Location: Longboat Key
Keyword(s): Martha B. King Middle
Keyword(s) Middle School: Martha B. King Middle
Do Not Show Listings
4540 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228
$595,000192 Days on yellowkey MLS ID: A4667631
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1312 Built: 1975 Tax: $9,451 (2024)Community: Windward BayCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,451
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: MOTIVATED SELLER! FULLY FUNDED RESERVES FOR 2026! PET FRIENDLY! NO UPCOMING SPECIAL ASSESSMENTS! 3 BEACH ACCESS POINTS! MILESTONE INSPECTION PASSED! Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering luxury Longboat Key living at its finest with preserved mangrove and Sarasota Bay views. Every detail has been thoughtfully updated ,this home has been renovated from top to bottom, featuring new flooring, new plumbing, new electrical, new lighting, hurricane-impact windows with shutters for peace of mind and MORE! The brand-new kitchen showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, creating a beautiful space that opens to the bright and airy living area. Both bathrooms have been updated with modern finishes and quarts countertops as well. A Murphy bed in the office area adds versatility, perfect for guests or additional workspace. Enjoy deeded beach access directly across the street for endless days on the sand, or take advantage of boat slips available for residents, ideal for boaters looking to explore Sarasota Bay and the Gulf. Windward Bay is a pet-friendly, amenity-rich community offering multiple pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and walking paths along the bayfront. Perfectly situated near world-renowned restaurants on Longboat Key, St. Armands Circle, and Anna Maria Island, this home combines effortless luxury with the ultimate coastal convenience. Move-in ready and maintenance-free, your Longboat Key lifestyle awaits!
Listing is courtesy of: VRI HOMES (800-531-2885)
Listing Agent: Paulina Vasiliev, Pllc (941-225-5383)
4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228
$399,00094 Days on yellowkey MLS ID: A4678473
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,196 Tax: $4,937 (2025)Community: Longboat HarbourCondo
Taxes:$4,937
Tax Year: 2025
Remarks: Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring elegant granite countertops, state-of-the-art appliances, and a spa-like shower that redefines luxury. Your perfect beach days await with exclusive private beach access, complete with a dedicated beach house that offers showers and restrooms for your convenience. For boating enthusiasts, the Longboat Key Yacht Club provides convenient boat slips and kayaks, giving you immediate access to the pristine waters of the bay. Stay energized and engaged with an array of top-tier amenities, including tennis courts, shuffleboard, a rejuvenating sauna, and a fully equipped gym. Join a dynamic social scene filled with workshops, a cozy library, an inspiring art studio, and clay classes, plus the warm camaraderie of the Book Buddies club that fosters connections. With four inviting swimming pools, a grand banquet hall for gatherings, a fun game room for entertainment, and convenient private beach parking, every day feels like a luxurious getaway. This is more than just a condo; it’s a lifestyle experience you truly deserve. Don’t let this extraordinary Longboat Key oasis pass you by! Schedule your showing today and discover if it’s your perfect match!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Rademacher (612-965-6188)
6841 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$1,050,000123 Days on yellowkey MLS ID: A4674302
0 Days Off yellowkey (back on 4/9/2026)
REDUCED by $45,000 (4.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1935 Tax: $13,113 (2025)Community: Longbeach On Longboat KeySpa: NoSingle Family
Taxes:$13,113
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Rarely does a property offer this much land, waterfront, and location value within the cherished Longbeach community of Longboat Key. Located on the desirable Manatee County side of the island, this original 1935 coastal cottage sits on an oversized .34+ acre waterfront lot with approximately 78 feet of frontage and an impressive 192-foot depth—dimensions increasingly difficult to find on Longboat Key. Enjoy direct, bridge-free boating to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America, making it an exceptional opportunity for boaters, investors, or those looking to build a future waterfront estate. All just moments from the beach and within walking distance of the charm and character of Longbeach Village. Enjoy a short walk to the beach, no HOA fees, and flexible rentals with one-month minimums allowed up to 12 times per year. RSF-6 zoning (buyer to verify) allows up to six units per acre, offering potential for a primary home with guest house, pool, and spa. An existing dock (currently damaged) already has water and electric, and the lot provides ample space for a large lap pool and outdoor entertaining. Over $100,000 in capital improvements include a shingle roof (2023), and extensive interior updates completed in 2025 following storm remediation, including all new flooring, paint, cabinetry, and drywall. Additional upgrades include a new 2.5-ton AC system (2024), electrical improvements with a 200-amp panel and grounding, water heater (2025), hurricane impact windows in most rooms, including the primary bedroom, kitchen, both bathrooms, and living room, a sizable upgrade to the home. Private irrigation well, providing peace of mind, long-term efficiency and conveniences of moving right in to enjoy this exceptional home and property! Offering two bedrooms, two bathrooms, and approximately 1,180 square feet, the home retains timeless island character with original cypress walls and ceilings, abundant windows, and a wood-burning fireplace that anchors the living space. A standout feature is the 15x33 rear-facing covered and screened lanai, providing approximately 510 square feet of under-roof outdoor living with pitched ceilings, fans, sun shades, and fully pocketing sliding glass doors, with the flexibility to incorporate this space into additional interior living if desired. The updated half-galley kitchen features shaker wood cabinetry, soft-close drawers, light quartz countertops, an LG stainless steel appliance package, deep stainless sink, pull-outs, and lazy Susan, all overlooking the front stoop and lawn. The spacious primary ensuite measures approximately 10x22 and includes room for seating or office use, dual sinks, his-and-hers closets, and a shower/tub combination. A shared full bath offers inlaid tile flooring and a walk-in shower with marble step. Wood flooring runs throughout with tile in the bathrooms, offering NO carpeting. Additional features include a shell and paver driveway, French front door, expansive fully pocketed sliding glass doors, gutters, fenced yard, and a one-car carport (that houses the washer, dryer and hot water heater). One of the last remaining original cottages in the Whitney Beach / LongBeach area, this property offers a compelling opportunity to restore historic charm, reimagine the footprint, or create a refined waterfront estate defined by location, land, boating, beach access, flexibility, and vision. SELLER financing terms available upon request.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Shayla Twit (941-544-7690)
729 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$449,00039 Days on yellowkey MLS ID: A4685189
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $1,994 (2025)Community: Saint Judes AptsSpa: NoCondo
Taxes:$1,994
Remarks: Live that Longboat Key waterfront lifestyle and have your own boat lift without the multi-million dollar price. Cute and conveniently located, this on-grade one bedroom condominium unit that is located on a saltwater canal on Longboat Key, features its own 10,000 lb boat lift, and is one block to the gulf beaches and adjacent to Durante Park. Everything new in 2025, including a washer and dryer and hot water demand unit. The condo is completely furnished with an updated living space, complete with open kitchen that features granite countertops, stainless steel appliance and plenty of storage. The modern wood-look tile and updated sliders and windows make for an open feeling living area. There is a paver patio and dock behind the condo for enjoying the sunsets on the canal. A number of shops and restaurants within walking distance. Schedule your showing today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steven Schield (941-650-1010)
765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$1,499,90059 Days on yellowkey MLS ID: A4683420
REDUCED by $80,100 (5.1%) on 04/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1900 Built: 1963 Tax: $14,125 (2025)Community: Longboat KeySpa: NoSingle Family
Taxes:$14,125
Remarks: Best Waterfront Value on Longboat Key – CANAL-FRONT Home with Deeded Private Beach Access. Exceptional opportunity to own a fully renovated CANAL-FRONT residence on highly sought-after Longboat Key. Notably, the property was appraised prior to renovation completion for more than the original asking price, creating a rare built-in equity opportunity. This 4-bedroom, 2-bathroom coastal retreat offers the perfect blend of luxury, location, and lifestyle, complete with DEEDED PRIVATE BEACH ACCESS to the Gulf of America. Positioned along 132 linear feet of canal frontage, the property features a seawall and kayak launch (2020) and provides direct boating access to Sarasota Bay and beyond. The home has undergone a comprehensive interior and exterior renovation, with virtually everything NEW apart from the home’s foundation, delivering exceptional move-in-ready peace of mind. 2025 Improvements Include: • New roof (2025) • New flooring (2025) • New interior walls (2025) • Full home renovation – interior & exterior (2025) • New AC systems (2025) • New decking (2025) • New cabinets (2025) • New landscaping (2025) • New electrical systems (2025) Major System & Feature Upgrades: • Electrical panel (2022) • New plumbing (2022) • Commercial-grade whole-home surge protector (2022) • Tankless gas water heater (2022) • New sliding glass doors (2022) • New impact windows (2022–2023) • Impact-rated garage doors (2022) • New pavers (2022) • New ductwork (2020) • Seawall & kayak launch (2020) PGT high-impact sliding glass doors, new impact windows, and impact-rated French doors enhance storm protection, energy efficiency, and natural light. Interior highlights include vaulted ceilings, expansive water views, two electric fireplaces, and elegant wood-look ceramic tile flooring throughout. The bright, open layout is designed for effortless coastal living. The beautifully updated kitchen features solid wood cabinetry, soft-close hardware, marble-look quartz countertops, a gas stove, premium stainless-steel appliances, a copper hood, and a copper farmhouse sink. Updated bathrooms showcase sophisticated Italian marble-look ceramic tile, including an alcove soaking tub in the primary suite and a walk-in rain shower. Outdoor living is elevated by a spacious screened porch overlooking the canal and backyard. The yard is enclosed with sleek black aluminum fencing and offers ample room for a future pool. Additional Highlights: • Higher elevation than many ground-level Longboat Key homes • 132 ft of canal frontage • Direct boating access • Deeded PRIVATE beach access Ideally located near Cedars East Tennis Resort & Club, offering nine tennis courts, three pickleball courts, and a large community lap pool, as well as Joan Durante Park (34 acres). Dining, shopping, and island amenities are all within close proximity. Offered fully furnished / TURNKEY, this home is ready for immediate enjoyment as a primary residence, vacation retreat, or investment opportunity. Boating + Beach + Extensive 2025 Renovation = Rare Longboat Key Opportunity. Schedule your private tour today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kalison Nix (941-900-9189)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$545,000108 Days on yellowkey MLS ID: A4676730
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? And could you even imagine you could have it for $615,000?! With one owner for the last 29 years, this is your unique opportunity to purchase this fully renovated beachfront walkout 1 bedroom, 1 bath condo in the beach to bay island community of Covert II - and hang onto it like these owners have! With this fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
576 SUTTON PL, LONGBOAT KEY, FL 34228
$359,000122 Days on yellowkey MLS ID: A4675729
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1972 Tax: $6,222 (2024)Community: Sutton PlaceSpa: YesCondo
Taxes:$6,222
High School: Manatee High
Remarks: Best Beach Villa Value on Longboat Key! - Experience effortless coastal living in this lovely 2-bedroom, 2-bath end-unit bayside villa offering the highly sought-after Bay-to-Beach lifestyle on Longboat Key. Beautifully appointed and sold turnkey, this ground-floor residence is truly Martha Stewart–perfect—move-in ready and designed for relaxed elegance. The villa welcomes you with an enclosed den/Florida room, a serene retreat where you can unwind while enjoying tranquil views of lush greenery and native birdlife. Hurricane impact windows and doors throughout ensure peace of mind while maintaining a quiet, comfortable interior. The open-concept living space is ideal for both everyday living and entertaining. A spacious family room and dining area flow seamlessly from the renovated kitchen, which features rich maple cabinetry, solid granite countertops, and an inviting, functional layout. Every detail has been thoughtfully curated, from custom cornices and blinds to coordinated bedding and decorative pillows—straight out of Serena & Lily. Additional highlights include a separate laundry room with pantry storage, complete with a garden door that opens to peaceful landscaping and provides direct access to the private marina, kayak storage, and an electric kayak launch—perfect for embracing the boating lifestyle right outside your door. This pet-friendly villa offers unmatched convenience and value with a private carport, extra guest parking just steps away, a new washer and dryer, a recently upgraded air-conditioning system and tankless water heater. Just across Gulf of Mexico Drive, enjoy exclusive access to your private beach facility, featuring gated parking, restrooms, showers, and chair storage—true resort-style living. Spend your days boating, kayaking, or soaking up the sun, then end each evening watching breathtaking sunsets over the sugar-sand beaches of the Gulf. This exceptional Longboat Key villa is move-in perfect and ready to enjoy—just bring your flip-flops. Opportunities like this are rare, and this one will not last long.
Listing Agent: Kathy Callahan (941-900-8088)
4621 GULF OF MEXICO DR #16B, LONGBOAT KEY, FL 34228
$649,900486 Days on yellowkey MLS ID: A4632978
3 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1972 Tax: $7,292 (2024)Community: Longboat Key Casa Del MarSpa: NoCondo
Taxes:$7,292
Remarks: Under contract-accepting backup offers. Imagine the serene sands of the Gulf, just steps away, offering the ideal blend of luxury and opportunity with rental income while you're away. An on-site rental office ensures seamless bookings for your beautifully renovated condominium with new A/C at Casa Del Mar. You and your guests will relish the gulf-front pool, tennis courts with pickleball, grilling area and picnic tables, all while basking in the soothing embrace of the gulf waters as the simple, fulfilling life awaits. For those who wish to travel light, the unit is turnkey furnished, fully equipped, and ready to provide your ideal beach getaway. Upgrades include new kitchen and baths, quartz countertops and tile throughout, and stainless-steel appliances. The unit comes with a washer and dryer. just a short drive to local restaurants, Anna Maria Island, local parks, grocery shopping, CVS, places of worship, banks, world-renowned St, Armands Circle, top-rated Sarasota and all it offers.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,00018 Days on yellowkey MLS ID: A4688632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1971 Tax: $2,179 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,179
Remarks: 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
4350 CHATHAM DR #205, LONGBOAT KEY, FL 34228
$259,90073 Days on yellowkey MLS ID: A4681134
0 Days Off yellowkey (back on 4/4/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 667 Built: 1969 Tax: $4,627 (2024)Community: Longboat HarbourCondo
Taxes:$4,627
Remarks: Under contract-accepting backup offers. Resort-style living at Longboat Harbour! This move in ready one bedroom, one bath condo is one of the best get-aways in the area. From your lanai, the serene view down the canal makes for a great place to have your morning coffee or enjoy a sunset cocktail. Steps away, you have private gated access to the Gulf beaches including a pavilion with washrooms, lockers and parking. If you like, this condo can be an incredible investment opportunity, earning rental income from day one. In 2025 the A/C unit was replaced, water heater 2023. In 2025, all the roofs were replaced, along with the elevators in Building E. There is private storage, assigned covered parking, and plenty of guest parking. The pool nearest you has been resurfaced and new pavers added throughout the complex. Longboat Harbour is a friendly community with numerous amenities and an on-site management team. It boasts four heated pools, tennis and pickleball courts, putting green, and kayak storage with launch. For boating enthusiasts, slips are available for powerboats and sailboats up to 34 feet on a first-come, first-served basis. At the clubhouse there is a fully equipped gym (with sauna and lockers) and the renovated community room overlooking the bay hosts many social occasions and private parties. Whether for a warm winter getaway, year-round residence or investment opportunity, Longboat Harbour is resort-style living at its best!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Tracey Fiedler (303-809-2582)
691 GULF BAY RD, LONGBOAT KEY, FL 34228
$950,00053 Days on yellowkey MLS ID: A4684077
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1581 Built: 1976 Tax: $9,082 (2024)Community: Bailey-DobsonSingle Family
Taxes:$9,082
Remarks: Tucked away on one of Longboat Key’s most unexpectedly serene streets, this elevated 3-bedroom island home offers something increasingly rare: space, privacy, nature, and convenient coastal living, all in one place. Set at the end of a quiet, dead-end road that gently meets Sarasota Bay, with deeded access to both the beach and the bay just moments away. Life here unfolds at an unhurried pace. Mornings begin on the porch with filtered sunlight and birdsong drifting in from Joan M. Durante Park, the 32-acre preserve that borders the property and wraps the street in natural beauty. Winding trails, mangroves, boardwalks, and bayfront docks become an extension of your backyard, offering a daily connection to the outdoors that feels both grounding and restorative. Inside, the home has been thoughtfully remodeled and is truly move-in ready, blending a relaxed coastal feel with modern comfort. The open-concept layout is light-filled and welcoming, anchored by a beautifully updated kitchen with quartz countertops, a generous island, and ample storage, perfect for everyday living or hosting friends who linger long after sunset. The primary suite is privately positioned, while additional bedrooms flex easily as guest space, a home office, or a creative retreat. Below, the spacious under-house garage offers exceptional versatility with room for cars, bikes, kayaks, paddleboards, or even a home gym, making island adventures effortless. At the entrance to the street, island life comes alive with Euphemia Haye Restaurant and The Haye Loft, ideal for impromptu dinners or sunset drinks without ever getting in the car. Beaches, boating, and quiet moments by the bay are all just part of the rhythm here. This is a home for those who value privacy without isolation, nature without sacrifice, and a lifestyle that feels intentional, calm, and deeply connected to Longboat Key.
Listing Agent: Angela Scott (941-928-7462)
515 FOREST WAY, LONGBOAT KEY, FL 34228
$1,420,00087 Days on yellowkey MLS ID: A4679679
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2880 Built: 1989Monthly Fee: $1,698 Tax: $4,802 (2025)Community: Cedars East Sec 2Condo
Taxes:$4,802
Remarks: NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
761 NORTON ST, LONGBOAT KEY, FL 34228
$4,390,00088 Days on yellowkey MLS ID: A4677200
Bed: 4 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 4674 Built: 2004 Tax: $14,281 (2024)Community: Sleepy Lagoon Park 2Single Family
Taxes:$14,281
Remarks: Tucked along a quiet canal in Longboat Key’s Sleepy Lagoon Park, 761 Norton Street delivers the kind of waterfront lifestyle that’s increasingly rare—equal parts boating-centric, resort-style, and built for hosting at scale. With 4 bedrooms, 4 ensuite baths, 3 half baths, and 4,674 square feet under air, the home is thoughtfully designed for those who want space and flexibility without sacrificing flow, comfort, or privacy, ideal for multi-generational living, extended stays, and entertaining without compromise. Constructed for exceptional strength and durability, this home offers solid concrete block walls on all levels with reinforced rebar, and hurricane-rated windows and doors. A travertine foyer filled with natural light and a planter with water feature sets the tone, complemented by a 5-stop elevator. This home features smart home functionality. The living level features an open-concept eat-in kitchen, appointed with wood cabinetry, stainless steel KitchenAid appliances, a beverage cooler, and cooktop, created to serve both everyday ease and elevated entertaining. Designed to maximize indoor-outdoor living, the home opens to a travertine pool deck anchored by an infinity-edge pool and spa, an outdoor shower, and an outdoor kitchen with a Coyote grill, a true backyard retreat that feels like a private resort. For boating enthusiasts, the property’s canal-front setting is enhanced by a 28,000-lb boat lift and lift for two jet skis, offering exceptional convenience for water access and day-to-day coastal living. Inside, architectural details add warmth and dimension, including a two-tone tray ceiling, travertine fireplace, and curated art niches along the hallway. Guest accommodations are generous and private, including multiple en-suite bedrooms with walk-in closets. One suite offers a walk-in shower and vanity, while another features a more spa-like bath with a Jacuzzi tub, dual vanities, a walk-in shower, and a water closet with a bidet. Adding to the home’s standout appeal is its rare, mirrored design, featuring an additional living level with a second kitchen/bar/living arrangement, as well as matching guest suites, creating two complete living experiences under one roof. Whether hosting seasonal guests, accommodating extended family, or simply wanting room to spread out, the layout provides the ultimate “together-but-separate” lifestyle. Additional highlights include a 4-car tandem garage, solid, poured concrete construction and a prime Longboat Key location. Experience the best of island living at this canal-front address featuring seamless access to the Bay, Intracoastal Waterway and Gulf waters. Just minutes away from St. Armand’s Circle, the new St. Regis, downtown Sarasota, and Anna Maria Island, you’re perfectly positioned near celebrated restaurants, boutique shopping, and culture. And from your own dock, the boating lifestyle becomes part of everyday life, with restaurants visible across the way and just a quick boat ride from home, it’s easy to head out for lunch, sunset cocktails, or a spontaneous evening on the water.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
5924 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$849,500341 Days on yellowkey MLS ID: A4651805
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1359 Built: 1955 Tax: $11,764 (2024)Community: Fractional SubSingle Family
Taxes:$11,764
Remarks: Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key. Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room. An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures. Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.
Listing is courtesy of: JOHN DONATO REAL ESTATE INC (941-504-4987)
Listing Agent: John Donato (941-504-4987)
5920 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$1,749,500341 Days on yellowkey MLS ID: A4652254
Bed: 2 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2823 Built: 1973 Tax: $8,478 (2024)Community: Longboat KeySingle Family
Taxes:$8,478
Remarks: DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house on the barrier island of Longboat Key. You can enjoy a 3-minute walk to the beach using your private beach access or step outside and enjoy the canal on your trex dock. The uncrowded beach with natural surroundings, fine sand beaches, warm breezes, and clear turquoise waters is truly a special place. Entering the home, you are greeted by terrazzo floors, stunning 2 story foyer and a water view of the canal. All new wood kitchen cabinets including island and coffee bar with quartz countertops making this a great area to entertain guests. All 3 bathrooms have been completely renovated and include custom tile showers. Large master bedroom with en-suite bathroom. An enclosed lanai overlooking the canal is a perfect spot for an office or tropical retreat. Large living room with wood burning fireplace and new tile flooring provides a relaxing space. New kitchen and bath fixtures throughout. Ceiling fans in each room. Being in the middle of LBK provides easy access to Anna Maria Island and Bradenton to the north, St. Armands and Sarasota to the south. SRQ airport is less than 45 minutes. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway, deeded beach and canal access with 5924 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together (or use one as a rental for an ongoing revenue stream}. The property is being sold as-is. Please use AS IS Residential Contract for Sale and Purchase_FloridaRealtors-FloridaBar-ASIS-7.xdp
635 MARBURY LN, LONGBOAT KEY, FL 34228
$1,945,00069 Days on yellowkey MLS ID: A4681616
REDUCED by $50,000 (2.5%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2446 Built: 1958 Tax: $22,205 (2024)Community: Sleepy Lagoon Park 2Single Family
Taxes:$22,205
Remarks: Come savor laid-back luxury and the island lifestyle that Longboat Key is known for in this tranquil, seaside retreat. AND listed more than $100,000. under a current appraisal! This home is a decorators dream! Completely remodeled with a brand new kitchen, all new flooring, 4 bedrooms and 3 baths in an open and inviting space. The line is blurred between indoor and outdoor living with a gorgeous sparkling pool just beyond the mahogany French doors, surrounded by tropical plants and situated on a fabulous canal. For the boaters, you have a 14,000 lb. lift and no fixed bridges to the Gulf of Mexico, making your day on the water an easy experience. Nightly sunsets at the neighborhood beach is just a short walk away and something to make a regular habit of! A short distance to multiple restaurants, shopping, 12 miles of biking paths, and the incredible Joan Durante Park on the Bay only add to the remarkable quality of life living on an island can provide. When you’re ready for something more, St.Armands Circle and the cultural mecca of Downtown Sarasota is just a short drive away. This extraordinary home is a true island paradise you must come see.
6322 LAGUNA DR #1, LONGBOAT KEY, FL 34228
$2,499,900178 Days on yellowkey MLS ID: A4669170
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2886 Built: 2001 Tax: $12,100 (2024)Community: Laguna Yacht Village A CondoSingle Family
Taxes:$12,100
Remarks: Welcome to Laguna Yacht Village on beautiful Longboat Key- a gated waterfront community located across the street from the beach, with private bay access. This fully furnished turnkey home is perfectly positioned to embrace the island lifestyle, with fantastic gulf views from almost every room. The home includes a deeded deep-water dock (Slip #6- boat lift included), located in a protected lagoon just minutes from the Intracoastal Waterway and Gulf of Mexico with no fixed bridges, making it a boater’s dream. This modern Key West inspired three story single residence with an oversized 3-car garage features four bedrooms, three full baths, and over 2,886 square feet of beautifully designed living space. Perfectly positioned to embrace the island lifestyle, this home includes a deeded deep-water dock (Slip #6) located in a protected lagoon just minutes from the Intracoastal Waterway and Gulf of Mexico — with no fixed bridges, making it a boater’s dream. Step inside and experience a harmonious blend of coastal elegance and comfort. Expansive living areas feature soaring ceilings, an abundance of natural light, and sophisticated finishes throughout. The culinary-inspired kitchen, designed in timeless style, boasts custom cabinetry, quartz countertops, and an oversized central island — the ideal space for hosting and entertaining. The primary suite, complete with a study, serves as a serene retreat with dual vanities, a hydro-massage soaking tub, and a walk-in glass-enclosed shower for the ultimate spa-like experience. Multiple balconies, including an elevated screened patio off the main level, provide refreshing sea breezes and captivating water views of the Gulf. A ground-floor patio further extends the outdoor living experience. The oversized garage provides ample storage for beach gear and boating essentials. The gated community features a resort-style pool offering a true lock-and-leave lifestyle. Residents will appreciate convenient proximity to Longboat Key’s pristine beach, award-winning island restaurants, boutique shopping, and parks — all while being a short drive from the cultural heart of downtown Sarasota and St. Armands Circle.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Brandy Loebker (941-404-4737)
4825 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$839,900201 Days on yellowkey MLS ID: A4667044
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,897 (2024)Community: Westchester AptsCondo
Taxes:$11,897
Remarks: Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.
701 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$259,000110 Days on yellowkey MLS ID: O6370226
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $3,873 (2024)Community: Saint Judes AptsCondo
Taxes:$3,873
Remarks: DIRECT WATERFRONT OPPORTUNITY IN LONGBOAT KEY! Here's your rare chance to own a waterfront property with direct access to the Intercoastal Waterway! Perfectly located for vacation rentals, this canal-front 1-bedroom, 1-bathroom end unit offers incredible potential for income, especially with high demand bookings from January to April. This property boasts 21 feet of water frontage and a newly installed seawall (June 2021). Enjoy the Florida lifestyle with easy access to boating, kayaking, and fishing. Additional outdoor amenities include a paver patio. Just steps away from a private beach access, kayak launch, and deeded beach entry. The property also has direct access to the scenic Joan M. Durante Park, with 32 acres of walking trails, gardens, recreational areas, and breathtaking Sarasota Bay views. Take a short walk to top-rated restaurants, shops, a deli, bike and kayak rentals, and more. Plus, you're just a short drive to St. Armands Circle and Anna Maria Island! This is the most economical waterfront property you'll find in all of Longboat Key!
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Filitsa Sterner Mistretta (941-928-3666)
771 MARBURY LN, LONGBOAT KEY, FL 34228
$2,500,00034 Days on yellowkey MLS ID: A4686401
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3016 Built: 1985 Tax: $24,092 (2025)Community: Sleepy Lagoon Park 2Single Family
Taxes:$24,092
Remarks: One or more photo(s) has been virtually staged. Boaters will love this spacious elevated home in a premier waterfront location on Longboat Key with dock, lift and by boat it is just four homes from the intercoastal, open bay waters and a short boat ride to the Gulf. Built for large gatherings, this home is beautifully designed with loads of gathering and entertaining spaces. The open plan home was thoughtfully designed with five bedrooms, four with en-suite baths. The kitchen features custom wood cabinets and granite countertops. Entertaining will be a breeze with two large gathering spaces, including a great room with dining area and adjacent bonus room that would be a wonderful media or game room. Ground level highlights include two bonus areas and a huge four-car garage. The composite dock has a 10,000-pound boat lift, water and electric. Recent updates include hurricane windows and doors (2025), metal roof (2025), pool equipment and pool heater (2025) and interior freshly painted. This location on Longboat Key can't be beat with community beach access just across the street, and a heated pool and boating in your own backyard. This is the ideal home to create wonderful island memories.
Listing Agent: Holly Switow (941-735-3186)
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