Longboat Key Homes with Private Entrance Exterior Features

Longboat Key Homes with Private Entrance Exterior Features

Welcome to Longboat Key, Florida – a slice of paradise nestled along the stunning Gulf Coast. Renowned for its pristine beaches, vibrant sunsets, and a laid-back lifestyle, Longboat Key is the ultimate destination for those seeking both relaxation and adventure. This charming barrier island boasts a unique blend of natural beauty and upscale living, making it a haven for families, retirees, and seasonal residents alike.

As you explore the enchanting neighborhoods of Longboat Key, you’ll discover an array of exquisite homes that perfectly embody the coastal lifestyle. One standout feature of many properties here is the private entrance. Imagine coming home to your own secluded sanctuary, where you can unwind in peace after a day of enjoying the sun and surf. These homes often showcase stunning exterior features, from lush landscaping to elegant facades, all designed to provide both privacy and curb appeal.

The allure of Longboat Key extends beyond its beautiful homes. With world-class dining, boutique shopping, and a plethora of outdoor activities, residents enjoy a vibrant community atmosphere. Whether you’re indulging in fresh seafood at a waterfront restaurant, exploring the local art scene, or taking a leisurely stroll along the beach, there’s always something to keep you entertained.

In Longboat Key, your dream home awaits, complete with a private entrance that offers a perfect blend of luxury and tranquility. Experience the best of Florida living in this idyllic coastal paradise, where every day feels like a vacation. Come and discover why Longboat Key is not just a place to live, but a lifestyle to embrace!

Newest Longboat Key Homes with Private Entrance Exterior Features

2352 Harbour Oaks Drive, Longboat Key
$1,249,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
Move right into this serene, spacious and furnished Longboat Key one-level villa, with its tastefully renovated interiors and new (2025) tile roof. This beautiful home offers 3 bedrooms, 2.5 baths, 2,487 square ft of updated interior space, with approximately 800 additional square feet including the expansive two-level lanai and deck overlooking a peaceful pond. No detail has been spared. The gracious living room and dining room, accented by a contemporary crystal chandelier and long-plank porcelain flooring, lead into the great room and kitchen. White quartz countertops and soaring ceilings highlight the chef's open kitchen, which is conveniently positioned so you can converse with friends and family in the adjacent the great room. The great room is centered around a fireplace, wine and coffee bar, and entertainment center. Mood LED lighting enhances the ambiance of the space. Both the great room and primary bedroom have automated blinds and sliding doors that open to the spacious hardy plank screened lanai. The primary ensuite bath features double vanities, a rainforest shower with wall jets, 10-jet jacuzzi soaking tub and custom lighting. Two more bedrooms with Jack & Jill bathroom outfitted with tub and shower, and a sophisticated powder room complete the home. This home provides ample storage, with 8 closets, a laundry room, and a two car garage with additional storage shelves and epoxy flooring. Imagine grilling outdoors while you relax on your shaded, screened lanai and enjoy the peaceful water views. Living in Bay Isles you will enjoy a true resort lifestyle with access to the community pool just a few steps away, deeded access to the nearby private Bay Isles beach club on the Gulf, optional golf, tennis or social membership in the Longboat Key Club, a marina, and miles of scenic paths for walking and cycling--all in a gated, maintenance free community. You are only minutes from the Longboat Key Club with its 45 holes of golf and Gulf side resort pool, the Longboat Key Tennis center, and a short drive to the shops, restaurants and cultural attractions of St. Armand's and Sarasota. Simply move in, unpack and enjoy your Longbboat life.

2352 Harbour Oaks Drive, Longboat Key

2110 Harbourside Drive Unit 523, Longboat Key
$628,000
3 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
Best value with SRQ Bay Views- great location. 3 bedrooms. Discover a relaxed island lifestyle at The Atrium in Bay Isles, where expansive water views and a generous, comfortable floor plan meet in this three-bedroom, two-bath residence. With 2,031 square feet of living space, this home offers room to gather and enjoy Longboat Key's natural beauty. A broad wraparound, covered balcony extends the living space outdoors and frames sweeping views across Sarasota Bay and the surrounding waterways. Start the day with coffee as the light moves across the water, or settle in at day’s end to watch the colors shift over the bay. The balcony’s generous proportions create multiple places to dine, read, or simply take in the coastal setting. Inside, the open living and dining area is designed for easy everyday living and entertaining. High ceilings, an open floor plan, and a wall of windows bring in natural light and keep the water view in focus. The spacious kitchen offers abundant cabinetry, stainless steel appliances, and a double oven, with plenty of room to prepare a casual breakfast or host a dinner with friends. A separate laundry room adds convenience. The primary suite provides a peaceful retreat, with a walk-in closet and a private bath. Two additional bedrooms offer flexibility for guests, a home office, or hobbies, while the second full bath serves both visitors and residents. Offered with furnishings negotiable, the residence gives its next owner the opportunity to make the space their own. The Atrium’s amenities support an active, easygoing island routine. Residents enjoy a gated setting with elevator access, a fitness center, a community pool, and tennis courts. Deeded beach access makes it easy to spend time on the Gulf of Mexico, while the community’s bayfront setting offers a different perspective on the island’s waters. A one-car garage and guest parking provide practical convenience. Located within Bay Isles on Longboat Key, the property is close to the island’s beaches, golf, boating, dining, and shopping. St. Armands Circle and downtown Sarasota are close, with restaurants, boutiques, cultural attractions, and waterfront events within reach. Whether you are looking for a full-time island home, a seasonal escape, or a place to enjoy between travels, this residence offers generous space, memorable bay views, and access to the best of the Longboat Key lifestyle.

2110 Harbourside Drive Unit 523, Longboat Key

6610 Gulf Of Mexico Drive, Longboat Key
$22,000,000
4 Beds ⋅ 7 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Introducing a rare legacy estate defined by architectural distinction, extraordinary waterfront, and an exceptional sense of privacy. 6610 Gulf of Mexico Drive is the pinnacle of architectural ingenuity designed by world-renowned visionary Carl Abbott, one of the most highly decorated architects in the Florida/Caribbean region. Known for naming his most valued accomplishments, Abbott designated this spectacular residence the “House of Columns”—a remarkable expression of art in architecture inspired by the land and its surrounding natural beauty. Including the adjacent lot at 6630 Gulf of Mexico Drive further enhances the offering, providing the opportunity to construct a guest house or secondary structure—an appealing option for multigenerational living, visiting guests, or staff accommodations. Set along Sarasota’s most coveted barrier island, the property represents a singular convergence of design, landscape, and place—an enduring residential landmark of remarkable presence and provenance. A long, private drive through a dense canopy of palms and native foliage leads to this nearly five-acre peninsula property with expansive bay frontage and exceptional seclusion. Endless expanses of water and sky form a breathtaking backdrop, while the ever-shifting light throughout the day casts the home and acreage in a constantly evolving palette. Designed for multilevel living, the 6,891-square-foot home features the main living structure with separate wings connected by enclosed bridges. Walls of glass dissolve the boundaries between interior and landscape, revealing lush grounds and a brilliant bay panorama that unfolds endlessly toward the horizon. A beautifully crafted pool surrounds nearly half of the home’s exterior and mirrors the tranquil movement of the water beyond. Clean architectural lines, soaring interior volumes, and a thoughtful interplay of solid and transparent forms create a cohesive relationship between the interior and exterior. Ceilings reaching up to 21 feet allow natural light to move freely throughout the home. Every space reveals a considered balance of visual drama and functional design. With every turn, another exquisite detail reveals itself—thoughtfully composed, beautifully nuanced, and presented with quiet grandeur. As daylight fades, exterior lighting transforms the grounds into a resort-like setting, creating an inviting atmosphere where every gathering becomes a memorable experience. A private dock with two lifts provides direct access to the protected shoreline of Sarasota Bay and the Intracoastal Waterway, supporting a seamless boating lifestyle. An elevator serves the home’s multiple levels, while Lutron lighting and automated shades allow the residence to respond intuitively to changing daylight. The owner’s garage provides convenient access to the interior elevator and an additional air-conditioned four-bay garage with a generous workspace brings the total capacity to six vehicles. A whole-home generator provides added continuity and peace of mind. Impeccably maintained by its original owner, the residence reflects an uncommon level of care and stewardship. Estates of this size and caliber, architectural clarity, substantial waterfront, established boating infrastructure, development flexibility, and meticulously maintained condition are exceptionally rare. This impressive property exudes a sense of timelessness and is distinguished by its design, scale, privacy, and extraordinary location.

6610 Gulf Of Mexico Drive, Longboat Key

2151 Gulf Of Mexico Drive Unit 4, Longboat Key
$4,100,000
4 Beds ⋅ 4 Baths ⋅ En Provence SubDv. ⋅ 34228 Zip Code
Gulf-front living with the privacy of a villa. Residence 4 at En Provence is one of just 21 homes in an exclusive, guard-gated French-Mediterranean enclave on nearly six acres of Longboat Key beachfront. Fully furnished and designer-decorated, this coastal retreat encompasses approximately 3,800 square feet with 4 bedrooms, 3.5 baths and a home office. A private elevator opens to the foyer, introducing interiors appointed with marble floors, crown molding and tray ceilings. Views of palms, the pool pavilion and the open Gulf frame the living and dining spaces. The kitchen features a gas cooktop, double wall ovens and an adjoining butler’s pantry with a wet bar and wine refrigerator. Gulf-front balconies extend the living areas outdoors, including a summer kitchen with a built-in grill. The primary suite features a private balcony entrance, a walk-in closet and a spa bath with a jetted tub and walk-in shower. Each additional bedroom also includes a walk-in closet. A private two-car garage and storage locker complete the residence. With its limited number of residences, expansive grounds and 24-hour gated security, En Provence offers an exceptional sense of privacy. The pet-friendly community features a heated pool and spa, beach access with chair and umbrella service, a clubhouse with social and dining rooms, and a fitness center. Enjoy a secluded beachfront lifestyle just minutes from St. Armands Circle, Longboat Key Club golf and Sarasota’s dining and culture.

2151 Gulf Of Mexico Drive Unit 4, Longboat Key

2141 Harbourside Drive Unit 1203, Longboat Key
$1,399,000
3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code
Welcome to an exceptional turnkey, furnished, and newly renovated villa in Harbour Oaks, ideally located within Bay Isles in the heart of Longboat Key. This end-unit residence offers the right blend of natural warmth, contemporary finishes, and curated style. With high ceilings, abundant natural light, and a spacious floor plan, the home feels remarkably open and inviting. Note: All new impact-windows and doors. Warm hickory wood floors extend throughout the living areas, adding richness and character to the home's fresh, contemporary design. The impressive kitchen features an oversized island with a dramatic waterfall-edge quartz countertop in a concrete-inspired finish that is both beautiful and requires no maintenance. Stainless steel GE Café appliances complement the kitchen, while a custom coffee bar with floating shelves and a stunning backsplash adds another layer of style and functionality. For evening entertaining, the custom built-in bar is a standout feature, topped with a beautiful live-edge Saman wood countertop. It is the perfect place to pour a cocktail and enjoy the relaxed Longboat Key lifestyle. The spacious dining area is adjacent to a beautiful atrium that fills the home with magnificent natural light. Newly tiled with stone. It is screened overhead, allowing the sliders to be opened, creating a wonderful connection to the outdoors and inviting fresh air into the dining and living space. The oversized screened lanai is another exceptional feature, with brand-new stone pavers and a new panoramic screen enclosure. Lush new greenery surrounds the lanai, creating a private tropical setting that feels like your own outdoor retreat. The primary suite is a luxurious sanctuary with three closets, including a walk-in, all outfitted with customized shelving for exceptional organization. The beautifully renovated primary bath features Carrera marble countertops, dual sinks, warm gold fixtures, and a separate water closet. The spacious second bedroom offers a private ensuite bath with a marble-floored shower, Carrera marble vanity top, and a separate water closet. The generous third bedroom is currently used as a fitness room but offers ample space for a comfortable bedroom, along with a generous closet. Storage is abundant throughout the home. A beautifully appointed powder room serves guests. As an end unit, this villa enjoys a large manicured grass side yard and an enviable location just steps from the community pool. This home has an attached 2-car garage with a new epoxy-coated floor and an additional fridge.  An especially wonderful benefit of living in Bay Isles is automatic membership in the Bay Isles Beach Club, just minutes away on Longboat Key's beautiful sandy beaches. Enjoy five acres of beachfront, gated parking, beach chair storage, newly renovated restrooms, grills and picnic tables—a wonderful setting for family and friends to gather, sunset strolls, and memories to last a lifetime. Close proximity to the Longboat Key Club with 45 holes of golf, 5 private restaurants, and a world-class tennis and pickleball facility. This residence is more than a renovation; it is a completely reimagined home where thoughtful design, beautiful materials, and the ease of living the good life on Longboat Key come together beautifully.

2141 Harbourside Drive Unit 1203, Longboat Key

3710 Gulf Of Mexico Drive Unit A3, Longboat Key
$525,000
2 Beds ⋅ 2 Baths ⋅ Gulfshore Of Longboat Key SubDv. ⋅ 34228 Zip Code
DIRECT GULF FRONT/OCEAN VIEWS, FULLY FURNISHED, ELEVATED, AND BRING YOUR BOAT (BOAT SLIP opportunity for a small monthly rental fee at the NEW community marina) Beach Retreat with numerous improvements. Longboat Key living doesn't get any better than this. Located in a highly desirable waterfront co-op community, this home was raised 4 ft to enjoy more of the beautiful ocean views. All new windows with the front windows replaced with large picture windows for year round gulf/ocean views. Additional new updates include all new windows, new window coverings, new doors, new kitchen remodel which includes new countertops and painted cabinets, new bedroom fans, newly redone dining area, refreshed outdoor bathhouse, (included for description purposes as 1 of 2 bathrooms), new HVAC duct work and heating element, new Astro turf lawn, new outdoor lighting, newly painted interior, beautifully redone outdoor patio. Gulfshore of Longboat Key is perfectly situated between the Gulf of America and the Bay for beach to bay access. It has approximately 450-500 ft of private deeded beach access on the powdery sand and views of the turquoise blue water. It also has a new marina on Sarasota Bay, a large, heated community pool, a remodeled clubhouse with a commerical kitchen, a well-maintained community with a professional on-site manager, and very reasonable HOA fees! Gulfshores is a 55+ community and does not permit pets or rentals. Come live The Longboat Key Life.

3710 Gulf Of Mexico Drive Unit A3, Longboat Key

6561 Bayou Hammock Road, Longboat Key
$3,495,000
4 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34228 Zip Code
Beyond the gates of Bayou Hammock, where just 13 residences share one of north Longboat Key’s most private waterfront settings, a true coastal retreat awaits. Arrive through one of two private gated entrances, where refreshed tropical landscaping and a charming butterfly garden welcome you home. Set on an expansive 0.83-acre lot with approximately 150 feet of direct canal frontage, the property offers sailboat water and room to accommodate vessels up to approximately 70 feet. Thoughtfully reimagined by the current owner, the beautifully renovated bungalow blends timeless Old Florida character with modern comfort. The 3-bedroom, 3-bathroom main residence is complemented by an attached guest casita with its own bedroom and bathroom, creating a total of 4 bedrooms, 4 bathrooms, and approximately 2,600 square feet of air-conditioned living space. Distinctive keystone accents will continue to develop a rich, natural patina in the coastal climate, while impact-rated windows and doors, a new standing-seam metal roof, and an attached one-car garage provide lasting value and peace of mind. Life here unfolds outdoors. Begin the morning beside the pool, rinse off beneath the outdoor shower after an afternoon on the water, or step onto the brand-new dock and set out from one of two new boat lifts, one 20,000lb and one 10,000lb. Spend the day boating, fishing, and exploring the surrounding waterways before returning to your own peaceful hideaway. Just moments from the beaches, dining, and relaxed charm of north Longboat Key and nearby Anna Maria Island, this exceptional property is also zoned for Anna Maria Elementary School. More than a waterfront home, it is a private island sanctuary offering rare space, remarkable boating access, and an unhurried way of life.

6561 Bayou Hammock Road, Longboat Key

1591 Gulf Of Mexico Drive Unit 618, Longboat Key
$12,500,000
4 Beds ⋅ 6 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Experience an extraordinary standard of beachfront luxury from this spectacular penthouse residence at the prestigious St. Regis Longboat Key. Showcasing breathtaking panoramic views of the Gulf of Mexico and Sarasota Bay, this exceptional home offers an unparalleled blend of sophistication, privacy, and world-class design. Spanning approximately 5,320 square feet, the residence features four spacious bedrooms, five full baths, and one half bath, thoughtfully designed to provide the ultimate in comfort and elegance. Expansive walls of glass frame mesmerizing water views from nearly every room, while the spectacular 1736 square foot wraparound terrace creates seamless indoor-outdoor living. Enjoy your own private plunge pool, outdoor gas grill, and multiple entertaining areas perfectly positioned to capture stunning sunrises over the bay and unforgettable sunsets across the Gulf. The interiors have been exquisitely curated by award-winning interior designer Kurt Lucas, with every detail reflecting impeccable craftsmanship, timeless elegance, and refined coastal luxury. The residence is offered fully furnished, allowing for an effortless transition into an exceptional waterfront lifestyle. Additional features include a private three-car garage. The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience the finest in luxury living at The St. Regis Longboat Key.

1591 Gulf Of Mexico Drive Unit 618, Longboat Key

760 Longboat Court, Longboat Key
$840,000
3 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, high-end updates. Located just steps from the island's finest beaches, bay access points, and local dining, this coastal sanctuary sits on a private, oversized 9,400 sq. ft. lot surrounded by lush tropical landscaping. Inside, classic details like white tongue-and-groove ceilings, a cozy masonry wood-burning fireplace, and warm Saltillo tile floors complement a fully updated gourmet kitchen equipped with solid-surface countertops, custom shaker cabinetry, gas cooking, and striking tile flooring and backsplash. The main living space features a bright open layout, with vintage charm mixed with today's luxuries. Charming enclosed Florida Room sets the vibes with its panoramic views of the lush, tropical gardens. Oversized primary bedroom radiates the beach cottage vibes you're looking for. Spa-inspired bathrooms with frame-less glass showers, and stylish finishes throughout. The guest bedroom, currently used as a den, features walls of glass and continued vintage charm. Adding incredible versatility, an adjoining mother-in-law suite complete with its own kitchenette offers private accommodations for extended family, guests, or flexible living space. This area was designed to be both an extension of the primary living space with its continuous flow or, with its separate entrance, it's ideal for guests seeking privacy. Step outside into your private backyard oasis featuring a paver patio, lush gardens, an outdoor lounge area, and a private hot tub (2025) - perfect for relaxing after a day on the water. The oversized backyard is completely fenced and secured ready for the dream pool ($10K pool builder credit and permit convey). This residence features extensive, high-quality updates designed for modern comfort and efficiency. Recent improvements include, Energy & Climate: A 10kW solar panel system (2021), a new central air conditioning system (2025), and a mini-split system (2024). Interior & Structural: Comprehensive kitchen and bathroom renovations, new weather-grade subflooring in the cottage, and upgraded electrical service featuring an EV car charger and Cat-6W wiring throughout. Technology & Entertainment: A whole-home Bose integrated audio system. Utilities & Appliances: Completely updated cottage plumbing, instant hot water heater and a full suite of new appliances, including a washer and dryer. Windows: Replacement cottage windows installed in 2020 and new impact windows in the Mother-in-Law Suite. New interior paint and lighting (2026). Exterior Improvements: New landscaping, irrigation, electrical, and fencing just installed. Discover contemporary elegance blended with classic Florida island charm in one of Longboat Key's most sought-after historic areas. Set within a vibrant, golf-cart-accessible neighborhood, this exceptional property puts you close to local cafés, waterfront dining, unique boutiques, fitness facilities, and fishing piers. Enjoy convenient access to Sarasota Bay with a nearby boat launch and kayak areas, while pristine Gulf beaches are only minutes away - all with the freedom of no mandatory HOA. A very favorable VA assumable loan is an option. Schedule a visit to experience the unique lifestyle and character of this remarkable home firsthand.

760 Longboat Court, Longboat Key

1561 Gulf Of Mexico Drive Unit 404, Longboat Key
$12,400,000
3 Beds ⋅ 4 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Presented in the most coveted beachfront enclave at The St. Regis Longboat Key Resort, this is a rare opportunity to own a spectacular residence in the prestigious Armand building — the closest to the Gulf, with breathtaking, unobstructed views of the Gulf of Mexico. Encompassing nearly 5,000 square feet and offered fully furnished, this extraordinary home was masterfully designed by the award-winning Rowland and Broughton of Aspen, Colorado. Thoughtfully curated throughout, it lives like a private single-family home while enjoying the legendary St. Regis services and amenities, including butler service and in-residence dining. The gracious great room is designed for effortless entertaining, featuring porcelain wood plank flooring and dramatic accordion doors that fully retract to a sprawling terrace with a private gas grill and panoramic views of the Gulf, resort, and saltwater lagoon — creating seamless indoor-outdoor living. The chef’s kitchen is a true showpiece, anchored by a large statement island clad in exquisite Pininfarina Crystal quartzite with a dramatic waterfall edge — blending sculptural beauty with everyday functionality. The space is impeccably appointed with dual Cove dishwashers, a Wolf six-burner cooktop, Wolf double ovens and microwave, and a Sub-Zero refrigerator. A charming breakfast area offers built-in storage and shelving, along with an ice maker and beverage refrigerator for ultimate convenience. A private club room provides the perfect setting for lounging or game day gatherings, highlighted by custom built-ins and striking in-wall wine storage. The luxurious owner’s suite captures sweeping Gulf views and opens directly onto the expansive terrace. A stunning feature wall wrapped in Bijou Knits wallpaper by Phillip Jeffries adds refined texture and sophistication, complementing the custom built-ins that define this serene retreat. The spa-inspired bath features dual oversized vanities (including a dedicated makeup area), illuminated mirrors, a soaking tub, seamless glass shower, two private water closets with Toto electric toilets, and custom closets. Two additional guest suites offer comfort and privacy. The second features custom built-ins with a king Murphy bed, integrated desk, generous closets, and a bath with double vanities and glass shower, opening to terrace views of Sarasota Bay. The third is equally spacious, also opening to the terrace with bay views and offering double vanities and custom closets. An elegant laundry room continues the home’s elevated aesthetic with custom cabinetry, a utility sink, and SM Quartz by Santa Margherita countertops. Throughout, porcelain wood plank floors, electronic shades, and a state-of-the-art Crestron smart home system enhance everyday living. The integrated technology package — valued at approximately $400,000 — controls lighting, blinds, televisions, and music throughout the home. This is an exceptional opportunity to own one of the most refined residences on Longboat Key — where five-star resort living meets the privacy and comfort of a grand coastal home. Residents enjoy a private clubhouse with fitness center, resident-only pool and spa, St. Regis Butler and Concierge services, an oceanfront spa, dining venues, beachfront cabanas, lazy river, and saltwater lagoon. Set on 17 acres of pristine beachfront just 3.5 miles from St. Armands Circle, this home invites you to embrace the legendary St. Regis lifestyle.

1561 Gulf Of Mexico Drive Unit 404, Longboat Key

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