
/2
$1,230,000 Sold Feb 20, 2026

5354 Calle Florida, Sarasota, FL 34242
- 4 Beds
- 3.5 Baths
- 2,659 Sq Ft
- Built 1954
Last Sold Summary
- 7% Below List Price
- $463/SF
- 96 Days On Market
Current Estimated Value $1,212,894

Last Listing Agent Angelica Ridley KW COASTAL LIVING III

5354 Calle Florida, Sarasota, FL 34242

/53
Est $494,373 Not Listed For Sale

44 Sandy Cove Rd Unit A4, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 561 Sq Ft
- Built 1968
44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

Last Sold Summary
- 13% Below List Price
- $1,007/SF
- 3 Days On Market
Last Sold Price $565,000

Last Listing Agent Veronica Murphy KELLER WILLIAMS ON THE WATER S

/99
$5,392,000 New Construction
- 4 Beds
- 6 Baths
- 4,220 Sq Ft
4819 Higel Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths

Cassandra Meyer

BRIGHT REALTY

(941) 394-0863

4819 Higel Ave, Sarasota, FL 34242
/27
$6,000 per month
- 2 Beds
- 2 Baths
- 1,180 Sq Ft
- Condo for Rent
6052 W Peppertree Way Unit 235B, Sarasota, FL 34242

This property is a 30 night minimum. 6052 WPW is a Large Garden condo, located approximately 50 yards away from Crescent BeachOpen porch lanai with a 6 person table. Recessed lighting in both bathrooms. Master bathroom has a seat. Recessed lighting in the kitchen. This unit has access to a private garageApprox. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
/2
$650,000 Sold Jul 14, 2025

4510 Banan Place, Sarasota, FL 34242
- Land
- 0.24 Acre
- $2,708,333 per Acre
Last Sold Summary
- 13% Below List Price
- 163 Days On Market
Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

4510 Banan Place, Sarasota, FL 34242

/2
Est $540,627 Not Listed For Sale

1257 S Portofino Dr Unit 406, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Built 1968
1257 S Portofino Dr Unit 406, Sarasota, FL 34242

Last Sold Summary
- 8% Below List Price
- $630/SF
- 22 Days On Market
Last Sold Price $585,000

Last Listing Agent Curtis Ware KW COASTAL LIVING III

/9
$4,800,000 New Construction
- 4 Beds
- 5.5 Baths
- 3,765 Sq Ft
533 Venice Ln, Sarasota, FL 34242

Under Construction. New Construction. This stunning new waterfront home is perfectly positioned on Siesta Key’s Grand Canal, offering excellent boating water with quick access to Sarasota Bay. The residence features 4 bedrooms, 5 full baths (including a pool bath), and 1 half bath, along with two laundry rooms conveniently located on the first and third floors. A spacious third-floor loft

Cassandra Meyer

BRIGHT REALTY

(941) 206-4697

533 Venice Ln, Sarasota, FL 34242
/28
$10,200 per month
- 2 Beds
- 2 Baths
- 1,180 Sq Ft
- House for Rent
6042 W Peppertree Way Unit 224B, Sarasota, FL 34242

his is a 3 bedroom, 2 bathroom, ground floor condo. Sleeps 6How about this location!! Gulf-side close to the Beach, Pool, Clubhouse and Fitness room.Lanai faces due west and you still have your privacy. Split Level unit with your own private one car garage, soaring living room ceiling, open kitchen silestone countertops throughout, new a/c, lanai has its own a/c split system; full size

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6042 W Peppertree Way Unit 224B, Sarasota, FL 34242
/2
$680,000 Sold Jun 12, 2025

1155 Lake House Cir Unit C119, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
- Built 1981
Last Sold Summary
- $503/SF
- 8 Days On Market
Current Estimated Value $659,753

Last Listing Agent Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

1155 Lake House Cir Unit C119, Sarasota, FL 34242

/77
Est $646,836 Not Listed For Sale

6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
- Built 1968
6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

Last Sold Summary
- 10% Below List Price
- $669/SF
- 20 Days On Market
Last Sold Price $715,000

Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

/11
$4,950,000 New Construction
- 4 Beds
- 5.5 Baths
- 4,158 Sq Ft
527 Venice Ln, Sarasota, FL 34242

Under Construction. Be the first owner of this exceptional new construction home. Enjoy gorgeous, wide Grand Canal views with quick access to Sarasota Bay—a true boater’s dream. This home showcases high-end construction at its core, featuring a standing seam metal roof, hurricane-impact windows and sliders, elegant stone detailing, and meticulous craftsmanship throughout—no detail has been

Cassandra Meyer

BRIGHT REALTY

(941) 390-2066

527 Venice Ln, Sarasota, FL 34242
/16
$10,770 per month
- 4 Beds
- 4 Baths
- 1,552 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 52B, Sarasota, FL 34242

Villa 52N at Aloha Kai offers the perfect escape for your next beach vacation, featuring three comfortable bedrooms and the convenience of an in-unit washer and dryer. Located on Siesta Key—a popular barrier island along Florida’s breathtaking West Coast—this villa is part of Aloha Kai, a family-friendly, gated resort community nestled in the heart of Crescent Beach, consistently ranked the

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 52B, Sarasota, FL 34242
/2
$729,000 Sold Oct 17, 2025

1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Built 1988
Last Sold Summary
- 6% Below List Price
- $570/SF
- 96 Days On Market
Current Estimated Value $711,245

Last Listing Agent Gina LaRouche COLDWELL BANKER REALTY

1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242

/66
Est $554,210 Not Listed For Sale

23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 561 Sq Ft
- Built 1967
23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

Last Sold Summary
- 21% Below List Price
- $1,246/SF
- 24 Days On Market
Last Sold Price $699,000

Last Listing Agent Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

/60
$2,249,000
- 4 Beds
- 2.5 Baths
- 2,774 Sq Ft
5361 Siesta Ct, Sarasota, FL 34242

Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior doors with switchable

David James CHARLES RUTENBERG REALTY INC

5361 Siesta Ct, Sarasota, FL 34242
/15
$8,010 per month
- 1 Bed
- 1 Bath
- 975 Sq Ft
- House for Rent
6061 E Peppertree Way Unit 116, Sarasota, FL 34242

This property is a 30 night minimum.This 2 bedroom, 1 bath is a second floor garden unit on the bay side of Midnight Pass, and is approximately 15 yards from the Intracoastal waterway.The master bedroom has a queen bed and a 40 inch TV. The master bathroom has a tub/shower combination with a sliding glass door.The guest bedroom has 2 twin beds, a ceiling fan, and window with natural

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6061 E Peppertree Way Unit 116, Sarasota, FL 34242
/2
$460,000 Sold Dec 04, 2025

5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
- Built 1975
Last Sold Summary
- 4% Below List Price
- $455/SF
- 92 Days On Market
Current Estimated Value $458,834

Last Listing Agent Janet Trefry RE/MAX ALLIANCE GROUP

5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242

/41
Est $647,265 Not Listed For Sale

141 Avenida Messina Unit 3, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
- Built 1966
141 Avenida Messina Unit 3, Sarasota, FL 34242

Last Sold Summary
- 14% Below List Price
- $741/SF
- 1 Day On Market
Last Sold Price $752,500

Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

/69
$2,695,000
- 5 Beds
- 3.5 Baths
- 3,205 Sq Ft
430 Island Cir, Sarasota, FL 34242

Welcome to 430 Island Circle, where island living feels both luxurious and refreshingly relaxed. Set on Palm Island, the “heart of Siesta Key”, just moments from the sugar-white sands of Siesta Key Beach, this home offers the perfect balance of modern comfort and coastal charm. Completely reimagined from top to bottom, this five bedroom, three and a half bathroom residence opens with sun-filled

Jesse Bauer KW COASTAL LIVING III

430 Island Cir, Sarasota, FL 34242
/27
$5,200 per month
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 602, Sarasota, FL 34242

Enjoy Gulf of Mexico views from our recently renovated penthouse apartment on Siesta Key. You will have access to the #1 beach in the US with white powder sand and warm gulf waters. Enjoy beautiful views of the gulf from our full-length lanai and both bedrooms.The condominium offers multiple heated swimming pools, beach side and bay side grills, fishing pier, and a recently renovated exercise

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1255 E Peppertree Dr Unit 602, Sarasota, FL 34242
/2
$865,000 Sold Mar 05, 2026

315 Avenida de Paradisio, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
- Built 1971
Last Sold Summary
- 9% Below List Price
- $591/SF
- 105 Days On Market
Current Estimated Value $953,976

Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

315 Avenida de Paradisio, Sarasota, FL 34242

/2
Est $928,216 Not Listed For Sale

1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,660 Sq Ft
- Built 1988
1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

Last Sold Summary
- 3% Below List Price
- $577/SF
- 124 Days On Market
Last Sold Price $958,000

Last Listing Agent Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

/90
$2,450,000 Open Thu 11AM - 2PM
- 3 Beds
- 2 Baths
- 2,276 Sq Ft
4508 Woodside Rd, Sarasota, FL 34242

Luxury Exclusive Living – Boaters’ Paradise Welcome to 4508 Woodside Rd., a true waterfront retreat on Siesta Key offering privacy, boating convenience, and refined coastal living. Positioned on one of the deepest canals on the island, this home delivers three-minute access to the Intracoastal and Sarasota Bay. With 95 feet of water frontage and a 75-foot new dock, this is a legitimate boater’s

Derek Edwards KELLER WILLIAMS ON THE WATER S

4508 Woodside Rd, Sarasota, FL 34242
/31
$7,000 per month
- 2 Beds
- 11 Baths
- 1,200 Sq Ft
- Condo for Rent
1200 E Peppertree Ln Unit 303, Sarasota, FL 34242

This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
/2
$800,000 Sold Dec 19, 2025

6300 Midnight Pass Rd Unit 2, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 1969
Last Sold Summary
- 6% Below List Price
- $617/SF
- 127 Days On Market
Current Estimated Value $786,590

Last Listing Agent Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

6300 Midnight Pass Rd Unit 2, Sarasota, FL 34242

/2
Est $2,410,995 Not Listed For Sale

1358 Roberts Bay Ln, Siesta Key, FL 34242
- 4 Beds
- 6 Baths
- 5,034 Sq Ft
- Built 1978
1358 Roberts Bay Ln, Siesta Key, FL 34242

Last Sold Summary
- 7% Below List Price
- $516/SF
- 0 Days On Market
Last Sold Price $2,600,000

Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

/66
$525,000 Open Fri 1PM - 3PM
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
4660 Ocean Blvd Unit Q1, Sarasota, FL 34242

PRICED TO SELL! New hurricane-impact sliders have been ordered and will be installed prior to closing. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath

Halie Monde KW COASTAL LIVING III

4660 Ocean Blvd Unit Q1, Sarasota, FL 34242
/32
$8,300 per month
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
- Condo for Rent
1200 E Peppertree Ln Unit 402, Sarasota, FL 34242

This condo is a 30-night minimum.Condo 1200-402 at Peppertree Bay on Siesta KeyThis 2 bedroom, 2 bathrooms recently remodeled, is only steps away from Crescent Beach and is located on the 4th floor.This condo comfortably sleeps 6 guests.The master King bedroom is equipped with a 43'' Smart TV for your entertainment and a ceiling fan. The master bathroom has a walk-in

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
/2
$4,000,000 Sold Jun 26, 2025

645 Beach Rd, Siesta Key, FL 34242
- 4,989 Sq Ft
- Built 2018
Last Sold Summary
- 19% Below List Price
- $802/SF
- 441 Days On Market
Current Estimated Value $3,903,309

Last Listing Agent Cole Collins COLDWELL BANKER REALTY

645 Beach Rd, Siesta Key, FL 34242

/68
Est $538,245 Not Listed For Sale

1600 Cove II Place Unit 421, Sarasota, FL 34242
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
- Built 1979
1600 Cove II Place Unit 421, Sarasota, FL 34242

Last Sold Summary
- 8% Below List Price
- $677/SF
- 4 Days On Market
Last Sold Price $582,000

Last Listing Agent Brian Livesey WATERSIDE REALTY LLC

/100
$2,499,000 Open Sat 11AM - 2PM
- 4 Beds
- 3 Baths
- 3,541 Sq Ft
5012 Higel Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts

Rachelle Tirey PREFERRED SHORE LLC

5012 Higel Ave, Sarasota, FL 34242
/21
$8,010 per month
- 2 Beds
- 2 Baths
- 1,314 Sq Ft
- Townhouse for Rent
6023 W Peppertree Way Unit 235, Sarasota, FL 34242

This property is a 30 night minimum.6023 WPW is a Gulf-side Townhouse unit, located approx. 60 yards away from Crescent Beach.Living room TV is mounted on the wall. This unit will have a flight of stairs.Approx. 1400 Sq. Ft. (1500 including the lanai) Condo Summary:Bedding: Master Bedroom: King - Guest Bedroom: 2 TwinsElectronics: Living-room: 32 inch Flat Panel - Master

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6023 W Peppertree Way Unit 235, Sarasota, FL 34242
/2
$1,200,000 Sold Apr 25, 2025

5602 Cape Leyte Dr, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,111 Sq Ft
- Built 1960
Last Sold Summary
- 9% Below List Price
- $568/SF
- 50 Days On Market
Current Estimated Value $1,183,639

Last Listing Agent Ben Angerami PREMIER SOTHEBY'S INTERNATIONAL REALTY

5602 Cape Leyte Dr, Sarasota, FL 34242

/42
Est $785,035 Not Listed For Sale

5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 816 Sq Ft
- Built 1970
5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

Last Sold Summary
- 15% Below List Price
- $1,134/SF
Last Sold Price $925,000

Last Listing Agent Charles Totonis PREMIER SOTHEBY'S INTERNATIONAL REALTY

Showing Results 121 - 160, Page 4 of 18

Florida Sarasota County Siesta Key

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Siesta Key, FL Homes

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