Vintage homes for sale & real estate in Longboat Key, FL

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ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
One or more photo(s) has been virtually staged. Presenting a stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. This sophisticated, move-in ready home offers an abundance of good vibes and professional quality, available now on the highly sought-after North End of exclusive Longboat Key. Sleek, chic, and absolutely move-in ready, this property is an instant atmosphere setter. From the moment you step inside, you'll feel the coastal modern bliss. Enjoy the clean, modern lines, vaulted ceilings, and stunning stone tile floors, all bathed in gorgeous southern sun light. The upgraded kitchen and bathrooms sparkle with new features, compleme

$840,000

3 beds3 baths1,387 sq ft

624 Saint Judes Dr, Longboat Key, FL 34228

Private back gate • Upgraded kitchen • 6,600 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!

$4,499,000

3 beds2 baths1,173 sq ft

2819 Gulf OF Mexico Dr, Longboat Key, FL 34228

Gulf-front lot • Downtown sarasota • White-sand beaches

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Step back in time and experience the “Old Florida Lifestyle” in the heart of Longboat Key’s historic Longbeach Village! Tucked away on the northernmost end of the island, this rare property features two charming Key West–style beach cottages on one lot, surrounded by lush tropical landscaping for a truly private island retreat. The main updated cottage offers a light-filled, open floor plan with 2 bedrooms, 2 bathrooms, a den, laundry room, and spacious living area. The kitchen was tastefully updated in 2021 with quartz countertops, hardwood cabinets, and newer appliances, complete with a breakfast bar for casual dining. Open the windows and let the coastal breeze fi

$675,000

3 beds3 baths1,564 sq ft

660 Linley St, Longboat Key, FL 34228

5,506 sq ft lot • Built 1952 • Listed 81 days

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Rare opportunity, two fully furnished TWIN residences (TWO UNITS BEING SOLD AS ONE 4473+4477 Gulf of Mexico Drive ). Directly on the pristine shores of Longboat Key! Combined 8 bedrooms, 8 Bathrooms. Spanning nearly 6,000 sq. ft. , on . 58 GULF-FRONT acres, this two-story property offers mirror-image residences, each thoughtfully decorated with both modern and timeless designs. A true investment gem—live in one, rent the other, enjoy a multi-generational retreat, or explore redevelopment potential on this premier beachfront site. Direct Gulf-front access — step onto the sand from your back door. Sweeping water views from nearly every room! State-of-the-art kitchens with high-en

$10,900,000

8 beds8 baths5,886 sq ft

4473 Gulf OF Mexico Dr #4473, Longboat Key, FL 34228

Gulf-front access • Impact-rated windows • Pavered decks

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
One or more photo(s) has been virtually staged. Welcome to an exceptional mid-century modern waterfront residence in Buttonwood Harbor, custom renovated from the ground up to deliver luxury coastal living. Situated on a deepwater canal with direct Gulf access, this 3-bedroom, 2-bath home offers timeless mid-century architecture, exceptional boating access, and thoughtfully integrated modern upgrades. Boaters will appreciate the private dock with a 13,000-pound boat lift, electricity, water, dock lighting, a raised seawall cap, and effortless navigation to open water. Inside, the open-concept layout centers on a spectacular chef’s kitchen featuring custom shaker cabinetry, high-end app

$1,599,000

3 beds2 baths2,265 sq ft

619 Buttonwood Dr, Longboat Key, FL 34228

Lavish soaking tub • 0.26 acre lot • 2 garage spots

Property at 711 Russell St, Longboat Key, FL 34228, 3 beds, 2 baths

$975,000

3 beds2 baths1,862 sq ft

711 Russell St, Longboat Key, FL 34228

Property at 608 Saint Judes Dr, Longboat Key, FL 34228, 4 beds, 3 baths

$989,000

4 beds3 baths2,106 sq ft

608 Saint Judes Dr, Longboat Key, FL 34228

Property at 552 Juan Anasco Dr, Longboat Key, FL 34228, 3 beds, 3.5 baths

$1,397,849

3 beds3.5 baths1,846 sq ft

552 Juan Anasco Dr, Longboat Key, FL 34228

Property at 5924 Gulf OF Mexico Dr, Longboat Key, FL 34228, 2 beds, 2 baths

$949,000

2 beds2 baths1,359 sq ft

5924 Gulf OF Mexico Dr, Longboat Key, FL 34228

Property at 766 Saint Judes Dr N, Longboat Key, FL 34228

$799,000

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766 Saint Judes Dr N, Longboat Key, FL 34228

Property at 6453 Gulfside Rd, Longboat Key, FL 34228

$4,550,000

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6453 Gulfside Rd, Longboat Key, FL 34228

Property at 580 Neptune Ave, Longboat Key, FL 34228

$950,000

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580 Neptune Ave, Longboat Key, FL 34228

Property at 6981 Lois Ave, Longboat Key, FL 34228

$649,000

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6981 Lois Ave, Longboat Key, FL 34228

Property at 6516 Bayou Hammock Rd, Longboat Key, FL 34228

$5,600,000

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6516 Bayou Hammock Rd, Longboat Key, FL 34228

Property at 620 Jackson Way, Longboat Key, FL 34228

$2,550,000

— beds— baths— sq ft

620 Jackson Way, Longboat Key, FL 34228

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NEW 11 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
NO RENTAL RESTRICTIONS and GREAT RENTAL HISTORY! Turn-key furnished second-floor condo located within the Ramada by Wyndham Sarasota Waterfront Resort. Updated interior with added kitchen area, laminate and tile flooring, fresh paint, and newer mid-sized refrigerator and microwave. Strong year-round rental demand makes this an excellent income-producing property and an easy, low-maintenance way to own in Florida. Enjoy resort amenities including a waterfront restaurant/tiki bar, fitness room, community laundry, security, and direct access to Gulf waters. HOA fee includes all utilities. Minutes to SRQ Airport, shopping, dining, and world-class beaches.

$130,000

1 bed1 bath348 sq ft

7150 N Tamiami Trl Unit S611, Sarasota, FL 34243

Turn-key furnished • Fresh paint • Updated interior

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Amazing Opportunity in the heart of Bradenton. ONE PROPERTY. .. TWO HOMES. This property has two separate units by a little hallway - both are totally renovated. Live in one, rent out the other part of the home or share with your family. Investors will have a great opportunity here to rent out both. Discover your dream multigenerational living space, where comfort, style, and functionality come together in perfect harmony. This updated pool property is ideal for families seeking a shared living arrangement or an investment opportunity. This house is a spacious 4-bedroom plus office/playroom space, 2-bathroom sanctuary, encompassing 2,532 square feet of thoughtfully designed space. The inter

$479,000

4 beds2 baths1,904 sq ft

4530 19th Street Cir W, Bradenton, FL 34207

Totally renovated • Spacious backyard • Two separate units

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
You are going to fall in love with this charming, updated gem in Bayshore Gardens! This lovely home features 2 bedrooms, 1.5 baths, a comfortable living room, a bright kitchen, and a generously sized flex room—perfect as a dining room (as it’s currently used), office, hobby space, workout room, or whatever best fits your lifestyle. Enjoy peace of mind with major improvements already done for you, including a newer roof (2019), tankless water heater, stainless-steel appliances, and mostly updated bathrooms. The abundance of windows fill the home with natural light, creating a space that feels both cozy and open. Flooring is easy to maintain—tile throughout, with laminate in

$299,900

2 beds1.5 baths1,036 sq ft

2011 Harvard Ave, Bradenton, FL 34207

Newer roof • Natural light • Updated bathrooms

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Discover an exceptional opportunity for true waterfront living with direct, no-bridge access to Sarasota Bay. This beautifully updated 3-bedroom, 2-bath home sits on one of the widest points of the saltwater canal, offering quick and unobstructed access for boating, kayaking, and paddle boarding. Inside, the home features a fully remodeled kitchen with new appliances, updated bathrooms, and a renovated primary suite designed for comfort and style. Vaulted ceilings create an open, airy feel, while the newer roof and updated windows contribute to the home’s move-in-ready appeal. Fresh exterior landscaping elevates curb appeal, and a separate workshop along with a dedicated laundry room

$589,000

3 beds2 baths1,664 sq ft

6715 Georgia Ave, Bradenton, FL 34207

Newer roof • Updated windows • Waterfront living

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Stylish studio at Sarasota Cay Club inside the Ramada by Wyndham on Tamiami Trail! This turnkey first-floor unit is fully furnished with a king bed, desk, and storage closet—perfect as a dorm room or short term stays for the business travelers. HOA fees include all utilities (electric, cable, internet, water, sewer, phone, pest control, exterior maintenance), making ownership hassle-free. Great investment property as well given that short-term rentals are allowed and can be listed on Airbnb or VRBO for income potential. Enjoy resort-style amenities: a large pool, tiki bar, on-site restaurants, and lovely water views throughout the property. Just 10 miles from Sarasota Airport, this is

$99,000

1 bed1 bath348 sq ft

7150 N Tamiami Trl Unit S515, Sarasota, FL 34243

Turnkey unit • Investment property • Fully furnished

OPEN SUN, 12PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
This Meticulously Renovated 3BR/2Bath home on . 35 acre is currently an AirBnB. A detailed and stylish recent renovation with high-end finishings included a new roof in 2023, completely new kitchen with SS appliances, Calcutta quartz countertops and a marble backsplash. Both bathrooms were renovated in a similar style. The entire home features new floors, new light fixtures, window trim, crown moldings, baseboards, updated electrical and new paint throughout! Too many upgrade details to list, you have to see it! The INCREDIBLE designer back yard includes a SPA with a waterfall feature, and new vinyl fence throughout. The back yard has a separate area for storage of boats, RV's or other big

$439,900

3 beds2 baths1,416 sq ft

3401 28th St W, Bradenton, FL 34205

New kitchen • New roof • New vinyl fence

Property at Undisclosed address, Bradenton, FL 34207, 4 beds, 3 baths

$425,000

4 beds3 baths2,100 sq ft

Undisclosed address, Bradenton, FL 34207

Property at 10315 Cortez Rd W Unit 1B, Bradenton, FL 34210, 2 beds, 1 bath

$149,900

2 beds1 bath1,012 sq ft

10315 Cortez Rd W Unit 1B, Bradenton, FL 34210

Property at 1907 Harvard Ave, Bradenton, FL 34207, 3 beds, 1.5 baths

$320,000

3 beds1.5 baths1,026 sq ft

1907 Harvard Ave, Bradenton, FL 34207

Property at 4709 Mineola St, Bradenton, FL 34207, 3 beds, 2 baths

$439,900

3 beds2 baths1,566 sq ft

4709 Mineola St, Bradenton, FL 34207

Property at 6835 Georgia Ave, Bradenton, FL 34207, 4 beds, 3 baths

$1,150,000

4 beds3 baths2,498 sq ft

6835 Georgia Ave, Bradenton, FL 34207

Property at 1712 63rd Ave W, Bradenton, FL 34207, 2 beds, 2 baths

$329,000

2 beds2 baths988 sq ft

1712 63rd Ave W, Bradenton, FL 34207

Property at 1811 Marilyn Ave, Bradenton, FL 34207, 3 beds, 2 baths

$375,000

3 beds2 baths1,052 sq ft

1811 Marilyn Ave, Bradenton, FL 34207

Property at 7230 Shepherd St, Sarasota, FL 34243, 2 beds, 2 baths

$450,000

2 beds2 baths1,415 sq ft

7230 Shepherd St, Sarasota, FL 34243

Property at 912 68th Ave W, Bradenton, FL 34207, 2 beds, 2 baths

$190,000

2 beds2 baths1,270 sq ft

912 68th Ave W, Bradenton, FL 34207

Property at 355 S Shore Dr, Sarasota, FL 34234, 3 beds, 3 baths

$2,695,000

3 beds3 baths3,276 sq ft

355 S Shore Dr, Sarasota, FL 34234

Property at 4516 57th St W, Bradenton, FL 34210, 3 beds, 2 baths

$309,900

3 beds2 baths1,225 sq ft

4516 57th St W, Bradenton, FL 34210

Property at 335 N Washington Dr, Sarasota, FL 34236

$995,000

— beds— baths— sq ft

335 N Washington Dr, Sarasota, FL 34236

Property at 259 John Ringling Blvd, Sarasota, FL 34236

$2,700,000

— beds— baths— sq ft

259 John Ringling Blvd, Sarasota, FL 34236

Property at 103 12th St S, Bradenton Beach, FL 34217

$1,200,000

— beds— baths— sq ft

103 12th St S, Bradenton Beach, FL 34217

Based on information submitted to the MLS GRID as of Sat Dec 06 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Longboat Key

There are currently 15 vintage homes for sale in Longboat Key at a median listing price of $1.25M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Longboat Key stay on the market for 71 days. Popular neighborhoods include Longboat Key Club, The Terraces at Wild Oak Bay, Bay Shore Gardens, Longboat Harbour, and Spanish Main Yacht Club Condominiums. This map is refreshed with the newest listings in Longboat Key every 15 minutes.

In the past month, 33 homes have been sold in Longboat Key. In addition to houses in Longboat Key, there were also 265 condos, 5 townhouses, and 1 multi-family unit for sale in Longboat Key last month. Find your dream home in Longboat Key using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Longboat Key are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Longboat Key. Our Longboat Key real estate stats and trends will give you more information about home buying and selling trends in Longboat Key. If you're looking to sell your home in the Longboat Key area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Longboat Key with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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