Longboat Key Homes under $500,000

Longboat Key Homes under $500,000

Welcome to Longboat Key, Florida—a stunning barrier island that embodies the essence of coastal living. Nestled between the azure waters of the Gulf of Mexico and the tranquil bays of Sarasota, Longboat Key is a paradise for those seeking sun, sand, and a welcoming community. Known for its pristine beaches, lush landscaping, and vibrant local culture, this idyllic location offers a lifestyle that is both relaxing and invigorating.

For homebuyers looking to invest in this slice of paradise, you’ll be delighted to discover that Longboat Key offers a range of homes under $500,000. These properties provide an incredible opportunity to enjoy the luxurious lifestyle of coastal living without breaking the bank. Whether you’re searching for a cozy condo with breathtaking views or a charming single-family home just a short stroll from the beach, there’s something for everyone in this vibrant community.

Imagine waking up to the sound of waves and enjoying your morning coffee on a sun-drenched patio. With a variety of recreational activities, including world-class golfing, boating, and dining, Longboat Key is perfect for both relaxation and adventure. The island is also conveniently located near the cultural attractions of Sarasota, including art galleries, theaters, and fine dining.

Discover the beauty of Longboat Key and explore the affordable homes that await you. Your dream of coastal living is just a step away—let Longboat Key welcome you home!

Newest Longboat Key Homes under $500,000

6750 Gulf Of Mexico Drive Unit 178, Longboat Key
$449,000
2 Beds ⋅ 2 Baths ⋅ Whitney Beach SubDv. ⋅ 34228 Zip Code
Whitney Beach Community – Turnkey Furnished. Enjoy the best of beach-to-bay living in Whitney Beach on Longboat Key’s peaceful north end. This two-bedroom, two-bath corner residence offers Gulf views from the front terrace and the privacy and natural light of an end unit. Ideally situated on the second floor, this 1,241-square-foot, pet-friendly home features hurricane-impact windows and shutters, inviting living spaces, and a spacious screened lanai overlooking a sparkling pool and lush tropical surroundings. The open kitchen and living area create an easy flow for everyday living and entertaining, while two generously sized bedrooms, each with an en-suite bath, provide comfortable retreats for owners and guests. Thoughtful updates complement the home’s bright, airy feel. Start your morning with coffee on the lanai, unwind with a favorite book, or simply enjoy the birds and wildlife just beyond your door. Whitney Beach offers access to both the Gulf of Mexico and Sarasota Bay. A short stroll across Gulf of Mexico Drive leads to deeded private beach access, where white sand, turquoise water, and community beach chairs await. On the bay side, enjoy fishing from the docks or exploring the shoreline by kayak. Community amenities include three pools, tennis and pickleball courts, shuffleboard, barbecue stations, kayak storage and launch facilities, and walking paths through beautifully landscaped grounds. Boat slips are available through community assignment or sublease, subject to availability. Located next to Whitney Plaza with restaurants, coffee shops, boutiques, and fitness and Pilates studios adding convenience to this relaxed island setting. With rentals permitted for a minimum of two months, six times annually, this inviting residence offers flexibility as a seasonal getaway or a place to settle in and savor Longboat Key living.

6750 Gulf Of Mexico Drive Unit 178, Longboat Key
4330 Falmouth Drive Unit 107, Longboat Key
$399,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
First time on the market in 25 years with OWNER FINANCING AVAILABLE, 40% down, 5.5% interest on balloon note or amortization, all negotiable. This turnkey, first-floor, two-bedroom, two-full-bath condominium in gated Longboat Harbour has hosted a lifetime of memories and is ready for its next chapter. Freshly painted and move-in ready, it opens through a glass-enclosed lanai straight onto the lawn and harbor, with boats docked a short distance away and Sarasota Bay beyond. Tile floors, plantation shutters and a bright kitchen with a pass-through to the dining area keep life easy. Being on the ground floor, you skip the elevator and stairs and enter right out to the pool, your covered parking and the path to the beach. Owners report no flood damage in their 25 years of ownership. Amenities include heated pools, a fitness center, a sauna, billiards and game rooms, a clubhouse, a putting green, shuffleboard, a fishing pier, grills, kayak storage and a private Gulf-side beach house across Gulf of Mexico Drive with parking, restrooms, showers and gear storage. Bayside sunrises, Gulf sunsets, Publix and dining nearby and SRQ about 13 miles. Owner financing is available; ask for the terms. Quick close is possible. Approximately $15,000 in 2027 rental bookings are already in place, according to the current owner.

4330 Falmouth Drive Unit 107, Longboat Key
693 Spanish Drive N Unit 24, Longboat Key
$423,750
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Spanish Main Yacht Club is a 55+ community. There are 213 villa, ground-level attached condo units in this condo complex. It has a marina with boat docks, a clubhouse, swimming pool, shuffleboard courts, and private beach access. Signs are not permitted and the streets are private and maintained by the Association. Roof maintenance and replacement are the responsibility of individual unit owners. All marina and boating inquiries should be directed to the Dock Master, Ross Wenum. Docks and slips are allowed on a first come first serve basis with sizes from 14 feet to 40 feet. It has its own marina with direct access to Sarasota Bay. The boat must be fully owned by the unit owner, and the unit owner must be in residence 155 days of the calendar year. There is a $750 non-refundable application fee for a dock or boat slip. Small boats are $200 a year, medium boats are $250 a year and large boats are $300 a year. The monthly condo fee covers the insurance for the community common elements and exterior of the buildings, all property management, water, sewer, trash collection, lawn mowing, palm tree trimming, general maintenance of the common grounds and pool, and exterior painting. Unit owners are separately responsible for electricity, cable/internet, pest control, landscaping around their villas, and their unit property taxes. There is an area off the entrance to the right - the boneyard, named because of the historical bones found there. There is a maintenance building, a vehicle wash area, a community dumpster, overflow parking for extra vehicles, boat trailers, and RV's. This two-bedroom, two bathroom unit is 1,429 square feet of air-conditioned space with Kitchen, Living Room/Dining Room combination and an additional 225 square foot glassed-enclosed rear lanai (porch), for a total of 1,765 under roof. The current jalousie windows will be replaced with new hurricane windows in the near future and this has been paid for. Off this lanai is the inside utility room 7 x 9 with washer/dryer hook up (washer/dryer not included), and ample extra storage space. Each unit has its own carport with a 5 x 7 storage closet attached to the carport. The previous washer/dryer hookup is still there as is the new hot water heater. This unit has been totally renovated after the hurricanes of 2024 and has an all new interior inside the unit, new everything - flooring, painting, ceilings, all new stone countertops in Kitchen and both bathrooms, many new hurricane windows, new sliding glass doors and new front entry door. All new appliances, Kitchen, bathrooms, fixtures, plumbing and electricity, ceiling fans, HVAC system with the air-handler in the hallway attic and the condenser on the roof. This unit has not been lived in since the renovation has been completed. The unit is vacant, on Supra lockbox, easy to preview, show and buy. We are currently priced at $423,750 which is the lowest list price of the twelve units currently for sale.

693 Spanish Drive N Unit 24, Longboat Key
738 Spanish Drive S Unit 98, Longboat Key
$495,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Discover the best of Longboat Key living in this freestanding, well-maintained 2-bedroom, 1.5-bath freestanding villa in the sought-after Spanish Main Yacht Club. With about 1,200 sq ft of living space plus an enclosed Florida room, this light-filled home features plantation shutters, terrazzo flooring and an updated kitchen with wood cabinetry and granite counters. Outside, enjoy a covered carport, private entrance and a private back yard with added privacy, plus block construction and a tile roof. Spanish Main Yacht Club offers deeded private beach access, a heated community pool, clubhouse, shuffleboard, kayak storage and a 40-slip private marina — just a short stroll from Gulf sunsets and minutes from St. Armand's Circle and Sarasota dining and shopping. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually. Check out the videos of the home and the community now, then call for a tour!

738 Spanish Drive S Unit 98, Longboat Key
2600 Harbourside Drive Unit Q8, Longboat Key
$189,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
**NO LONGBOAT KEY CLUB MEMBERSHIP REQUIRED!** A rare and highly desirable opportunity to own a 48' x 21' deep-water slip at the prestigious Longboat Key Club Moorings without the expense or obligation of club membership! This valuable distinction offers owners the flexibility to enjoy a world-class marina while avoiding mandatory club membership fees. Accommodating vessels up to 43' long and 19' wide, this ideally located slip boasts stunning Sarasota skyline views and direct access to Sarasota Bay and the Intracoastal Waterway. Longboat Key Club Moorings offers a resort-style marina experience within an elegant Mediterranean-inspired waterfront village, complete with on-site dining, shopping, social activities, professional maintenance, and concierge services. Conveniently located near Publix, CVS, and specialty shops, the marina combines luxury with everyday convenience. Slip amenities include electric, water, and wireless internet access. For those interested, Longboat Key Club membership remains entirely optional, with the opportunity to join at any time. All vessels require Association Board approval prior to entering the marina, and allowable beam depends on vessel specifications. Enjoy the prestige and convenience of Longboat Key Club Moorings with the freedom of ownership without mandatory club membership!

2600 Harbourside Drive Unit Q8, Longboat Key
845 Spanish Drive N Unit 845, Longboat Key
$450,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Positioned directly across from the marina and boat slips, this updated villa in Spanish Main Yacht Club enjoys beautiful marina views and puts boating and waterfront access just steps from your front door, while offering the relaxed island lifestyle and everyday convenience of a 55+ waterfront community on Longboat Key. The villa features 2 bedrooms, 2 bathrooms, and a flexible third room that could potentially be converted into a third bedroom, giving you added space for guests, a home office, workout area, or den. Tile flooring runs throughout, while the renovated kitchen features quartz countertops, stainless steel appliances, new cabinetry, and dovetail soft-close drawers. The primary suite offers its own private bath and walk-in closet, while the guest bedroom and second bath are positioned separately for added privacy. The home also features an interior washer and dryer combo, offering added everyday convenience compared with the exterior laundry setups found in many neighboring units. Spanish Main Yacht Club offers a community pool, clubhouse, marina, water access, and deeded beach access just across Gulf of Mexico Drive. Additional parking across the street provides extra convenience for guests and visitors. Here, days can be spent enjoying the marina views, relaxing at the private beach, lounging by the pool, or heading out on the water, with local dining, parks, and island conveniences nearby. Boat slips are available separately through the association as availability allows. Whether you’re looking for a full-time residence or seasonal retreat, this villa offers the updates, setting, and waterfront lifestyle that make Spanish Main Yacht Club such a special place to enjoy Longboat Key.

845 Spanish Drive N Unit 845, Longboat Key
554 Spanish Drive S, Longboat Key
$425,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.

554 Spanish Drive S, Longboat Key
600 Sutton Place Unit 101B, Longboat Key
$319,000
1 Beds ⋅ 1 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code
Waterfront condo with Sarasota Bay views! Perfectly positioned along Sarasota Bay on **Longboat Key** and just steps from the turquoise waters of the **Gulf of Mexico**, this exceptional community offers the ultimate coastal lifestyle in an unbeatable location. Current owners have never had water intrusion from any hurricanes. This spacious ground-floor corner residence features an expansive open-concept layout designed to comfortably accommodate up to six guests. The beautifully remodeled kitchen showcases stainless steel appliances, a brand-new range, granite countertops, stone backsplash, recessed lighting, and solid wood cabinetry — blending modern style with everyday functionality. A charming nook provides the perfect space for additional sleeping accommodations or a cozy retreat to enjoy serene bay views. Impact-rated sliding glass doors open seamlessly to the outdoors and are complemented by brand-new Shade Store cellular window treatments. Relax while taking in peaceful water and pool views from the comfort of your living space. The spacious primary bedroom features custom cellular shades with top and bottom openings to maximize natural light and views, along with a walk-in closet complete with built-ins. The ensuite bath has been thoughtfully updated with a newer vanity and a brand-new shower remodel (2025), offering a fresh, modern feel. Furnishings are optional and tastefully curated with designer touches, making this property move-in or rental ready. Exceptional Community Amenities - Residents enjoy a truly unique waterfront lifestyle: Two heated pools, Marina and clubhouse, Available boat slips for rent, fish-cleaning station, Kayak storage with electric launch, BBQ grilling areas, Car wash station, Lighted assigned carport parking, Elevator access, Private storage unit (3rd floor), Laundry facility (2nd floor), exclusive deeded beach access on Longboat Key, featuring a pavilion, storage lockers, indoor showers, and restrooms. Enjoy watching dolphins and manatees from the bayfront grounds, spend your days fishing or kayaking, or relax on the sugar-sand beaches just across the street. The community is also in the planning stages of adding a brand-new state-of-the-art fitness center. Shopping and dining are just minutes away at the renowned **St. Armands Circle**. Experience the best of both worlds — Gulf-front beach days and tranquil bayfront evenings. This is coastal living at its finest.

600 Sutton Place Unit 101B, Longboat Key
408 Gulf Of Mexico Drive Unit 2207, Longboat Key
$49,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #2207 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 premium slip accommodates boats up to 28 feet in length, with a maximum height of 7'8" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2207, Longboat Key
408 Gulf Of Mexico Drive Unit 1206, Longboat Key
$65,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #1206 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 premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8'4" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 1206, Longboat Key
408 Gulf Of Mexico Drive Unit 2114, Longboat Key
$39,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #2114 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 premium slip accommodates boats up to 23.5 feet in length, with a maximum height of 7'2" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2114, Longboat Key
2800 Harbourside Drive Unit E-21, Longboat Key
$385,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-21, Longboat Key
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