Longboat Key, FL Homes

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  /17

  $589,000

  • Land
  • 0.19 Acre
  • $3,100,000 per Acre

  620 Companion Way, Longboat Key, FL 34228

  A fabulous opportunity to build your dream home on the lowest priced single family vacant lot in all of Longboat Key! Enjoy deeded beach access just across Gulf of Mexico Drive. Surrounded by multi million dollar homes and with walking or biking distance to multiple restaurants, shopping, Cedars Tennis club, and the tree lined splendor of Joan Durante Park, this is where your island living dream

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  620 Companion Way, Longboat Key, FL 34228
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  /55

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Condo for Rent

  3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You

  Andy Moore GULF COAST REALTY & MANAGEMENT

  3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  /2

  $1,150,000 Sold Jan 08, 2026

  4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft
  • Built 1980

  Last Sold Summary

  • 15% Below List Price
  • $693/SF
  • 117 Days On Market

  Last Listing Agent Ian Greenberg BRISTA REALTY LLC

  4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /49

  Est $839,744 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /52

  $485,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  4440 Exeter Dr Unit 204, Longboat Key, FL 34228

  Unmatched Intracoastal Views + Premium Upgrades + New Roof = Exceptional Value! The standout feature is a fully enclosed lanai with brand-New Hurricane-Impact sliding doors (2025) ,New HVAC system (2025-valued at $16,000), a New water heater(2025), Fresh interior paint, and new king-size bedding in the primary suite(2025). Combined with the in-kitchen washer & dryer and a bidet, this residence is

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4440 Exeter Dr Unit 204, Longboat Key, FL 34228
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  /39

  $30,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,230 Sq Ft
  • House for Rent

  6925 Longboat Dr S, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful decor

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  6925 Longboat Dr S, Longboat Key, FL 34228
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  /2

  $435,000 Sold Dec 19, 2025

  1965 Gulf of Mexico Dr Unit G5304, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 933 Sq Ft
  • Built 1977

  Last Sold Summary

  • 13% Below List Price
  • $466/SF
  • 112 Days On Market

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  1965 Gulf of Mexico Dr Unit G5304, Longboat Key, FL 34228
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  /47

  Est $1,275,546 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  1135 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  1135 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /27

  $550,000

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  5841 Gulf of Mexico Dr Unit 236, Longboat Key, FL 34228

  Enjoy relaxed coastal living in this turnkey furnished 1 bedroom, 1 bath residence located in the Gulf front community of Silver Sands Gulf Beach Resort. This first floor unit features an open living and dining layout that extends to a private screened lanai overlooking the communities tropical landscaping. Recent improvements include a new A/C system, new kitchen appliances, and a new hot water

  Stephen Strong MICHAEL SAUNDERS & COMPANY

  5841 Gulf of Mexico Dr Unit 236, Longboat Key, FL 34228
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  /41

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • Property for Rent

  1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228

  Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
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  /2

  $925,000 Sold Dec 15, 2025

  1000 Longboat Club Rd Unit 1103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $656/SF
  • 17 Days On Market

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  1000 Longboat Club Rd Unit 1103, Longboat Key, FL 34228
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  /18

  Est $236,131 Not Listed For Sale

  • Studio

  2600 Harbourside Dr Unit K-01, Longboat Key, FL 34228

  2600 Harbourside Dr Unit K-01, Longboat Key, FL 34228
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  /77

  $699,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true

  John Esser KELLER WILLIAMS ON THE WATER S

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /72

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Condo for Rent

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and

  C. Alison Hunter JENNETTE PROPERTIES INC

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
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  /2

  $9,795,000 Sold Jun 27, 2025

  1561 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 4,992 Sq Ft
  • Built 2024

  Last Sold Summary

  • $1,962/SF
  • 0 Days On Market

  Last Listing Agent Georgia Kopelousos COLDWELL BANKER REALTY

  1561 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /91

  Est $1,996,355 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,485 Sq Ft

  2165 Gulf of Mexico Dr Unit 125, Longboat Key, FL 34228

  2165 Gulf of Mexico Dr Unit 125, Longboat Key, FL 34228
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  /55

  $1,295,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,239 Sq Ft

  3543 Mistletoe Ln, Longboat Key, FL 34228

  Under contract-accepting backup offers. Located in the gated waterfront community of Coreys Landing within Bay Isles, this beautifully maintained 3BR residence offers refined design, comfort, and privacy. A paver walkway and lush tropical landscaping lead to the home’s centerpiece - a private courtyard pool surrounded by high privacy walls and tropical foliage, creating a tranquil space for

  Bruce Myer COLDWELL BANKER REALTY

  3543 Mistletoe Ln, Longboat Key, FL 34228
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  /30

  $11,769 per month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228

  ..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
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  /2

  $505,000 Sold Dec 15, 2025

  1945 Gulf of Mexico Dr Unit M2207, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $469/SF
  • 139 Days On Market

  Last Listing Agent Harold Kaufman PREFERRED SHORE LLC

  1945 Gulf of Mexico Dr Unit M2207, Longboat Key, FL 34228
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  /53

  Est $841,542 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  Unlisted Address

  Unlisted Address
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  /30

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft

  620 Spanish Dr N, Longboat Key, FL 34228

  Some Photo's have been virtually staged. Don't miss this rare opportunity to own a renovated standalone villa with a lake view on Longboat Key! This very light, bright, and charming 2 bedroom 2 bath home is almost ready for occupancy at an exceptionally low price. As you enter the home, you can see a lovely lake view through the large back windows. The rear, shady, landscaped patio is a perfect

  Adrienne Scott MICHAEL SAUNDERS & COMPANY

  620 Spanish Dr N, Longboat Key, FL 34228
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  /23

  $9,587 per month

  • 3 Beds
  • 2.5 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

  THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
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  /2

  $440,000 Sold Feb 02, 2026

  106 Twin Shores Blvd, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 763 Sq Ft
  • Built 1950

  Last Sold Summary

  • $577/SF
  • 0 Days On Market

  Last Listing Agent Kelly Fullick COLDWELL BANKER REALTY

  106 Twin Shores Blvd, Longboat Key, FL 34228
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  /63

  Est $1,467,461 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,530 Sq Ft

  621 Buttonwood Dr, Longboat Key, FL 34228

  621 Buttonwood Dr, Longboat Key, FL 34228
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  /67

  $750,000

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft

  490 N Shore Rd Unit 6, Longboat Key, FL 34228

  This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a small, waterfront, boutique midrise building containing only 9 residences: this is island living at its best! It features two bedrooms and 2 and a half

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  490 N Shore Rd Unit 6, Longboat Key, FL 34228
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  /24

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228

  Available March 2026. Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico . The master suite features a

  Shaun Cumston STERLING REALTY

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
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  /2

  $1,000,000 Sold Apr 25, 2025

  3360 Bayou, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1981

  Last Sold Summary

  • 23% Below List Price
  • $520/SF
  • 5 Days On Market

  Current Estimated Value $1,330,510

  Last Listing Agent Stephen Strong MICHAEL SAUNDERS & COMPANY

  3360 Bayou, Longboat Key, FL 34228
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  /61

  Est $1,147,335 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /67

  $4,995,000

  • 3 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  681 Old Compass Rd, Longboat Key, FL 34228

  Welcome to a crisp & clean Florida ranch. Located in popular Emerald Harbor which is a bayside enclave of just 82 homes. Homes are located on broad lagoon-style canals that provide direct boating access to Sarasota Bay. 20 ft. private Beach access is a real bonus for sunworshippers. This 3 bedroom 3.5 bath custom home blends Dutch Cape and West Indies architectural style. It is a split design

  Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  681 Old Compass Rd, Longboat Key, FL 34228
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  /25

  $5,835 per month

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will

  Andy Moore GULF COAST REALTY & MANAGEMENT

  3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
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  /48

  $1,170,000 Sold Mar 11, 2025

  4825 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $840/SF
  • 94 Days On Market

  Current Estimated Value $1,083,595

  Last Listing Agent Michael Albano, PA COLDWELL BANKER REALTY

  4825 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /45

  Est $1,027,989 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228
• 

  

  /54

  $5,280,000

  • 4 Beds
  • 6 Baths
  • 4,145 Sq Ft

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228

  Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers

  Toni Zarghami KW COASTAL LIVING III

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /75

  $25,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft
  • Condo for Rent

  455 Longboat Club Rd Unit 1, Longboat Key, FL 34228

  This EXQUISITE 3 bedroom - 3 1⁄2 bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom appointments throughout. Natural light fills the condo from the moment you enter the foyer and a large skylight is overhead. Floor to ceiling windows frame the 14’ ceiling’s perimeter creating a

  Teresa Ribaudo JENNETTE PROPERTIES INC

  455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
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  /2

  $640,000 Sold Oct 07, 2025

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $459/SF
  • 11 Days On Market

  Current Estimated Value $827,768

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /28

  Est $2,941,335 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /5

  $43,500

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228

  Welcome to Slip #2112 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6''Lx8'6''Wx7'2''H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228
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  /12

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228

  LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
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  /2

  $3,170,000 Sold Aug 08, 2025

  689 Lands End Dr, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 3,254 Sq Ft
  • Built 2005

  Last Sold Summary

  • 17% Below List Price
  • $974/SF
  • 140 Days On Market

  Current Estimated Value $3,102,663

  Last Listing Agent Matthew Voss PREFERRED SHORE LLC

  689 Lands End Dr, Longboat Key, FL 34228
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  /67

  Est $1,511,077 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

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