Longboat Key Homes with Rain Gutters Exterior Features

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

539 Forest Way Unit 539, Longboat Key

$599,900

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with recently install hurricane rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front.

521 Forest Way, Longboat Key

$1,495,000

3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code

3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key

$795,000

3 Beds ⋅ 2 Baths ⋅ Club Longboat Beach & Tennis SubDv. ⋅ 34228 Zip Code

Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s established and sought-after beachfront communities. This beautifully updated three-bedroom, two-bath residence is offered turnkey furnished, making it an exceptional opportunity for a full-time residence, coastal retreat or potential income-producing investment. In desirable Building 1, this spacious first-floor residence offers approximately 1,484 square feet of comfortable, thoughtfully designed living space with the rare convenience of no elevators or long walks. The open, split-bedroom floor plan features wide-plank flooring, a light and inviting coastal palette, and an easy flow for everyday living and entertaining. The updated kitchen is the heart of the home, featuring crisp white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash and a large center island with seating. Floor-to-ceiling sliders in the great room open to a private, lushly landscaped patio, extending the living space outdoors and creating a peaceful place to enjoy the Longboat Key lifestyle. The spacious primary suite offers direct patio access, a beautifully updated bath with walk-in glass shower and generous closet space. Two additional bedrooms provide flexibility for family and guests, including a den/third bedroom with Murphy bed. A second full bath, full-size washer and dryer, additional laundry cabinetry and abundant storage complete the interior. Just outside your front door is a private storage room and covered parking space, with ample additional guest and resident parking throughout the community. Club Longboat offers approximately 750 feet of direct Gulf-front beach and an exceptional resort-style lifestyle. Amenities include eight Har-Tru tennis courts, several lighted for evening play, an on-site tennis professional, pickleball, two heated swimming pools including separate adult and family pool areas, spa/whirlpool, sauna, beach chairs and umbrellas, grilling areas, bocce, fishing, on-site management and an active social calendar. A new clubhouse with fitness and social spaces is also planned as part of the community’s hurricane restoration, with exciting improvements ahead. Owners enjoy a welcoming community with regular social events, including Friday happy hours and seasonal celebrations. Club Longboat is also pet-friendly for owners and offers exceptional rental flexibility, with a 30-day minimum and up to 12 leases per year. For buyers looking to offset ownership costs, this residence offers a particularly compelling advantage, such as a proven rental history with substantial demand and future bookings potential. The combination of a three-bedroom floor plan, turnkey furnishings, direct Gulf access and flexible leasing has made this an exceptionally desirable rental. Ideally on the Gulf side of Longboat Key, you are minutes from outstanding dining, boating, golf and recreation, with the shops and restaurants of St. Armands Circle and the arts and culture of downtown Sarasota just a short drive away. Whether you are searching for a turnkey beach home, seasonal escape or investment property, this beautifully furnished Club Longboat residence offers the combination buyers want most, direct gulf access, resort-style amenities, three bedrooms, rental flexibility and unmistakable lifestyle of Longboat Key. Simply arrive, unpack and head to the beach.

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

$3,999,990

5 Beds ⋅ 5 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.

560 Chipping Lane, Longboat Key

$525,000

2 Beds ⋅ 2 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

Beautifully renovated waterfront unit at 729 St. Jude’s Way with gorgeous water views and a boat dock, plus easy access to the Intracoastal Waterway. Renovated from top to bottom, this move-in-ready home features all-new flooring, a beautifully updated kitchen and bathroom, and brand-new appliances. Ideally located near a variety of restaurants, beautiful beaches, downtown Sarasota, and Anna Maria Island. Enjoy the perfect blend of waterfront living, modern updates, and convenient access to everything the area has to offer!

729 Saint Judes Drive S Unit 2, Longboat Key

$2,675,000

4 Beds ⋅ 4 Baths ⋅ Coreys Landing SubDv. ⋅ 34228 Zip Code

Freshly updated and directly overlooking Sarasota Bay, this four-bedroom waterfront residence in guard-gated Corey’s Landing returns to the market with significant interior enhancements just completed. Most notably, beautiful brand-new oversized porcelain tile flooring now extends throughout the main living areas, creating a fresh, sophisticated look while visually connecting the home’s open living spaces. The fireplace wall has also been thoughtfully scaled back, opening the sightlines and creating a more effortless flow between the living room, dining room and eat-in kitchen. These new improvements complement an exceptional Longboat Key lifestyle centered around the water. Located behind the gates of Bay Isles, the more than 3,100-square-foot residence combines direct Sarasota Bay frontage, updated dock with 14,000-lb boat lift and deeded access to the private Bay Isles Beach Club on the Gulf of Mexico—a particularly desirable combination for those seeking both boating and beach access. The newly updated main level is designed to draw your attention toward the bay. The oversized porcelain tile provides a clean, cohesive foundation throughout the common areas, while soaring ceilings, abundant natural light and walls of glass enhance the home's open, airy feel. The dramatic bayfront living room features cathedral ceilings, a gas fireplace and impact-rated sliding glass doors opening to the screened waterfront terrace, where wide water views create a beautiful backdrop for morning coffee, entertaining and evenings overlooking Sarasota Bay. The primary suite is conveniently located on the first floor, offering a spacious walk-in closet plus two additional closets and a private en-suite bath. Two additional guest bedrooms on this level—one currently used as a study—share a beautifully updated full bathroom. Upstairs, guests enjoy a private retreat with a loft-style bonus area featuring a built-in entertainment center and an oversized en-suite bedroom finished with elegant tilework. Extensive upgrades enhance comfort and long-term value, including a new tile roof (2023), two A/C systems (2022), remodeled kitchen and baths, recessed lighting, storm windows on the bayside, a new electrical panel, exterior lighting, updated landscaping, sprinkler system, and a new screen enclosure. Corey’s Landing offers a maintenance-free waterfront lifestyle with 24-hour guard-gated security, community tennis courts, and a heated pool and spa. Ownership also includes deeded access to the private Bay Isles Beach Club, where residents enjoy Gulf-front relaxation with pavilion seating, beachside gatherings, and direct access to the white sands of Longboat Key. Ideally positioned behind the gates of Bay Isles, this residence is moments from the Longboat Key Club’s championship golf and tennis facilities, nearby marinas, and island dining. St. Armands Circle, Lido Beach, and downtown Sarasota’s renowned cultural venues, galleries, waterfront parks, and restaurants are all within easy reach—bringing together boating, beach access, and the best of Sarasota’s coastal lifestyle.

3530 Mistletoe Lane, Longboat Key

$399,000

1 Beds ⋅ 1 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

Have you ever dreamed of living on the water on Longboat Key, with your boat just steps from your back door? Imagine starting your morning with coffee outside in front of your dock and breakfast in the sun-filled breakfast nook overlooking the canal, spending the afternoon boating or kayaking on Sarasota Bay, and ending the day with your toes in the sand along the Gulf. Here, that can simply be your everyday life. Beautifully remodeled two years ago and offered furnished, this 1-bedroom, 1-bath canal-front end unit is ready to enjoy from day one. The bright coastal interior features a renovated kitchen that opens to the living room, an updated bathroom, newer appliances, impact-resistant windows and doors, and beautiful tile flooring throughout. A wall of windows surrounding the breakfast nook draws your eye toward the water and creates the perfect spot to linger over breakfast. At the end of the day, retreat to the spacious bedroom, where a long window brings in plenty of natural light and offers another glimpse toward the water. But the real magic begins outside. Step out to your own waterfront setting with a two-year-old dock just beyond your door, new pavers and a seawall replaced in 2021. Grab one of the included kayaks for a peaceful paddle, cast a line from the dock, or hop aboard your boat and head out to Sarasota Bay and the Intracoastal Waterway. There's even room along the side of the property to store your boat trailer. And on Longboat Key, life on the water is only half the story. When you're ready for the beach, Gulf access is just a short walk away. Joan M. Durante Park is practically next door, offering 32 acres of trails, gardens and gorgeous Sarasota Bay views, while island restaurants, shops, a deli, and bike and kayak rentals are all close to home. Perfectly positioned between Sarasota and Anna Maria Island, you can head south toward St. Armands Circle and downtown Sarasota or north toward the laid-back charm of Anna Maria Island. A newer metal roof and flood insurance included in the HOA fee offer additional peace of mind. Parking is easy with paver parking out front plus your own carport. Whether you're searching for your own island retreat, a waterfront investment, or simply a place where boating, beach days and sunsets become part of your routine, this is your opportunity to experience the Longboat Key lifestyle you've been dreaming about.

707 Saint Judes Drive S Unit 1, Longboat Key

$589,900

2 Beds ⋅ 2 Baths ⋅ Longboat Arms SubDv. ⋅ 34228 Zip Code

Longboat Arms - 2BR / 2BA / 1,187 sq ft - Bring your boat and enjoy a slice of paradise! This lovely second-floor condo offers views of the bay, pool, and marina from the front. Open and light-filled, it features a covered front porch and was completely remodeled in 2017. Highlights include all-new hurricane-impact windows, a kitchen with stainless steel appliances and granite countertops, and a hall closet with washer/dryer hookup (or use the convenient laundry facility on the same floor). Tastefully decorated and move-in ready. Located in the low-density Longboat Arms community of just 45 residences with approximately 1,000 feet of waterfront and abundant green space. Enjoy covered parking, a private community boat ramp (perfect for boats, kayaks, paddleboards, jet skis), and offering boat dockage - available to residents on waitlist basis (currently open), heated pool, tennis court, outdoor amenities, and deeded Gulf beach access just across the street. The separate community building is currently undergoing extensive renovation. This is an outstanding opportunity for full-time living, a seasonal retreat, or a smart investment in one of mid-island Longboat Key’s most appealing bay-side communities. Don’t miss your chance to own in Longboat Arms — schedule your private showing today! "Furnishings available upon request"

3320 Gulf Of Mexico Drive Unit 206C, Longboat Key

$565,000

2 Beds ⋅ 2 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

Waterfront Longboat Key living with a private dock, direct Intracoastal boating access, extensive 2025 renovations, and proven seasonal rental performance. Welcome to 713 Saint Judes Drive S #2, a turnkey furnished 2-bedroom, 2-bath waterfront residence offering approximately 1,088 square feet in a desirable south Longboat Key location. Extensively renovated in 2025, the residence features a new kitchen with quartz countertops, updated cabinetry, and new appliances; renovated bathrooms; new flooring; a new HVAC system and water heater; upgraded electrical; extensive plumbing improvements; and new windows and exterior doors. Additional features include a private dock, one-car carport, interior laundry and storage area, and a metal roof. First offered for rent in November 2025, the property has already demonstrated strong seasonal rental performance, creating an appealing combination of waterfront living, boating access, recent renovations, and income potential. Enjoy convenient access to Longboat Key beaches, Sarasota Bay, waterfront dining, shopping, St. Armands Circle, and downtown Sarasota. Whether used as a seasonal retreat, full-time waterfront residence, vacation home, or income-producing property, #2 delivers a compelling combination of location, condition, private dockage, rental flexibility, and immediate enjoyment.

713 Saint Judes Drive S Unit 2, Longboat Key

$835,000

3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code

Welcome to this beautifully situated 2 or 3 bedroom 2.5-bath villa overlooking the second hole of the Harborside White Egret Golf Course. Designed with an inviting sense of openness, the residence features soaring vaulted ceilings accented by rich wood beams, contemporary lighting, and skylights that fill the interior with abundant natural light. The thoughtfully designed floor plan creates an effortless flow between the living, dining, family, and kitchen areas, making the home equally suited to relaxed everyday living or entertaining. The spacious primary suite is privately positioned toward the rear of the home and offers direct access to the screened lanai. Step outside to enjoy tranquil views of the picturesque waterway, complete with fountains, with the manicured golf course providing a beautiful backdrop. Adjacent to the living and dining areas, a versatile additional room with its own closet and access to the second bath offers flexibility as a den, home office, or third bedroom. Additional features include a two-car garage, central vacuum system, and an updated pool deck surface. Ideally positioned to take advantage of the peaceful golf-course setting, this residence offers an exceptional opportunity to create a home in a desirable Bay Isles community. HUD Case #093-659100. Initial Disposition: IN, Equal Housing Opportunity.

2321 Harbour Oaks Drive, Longboat Key

$574,900

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

NEW AND IMPROVED PRICE! There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

508 Forest Way, Longboat Key

Longboat Key Homes with Rain Gutters Exterior Features

Newest Longboat Key Homes with Rain Gutters Exterior Features