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. An exceptional offering in the sought-after Longbeach neighborhood of Longboat Key. Located on the Manatee County side of the island, this original 1935 coastal cottage sits on an oversized . 34+ acre waterfront lot with approximately 78 feet of water frontage and an impressive depth of roughly 192 feet, offering direct, bridge-free access to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America. Enjoy the luxury of a short walk to the beach, no HOA fees, and flexible rental terms with a one-month minimum allowed up to 12 times annually. RSF-6 zoning (Single-Family Medium-High Density) allows up to six units an acre (buyer to verify

$1,190,000

2 beds2 baths1,180 sq ft

6841 Longboat Dr S, Longboat Key, FL 34228

Water frontage • No hoa fees • 0.35 acre lot

3D WALKTHROUGH

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 99 days

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
This premier lot and midcentury property, with one of the nicest pools in the area, is ready for its next visionary owner seeking the best of island living on beautiful Longboat Key. It's an ideal opportunity to renovate or build your dream home in the heart of the pedestrian and golf-cart friendly historic Longbeach Village with numerous waterfront restaurants and shops nearby. Located on Longboat Key's north end, this charming midcentury cedar-framed residence is set back on an expansive elevated lot with a deep front yard. The property boasts a private oasis in the rear, complete with a generous resort pool & spa and low-maintenance lawn. Previously updated to blend modern convenie

$975,000

3 beds2 baths1,862 sq ft

711 Russell St, Longboat Key, FL 34228

Heated pool • 0.27 acre lot • Pool

Property at 4473 Gulf OF Mexico Dr #4473, Longboat Key, FL 34228, 8 beds, 8 baths

$10,900,000

8 beds8 baths5,886 sq ft

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

Property at 619 Buttonwood Dr, Longboat Key, FL 34228, 3 beds, 2 baths

$1,599,000

3 beds2 baths2,265 sq ft

619 Buttonwood Dr, Longboat Key, FL 34228

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

$1,239,552

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 6549 Gulf OF Mexico Dr, Longboat Key, FL 34228

$1,900,000

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6549 Gulf OF Mexico Dr, Longboat Key, FL 34228

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

$5,400,000

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6516 Bayou Hammock Rd, 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 620 Jackson Way, Longboat Key, FL 34228

$2,550,000

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620 Jackson Way, Longboat Key, FL 34228

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NEW 19 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Lowest price 3/2 block home by nearly 130k! Property needs FULL rehab and trash-out. No HOA!! Located in a quiet neighborhood just under 30 minutes from Manatee beach! Close to major roads, shopping and dining. Cash only. Sold AS-IS. All inspections must be done prior to offering. Seller will not remove any personal property.

$199,900

3 beds2 baths1,438 sq ft

2303 Lehigh Ave, Bradenton, FL 34207

Close to dining • Quiet neighborhood • Close to major roads

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
YOUR BUNGALOW in Paradise. Still has a lot of vintage charm, but with many updates to this 2 Bedroom, 1.5 Bath Mobile Home in the highly desired, active 55+ Trailer Estates community. Just steps from the heart of the social scene to access the community pool, recreation buildings, shuffleboard, fitness center, and all the wonderful park amenities. New luxury vinyl floors throughout. Second bedroom has new ensuite half bath. 10'x7' Laundry shed with washer/dryer, plus new 7x7 storage shed. A/C 2017. WDO treated in 2019. You own the land. No lot rent, Park Fees are included into annual real estate taxes. Boaters have direct access to Sarasota Bay from the Marina. Trailer Estates community off

$154,900

2 beds1.5 baths880 sq ft

1912 Iowa Ave, Bradenton, FL 34207

Fitness center • Community pool • Storage shed

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
LIDO BEACH – Rare Opportunity! Owned by the same family for 36 years, this property is located on one of the most coveted streets on Lido Key—South Polk Drive—surrounded by multi-million-dollar homes. Just one block to the pristine sands of Lido Beach and one block to the world-class shopping and dining of St. Armands Circle, the location is unmatched. Positioned across from the open bay and canal-front residences, this property offers incredible potential. With a one-week rental minimum, it’s an excellent investment opportunity. Plus, there are no HOA fees. Whether you choose to remodel or build the magnificent home of your dreams, the true value lies in the land. T

$1,495,000

3 beds2 baths1,422 sq ft

554 S Polk Dr, Sarasota, FL 34236

One block to beach • No hoa fees • 7,202 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
Experience the best of beach living in this beautifully renovated home near the sugar-white sands of Lido Beach and the upscale shops and restaurants of St. Armands Circle. Positioned between these two renowned destinations, this desirable address offers effortless access to both. Offering three bedrooms and three and one-half baths, this bright and airy residence blends timeless charm with modern functionality, and is zoned for seven-day minimum rentals, making it an exceptional opportunity for investors and lifestyle buyers alike. The open-concept layout is highlighted by a soaring 14-foot beam ceiling, skylight windows, and a fireplace that adds warmth and character. A wall of sliding gl

$2,350,000

3 beds3.5 baths2,272 sq ft

444 S Polk Dr, Sarasota, FL 34236

Skylight windows • Renovated home • 14-foot beam ceiling

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
If you’ve been hoping for a simple, easygoing lifestyle in a welcoming coastal community, this home makes it possible. Offers 1% lender credit at closing. Fully furnished and move-in ready, this turnkey property provides everything you need without any fuss—perfect for anyone seeking a winter escape or a comfortable year-round residence. Located in the popular 55+ cooperative of Paradise Bay Estates, this charming 1-bedroom, 1-bath home features a bright dinette area surrounded by windows that bring in plenty of natural light. The propane range and water heater keep utility costs efficient, while two mini-split systems—only two years old—provide dependable heating an

$80,000

1 bed1 bath363 sq ft

10315 Cortez Rd W Unit 62-4, Bradenton, FL 34210

Turnkey property • Bright dinette area • Large pool

ABOUT THIS HOME
Vintage Home for sale in Longboat Key, FL:
NO RENTAL RESTRICTIONS at this studio condo in Sarasota, Florida! Enjoy staying in this updated unit which is located inside a waterfront community with direct access to the GULF WATERS. This studio has a full bathroom and microwave with mini fridge. With no minimum rental restrictions, you can enjoy the unit whenever you like or rent it out through AIRBNB, VRBO, or the onsite program. These condos surround a marina with gulf access. Enjoy stepping out onto the dock, into your boat or kayak, hop aboard a fishing charter, or simply sip on something tropical while watching the beautiful sunsets over the water. Owners are able enjoy the Ramada Hotel's Resort Lifestyle with amenities that incl

$95,000

0 beds1 bath348 sq ft

7150 N Tamiami Trl Unit S523, Sarasota, FL 34243

Dock access • $715 HOA • Community pool

Property at 1017 51st Avenue Dr W, Bradenton, FL 34207, 1 bed, 1 bath

$80,000

1 bed1 bath440 sq ft

1017 51st Avenue Dr W, Bradenton, FL 34207

Property at Undisclosed address, Bradenton, FL 34207, 3 beds, 2 baths

$425,000

3 beds2 baths1,400 sq ft

Undisclosed address, Bradenton, FL 34207

Property at 3407 29th St W, Bradenton, FL 34205, 3 beds, 2 baths

$529,900

3 beds2 baths1,525 sq ft

3407 29th St W, Bradenton, FL 34205

Property at 110 6th St S, Bradenton Beach, FL 34217, 3 beds, 2.5 baths

$3,299,000

3 beds2.5 baths2,237 sq ft

110 6th St S, Bradenton Beach, FL 34217

Property at 2307 N Wellesley Dr, Bradenton, FL 34207, 3 beds, 2 baths

$449,900

3 beds2 baths1,470 sq ft

2307 N Wellesley Dr, Bradenton, FL 34207

Property at 5703 18 St W, Bradenton, FL 34207, 4 beds, 2 baths

$449,000

4 beds2 baths1,650 sq ft

5703 18 St W, Bradenton, FL 34207

Property at 4507 123rd St W, Cortez, FL 34215

$1,295,000

0 beds— baths2,762 sq ft

4507 123rd St W, Cortez, FL 34215

Property at 5812 22nd St W, Bradenton, FL 34207, 3 beds, 1.5 baths

$309,000

3 beds1.5 baths1,403 sq ft

5812 22nd St W, Bradenton, FL 34207

Property at 4530 19th Street Cir W, Bradenton, FL 34207, 4 beds, 2 baths

$469,000

4 beds2 baths1,904 sq ft

4530 19th Street Cir W, Bradenton, FL 34207

Property at 2011 Harvard Ave, Bradenton, FL 34207, 2 beds, 1.5 baths

$299,900

2 beds1.5 baths1,036 sq ft

2011 Harvard Ave, Bradenton, FL 34207

Property at 6715 Georgia Ave, Bradenton, FL 34207, 3 beds, 2 baths

$589,000

3 beds2 baths1,664 sq ft

6715 Georgia Ave, Bradenton, FL 34207

Property at 7150 N Tamiami Trl Unit S515, Sarasota, FL 34243, 1 bed, 1 bath

$99,000

1 bed1 bath348 sq ft

7150 N Tamiami Trl Unit S515, Sarasota, FL 34243

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

Based on information submitted to the MLS GRID as of Tue Dec 23 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 16 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 69 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 270 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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