Siesta Key, FL Homes

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  /44

  $115,000

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft

  915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242

  Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 4-7), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on America’s

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 842-0963

  915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242
• 

  

  

  /25

  $12,296 Per Month

  • 2 Beds
  • 2 Baths
  • 1,319 Sq Ft
  • House for Rent

  6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

  Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
• 

  

  /2

  $1,300,000 Sold Jan 30, 2026

  5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,471 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Below List Price
  • $884/SF
  • 107 Days On Market

  Current Estimated Value $1,312,451

  Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242
• 

  

  /2

  Not Listed For Sale

  915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,255 Sq Ft
  • Built 2009

  915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

  Last Sold Summary

  • $8/SF
  • 40 Days On Market

  • Last Sold Price $17,000
  • Jan 29, 2025

  Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN
• 

  

  

  /51

  $60,000

  • 4 Beds
  • 4 Baths
  • 2,625 Sq Ft

  915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242

  Fractional Ownership. Experience elevated beachfront living with this Deluxe, Guaranteed Gulf View, Spring (April) Fractional Ownership opportunity—offering one-sixteenth ownership on Siesta Key Beach, consistently ranked as America’s #1 beach. This rare fractional real estate offering delivers luxury coastal living, prime spring usage, and true Gulf-front views without the full-ownership price

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 369-8950

  915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242
• 

  

  /27

  $5,200 Per Month

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

  1255 E Peppertree Dr Unit 602, Sarasota, FL 34242

  Enjoy Gulf of Mexico views from our recently renovated penthouse apartment on Siesta Key. You will have access to the #1 beach in the US with white powder sand and warm gulf waters. Enjoy beautiful views of the gulf from our full-length lanai and both bedrooms.The condominium offers multiple heated swimming pools, beach side and bay side grills, fishing pier, and a recently renovated exercise

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 602, Sarasota, FL 34242
• 

  /2

  $1,100,000 Sold Jun 27, 2025

  4857 Primrose Path, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,519 Sq Ft
  • Built 1957

  Last Sold Summary

  • 37% Below List Price
  • $437/SF
  • 83 Days On Market

  Current Estimated Value $1,048,333

  Last Listing Agent Nadiya Marisol-Pote DALTON WADE INC

  4857 Primrose Path, Sarasota, FL 34242
• 

  /2

  Est $762,316 Not Listed For Sale

  5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,211 Sq Ft
  • Built 1976

  5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

  Last Sold Summary

  • 4% Below List Price
  • $654/SF
  • 80 Days On Market

  • Last Sold Price $792,000
  • Apr 01, 2025

  Last Listing Agent Kelli Eggen COLDWELL BANKER REALTY
• 

  

  /90

  $6,400,000

  • 12 Beds
  • 11 Baths
  • 5,313 Sq Ft

  662 Calle Del Otono, Siesta Key, FL 34242

  Charming mini-resort with lagoon-style pool and waterfall, sun decks, tropical landscaped gardens. Just steps from Siesta Key Public Beach. Free Trolley transports guests to Siesta Key Village for shopping, dining and a supermarket. Income Producing Property priced to sell at a Seven Cap. Two lots, 19 & 20 with 2 Duplexes.

  

  Tonna Gruber

  COLDWELL BANKER REALTY

  (941) 732-8615

  662 Calle Del Otono, Siesta Key, FL 34242
• 

  

  /41

  $7,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

  Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
• 

  /2

  $650,000 Sold Jul 30, 2025

  813 Plymouth St, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,919 Sq Ft
  • Built 1953

  Last Sold Summary

  • 43% Below List Price
  • $223/SF
  • 130 Days On Market

  Current Estimated Value $1,005,948

  Last Listing Agent Georgia Salaverri COMPASS FLORIDA LLC

  813 Plymouth St, Sarasota, FL 34242
• 

  

  /47

  Est $2,245,299 Not Listed For Sale

  6906 Bochi Cir, Sarasota, FL 34242

  • 4 Beds
  • 4.5 Baths
  • 4,358 Sq Ft
  • Built 2012

  6906 Bochi Cir, Sarasota, FL 34242

  Last Sold Summary

  • 8% Above List Price
  • $476/SF
  • 228 Days On Market

  • Last Sold Price $2,075,000
  • May 02, 2023

  Last Listing Agent Malia Smiley KELLY RIGHT REAL ESTATE
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  /52

  $59,000

  • 3 Beds
  • 3 Baths
  • 1,780 Sq Ft

  915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242

  Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 271-5462

  915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242
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  /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 Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 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 portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

  Margaret Young JENNETTE PROPERTIES, INC.

  1257 S Portofino Dr Unit 36, Sarasota, FL 34242
• 

  /2

  $3,000,000 Sold Oct 15, 2025

  137 Big Pass Ln, Sarasota, FL 34242

  • 5 Beds
  • 4.5 Baths
  • 4,486 Sq Ft
  • Built 2006

  Last Sold Summary

  • 30% Below List Price
  • $669/SF
  • 148 Days On Market

  Last Listing Agent Dion Souza SARABAY REAL ESTATE INC

  137 Big Pass Ln, Sarasota, FL 34242
• 

  

  /68

  Est $638,946 Not Listed For Sale

  101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

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

  101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

  Last Sold Summary

  • 2% Below List Price
  • $515/SF
  • 51 Days On Market

  • Last Sold Price $655,000
  • Apr 26, 2024

  Last Listing Agent Daria Fairchild COLDWELL BANKER REALTY
• 

  

  /59

  $635,000

  • 2 Beds
  • 1 Bath
  • 1,373 Sq Ft

  5019 Commonwealth Dr, Sarasota, FL 34242

  PRICED to Sell! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision whether you’re

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 842-0059

  5019 Commonwealth Dr, Sarasota, FL 34242
• 

  

  /22

  $6,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,288 Sq Ft
  • House for Rent

  5157 Sandy Beach Ave, Sarasota, FL 34242

  Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee at LeLu Coffee Lounge. 4 bedrooms and 2.5 baths brings you back inside with a

  Joseph Meszaros M&M PROPERTY MANAGEMENT GROUP

  5157 Sandy Beach Ave, Sarasota, FL 34242
• 

  /2

  $1,640,000 Sold Mar 24, 2026

  5880 Midnight Pass Rd Unit 710, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,713 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $957/SF
  • 27 Days On Market

  Current Estimated Value $1,670,634

  Last Listing Agent Kristina Rain MICHAEL SAUNDERS & COMPANY

  5880 Midnight Pass Rd Unit 710, Sarasota, FL 34242
• 

  

  /84

  Est $619,211 Not Listed For Sale

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1970

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  Last Sold Summary

  • 14% Below List Price
  • $560/SF
  • 86 Days On Market

  • Last Sold Price $717,500
  • Dec 22, 2023

  Last Listing Agent Lisa Garcia COLDWELL BANKER REALTY
• 

  

  /99

  $5,392,000 New Construction

  • 4 Beds
  • 6 Baths
  • 4,220 Sq Ft

  4819 Higel Ave, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 394-0863

  4819 Higel Ave, Sarasota, FL 34242
• 

  

  /31

  $7,000 Per Month

  • 2 Beds
  • 11 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1200 E Peppertree Ln Unit 303, Sarasota, FL 34242

  This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
• 

  /2

  $452,000 Sold Dec 18, 2025

  73 Avenida Messina Unit 15, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $1,108/SF

  Current Estimated Value $457,612

  Last Listing Agent Maxwell Mann MICHAEL SAUNDERS & COMPANY

  73 Avenida Messina Unit 15, Sarasota, FL 34242
• 

  /2

  Not Listed For Sale

  915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242

  • 2 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Built 2009

  915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242

  Last Sold Summary

  • $7/SF
  • 159 Days On Market

  • Last Sold Price $13,000
  • Feb 12, 2025

  Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN
• 

  

  /9

  $4,800,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,765 Sq Ft

  533 Venice Ln, Sarasota, FL 34242

  Under Construction. New Construction. This stunning new waterfront home is perfectly positioned on Siesta Key’s Grand Canal, offering excellent boating water with quick access to Sarasota Bay. The residence features 4 bedrooms, 5 full baths (including a pool bath), and 1 half bath, along with two laundry rooms conveniently located on the first and third floors. A spacious third-floor loft

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 206-4697

  533 Venice Ln, Sarasota, FL 34242
• 

  

  /30

  $3,500 Per Month

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

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242

  BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai,

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242
• 

  /2

  $990,000 Sold Jun 25, 2025

  20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • Built 1973

  Last Sold Summary

  • 38% Below List Price
  • $676/SF
  • 117 Days On Market

  Current Estimated Value $1,034,510

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 306, Sarasota, FL 34242
• 

  /2

  Est $1,380,943 Not Listed For Sale

  312 Calle Miramar Unit S1, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 2008

  312 Calle Miramar Unit S1, Sarasota, FL 34242

  Last Sold Summary

  • 8% Below List Price
  • $984/SF
  • 1 Day On Market

  • Last Sold Price $1,495,000
  • Aug 05, 2024

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY
• 

  

  /11

  $4,950,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 4,158 Sq Ft

  527 Venice Ln, Sarasota, FL 34242

  Under Construction. Be the first owner of this exceptional new construction home. Enjoy gorgeous, wide Grand Canal views with quick access to Sarasota Bay—a true boater’s dream. This home showcases high-end construction at its core, featuring a standing seam metal roof, hurricane-impact windows and sliders, elegant stone detailing, and meticulous craftsmanship throughout—no detail has been

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 390-2066

  527 Venice Ln, Sarasota, FL 34242
• 

  

  /16

  $8,370 Per Month

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242

  Villa 45 at Aloha Kai is a light-filled coastal retreat featuring an updated kitchen that perfectly complements its bright, beachy furnishings. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king bed and two twin beds, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
• 

  /2

  $400,000 Sold Aug 20, 2025

  6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft
  • Built 1974

  Last Sold Summary

  • 26% Below List Price
  • $300/SF
  • 86 Days On Market

  Current Estimated Value $428,256

  Last Listing Agent Julia Montei COLDWELL BANKER REALTY

  6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242
• 

  

  /27

  Est $714,823 Not Listed For Sale

  5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Built 1975

  5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

  Last Sold Summary

  • 10% Below List Price
  • $762/SF
  • 0 Days On Market

  • Last Sold Price $795,000
  • Jun 07, 2024

  Last Listing Agent Linda Stowe Michael Saunders
• 

  

  /60

  $2,249,000

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  5361 Siesta Ct, Sarasota, FL 34242

  Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior doors with switchable

  David James CHARLES RUTENBERG REALTY INC

  5361 Siesta Ct, Sarasota, FL 34242
• 

  

  /10

  $8,340 Per Month

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242

  C6 is a lovely unit, has been remodeled and is awaiting your arrival. It can accommodate up to 6. The spacious living room/dining room has all new furniture, including a large couch, two recliners, coffee, and end tables. In the dining area you will find a new dining table and chairs and a ceiling fan. There is also a wall-mounted 55” UHD Smart TV. The very large Master Bedroom has a king-size

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
• 

  /2

  $1,230,000 Sold Feb 20, 2026

  5354 Calle Florida, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 2,659 Sq Ft
  • Built 1954

  Last Sold Summary

  • 7% Below List Price
  • $463/SF
  • 96 Days On Market

  Current Estimated Value $1,213,115

  Last Listing Agent Angelica Ridley KW COASTAL LIVING III

  5354 Calle Florida, Sarasota, FL 34242
• 

  

  /53

  Est $497,214 Not Listed For Sale

  44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • Built 1968

  44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

  Last Sold Summary

  • 12% Below List Price
  • $1,007/SF
  • 3 Days On Market

  • Last Sold Price $565,000
  • May 23, 2024

  Last Listing Agent Veronica Murphy KELLER WILLIAMS ON THE WATER S
• 

  

  /75

  $2,450,000

  • 3 Beds
  • 2 Baths
  • 2,276 Sq Ft

  4508 Woodside Rd, Sarasota, FL 34242

  Luxury Waterfront Living - Now Priced to Move Welcome to 4508 Woodside Rd., a true boater’s paradise on Siesta Key offering privacy, deep-water access, and refined coastal living. Positioned on one of the island’s deepest canals, this exceptional waterfront property provides quick access to the Intracoastal Waterway and Sarasota Bay, featuring 95 feet of waterfrontage and a 75-foot dock designed

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  4508 Woodside Rd, Sarasota, FL 34242
• 

  

  /76

  $2,950 Per Month

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Condo for Rent

  1700 Cove II Place Unit 310, Sarasota, FL 34242

  Available 2950.00 Monthly - April 20th 2026 through December 31st 2026... Not Available 2027 Jan through April 15th 2027 Stunning Water Views & Deeded Beach Access | Siesta Keyplus taxes and fees. Live your Dream on Siesta Key for the Summer...Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and

  Robert Bevington SHOWTIME REALTY

  1700 Cove II Place Unit 310, Sarasota, FL 34242
• 

  /2

  $575,000 Sold Apr 27, 2026

  5830 Midnight Pass Rd Unit 94, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 921 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $624/SF
  • 56 Days On Market

  Current Estimated Value $594,169

  Last Listing Agent Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY

  5830 Midnight Pass Rd Unit 94, Sarasota, FL 34242
• 

  /2

  Est $532,758 Not Listed For Sale

  1257 S Portofino Dr Unit 406, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Built 1968

  1257 S Portofino Dr Unit 406, Sarasota, FL 34242

  Last Sold Summary

  • 9% Below List Price
  • $630/SF
  • 22 Days On Market

  • Last Sold Price $585,000
  • Dec 19, 2024

  Last Listing Agent Curtis Ware KW COASTAL LIVING III

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