Siesta Key, FL Homes

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  $1,275,000

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  6140 Midnight Pass Rd Unit 407, Sarasota, FL 34242

  Nestled on the renowned Crescent Beach, Horizon’s West offers a truly exceptional Siesta Key beachfront living experience, where breathtaking Gulf views and unforgettable sunsets become part of everyday life. This beautiful 2-bedroom, 2-bathroom condominium, located on the fourth floor, delivers luxury, privacy, and a prime Gulf-front location on Siesta Key. This updated, turn-key furnished condo

  Brian Partie ENGEL + VOELKERS SARASOTA

  6140 Midnight Pass Rd Unit 407, Sarasota, FL 34242
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  /14

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 202, Sarasota, FL 34242

  Second-Floor Condo in Sought-After Peppertree Bay. 30 day minimum stay. Starting between $250-$347/night!Welcome to this beautifully maintained second-floor condo located in the highly desirable Peppertree Bay community on Siesta Key. Offering a tranquil pond view, this residence provides a peaceful coastal retreat just steps from the Gulf.The condo features a full kitchen equipped with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 202, Sarasota, FL 34242
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  $325,000 Sold Dec 31, 2025

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $256/SF
  • 25 Days On Market

  Last Listing Agent Julie Froeschle BERKSHIRE HATHAWAY HOMESERVICE

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242
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  /2

  Est $8,416,775 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 6,838 Sq Ft

  241 Cedar Park Cir, Sarasota, FL 34242

  241 Cedar Park Cir, Sarasota, FL 34242
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  /58

  $1,250,000 Open Sat 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft

  4822 Ocean Blvd Unit 9A, Sarasota, FL 34242

  In a word...Stunning. Introducing this fully renovated and stylishly furnished 9th floor condominium offering refined Gulf-front living on Siesta Key, where breathtaking sunsets and gentle Gulf breezes set the tone for everyday life. This beautifully redesigned 1,435-square-foot residence features two bedrooms and two full baths and was completely renovated in 2020 with quality finishes and

  Darlene Gamble FINE PROPERTIES

  4822 Ocean Blvd Unit 9A, Sarasota, FL 34242
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  /26

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 702, Sarasota, FL 34242

  This property is a 30 night minimum. This 2 bedroom, 2 bath is in a Gulf-side High-rise unit, located approximately 175 yards from Crescent Beach.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and beautiful views of the beach through the lanai sliding glass doors. The master bathroom has a tub/shower combination with updated finishes and grab bars.The guest bedroom has a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 702, Sarasota, FL 34242
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  /2

  $1,259,000 Sold Jul 16, 2025

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1973

  Last Sold Summary

  • 10% Below List Price
  • $982/SF
  • 61 Days On Market

  Current Estimated Value $1,196,185

  Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242
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  /66

  Est $467,788 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft

  1300 N Portofino Dr Unit 202, Sarasota, FL 34242

  1300 N Portofino Dr Unit 202, Sarasota, FL 34242
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  /37

  $599,000 Pending

  • 1 Bed
  • 1 Bath
  • 1,040 Sq Ft

  5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242

  Under contract-accepting backup offers. Located in the highly sought-after Gulf Haven Community, this beautifully renovated residence offers a rare opportunity to enjoy private beachfront living on the sugar-white sands of world-famous Siesta Key Beach, shared exclusively by just 50 owners. No crowds, no competition for space for your beach chair or blanket, just pure relaxation. With over 1,000

  Keith Redding WILLIAM RAVEIS REAL ESTATE

  5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242
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  /24

  $11,105 per month

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft
  • Apartment for Rent

  1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242

  This property is a 30 night minimum. This 2 bedroom, 2 full bath unit is located in a Gulfside Highrise, only steps from Crescent Beach. An open concept living space flows nicely from the formal dining to spectacular views of Peppertree Pond on the lanai. The living area has plenty of comfortable seating for the entire family, a 55" Smart TV, and glass door lanai access. The kitchen has been

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242
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  /2

  $990,000 Sold Apr 03, 2025

  5159 Oakmont Place, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,953 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $507/SF
  • 47 Days On Market

  Current Estimated Value $931,157

  Last Listing Agent Jenni Burnette COLDWELL BANKER REALTY

  5159 Oakmont Place, Sarasota, FL 34242
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  /2

  Est $449,615 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  6415 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  6415 Midnight Pass Rd Unit 206, Sarasota, FL 34242
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  /37

  $1,095,000

  • 4 Beds
  • 3.5 Baths
  • 2,314 Sq Ft

  5151 Saint Albans Ave, Sarasota, FL 34242

  Charming Coastal Oasis in the Heart of Siesta KeyNestled on a serene, tree-lined property, this inviting 4-bedroom, 3.5-bath beach-style home offers the perfect blend of tranquility, charm, and central location. Step into a spacious, light-filled living area with an open kitchen layout—ideal for hosting friends and making family memories. Freshly updated with new paint, gleaming quartz

  Dianne Anderson COMPASS FLORIDA LLC

  5151 Saint Albans Ave, Sarasota, FL 34242
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  /27

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 701, Sarasota, FL 34242

  2 BR -- 2 BA -- 4 Person Max -- High Rise -- Beach ViewThis property is a 30 night minimum.This 2 bedroom, 2 bath is in a Gulf-side High-rise unit, located approximately 175 yards from Crescent Beach.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and beautiful views of the beach through the lanai sliding glass doors. The master bathroom has a tub/shower combination

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 701, Sarasota, FL 34242
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  /2

  $700,000 Sold Dec 08, 2025

  4637 Ocean Blvd, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,065 Sq Ft
  • Built 1952

  Last Sold Summary

  • 20% Below List Price
  • $339/SF
  • 73 Days On Market

  Last Listing Agent Albert Wooster ALBERT WOOSTER & COMPANY

  4637 Ocean Blvd, Sarasota, FL 34242
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  /32

  Est $1,421,201 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,277 Sq Ft

  4708 Ocean Blvd Unit E1, Sarasota, FL 34242

  4708 Ocean Blvd Unit E1, Sarasota, FL 34242
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  /18

  $799,900 Pending

  • Land
  • 0.18 Acre
  • $4,443,889 per Acre

  0 Avenida Leona, Siesta Key, FL 34242

  Under contract-accepting backup offers. 20% Down Seller Financing Offered. Design Your Legacy on Siesta Key – Premier Waterfront Lot in Siesta ManorWelcome to Lot 17 on Avenida Leona—an extraordinary opportunity to create your own masterpiece in one of Florida’s most coveted coastal enclaves. Nestled along a private, tree-lined lane in Siesta Manor, this canal-front parcel offers the rare

  Ron Pepka KW SUNCOAST

  0 Avenida Leona, Siesta Key, FL 34242
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  /26

  $6,650 per month

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 705, Sarasota, FL 34242

  This property is a 30 night minimum.1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach.Open kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai). Condo

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
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  $1,700,000 Sold Aug 21, 2025

  1031 Contento St, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft
  • Built 1971

  Last Sold Summary

  • 3% Below List Price
  • $917/SF
  • 24 Days On Market

  Current Estimated Value $1,639,055

  Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1031 Contento St, Sarasota, FL 34242
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  /67

  Est $1,695,777 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,063 Sq Ft

  4960 Commonwealth Dr, Sarasota, FL 34242

  4960 Commonwealth Dr, Sarasota, FL 34242
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  /45

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  1358 Moonmist Dr Unit B4, Sarasota, FL 34242

  Exceptional waterfront villa on the Intracoastal Waterway in the heart of Siesta Key. Located in the highly sought-after Polynesian Gardens, this rare 3-bedroom residence offers the space and feel of a single-family home with the ease of condominium living. Designed for seamless indoor-outdoor coastal living, the open great room is anchored by massive 10' x 9' Euro Vista folding doors, flanked by

  Nadiya Marisol-Pote DALTON WADE INC

  1358 Moonmist Dr Unit B4, Sarasota, FL 34242
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  /20

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 53, Sarasota, FL 34242

  Starting at $179/night! Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, featuring a king-sized bed in the primary suite and a comfortable sleeper sofa in the living area. This stylish retreat boasts a fully equipped kitchen adjoining a spacious dining area, ideal for entertaining or relaxing meals. Enjoy the convenience of a private carport just steps from your door, while

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 53, Sarasota, FL 34242
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  $875,000 Sold Sep 25, 2025

  5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1979

  Last Sold Summary

  • 20% Below List Price
  • $643/SF
  • 493 Days On Market

  Current Estimated Value $863,385

  Last Listing Agent Carol Thomas MICHAEL SAUNDERS & COMPANY

  5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242
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  /36

  Est $1,331,062 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft

  5790 Midnight Pass Rd Unit 608, Sarasota, FL 34242

  5790 Midnight Pass Rd Unit 608, Sarasota, FL 34242
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  /39

  $705,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  6263 Midnight Pass Rd Unit 105, Sarasota, FL 34242

  Huge Price Reduction!! Stunning Beach-to-Bay Condo on Siesta Key – 2 Bed, 2 Bath Excelsior Beach to Bay Condo Discover your perfect slice of paradise at this beautifully appointed 2-bedroom, 2-bathroom condo located in the coveted Excelsior Beach to Bay community on Siesta Key. This light-filled retreat offers the ultimate Florida lifestyle, with private beach access to the powdery white sands of

  Randy Owens COLDWELL BANKER REALTY

  6263 Midnight Pass Rd Unit 105, Sarasota, FL 34242
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  /25

  $7,650 per month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242

  Starting at $255/night! Experience the ultimate beachfront getaway at Villa 40, a beautifully appointed 2-bedroom, 2-bathroom condo at Casa Mar, thoughtfully designed to accommodate up to six guests in comfort and style. This spacious retreat features a king bed in the primary bedroom, two twin beds in the second bedroom, and a queen air mattress for added flexibility. The fully equipped kitchen

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
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  $8,100,000 Sold Feb 27, 2025

  3960 Roberts Point Rd, Sarasota, FL 34242

  • 4 Beds
  • 7 Baths
  • 5,282 Sq Ft
  • Built 2024

  Last Sold Summary

  • 9% Below List Price
  • $1,534/SF
  • 145 Days On Market

  Current Estimated Value $7,483,667

  Last Listing Agent Tammy Dentici BRIGHT REALTY

  3960 Roberts Point Rd, Sarasota, FL 34242
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  /35

  Est $637,047 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 940 Sq Ft

  915 Beach Rd Unit 114, Sarasota, FL 34242

  915 Beach Rd Unit 114, Sarasota, FL 34242
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  /90

  $1,365,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  445 Reid St, Sarasota, FL 34242

  Coastal Chic meets Contemporary Classic on Siesta Key. This 3-bed, 2-bath oasis with saltwater pool boasts 1,750 square feet under air, $100,000 in upgrades and $50,000+ in brand new designer furnishings from Crate & Barrel. In 2025, the owners installed new tile flooring throughout the home, all new appliances, new washer & dryer, new doors (except the front door), new water heater and pool

  Robin Leonardi MICHAEL SAUNDERS & COMPANY

  445 Reid St, Sarasota, FL 34242
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  /16

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 24, Sarasota, FL 34242

  Starting at $179/night! Step into your perfect beach getaway with this charming ground-floor 1-bedroom unit located in the sought-after Casa Mar complex, just off Midnight Pass Road and only steps from the sand. Relax on the screened lanai overlooking a peaceful courtyard, where two sparkling pools invite you to unwind in the Florida sunshine. A short stroll along the sidewalk brings you directly

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 24, Sarasota, FL 34242
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  $500,000 Sold Nov 21, 2025

  4189 Roberts Point Cir, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft
  • Built 1930

  Last Sold Summary

  • 38% Below List Price
  • $285/SF
  • 315 Days On Market

  Last Listing Agent Shane Lewis MICHAEL SAUNDERS & COMPANY

  4189 Roberts Point Cir, Sarasota, FL 34242
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  /76

  Est $622,025 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  5855 Midnight Pass Rd Unit 505, Sarasota, FL 34242

  5855 Midnight Pass Rd Unit 505, Sarasota, FL 34242
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  /51

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  1260 Dolphin Bay Way Unit 404, Sarasota, FL 34242

  ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a

  Mina Johnson MICHAEL SAUNDERS & COMPANY

  1260 Dolphin Bay Way Unit 404, Sarasota, FL 34242
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  /21

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 54, Sarasota, FL 34242

  Starting from $179/night! Experience the charm of Villa 54, a 1-bedroom, 1-bathroom retreat at Casa Mar. Relax in the luxurious king-sized bed in the master bedroom, complemented by a cozy sleeper sofa in the spacious living area. Prepare gourmet meals in the fully equipped kitchen that seamlessly flows into an elegant dining space, perfect for entertaining or quiet meals. Outside, enjoy the

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 54, Sarasota, FL 34242
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  /2

  $712,000 Sold Nov 21, 2025

  5600 Beach Way Dr Unit 304, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Below List Price
  • $602/SF
  • 72 Days On Market

  Last Listing Agent Janell Stuckwisch EXP REALTY LLC

  5600 Beach Way Dr Unit 304, Sarasota, FL 34242
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  /49

  Est $662,483 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  5855 Midnight Pass Rd Unit 209, Sarasota, FL 34242

  5855 Midnight Pass Rd Unit 209, Sarasota, FL 34242
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  /46

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  1260 Dolphin Bay Way Unit 301, Sarasota, FL 34242

  Discover this truly exceptional 3-bedroom, 3-bathroom condominium offering mesmerizing views of the Intracoastal Waterway. Redesigned with modern elegance, this home features a spacious chef's kitchen equipped with Sub Zero, Monogram, and Viking appliances, along with an impressive six-foot-tall built-in double-door wine cellar. This stunning residence boasts 9-foot ceilings, copious custom

  Mina Johnson MICHAEL SAUNDERS & COMPANY

  1260 Dolphin Bay Way Unit 301, Sarasota, FL 34242
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  /24

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 22, Sarasota, FL 34242

  Starting at $179/night. Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, where comfort and style meet just steps from the beach. The spacious primary suite features a king-sized bed, while the fully equipped kitchen flows seamlessly into a generous dining area and inviting living room, perfect for relaxing or entertaining. Step outside to enjoy a screened-in lanai furnished

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 22, Sarasota, FL 34242
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  /2

  $875,000 Sold May 19, 2025

  1900 Cove II Place Unit 135, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • Built 1979

  Last Sold Summary

  • $707/SF

  Current Estimated Value $827,493

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1900 Cove II Place Unit 135, Sarasota, FL 34242
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  /34

  Est $1,088,774 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft

  5579 Cape Aqua Dr, Sarasota, FL 34242

  5579 Cape Aqua Dr, Sarasota, FL 34242

Showing Results 441 - 480, Page 12 of 18