Siesta Key, FL Homes

/48
$850,000
- 2 Beds
- 2 Baths
- 1,163 Sq Ft
1055 W Peppertree Dr Unit 102AA, Sarasota, FL 34242

Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional

Tanya Stutzman REALTY HUB

1055 W Peppertree Dr Unit 102AA, Sarasota, FL 34242
/10
$8,970 per month
- 2 Beds
- 2 Baths
- 1,064 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242

This is a fun tropically decorated beach villa that will put a smile on your face when you walk in!! This unit can easily occupy up to 6. We have recently remodeled the kitchen and both bathrooms. The master bedroom features a king size bed with a new pillow top mattress. The master bath is new with a roman walk in shower. There is an LCD TV, DVD player and a nice closet. The second bedroom has a

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
/2
$870,000 Sold Apr 14, 2025

5780 Midnight Pass Rd Unit 408, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1979
Last Sold Summary
- 27% Below List Price
- $639/SF
- 79 Days On Market
Current Estimated Value $864,892

Last Listing Agent Betsy Campbell MICHAEL SAUNDERS & COMPANY

5780 Midnight Pass Rd Unit 408, Sarasota, FL 34242

/2
Est $572,786 Not Listed For Sale

5600 Beach Way Dr Unit 107, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
- Built 1970
5600 Beach Way Dr Unit 107, Sarasota, FL 34242

Last Sold Summary
- 9% Above List Price
- $444/SF
- 79 Days On Market
Last Sold Price $525,000

Last Listing Agent Glenn Zakaria NEW DOOR REAL ESTATE LLC

/62
$779,000
- 2 Beds
- 2 Baths
- 1,173 Sq Ft
6204 Midnight Pass Rd Unit 205, Sarasota, FL 34242

Welcome to your slice of paradise at Siesta Dunes Beach Community. This beautifully maintained 2-bedroom, 2-bath end-unit is located on the second floor and is offered turnkey furnished, making it ideal as a vacation getaway, investment property, or full-time residence. Being an end unit, the condo is filled with extra natural light and offers a charming peek-a-boo ocean view to remind you just

Christine Green COLDWELL BANKER REALTY

6204 Midnight Pass Rd Unit 205, Sarasota, FL 34242
/15
$8,970 per month
- 2 Beds
- 2 Baths
- 1,071 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242

Welcome to the newly renovated A04 Villa! Private entrance leads to the screened in lanai and open air space which includes the kitchen, dining area and comfortable seating to enjoy the large flat screen tv. The villa sleeps up to 6. 2 queen beds in the primary bedroom and 2 twin beds in the guest bedroom. Both bedrooms are also equipped with flat screen TVs. This large villa features 2

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
/2
$1,100,000 Sold Aug 05, 2025

554 Canal Rd, Sarasota, FL 34242
- 2 Beds
- 1 Bath
- 1,085 Sq Ft
- Built 1945
Last Sold Summary
- 21% Below List Price
- $1,014/SF
- 119 Days On Market
Current Estimated Value $1,107,222

Last Listing Agent Curtis Ware KW COASTAL LIVING III

554 Canal Rd, Sarasota, FL 34242

/72
Est $5,166,746 Not Listed For Sale

5119 Jungle Plum Rd, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 4,131 Sq Ft
- Built 2012
5119 Jungle Plum Rd, Sarasota, FL 34242

Last Sold Summary
- 14% Below List Price
- $1,452/SF
- 96 Days On Market
Last Sold Price $6,000,000

Last Listing Agent Rudy Dudon Michael Saunders

/55
$949,000
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
6063 E Peppertree Way Unit 111, Sarasota, FL 34242

Experience effortless coastal luxury in this brand-new residence, thoughtfully designed and new built from the studs on in. Professionally staged to showcase the very best of waterfront living. Offered fully furnished and truly turnkey, this stunning 2-bedroom, 2-bath home allows you to move right in—or begin generating rental income—without lifting a finger.Perfectly positioned on the

Eliza Miller PEPPERTREE BAY REALTY INC

6063 E Peppertree Way Unit 111, Sarasota, FL 34242
/12
$8,340 per month
- 2 Beds
- 1.5 Baths
- 836 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit D02, Sarasota, FL 34242

Newly furnished and redecorated with a beachy vibe! Both bedrooms have new premium mattresses. Master bedroom has a king size mattress with 1.5 bath ensuite Second bedroom is furnished with two twin mattresses. Flat screen TVs in both bedrooms. Living room has two new Lazy Boy sofa sleepers. Individual in villa wi-fi. Just steps to one of the large pools on Siesta Key or choose a day on the beach

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit D02, Sarasota, FL 34242
/2
$720,000 Sold Feb 05, 2026

0 Avenida Leona, Siesta Key, FL 34242
- Land
- 0.18 Acre
- $4,000,000 per Acre
Last Sold Summary
- 10% Below List Price
- 226 Days On Market
Last Listing Agent Ron Pepka KW SUNCOAST

0 Avenida Leona, Siesta Key, FL 34242

/2
Est $2,072,311 Not Listed For Sale

452 Canal Rd, Sarasota, FL 34242
- 5 Beds
- 3.5 Baths
- 3,384 Sq Ft
- Built 2008
452 Canal Rd, Sarasota, FL 34242

Last Sold Summary
- 6% Below List Price
- $650/SF
- 29 Days On Market
Last Sold Price $2,200,000

Last Listing Agent Joseph Kesslak COLDWELL BANKER REALTY

/54
$874,000
- 1 Bed
- 1 Bath
- 928 Sq Ft
5400 Ocean Blvd Unit 9-4, Sarasota, FL 34242

Discover coastal luxury at Beach Terrace, one of Siesta Key's most coveted addresses. Perfectly positioned at the end of the village with direct Gulf of Mexico frontage, this exceptional 1 bedroom, 1 bathroom corner residence offers an unparalleled beachfront lifestyle with breathtaking panoramic views that truly set it apart. This thoughtfully designed condominium showcases sweeping vistas that

Mickey Kiernan MICHAEL SAUNDERS & COMPANY

5400 Ocean Blvd Unit 9-4, Sarasota, FL 34242
/10
$8,970 per month
- 2 Beds
- 2 Baths
- 1,064 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242

Welcome to D18 one of the closest to the beach among the villas.” It consists of two bedrooms and two full bathrooms, each of which contain a walk-in shower. The master bedroom has a king size bed while the second bedroom has a twin and a queen bed. The villa owners regularly update the unit for the comfort of the guests, which includes a TV in the master bedroom and a large screen TV in the main

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
/2
$615,000 Sold Dec 26, 2025

6150 Midnight Pass Rd Unit 12, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 939 Sq Ft
- Built 1967
Last Sold Summary
- 5% Below List Price
- $655/SF
- 13 Days On Market
Current Estimated Value $634,323

Last Listing Agent Glenn Brown RE/MAX ALLIANCE GROUP

6150 Midnight Pass Rd Unit 12, Sarasota, FL 34242

/45
Est $1,420,761 Not Listed For Sale

313 Beach Rd Unit 313S1, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,555 Sq Ft
- Built 2009
313 Beach Rd Unit 313S1, Sarasota, FL 34242

Last Sold Summary
- 16% Below List Price
- $1,093/SF
- 82 Days On Market
Last Sold Price $1,700,000

Last Listing Agent Catherine Reali BRIGHT REALTY

/36
$599,000 Pending
- 2 Beds
- 1.5 Baths
- 780 Sq Ft
5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242

Under contract-accepting backup offers. Gulf-side living at its best! This cute-as-a-button 2-bedroom, 2-bath ground-floor unit has been completely remodeled from top to bottom, featuring new electrical and plumbing, impact windows and doors, stylish new flooring, beautifully updated baths, and a stunning new kitchen with quartz countertops, tile backsplash, countertop breakfast bar, and

Christine Green COLDWELL BANKER REALTY

5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242
/10
$7,500 per month
- 2 Beds
- 2 Baths
- 1,064 Sq Ft
- House for Rent
6154 Midnight Pass Rd Unit D06, Sarasota, FL 34242

Casa Blanca is within sight of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. Most Villas have a screened Lanai with table and chairs for dining and relaxing. Those without a lanai

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6154 Midnight Pass Rd Unit D06, Sarasota, FL 34242
/2
$640,000 Sold Oct 06, 2025

5369 Shadow Lawn Dr, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,348 Sq Ft
- Built 1961
Last Sold Summary
- 19% Below List Price
- $475/SF
- 78 Days On Market
Current Estimated Value $673,851

Last Listing Agent Nancy Drake ACCARDI & ASSOCIATES REAL ESTATE

5369 Shadow Lawn Dr, Sarasota, FL 34242

/100
Est $8,406,084 Not Listed For Sale

4300 Higel Ave, Sarasota, FL 34242
- 6 Beds
- 9 Baths
- 8,615 Sq Ft
- Built 2008
4300 Higel Ave, Sarasota, FL 34242

Last Sold Summary
- 44% Below List Price
- $1,741/SF
- 4 Days On Market
Last Sold Price $14,995,000

Last Listing Agent Mark Coppens EXP REALTY LLC

/77
$365,000 Pending
- 1 Bed
- 2 Baths
- 780 Sq Ft
1250 N Portofino Dr Unit 305, Sarasota, FL 34242

Under contract-accepting backup offers. $20,000 PRICE IMPROVEMENT!!! Relax in Paradise for under $400,000! MOTIVATED SELLER!!! Stunning, Oversized One Bedroom Waterfront condo with 2 full Bathrooms in the highly sought after Siesta Harbor community on Siesta Key! Whether you enjoy the sunrise over your morning coffee or work from your glass-enclosed lanai, enjoy beautiful views of the canal and

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1250 N Portofino Dr Unit 305, Sarasota, FL 34242
/18
$5,970 per month
- 1 Bed
- 1 Bath
- 696 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242

This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
/2
$965,000 Sold Apr 04, 2025

1271 Dockside Place Unit 215, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,737 Sq Ft
- Built 1982
Last Sold Summary
- 12% Below List Price
- $556/SF
- 165 Days On Market
Current Estimated Value $930,481

Last Listing Agent Debra Forkan COLDWELL BANKER REALTY

1271 Dockside Place Unit 215, Sarasota, FL 34242

/2
Est $1,689,698 Not Listed For Sale

3928 Roberts Point Rd, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Built 1951
3928 Roberts Point Rd, Sarasota, FL 34242

Last Sold Summary
- 10% Below List Price
- $1,017/SF
- 2 Days On Market
Last Sold Price $1,870,000

Last Listing Agent Wayne Cherry PROGRAM REALTY, LLC

/9
$1,900,000
- Land
- 0.35 Acre
- $5,428,571 per Acre
5174 Sandy Cove Ave, Sarasota, FL 34242

This oversized cul-de-sac lot has just been cleared and is currently permitted and the slab has been poured. In addition a new 275 foot seawall has also been completed along with a dock and 10,000 lb boat lift. This lot is ready for your new home plans or use the existing plans that have been permitted and approved. Plans with existing builder can be taken over if desired or design your own home

Troy Jenkins REALTY EXECUTIVES GALLERY

5174 Sandy Cove Ave, Sarasota, FL 34242
/12
$8,970 per month
- 2 Beds
- 2 Baths
- 900 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 59, Sarasota, FL 34242

Villa 59 at Aloha Kai invites you to kick back and escape the traffic and long lines—no need to leave the property! Enjoy the pristine beach, the refreshing pool, and your fully equipped kitchen, all designed to make your stay effortless and relaxing. The comfortable furnishings and soothing neutral colors create a welcoming atmosphere where you can truly feel at home. Savor your morning coffee

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 59, Sarasota, FL 34242
/2
$570,000 Sold Aug 01, 2025

5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1976
Last Sold Summary
- 12% Below List Price
- $495/SF
- 59 Days On Market
Current Estimated Value $557,226

Last Listing Agent Christine Green COLDWELL BANKER REALTY

5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242

/68
Est $513,683 Not Listed For Sale

1113 N Moonmist Ct Unit L3, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Built 1968
1113 N Moonmist Ct Unit L3, Sarasota, FL 34242

Last Sold Summary
- 13% Below List Price
- $654/SF
- 0 Days On Market
Last Sold Price $589,000

Last Listing Agent Helene Hyland COLDWELL BANKER REALTY

/29
$549,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242

Turnkey furnished 1 bedroom, 1 bathroom condo at Jamaica Royale on Siesta Key, offering a true hands-off investment opportunity with onsite rental office and future bookings already in place for 2026. This fully renovated condo features high-end finishes and thoughtful upgrades throughout, making it ideal as a vacation rental, second home, or full-time residence. The updated kitchen showcases

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242
/15
$8,970 per month
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 2, Sarasota, FL 34242

Villa 2 at Aloha Kai is beautifully situated on Siesta Key, a popular barrier island along Florida’s West Coast. This family-friendly, gated resort community is nestled in the heart of Crescent Beach, which is ranked as the number one beach in the continental United States. Known for its dazzling white quartz sand and vibrant emerald-green waters, Siesta Key is among Florida’s top vacation

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 2, Sarasota, FL 34242
/2
$963,000 Sold Feb 04, 2026

1013 W Peppertree Dr Unit 115, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
- Built 1974
Last Sold Summary
- 3% Below List Price
- $875/SF
- 1 Day On Market
Current Estimated Value $971,906

Last Listing Agent Karl Helbig SUNREAL ESTATE INC

1013 W Peppertree Dr Unit 115, Sarasota, FL 34242

/2
Est $505,963 Not Listed For Sale

6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
- Built 1974
6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

Last Sold Summary
- 5% Above List Price
- $440/SF
- 23 Days On Market
Last Sold Price $484,000

Last Listing Agent Kristin Gilardi EXP REALTY LLC

/40
$1,250,000
- 4 Beds
- 4 Baths
- 2,173 Sq Ft
604 Avenida de Mayo, Sarasota, FL 34242

Back on the market! Beautiful triplex that went through a total renovation 2024. A re-roof project was completed in 2022 and is under a transferable warranty. Property can be rented as 3 separate units - Studio, One Bedroom, Three Bedroom. Property could easily be converted to a duplex (2 BR / 1 BA + 3 BR / 2 BA) in the event the owner prefers to live in one unit and rent the other. Just a few

Dan DeSoto, Jr MICHAEL SAUNDERS & COMPANY

604 Avenida de Mayo, Sarasota, FL 34242
/13
$8,370 per month
- 2 Beds
- 1 Bath
- 672 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 3, Sarasota, FL 34242

Enjoy a relaxing getaway in Villa 3 at Aloha Kai, a cozy beach villa beautifully decorated with casual coastal charm. The screened porch provides the perfect spot for morning coffee, unwinding with a good book, or entertaining guests in the evening with a meal or cocktail. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 3, Sarasota, FL 34242
/2
$550,000 Sold Nov 12, 2025

5222 Winding Way, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,137 Sq Ft
- Built 1963
Last Sold Summary
- 3% Below List Price
- $484/SF
- 35 Days On Market
Current Estimated Value $572,072

Last Listing Agent Robert Moffatt MICHAEL SAUNDERS & COMPANY

5222 Winding Way, Sarasota, FL 34242

/71
Est $372,754 Not Listed For Sale

6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242
- 2 Beds
- 1 Bath
- 690 Sq Ft
- Built 1974
6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

Last Sold Summary
- 7% Below List Price
- $583/SF
- 42 Days On Market
Last Sold Price $402,000

Last Listing Agent Babette Paige COLDWELL BANKER REALTY

/84
$1,600,000
- 3 Beds
- 2.5 Baths
- 2,557 Sq Ft
5231 Siesta Cove Dr, Sarasota, FL 34242

Tucked inside the private enclave of Siesta Cove, this beautifully updated island home offers that rare blend of privacy, space, and an easy walk to world-famous Siesta Key Beach. Set on an oversized 0.35-acre lot, the property features 3 bedrooms, 2.5 baths, and more than 2,500 square feet of bright, open living space designed for both everyday comfort and effortless entertaining. Vaulted

Natalie Gutwein MICHAEL SAUNDERS & COMPANY

5231 Siesta Cove Dr, Sarasota, FL 34242
/30
$8,970 per month
- 2 Beds
- 1.5 Baths
- 887 Sq Ft
- House for Rent
6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242

Villa 1 at Aloha Kai is ideally situated on Siesta Key, a popular barrier island along Florida’s West Coast. Nestled within the family-friendly, gated resort community of Aloha Kai, it lies in the heart of Crescent Beach—ranked the number one beach in the continental United States. Renowned for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
/2
$1,150,000 Sold Oct 22, 2025

4915 Primrose Path, Sarasota, FL 34242
- 6 Beds
- 5 Baths
- 3,549 Sq Ft
- Built 1960
Last Sold Summary
- 38% Below List Price
- $324/SF
- 320 Days On Market
Current Estimated Value $1,192,942

Last Listing Agent Tony Andrews ANDREWS & ASSOCIATES REALTY

4915 Primrose Path, Sarasota, FL 34242

/82
Est $547,537 Not Listed For Sale

6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
- Built 1974
6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

Last Sold Summary
- $413/SF
- 64 Days On Market
Last Sold Price $550,000

Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

Showing Results 281 - 320, Page 8 of 18

Florida Sarasota County Siesta Key

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Siesta Key, FL Homes

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