Siesta Key, FL Homes

/59
$2,275,000
- 5 Beds
- 4 Baths
- 3,855 Sq Ft
2 Island Cir, Sarasota, FL 34242

*2 BUILDABLE WATERFRONT LOTS* Palm Island IS the "Heart of Siesta Key". Don't miss this rare opportunity to live in Siesta Key's most sought-after neighborhood and experience the quiet, friendly, yet close to everything community of Palm Island. Build your tropical dream home on one lot and sell the other, or go "all in" and create your ideal island estate on the 17,883 sq ft lot. If restoration

George Miller COLDWELL BANKER REALTY

2 Island Cir, Sarasota, FL 34242
/58
$8,000 per month
- 3 Beds
- 3 Baths
- 1,835 Sq Ft
- Condo for Rent
1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242

Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural

Andy Moore GULF COAST REALTY & MANAGEMENT

1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
/2
$650,000 Sold Aug 22, 2025
- 2,114 Sq Ft
- $307/SF
- 118 Days On Market
- 3 Beds
- 2 Baths
- Built 1971
670 Venice Ln, Sarasota, FL 34242

Imagine living in your dream home on world renowned Siesta Key....THIS PROPERTY IS BEING SOLD FOR LAND VALUE ONLY!!! The cul-de-sac location offers privacy with no homes across the street. Live the local’s lifestyle in Waterside East, an established community with very little rental traffic. Easy access to the north and south bridges. The current home on the property has a footprint of 3,173

Debbie Lane RE/MAX ALLIANCE GROUP

670 Venice Ln, Sarasota, FL 34242

/25
Not Listed For Sale
0 Commonwealth Dr Unit A4538307, Sarasota, FL 34242

0 Commonwealth Dr Unit A4538307, Sarasota, FL 34242

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

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 stainless-steel appliances. The primary bedroom

Christine Green COLDWELL BANKER REALTY

5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242
/33
$8,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242

Embrace coastal living in this inviting 2-bedroom, 2-bathroom first-level condo nestled within the prestigious Gulf & Bay Club Bayside in Siesta Key, Florida. Step inside to discover a thoughtfully designed space adorned with coastal-inspired décor and an abundance of natural light. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an ideal space for

Andy Moore GULF COAST REALTY & MANAGEMENT

1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
/2
$680,000 Sold Aug 21, 2025
- 1,163 Sq Ft
- $585/SF
- 4 Days On Market
- 2 Beds
- 2 Baths
- Built 1974
1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242

Welcome to Peppertree Bay, one of Siesta Key’s most coveted Gulf to Bay communities, where island living meets effortless elegance. This turnkey, beautifully reimagined 2 bedroom, 2 bathroom residence is nestled within the desirable midrise building on the beach side of the complex, offering the perfect combination of privacy, convenience, and resort style amenities. Just steps from Siesta Key’s

James Gammello WILLIAM RAVEIS REAL ESTATE

1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242

/19
Not Listed For Sale
0 Azure Way, Sarasota, FL 34242

0 Azure Way, Sarasota, FL 34242

/43
$1,199,900 Open Fri 1PM - 4PM
- 4 Beds
- 2 Baths
- 1,915 Sq Ft
567 Venice Ln, Sarasota, FL 34242

Under the canopy of grand oaks and banyan trees, this move-in-ready FURNISHED Siesta Key POOL home offers the perfect blend of luxury and coastal charm. Located minutes from the world-famous beach and village, this retreat has been redesigned for island living with almost every inch of the home renovated to perfection! A freshly painted exterior, paver driveway, and xeriscape landscaping create a

Conner Ashley PREFERRED SHORE LLC

567 Venice Ln, Sarasota, FL 34242
/34
$8,000 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242

Experience luxury waterfront living in this stunning 2-bedroom, 2-bathroom condo situated on the second level of Gulf & Bay Club Bayside in Siesta Key, Florida. Boasting breathtaking views of the bay, this meticulously designed residence boasts comfort. Step into a spacious living area adorned with coastal finishes and large windows that invite an abundance of natural light. The open-concept

Andy Moore GULF COAST REALTY & MANAGEMENT

1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
/2
$1,700,000 Sold Aug 21, 2025
- 1,853 Sq Ft
- $917/SF
- 24 Days On Market
- 3 Beds
- 2 Baths
- Built 1971
1031 Contento St, Sarasota, FL 34242

Designer waterfront retreat on Siesta Key. Welcome to your dream coastal getaway! Tucked away on a quiet cul-de-sac, just moments from the world-renowned, powdery quartz sands of Siesta Beach, this impeccably renovated and landscaped waterfront home captures the essence of laid-back luxury and island living. Boaters will delight in the deepwater Grand Canal access—just one fixed bridge to

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

1031 Contento St, Sarasota, FL 34242

/44
Est $624,465 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
5600 Beach Way Dr Unit 213, Sarasota, FL 34242

5600 Beach Way Dr Unit 213, Sarasota, FL 34242

/60
$679,000
- 2 Beds
- 2 Baths
- 1,160 Sq Ft
111 Whispering Sands Cir Unit V38, Sarasota, FL 34242

Set within one of the few 55+ private Gulf-front communities on Siesta Key, this beautifully updated two-bedroom, two-bath villa blends refined comfort with a relaxed coastal lifestyle. Every corner of this residence has been carefully renewed to create a light-filled, contemporary retreat just moments from the famous white powder sand and Siesta Village. Inside, the open-concept design showcases

Domanic Calamese KW COASTAL LIVING III

111 Whispering Sands Cir Unit V38, Sarasota, FL 34242
/38
$5,000 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242

Enjoy your vacation on Siesta Key in this spacious three bedroom/two bathroom vacation rental. This 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 Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.

Andy Moore GULF COAST REALTY & MANAGEMENT

1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242
/2
$400,000 Sold Aug 20, 2025
- 1,332 Sq Ft
- $300/SF
- 86 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1974
6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

PRICED FOR QUICK, AS-IS SALE - Lowest price per sq. foot condo on Island! Siesta Key Waterfront for a Great Price! TWO-STORY, 2 BEDROOMS, 3 BATHROOMS, & 1-WEEK RENTALS PERMITTED gem in the popular Bay Oaks community. This spacious condo features two oversized ensuite bedrooms, a guest half bath, and three private lanais—two of them covered, and two with stunning Intracoastal Waterway views. Sip

Julia Montei COLDWELL BANKER REALTY

6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

/2
Est $1,446,087 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,164 Sq Ft
5966 Midnight Pass Rd Unit G-73, Sarasota, FL 34242

5966 Midnight Pass Rd Unit G-73, Sarasota, FL 34242

/82
$660,000
- 2 Beds
- 2 Baths
- 1,287 Sq Ft
6415 Midnight Pass Rd Unit 505, Sarasota, FL 34242

Discover coastal luxury on Siesta Key with this beautifully renovated and fully turnkey-furnished condominium at the prestigious Anchorage Yacht and Tennis Club. Featuring two spacious bedrooms and two modern bathrooms, this residence perfectly blends comfort, style, and investment potential. Ideal for both personal enjoyment and rental income, Anchorage allows weekly rentals—52 weeks per

Cindy Taliaferro PREMIER SOTHEBY'S INTERNATIONAL REALTY

6415 Midnight Pass Rd Unit 505, Sarasota, FL 34242
/29
$5,700 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242

Charming 2 bedroom/ 2 bath Condo just a short walk to the beach. Come enjoy our key-west style condo with a very rare 2 car garage. Two swimming pools, tennis court, pickleball, workout room and fishing dock round out the amenities on our lushly landscaped property. Nestled between palm trees, this ground floor condo does not have a unit above it. Impeccably clean and comfortable with a fully

Andy Moore GULF COAST REALTY & MANAGEMENT

1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
/2
$550,000 Sold Aug 19, 2025
- 1,291 Sq Ft
- $426/SF
- 79 Days On Market
- 2 Beds
- 2 Baths
- Built 1975
6415 Midnight Pass Rd Unit 204, Sarasota, FL 34242

THE ANCHORAGE - PARADISE AWAITS: A UNIQUE CORNER CONDO WITH DEEDED ACCESS TO SIESTA KEY BEACH ....Experience coastal paradise at this stunning 2-bedroom, 2-bathroom corner condo offering three private balconies and coveted deeded access to TripAdvisor's #1 Rated Beach in the USA. This fully furnished retreat captures Florida's natural beauty through its unique double-aspect design,

Steven McNally ENGEL + VOELKERS SARASOTA

6415 Midnight Pass Rd Unit 204, Sarasota, FL 34242

/72
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,166 Sq Ft
1640 Summerhouse Ln Unit 502B, Sarasota, FL 34242

1640 Summerhouse Ln Unit 502B, Sarasota, FL 34242

/97
$5,649,000
- 3 Beds
- 5 Baths
- 4,294 Sq Ft
5362 Shadow Lawn Dr, Sarasota, FL 34242

Experience elevated coastal living in this award-winning “Marlin Model” by Nutter Custom Construction, perfectly positioned on Siesta Key’s coveted Grand Canal. Completed in 2023 and showcased as the builder’s signature home, this completely custom Yacht-Modern residence blends refined elegance, contemporary design, and exceptional waterfront functionality. With 4,294 sq. ft. under air and 6,405

Morgan Marziali NCC PROPERTIES LLC

5362 Shadow Lawn Dr, Sarasota, FL 34242
/34
$8,100 per month
- 2 Beds
- 2 Baths
- 1,420 Sq Ft
- Condo for Rent
1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242

Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedrooms and two bathrooms, this meticulously designed residence seamlessly blends coastal elegance with modern comfort.Step into a sunlit living space adorned with coastal-inspired décor,

Andy Moore GULF COAST REALTY & MANAGEMENT

1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242
/2
$1,170,000 Sold Aug 15, 2025
- 1,166 Sq Ft
- $1,003/SF
- 23 Days On Market
- 2 Beds
- 2 Baths
- Built 1968
6312 Midnight Pass Rd Unit 102S, Sarasota, FL 34242

Siesta Key Beachfront Gem - Just Like New! Welcome to your slice of paradise on world-famous Siesta Key Beach! This stunning 2 bedroom, 2 bath elevated first floor end unit offers the ultimate in coastal living with direct beach access and breathtaking Gulf views. Step into a fully remodeled interior, professionally remediated and redesigned from top to bottom--including stylish furnishings--so

Kristina Rain MICHAEL SAUNDERS & COMPANY

6312 Midnight Pass Rd Unit 102S, Sarasota, FL 34242

/48
Est $661,283 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
199 Whispering Sands Dr Unit 202, Sarasota, FL 34242

199 Whispering Sands Dr Unit 202, Sarasota, FL 34242

/31
$550,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
1140 S Moonmist Ct Unit M5, Sarasota, FL 34242

FULLY renovated and appointed, in 2025, villa. Offered turnkey furnished, ready to use or rent for the season! The Polynesian Gardens community is well located on Siesta Key's south end; Walking distance to shopping, dining, nightlife of Captain Curt's corner, coffee and ice cream shops, grocery store, public beach access, boat rentals, and all things Siesta Key! Grab a golf cart or Free Trolly

Heide Crino BLUESRQ REAL ESTATE INC

1140 S Moonmist Ct Unit M5, Sarasota, FL 34242
/24
$7,600 per month
- 2 Beds
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242

Gulf and Bay Club Bayside is one of the most attractive condominium units on Siesta Key. This beautifully remodeled unit offers luxury accommodations at a reasonable cost. Offering a beautiful lake view and steps to the resort-style pool. You will enjoy your stay every minute.Enjoy all of the luxurious amenities this unit has to offer, from comfortable King size bed to the comfy

Andy Moore GULF COAST REALTY & MANAGEMENT

1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
/2
$850,000 Sold Aug 15, 2025
- Land
- 0.22 Acre
- $3,863,636 per Acre
- 14 Days On Market
5443 Avenida Del Mare, Sarasota, FL 34242

ESTATE SALE 2 or 4 lots! Priced well below market value! Concrete block home with caged pool just 2 blocks to world famous Siesta Beach. Home did sustain some flooding, was cleaned and is now somewhat habitable. The value is in the land with two fully platted lots which may support 1 or 2 new homes. See also 5453 to the West with 2 more larger lots for a contiguous aggregation of 4 lots. Seller

Bob Stahlschmidt II BRIGHT REALTY

5443 Avenida Del Mare, Sarasota, FL 34242

/41
Est $1,248,421 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
19 Whispering Sands Dr Unit 1005, Sarasota, FL 34242

19 Whispering Sands Dr Unit 1005, Sarasota, FL 34242

/43
$1,350,000
- 2 Beds
- 2 Baths
- 1,642 Sq Ft
5880 Midnight Pass Rd Unit 906, Sarasota, FL 34242

Welcome to Unit 906 in the sought-after Casarina on Siesta Key! This top-floor unit offers stunning views of Siesta Beach and all the comforts of home. The interior has been tastefully updated with modern finishes and stylish decor. The unit is being sold furnished (minus few staging items). The kitchen has newer cabinets and upgraded appliances. Enjoy the spaciousness of the living/dining

Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

5880 Midnight Pass Rd Unit 906, Sarasota, FL 34242
/18
$7,700 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops

Andy Moore GULF COAST REALTY & MANAGEMENT

1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
/2
$690,000 Sold Aug 14, 2025
- 894 Sq Ft
- $772/SF
- 10 Days On Market
- 2 Beds
- 2 Baths
- Built 1968
6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242

Welcome to 6310 Midnight Pass Rd #405N, an exceptional opportunity to own a turnkey furnished, income-producing beach retreat in the highly sought-after Crescent Arms community on Siesta Key. This rarely available 2-bedroom, 2-bathroom condo offers partial Gulf views from the spacious screened lanai and is just steps from private deeded beach access to Siesta Beach—ranked the #1 beach in the USA

Halie Monde KELLER WILLIAMS ON THE WATER S

6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242

/2
Est $567,219 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
5600 Beach Way Dr Unit 107, Sarasota, FL 34242

5600 Beach Way Dr Unit 107, Sarasota, FL 34242

/19
$674,900
- 2 Beds
- 2 Baths
- 1,139 Sq Ft
1325 S Portofino Dr Unit 309, Sarasota, FL 34242

This is the one! 2/2 condo with beach access. Boat slips available - check with association. Completely furnished with Tommy Bahama furnishings. Water view. On a canal but can see toward Gulf of Mexico. Enjoy the Siesta Key life annually or use as a seasonal unit. You can also rent it but there are length and approval requirements. Storage unit and laundry area outside of unit on the same floor.

Kimberly Stanford VETERANS REALTY INC.

1325 S Portofino Dr Unit 309, Sarasota, FL 34242
/89
$4,700 per month
- 3 Beds
- 3 Baths
- 1,867 Sq Ft
- Condo for Rent
4900 Ocean Blvd Unit 501, Sarasota, FL 34242

Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the

Beth Dilley ASCENDIA REAL ESTATE

4900 Ocean Blvd Unit 501, Sarasota, FL 34242
/2
$3,990,000 Sold Aug 12, 2025
- 3,329 Sq Ft
- $1,199/SF
- 178 Days On Market
- 5 Beds
- 4 Baths
- Built 2024
4815 Featherbed Ln, Sarasota, FL 34242

Just Completed! This brand-new, custom waterfront home on Siesta Key is now move-in ready, built above current elevation code with a brand-new raised seawall and dock, offering an unparalleled display of high-end, designer finishes throughout. The home features a spacious, open-floor plan with 5 bedrooms, 4 full bathrooms, and a sizable chef's kitchen complete with custom-designed cabinetry, an

Marco Guadagnini PREFERRED SHORE LLC

4815 Featherbed Ln, Sarasota, FL 34242

/72
Est $4,725,055 Not Listed For Sale
- 4 Beds
- 4 Baths
- 4,131 Sq Ft
5119 Jungle Plum Rd, Sarasota, FL 34242

5119 Jungle Plum Rd, Sarasota, FL 34242

/58
$1,499,000
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

Beachfront Penthouse Condo on Siesta Key! Have you been waiting for an opportunity that’s just too good to pass up? This spacious two bedroom, two bathroom home offers a versatile layout perfect for personal use or entertaining family and friends. Recently renovated, this top-floor condo places you directly above Siesta Key's powdery quartz sands and offers unobstructed, breathtaking views of the

Christa Spalding COLDWELL BANKER REALTY

20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242
/29
$6,700 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242

This two bedroom, two bath ground floor unit is steps from the pool and short distance to the beach. Enjoy all of the amenities that Gulf and Bay Club Bayside has to offer, two swimming pools, 2 pickle-ball courts, tennis, workout room, fishing dock and walking path. Washer and Dryer and one car garage sets us apart from other Siesta Key condos and makes it feel more like a home away from home.

Andy Moore GULF COAST REALTY & MANAGEMENT

1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
/2
$400,000 Sold Aug 11, 2025
- 1,254 Sq Ft
- $319/SF
- 30 Days On Market
- 2 Beds
- 2 Baths
- Built 1969
7 Sandy Cove Rd Unit 9B, Sarasota, FL 34242

One or more photo(s) has been virtually staged. INVESTOR SPECIAL!! Incredible opportunity to own one of the most desirable condo units in all of Sandy Cove. This 2 bedroom 2 bath first floor unit with an attached garage and its own laundry room, is a rare find. This currently empty shell is begging for someone with a vision and a keen eye for an investment opportunity. All drywall, electrical and

Tim Koons-McGee MICHAEL SAUNDERS & COMPANY

7 Sandy Cove Rd Unit 9B, Sarasota, FL 34242

/45
Est $1,456,475 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,555 Sq Ft
313 Beach Rd Unit 313S1, Sarasota, FL 34242

313 Beach Rd Unit 313S1, Sarasota, FL 34242

Showing Results 241 - 280, Page 7 of 18

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