Siesta Key, FL Homes

/84
$6,850,000
- 3 Beds
- 4 Baths
- 2,454 Sq Ft
216 Tenacity Ln, Sarasota, FL 34242

Nestled along the pristine sands of Siesta Key, this multi-level beach house is a true gem offering an idyllic coastal lifestyle. Immaculate and beautifully designed, the property boasts expansive decks that capture spectacular western views of the beach and the shimmering Gulf of Mexico. As you enter the home, you are greeted by a large living room that serves as the heart of this coastal

Stephanie Church COLDWELL BANKER REALTY

216 Tenacity Ln, Sarasota, FL 34242
/60
$6,500 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 102, Sarasota, FL 34242

Available January to May 1, 2025! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Sauna, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1250 N Portofino Dr Unit 102, Sarasota, FL 34242
/2
$623,000 Sold Feb 28, 2025
- 1,352 Sq Ft
- $461/SF
- 37 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
1137 Lake House Cir Unit C215, Sarasota, FL 34242

Reduced! The Best Price for a 2 Bed with a Garage on the Key! Your place at the beach needs to be Our House at The Beach. This 2 bed 2 bath 2nd floor unit with it's own 1 car garage is beautifully updated with carefree bamboo floors in all the living space and ceramic tile in the baths, oversize crown moldings and base trim. It offers lake views with a fountain and a twenty-foot-wide balcony

Mike Winger RE/MAX PLATINUM

1137 Lake House Cir Unit C215, Sarasota, FL 34242

/63
Est $748,359 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

/59
$1,150,000
- 3 Beds
- 3 Baths
- 1,964 Sq Ft
396 Avenida Madera, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Welcome to 396 Avenida Madera! Nestled in the heart of the Siesta Key Village and walking distance to world renown Siesta Key Beach presents a rare opportunity to own prime land. The very last lot at the end of a cul-de-sac offers a novel setting for your tranquil escape to over 112 feet of direct saltwater canal access. Having had storm damages

Michael Nogueira LUXURY & BEACH REALTY INC

396 Avenida Madera, Sarasota, FL 34242
/43
$3,900 per month
- 3 Beds
- 2 Baths
- 1,645 Sq Ft
- Condo for Rent
4660 Ocean Blvd Unit B2, Sarasota, FL 34242

SIESTA KEY WATERFRONT UNIT AVAILABLE AS SHORT OR LONG TERM. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its location on the north end of the Key provides convenient

Margaret Young JENNETTE PROPERTIES, INC.

4660 Ocean Blvd Unit B2, Sarasota, FL 34242
/2
$8,100,000 Sold Feb 27, 2025
- 5,282 Sq Ft
- $1534/SF
- 145 Days On Market
- 4 Beds
- 7 Baths
- Built 2024
3960 Roberts Point Rd, Sarasota, FL 34242

Nestled within the coveted north end of Siesta Key, this extraordinary residence boasts a blend of modern & contemporary elegance. Situated on an expansive lot spanning approximately 0.45 acres along the scenic Roberts Point Rd, the home welcomes you through private gates into your own secluded sanctuary. Possessing a spacious driveway with garages accommodating up to 7 vehicles (5-car garage

Tammy Dentici BRIGHT REALTY

3960 Roberts Point Rd, Sarasota, FL 34242

/60
Est $1,445,519 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

/97
$1,725,000 Open Mon 12PM - 3PM
- 3 Beds
- 2 Baths
- 2,217 Sq Ft
1038 Contento St, Sarasota, FL 34242

Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The

Sara Leicht SARASELLSSARASOTA.COM

1038 Contento St, Sarasota, FL 34242
/14
$30,000 per month
- 3 Beds
- 3 Baths
- 3,395 Sq Ft
- House for Rent
95 Sandy Hook Rd S, Sarasota, FL 34242

6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry

Joseph Russo COURTYARD MODERN

95 Sandy Hook Rd S, Sarasota, FL 34242
/2
$850,000 Sold Feb 26, 2025
- 2,832 Sq Ft
- $300/SF
- 34 Days On Market
- 3 Beds
- 2 Baths
- Built 1952
4431 Ocean Blvd, Sarasota, FL 34242

Beautiful home located in the heart of picturesque Siesta Key. This home offers the perfect blend of island living and untapped potential. While recently impacted by Hurricanes Helene and Milton, this property remains a rare gem with endless possibilities to restore and reimagine your dream coastal retreat. Located just minutes from world-famous Siesta Key Beach, this property is your chance to

Shawn Judy FLORIDA SUN & SAND REALTY

4431 Ocean Blvd, Sarasota, FL 34242

/48
Est $1,746,841 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

/43
$599,900
- 2 Beds
- 2 Baths
- 1,160 Sq Ft
111 Whispering Sands Cir Unit V38, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Coastal Elegance in the Heart of Siesta Key Village — Fully Remodeled Villa with Private Beach Access.Welcome to Whispering Sands, an exclusive 55+ Gulf-front community offering unmatched serenity, luxury, and location. Nestled in a prime location in the heart of Siesta Key Village, this beautifully remodeled 2-bedroom, 2-bath villa is just steps

Anita Darvai Seaton OFFERMATE REAL ESTATE

111 Whispering Sands Cir Unit V38, Sarasota, FL 34242
/42
$8,500 per month
- 2 Beds
- 2 Baths
- 1,337 Sq Ft
- Condo for Rent
5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

** BOOKED JANUARY THROUGH MARCH 2025 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dining room combo and master bedroom! Gulf & Bay Club is located on Siesta Key Beach, voted #1 Beach in the USA! The spacious unit

Kayla Lamb NEXTHOME EXCELLENCE

5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
/2
$540,000 Sold Feb 26, 2025
- 1,165 Sq Ft
- $464/SF
- 30 Days On Market
- 2 Beds
- 2 Baths
- Built 1976
5855 Midnight Pass Rd Unit 511, Sarasota, FL 34242

Welcome to Harbor Towers Yacht & Racket Club on Siesta Key! This 2-bedroom, 2-bathroom condo offers an exciting opportunity to create your dream coastal retreat. While the interior needs updating, the potential is endless. The open floor plan offers a spacious living area, two generous bedrooms, and a Florida room perfect for taking in the serene surroundings. Sold fully furnished, this condo is

Molly Higdon KELLER WILLIAMS ON THE WATER S

5855 Midnight Pass Rd Unit 511, Sarasota, FL 34242

/57
Est $1,813,863 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

/67
$525,000
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
6157 Midnight Pass Rd Unit E65, Sarasota, FL 34242

The perfect opportunity for you to enjoy the Florida Lifestyle and make income! This 2-bed, 2-bath penthouse condo is being sold TURNKEY FURNISHED, all within walking distance to the sugary sands of SIESTA KEY BEACH. This condo is ideal for personal use or as an investment with WEEKLY RENTAL allowance and future bookings in place. The interior of the condo is tastefully decorated with a tropical

Roni-Marie Gold, PA COLDWELL BANKER REALTY

6157 Midnight Pass Rd Unit E65, Sarasota, FL 34242
/15
$7,500 per month
- 2 Beds
- 2 Baths
- 1,363 Sq Ft
- Condo for Rent
460 Beach Rd Unit A1, Sarasota, FL 34242

Available OCT- DEC. 2024 and APR. 2025. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take

Brenda Cozy COLDWELL BANKER REALTY

460 Beach Rd Unit A1, Sarasota, FL 34242
/2
$1,150,000 Sold Feb 25, 2025
- 1,446 Sq Ft
- $795/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
5300 Ocean Blvd Unit 704, Sarasota, FL 34242

Welcome to your dream coastal retreat! This condo offers breathtaking views of the Gulf of Mexico, placing you just steps away from a deeded beach access and the sparkling shoreline. Located in the vibrant heart of Siesta Key Village, this property offers unparalleled access to the best dining, shopping and entertainment, all just a few steps away from your door. Whether you're savoring the

Samantha Jennen PREFERRED SHORE LLC

5300 Ocean Blvd Unit 704, Sarasota, FL 34242

/64
Est $660,173 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

/29
$525,000
- 1 Bed
- 1 Bath
- 956 Sq Ft
1223 Siesta Bayside Dr Unit 1223D, Sarasota, FL 34242

Welcome to paradise on Siesta Key! This delightful elevated first-floor one-bedroom, one-bath unit in the highly sought-after Gulf and Bay Club Bayside combines comfort, style, and unbeatable convenience—with no flood or storm damage.Enjoy direct deeded beach access just across the street to world-famous Siesta Key Beach, and embrace true resort-style living with incredible amenities at your

Gigi Kuster COLDWELL BANKER REALTY

1223 Siesta Bayside Dr Unit 1223D, Sarasota, FL 34242
/91
$6,500 per month
- 2 Beds
- 2 Baths
- 1,123 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 301, Sarasota, FL 34242

Immaculate End Unit in the Marlin building, Ready for you to Enjoy through December 2025 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1250 N Portofino Dr Unit 301, Sarasota, FL 34242
/2
$3,850,000 Sold Feb 25, 2025
- 2,647 Sq Ft
- $1454/SF
- 19 Days On Market
- 4 Beds
- 4 Baths
- Built 1969
1290 Hidden Harbor Way, Sarasota, FL 34242

IMAGINE owning nearly 3/4 of an acre on the exquisite Sarasota Bayfront! Your imagination can become reality on the northern end of world-renowned Siesta Key! This incredible property is perfect for living the true island life that you imagine! This dream property is located in Hidden Harbor only minutes from the famous Siesta Key Village as well as the #1 Beach in the United States and is

Frank Pachinger RE/MAX ALLIANCE GROUP

1290 Hidden Harbor Way, Sarasota, FL 34242

/14
Est $1,097,174 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

/33
$1,000,000
- Land
- 0.28 Acre
- $3,571,429 per Acre
734 Canal Rd, Sarasota, FL 34242

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to build a new island retreat or remodel the existing structure, opportunity awaits, a prime 12,229-square-foot property in the sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create your dream

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

734 Canal Rd, Sarasota, FL 34242
/29
$7,000 per month
- 2 Beds
- 2 Baths
- 1,250 Sq Ft
- Condo for Rent
1255 E Peppertree Dr Unit 201, Sarasota, FL 34242

Bayside highrise Building with underground parking, elevator, turnkey furnished, secured building, washer and dryer nicely appointed Two heated pools, lighted tennis courts, fishing pier, fitness room and that Beautiful Siesta Beach. Restaurants, Shopping, Theater, Arts, Golfing, Bicycling whatever your pleasure you will find in Sarasota. Peppertree is a Gulf to Bay complex Available

Lisa Beach WATERSIDE REALTY LLC

1255 E Peppertree Dr Unit 201, Sarasota, FL 34242
/2
$2,600,000 Sold Feb 24, 2025
- 5,034 Sq Ft
- $516/SF
- 0 Days On Market
- 4 Beds
- 6 Baths
- Built 1978
1358 Roberts Bay Ln, Siesta Key, FL 34242

This splendid waterfront retreat on Siesta Key offers the ideal blend of luxury, comfort and coastal charm. In an enviable location known for world-renowned beaches and vibrant island living, this gracious two-story home features four bedrooms, four full baths and two half baths, creating an oasis for discerning buyers. The home showcases breathtaking views of the Intracoastal Waterway and bay

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

1358 Roberts Bay Ln, Siesta Key, FL 34242

/43
Est $754,760 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

/52
$1,000,000
- 3 Beds
- 2 Baths
- 1,412 Sq Ft
734 Canal Rd, Sarasota, FL 34242

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity awaits, a prime 12,229-square-foot property in the sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create your dream home in

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

734 Canal Rd, Sarasota, FL 34242
/49
$9,500 per month
- 2 Beds
- 2 Baths
- 1,489 Sq Ft
- Condo for Rent
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

***AVAILABLE MAY 2026*** one MONTH MIN***Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets. Available as a monthly rental, the interior boasts a decorative fireplace, reclining sofa, two walk-in closets, washer and dryer in

Anthony DeLuca AUDREY RAIN RENTALS, INC

6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
/2
$475,000 Sold Feb 24, 2025
- 787 Sq Ft
- $604/SF
- 68 Days On Market
- 1 Bed
- 1 Bath
- Built 1969
711 Beach Rd Unit 208, Sarasota, FL 34242

Location, Location! NO HURRICANE DAMAGE to this unit. Luxurious lifestyle awaits you with Glorious Unobstructed Breathtaking FULL GULF VIEWS of tranquil aqua waters and enchanting sunsets right from your own Condo. DIRECT BEACH VIEW & ACCESS + a convenient WALK to the VILLAGE full of restaurants, music and shopping. Only a handful of buildings have full VIEWS + LOCATION + BEACH. MINIMUM ONE WEEK

Yvonne Blackburn SUNSET REALTY

711 Beach Rd Unit 208, Sarasota, FL 34242

/41
Est $1,420,909 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

/60
$585,000
- 2 Beds
- 2 Baths
- 1,291 Sq Ft
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
$5,000 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1257 S Portofino Dr Unit 36, Sarasota, FL 34242

Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach

Margaret Young JENNETTE PROPERTIES, INC.

1257 S Portofino Dr Unit 36, Sarasota, FL 34242
/2
$730,000 Sold Feb 21, 2025
- 1,061 Sq Ft
- $688/SF
- 69 Days On Market
- 2 Beds
- 2 Baths
- Built 1969
1350 N Portofino Dr Unit 302, Sarasota, FL 34242

Stunning Direct Intracoastal Waterway Views. Experience breathtaking, direct views of the Intracoastal Waterway from this beautifully renovated 3rd-floor unit in the exclusive Tarpon Building. With only 8 units facing the water, this residence offers a rare opportunity to live in one of Siesta Harbor’s most coveted locations. This spacious 2-bedroom, 2-bathroom condo boasts a modern, open floor

Liza Knipe RE/MAX PLATINUM

1350 N Portofino Dr Unit 302, Sarasota, FL 34242

/33
Est $869,202 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,220 Sq Ft
6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242

6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242

/50
$2,800,000
- 3 Beds
- 3.5 Baths
- 2,468 Sq Ft
5024 Commonwealth Dr, Sarasota, FL 34242

Nestled in the quaint neighborhood along the Grand Canal on Siesta Key, this Key West style home offers the perfect blend of old-world charm and modern living. This exceptionally well-appointed custom-built home is being offered turnkey. The home's grand entrance welcomes you through a covered porch that leads to an oversized foyer. You are greeted with a spectacular open floor plan, where an

Gabi Charity CHARITY & WEISS INTERNATIONAL LLC

5024 Commonwealth Dr, Sarasota, FL 34242
/27
$6,400 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 107, Sarasota, FL 34242

This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring. Queen size bed in the Master with a walk in closet plus a full wall length closet. The guest bedroom has 2 single beds that can be combined to make a King. Updated bathrooms

Margaret Young JENNETTE PROPERTIES, INC.

1250 N Portofino Dr Unit 107, Sarasota, FL 34242
/2
$1,100,000 Sold Feb 21, 2025
- 2,550 Sq Ft
- $431/SF
- 64 Days On Market
- 4 Beds
- 3 Baths
- Built 1963
5624 Cape Leyte Dr, Sarasota, FL 34242

$100k PRICE REDUCTION. RARE LOCATION! Rare opportunity to live just five houses from the street entrance to famed Siesta Key public beach. No need for a car or to worry about parking. Just a 5 minute walk and you’ll be enjoying the beautiful quartz sand and crystal clear water. If that isn't enough, this rare parcel is situated between two properties, and has a direct bird's eye view of the

Amy Tanaka SILVER PALM REALTY

5624 Cape Leyte Dr, Sarasota, FL 34242

/59
Est $770,651 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242

6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242

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