Sarasota, FL Homes in ZIP Code 34242

• 

  

  

  /100

  $6,499,500

  • 10 Beds
  • 10 Baths
  • 7,052 Sq Ft

  1204 Derby Ln, Sarasota, FL 34242

  Welcome to an unparalleled luxury coastal retreat in the heart of SIESTA KEY, home to Tripadvisor’s #1 Beach in America! This turn-key luxury vacation rental boasts a potential $966,192 in first-year cash flow ($575,000+ from rental income and up to $391,192 from 100 percent bonus depreciation, reinstated by the Big Beautiful Bill), making it an extraordinary investment opportunity. Built in 2017

  Jeffrey Stuben CHARLES RUTENBERG REALTY INC

  1204 Derby Ln, Sarasota, FL 34242
• 

  

  

  /37

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,303 Sq Ft
  • Condo for Rent

  8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242

  Seasonal Property available on the top floor in Siesta Key, Look no further than "Island Reef" This Gulf to Bay location features the top floor PH unit directly overlooking the intercostal water way, just a short walk to the beach and very close to the Siesta key village and local dining. The property has a beautiful community pool, Tennis courts, shuffle board and much more. Entering the unit

  Lee Brewer RE/MAX ALLIANCE GROUP

  8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
• 

  

  /2

  $3,300,000 Sold Apr 10, 2025

  • 3,362 Sq Ft
  • $982/SF
  • 14 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2009

  317 Beach Rd, Sarasota, FL 34242

  ONE-OF-A-KIND IN THE HEART OF SIESTA KEY! With more than 3,300 square feet of beautifully designed living space, this meticulously maintained 4-bed, 3.5-bath single-family home is move-in ready and available for a quick close, as it sustained NO storm damage. From the moment you arrive, the classic architecture, tile roof and detailed craftsmanship are bound to leave a lasting impression. The

  Christa Spalding COLDWELL BANKER REALTY

  317 Beach Rd, Sarasota, FL 34242
• 

  

  

  /31

  Est $570,693 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6157 Midnight Pass Rd Unit E35, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit E35, Sarasota, FL 34242
• 

  

  

  /16

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft

  5880 Midnight Pass Rd Unit 202, Sarasota, FL 34242

  Seize this opportunity to own a second-floor condominium in the heart of Siesta Key, at one of the beach's widest, most breathtaking stretches. Spacious 1,500-square-foot getaway is mid-kitchen remodel, offered as-is at an unbeatable price for a swift sale, ideal for those eager to personalize their coastal escape! Choose your colors, finishes, and design touches to transform this gem into your

  Maureen Morris PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5880 Midnight Pass Rd Unit 202, 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

  $1,300,000 Sold Apr 10, 2025

  • 2,152 Sq Ft
  • $604/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1957

  530 Freeling Dr, Sarasota, FL 34242

  Beautiful value for premier Bay Island waterfront property on the prized north end of Siesta Key and a short drive to downtown Sarasota and Siesta beaches. Sad to say that this mid-century modern home with terrazzo floors had storm damage and is priced at lot value, ready to be remodeled or build new The back yard features stunning secluded bayou views with access to Roberts Bay by way of a

  Barbara May MICHAEL SAUNDERS & COMPANY

  530 Freeling Dr, Sarasota, FL 34242
• 

  

  /52

  Est $520,941 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242
• 

  

  /41

  $1,500,000

  • 3 Beds
  • 3 Baths
  • 1,658 Sq Ft

  5169 Oxford Dr, Sarasota, FL 34242

  Welcome to 5169 Oxford Drive, a beautifully renovated waterfront home located in the heart of Siesta Key, Sarasota. This 3-bedroom, 3-bathroom residence offers the perfect blend of coastal charm and modern luxury, thoughtfully updated in 2021 with high-end finishes throughout. Inside, you'll find over 2,000 square feet of open living space featuring soaring ceilings, crown molding, and luxury

  John Chalkias CHARLES RUTENBERG REALTY ORLANDO

  5169 Oxford Dr, 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

  $1,300,000 Sold Apr 10, 2025

  • Land
  • 0.27 Acre
  • $4,814,815 per Acre

  • 50 Days On Market

  546 Freeling Dr, Sarasota, FL 34242

  Incredible waterfront value. Bay Island is the premiere section on the north end of Siesta Key, a 10 minute drive to Southside Village shops and restaurants and 15 minutes to downtown or Siesta Village. Prized for its location, this canal front lot is cleared and ready to build on. The .27 acre lot with 85 feet of canal frontage (no bridges to the bay) is cleared, gated, has an inground swimming

  Barbara May MICHAEL SAUNDERS & COMPANY

  546 Freeling Dr, Sarasota, FL 34242
• 

  

  /23

  Est $530,766 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6157 Midnight Pass Rd Unit E01, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit E01, Sarasota, FL 34242
• 

  

  /17

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft

  782 Birdsong Ln, Sarasota, FL 34242

  SELLER FINANCING NOW AVAILABLE!!! Opportunity knocks in one of the most sought-after locations on Siesta Key! Roof in good shape and impact windows throughout the home. This prime property offers the perfect chance to create your ideal coastal retreat. Situated just moments from world-famous Siesta Key Beach, this lot presents a blank canvas for a stunning new build or a visionary renovation.

  Joey Lamielle RE/MAX ALLIANCE GROUP

  782 Birdsong Ln, Sarasota, FL 34242
• 

  

  /30

  $26,319 per month

  • 2 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  915 Seaside Dr Unit 512, Sarasota, FL 34242

  Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach. This beachfront sanctuary offers a fitness center, heated pool, outdoor grotto style whirlpool hot tub, bicycles, kayaks and barbecue grills, the tiki bar offers food from the famous Morton’s and cabanas to shield you from the sun when you want some shade. The unit has top of

  Andy Moore GULF COAST REALTY & MANAGEMENT

  915 Seaside Dr Unit 512, Sarasota, FL 34242
• 

  /2

  $2,300,000 Sold Apr 10, 2025

  • 4,071 Sq Ft
  • $565/SF
  • 299 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1979

  5422 Siesta Cove Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Home has sustained significant water damage on the first floor. Rehab or build your dream home on 90 feet of water frontage in Siesta Cove, a highly sought after neighborhood on the North end of Siesta Key. Unobstructed views of the Intracoastal, Phillippi creek and downtown. 10 minute walk to the public beach, biking distance to the village.

  Tori Harless COLDWELL BANKER REALTY

  5422 Siesta Cove Dr, Sarasota, FL 34242
• 

  

  /71

  Est $428,567 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242
• 

  

  /83

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242

  Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom condo is ideally situated and directly across the street from the

  ashley little WILLIAM RAVEIS REAL ESTATE

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242
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  /27

  $25,048 per month

  • 4 Beds
  • 3 Baths
  • 2,430 Sq Ft
  • House for Rent

  1140 Seaside Dr Unit 101, Sarasota, FL 34242

  Serenity at its finest! If luxury is calling, come indulge at the Beach House Residences for your ultimate beach vacation experiences. A place to escape and rediscover you. Renew your senses, inspire your mind and relax your body. Take advantage of the magnificent sunsets, tranquil waters, immense sunshine of world-renowned Crescent Beach. The most discerning traveler will appreciate the island

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1140 Seaside Dr Unit 101, Sarasota, FL 34242
• 

  /2

  $807,500 Sold Apr 09, 2025

  • 1,173 Sq Ft
  • $688/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  6202 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Nestled in the heart of Siesta Key, this beautifully updated and turnkey furnished corner garden unit at the iconic Siesta Dunes Resort offers the perfect blend of comfort, style, and location. Situated on the second floor, this 2-bedroom, 2-bathroom unit has been meticulously updated to provide a luxurious coastal retreat.Interior Features / updates include:*Luxury Vinyl Flooring

  Ryan Carson RE/MAX ALLIANCE GROUP

  6202 Midnight Pass Rd Unit 201, Sarasota, FL 34242
• 

  

  /82

  Est $597,012 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242
• 

  

  /100

  $5,000,000

  • 4 Beds
  • 4 Baths
  • 3,866 Sq Ft

  878 Freeling Dr, Sarasota, FL 34242

  Coastal Elegance on the Northern tip of Siesta Key. Discover timeless luxury in this waterfront estate nestled in the exclusive Bay Island enclave on Siesta Key's coveted North end. With panoramic views of Roberts Bay and the Intracoastal Waterway, this home captures the essence of Florida lifestyle- elegant, relaxed and designed for seamless indoor/outdoor living. Step inside to find all new

  Brian Livesey WATERSIDE REALTY LLC

  878 Freeling Dr, Sarasota, FL 34242
• 

  

  /96

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Condo for Rent

  1257 S Portofino Dr Unit 38, Sarasota, FL 34242

  Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice decor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

  Kay Esposito SIGNATURE REALTY ASSOCIATES

  1257 S Portofino Dr Unit 38, Sarasota, FL 34242
• 

  /2

  $1,125,000 Sold Apr 07, 2025

  • 1,645 Sq Ft
  • $684/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  1341 Siesta Bayside Dr Unit 1341B, Sarasota, FL 34242

  Nestled in the highly coveted Gulf & Bay Club Bayside, this 3-bedroom, 2-bathroom townhouse-style condominium offers breathtaking water views, resort-style living, and the flexibility of weekly rentals – perfect for personal enjoyment or as a lucrative income-producing property. Situated along the peaceful Intracoastal Waterway, this 1,645 sf. property blends comfort, luxury, and income potential

  Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

  1341 Siesta Bayside Dr Unit 1341B, Sarasota, FL 34242
• 

  

  /54

  Est $485,028 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit B31, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit B31, Sarasota, FL 34242
• 

  

  /43

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft

  310 Avenida Milano, Sarasota, FL 34242

  Discover the potential of this canal-front property, perfectly positioned just steps from Siesta Key Village and minutes from the island’s world-famous beach. This rare offering presents the perfect opportunity for visionaries, builders, or investors to renovate the existing home or build your custom luxury retreat in one of Sarasota’s most desirable coastal communities. With 75 linear feet of

  Domanic Calamese KW COASTAL LIVING III

  310 Avenida Milano, Sarasota, FL 34242
• 

  

  /57

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Condo for Rent

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

  Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot

  Beth Dilley ASCENDIA REAL ESTATE

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
• 

  /2

  $800,000 Sold Apr 04, 2025

  • 1,682 Sq Ft
  • $476/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  9393 Midnight Pass Rd Unit 704, Sarasota, FL 34242

  Rarely available–largest floor plan in The Pointe totally renovated with expansive 180-degree water views! Redesigned & remodeled for comfort & convenience, the exquisite finishes & details in this 7th floor coastal home will delight the most discerning buyers! All Impact Glass sliders & windows, porcelain tile throughout, abundant custom millwork & ample storage, a large full-sized laundry

  Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

  9393 Midnight Pass Rd Unit 704, Sarasota, FL 34242
• 

  

  /26

  Est $635,668 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242
• 

  

  /66

  $994,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  5353 Shadow Lawn Dr, Sarasota, FL 34242

  With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, world renown island of Siesta Key. Being offered Turnkey Finished negotiable, you are ready to move in and get to relaxing on this spacious lot of over a quarter acre of high and dry land. You will find yourself in a 3-bedroom, 2- bathroom ranch style

  Brittany McCord IRONGATE REALTY INC

  5353 Shadow Lawn Dr, Sarasota, FL 34242
• 

  

  /99

  $5,900 per month

  • 3 Beds
  • 3.5 Baths
  • 2,490 Sq Ft
  • Condo for Rent

  1660 Summerhouse Ln Unit 301, Sarasota, FL 34242

  LOCATION, LOCATION, LOCATION!!! Stunning large luxury condo located in the sought after community of Summer Cove on Siesta Key is available for an ANNUAL LEASE. This corner unit, light and bright property has been meticulously professionally decorated and it shows. Three bedrooms, three and a half bathrooms, turnkey furnished, three open lanais that face east and west, living room/kitchen/dining

  C. Alison Hunter JENNETTE PROPERTIES INC

  1660 Summerhouse Ln Unit 301, Sarasota, FL 34242
• 

  /2

  $965,000 Sold Apr 04, 2025

  • 1,737 Sq Ft
  • $556/SF
  • 165 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  1271 Dockside Place Unit 215, Sarasota, FL 34242

  Experience coastal living in this HIGH and DRY waterfront 3-bedroom, 2-bathroom condo on the sought-after Siesta Key. Perfectly positioned just steps from the renowned Siesta Key Beach, this second-floor gem offers unparalleled access to sun and sand, while a private boat slip and lift awaits your boating adventures.This turnkey-furnished condo is meticulously designed for both relaxation

  Debra Forkan COLDWELL BANKER REALTY

  1271 Dockside Place Unit 215, Sarasota, FL 34242
• 

  

  /35

  Est $437,387 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit A41, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit A41, Sarasota, FL 34242
• 

  

  /74

  $1,295,000

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft

  20 Whispering Sands Dr Unit 1201, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. A truly RARE offering, this TOP floor, GULF FRONT PENTHOUSE residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL

  Harriet Stopher COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 1201, Sarasota, FL 34242
• 

  

  /42

  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft
  • Condo for Rent

  6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

  Variable rent based on season

  Terry Dorrity INTEGRITY INVESTMENTS REALTY

  6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
• 

  /2

  $990,000 Sold Apr 03, 2025

  • 1,953 Sq Ft
  • $507/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  5159 Oakmont Place, Sarasota, FL 34242

  A HURRICANE SURVIVOR SUPERSTAR--NO DAMAGE HERE!! This CHARMING COASTAL HOME invites you to live the ultimate seaside dream! This home has been IMPECCABLY MAINTAINED and is in a GREAT LOCATION! Only 1.4 miles to the ICONIC #1 rated SIESTA KEY BEACH and 2.4 miles to SIESTA KEY VILLAGE. Surrounded by vibrant, beachy charm, this home offers the perfect escape- where relaxation meets adventure.

  Jenni Burnette COLDWELL BANKER REALTY

  5159 Oakmont Place, Sarasota, FL 34242
• 

  

  /42

  Est $755,510 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 969 Sq Ft

  9000 Blind Pass Rd Unit B313, Sarasota, FL 34242

  9000 Blind Pass Rd Unit B313, Sarasota, FL 34242
• 

  

  /46

  $1,795,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,511 Sq Ft

  4108 Roberts Point Rd, Sarasota, FL 34242

  Welcome to one of the most desirable streets on Siesta Key, Roberts Point Road. Just steps from Shell Beach and minutes from the north bridge, this home blends island charm with thoughtful updates, including a brand-new roof in 2024. Enter through a tranquil, private courtyard, ideal for quiet mornings or intimate entertaining before stepping into a stunning interior with soaring 22' ceilings and

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  4108 Roberts Point Rd, 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 April 1, 2026! 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, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 102, Sarasota, FL 34242
• 

  /2

  $2,200,000 Sold Apr 02, 2025

  • 2,635 Sq Ft
  • $835/SF
  • 81 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2003

  447 Canal Rd Unit 447, Sarasota, FL 34242

  Welcome to Grand Siesta! Rarely available Opportunity! Where else on Siesta Key can you find this unique location, offering Siesta Beach Access a block away, the Siesta Village two blocks away, directly on the Grand Canal with a boat lift, while all within the weekly rental zone. Paradise awaits at this fabulous, 3 bedroom/3.5 bath luxury townhouse. This amazing, spacious, luxury townhouse draws

  Joseph Kesslak COLDWELL BANKER REALTY

  447 Canal Rd Unit 447, Sarasota, FL 34242
• 

  

  /51

  Est $612,739 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 750 Sq Ft

  9000 Blind Pass Rd Unit B303, Sarasota, FL 34242

  9000 Blind Pass Rd Unit B303, Sarasota, FL 34242

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