Fairway Bay Homes with Tennis Court(s) Community Features

Welcome to Fairway Bay, a hidden gem nestled in the picturesque Longboat Key, Florida. This exclusive subdivision offers a unique blend of luxury living and a vibrant community atmosphere, making it the perfect place for those seeking a serene coastal lifestyle. With its stunning views and lush landscapes, Fairway Bay is a true paradise for nature lovers and outdoor enthusiasts alike.

One of the standout features of Fairway Bay is its impressive homes, many of which come with private tennis courts. Whether you're a seasoned player or just looking to enjoy a friendly match with neighbors, having a tennis court right in your backyard elevates your living experience. Imagine stepping outside, racket in hand, and enjoying a game under the warm Florida sun or hosting weekend tournaments with friends and family.

The community is thoughtfully designed, boasting a variety of amenities that cater to an active lifestyle. Residents can take advantage of the beautifully maintained tennis courts, perfect for honing your skills or engaging in some lighthearted competition. Additionally, the surrounding area offers pristine beaches, scenic walking trails, and access to the vibrant local culture that Longboat Key is known for.

Fairway Bay is not just a place to live; it's a lifestyle. With its prime location in Sarasota County, residents enjoy proximity to world-class dining, shopping, and entertainment options. Whether you're looking for a permanent residence or a seasonal retreat, Fairway Bay is the ideal choice for those who appreciate the finer things in life while enjoying the charm of a close-knit community. Come discover your dream home in this enchanting enclave today!

Newest Fairway Bay Homes with Tennis Court(s) Community Features

$1,195,000

3 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4700558 MLS ⋅ Active Status ⋅ Building 3 - Phase 1 BLDG.

Behind the gates of Bay Isles, this beautifully updated waterfront townhome in Fairway Bay offers the rare convenience of a private deepwater dock accommodating vessels up to 40’. From here, Sarasota Bay, waterfront dining and the Gulf are only minutes away by boat, while peaceful water views become part of the backdrop to everyday living. A stepped walkway welcomes you inside, where more than 2,100+/- sq. ft. unfolds across two thoughtfully designed levels. The moment you enter, soaring 2-story ceilings create an immediate sense of openness, while warm wood flooring, soft neutral tones and carefully selected finishes create an inviting atmosphere throughout. The living room centers around a striking linear fireplace, creating a natural gathering place for relaxing or entertaining. Nearby, the dining area transitions effortlessly into the reimagined kitchen, where white cabinetry with glass panel accents, stone countertops, tile backsplash, breakfast bar and a dedicated coffee station combine beauty with everyday function while keeping the space connected to the surrounding living areas. The primary suite offers a peaceful retreat with its own private terrace overlooking the bay, while the spa-inspired bath features an oversized soaking tub, rainfall steam shower and abundant natural light from an overhead skylight. Two additional bedrooms, along with flexible bonus areas for hobbies, fitness or music, provide comfortable accommodations for family and guests. Multiple terraces throughout the home create inviting places to enjoy the waterfront setting from sunrise through evening. A popular, bayfront and pet-friendly community, Fairway Bay offers a heated pool, spa, fitness center, clubhouse, tennis courts and scenic walking and biking paths. Optional membership to the Longboat Key Club provides access to championship golf, dining, tennis and an exceptional collection of island amenities.

1906 Harbourside Drive Unit 304, Longboat Key

$699,000

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4697798 MLS ⋅ Active Status ⋅ Fairway Bay BLDG.

Nestled in the attractive community of Fairway Bay in Bay Isles on Longboat Key is this fabulous 2BR/2BA elevated townhouse. This tastefully decorated condo residence is on one level above the oversized 2-car garage and is an end unit. It is beautifully maintained, in great condition and offered turnkey-furnished with upscale furnishing from Robb & Stucky. The spacious living room and dining room has high ceilings, crown molding, plantation shutters, a fireplace and a wet bar with built-ins. The updated kitchen completed in 2025 is a neutral palette with new white cabinetry, white quartz countertops, a super pull-out pantry, all new appliances and washer & dryer in the past 12 months. A/C replaced in 2020 & water heater in 2021. The flooring in the entire residence was recently replaced with luxury vinyl plank flooring. A spacious shaded screened lanai offers a peaceful garden view and is a short walk to the heated pool and the bay. The bathrooms have also been updated in 2025 with new flooring, new cabinets, fixtures and shower door. The primary bedroom suite is a quiet sanctuary offering ample room for your apparel with two walk-in closets and Hunter-Douglas window blinds. This townhouse affords plenty of room for guests and a large family to stay. There is a two-and-a-half garage with a large finished air-conditioned space on the ground floor giving you extra space. Community amenities include walking paths, 2 heated pools, a fitness room, tennis & pickle ball courts and a social room. The building will soon benefit from a new roof, which the seller has paid for. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulf front pavilion, grilling areas, and beautiful sandy beaches. Located within the Longboat Key Club, residents have the option to join golf, tennis, and social memberships, all just minutes from the boutiques and dining on world-renowned St. Armands Circle, downtown Sarasota’s cultural attractions and Harbourside Marina.

2000 Harbourside Drive Unit 1501, Longboat Key

$510,000

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4692494 MLS ⋅ Active Status ⋅ Fairway Bay 1 BLDG.

Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day. Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle. The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, New AC 2025, New Water Heater 2025, New Washer and Dryer 2025, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests. The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style. Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity. Fairway Bay, located within the desirable Bay Isles community, offers a lifestyle rich in amenities and natural beauty. Residents enjoy gated entry with 24-hour guard service, beautifully maintained grounds, resort-style pools, a clubhouse, fitness center, and tennis courts. Scenic walking and biking paths wind along the bay, while a kayak and paddleboard launch provides easy access to the water for outdoor enthusiasts. Ownership also includes exclusive access to a private beach club on the Gulf of Mexico, offering the rare advantage of experiencing both serene bayfront living and pristine Gulf beaches. Ideally situated near the renowned The St. Regis Longboat Key Resort, this residence is just moments from exceptional dining, shopping, and leisure experiences, further enhancing its appeal as both a full-time residence and seasonal escape. This is more than just a condominium—it is an opportunity to embrace the relaxed elegance, natural beauty, and effortless lifestyle that make Longboat Key one of Florida’s most coveted coastal destinations.

1930 Harbourside Drive Unit 122, Longboat Key

$539,000

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4688978 MLS ⋅ Active Status ⋅ Fairway Bay 1 BLDG.

Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This turnkey furnished move-in ready two-bedroom, two-bathroom residence presents an exceptional chance to enjoy the Longboat Key lifestyle along with the rare advantage of one under building garage parking space. Enjoy peaceful views of Sarasota Bay, surrounding mangroves, and native wildlife from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ready for immediate enjoyment as a primary home, seasonal retreat, or investment opportunity. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.

1932 Harbourside Drive Unit 242, Longboat Key

$1,175,000

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4689076 MLS ⋅ Active Status ⋅ M-2 BLDG.

Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in Fairway Bay—nestled on picturesque Longboat Key. From the moment you enter, you're greeted by a thoughtfully redesigned open floor plan, elevated ceilings, solid core doors, and impeccable high-end finishes. IT IS TRULY ONE OF A KIND! This condominium is truly one-of-a-kind! Exceptional Kitchen features include: Bertazzoni induction range, refrigerator, and dishwasher, built-in Miele plumbed espresso machine, sleek, low-profile custom cabinetry with quartz countertops, glass tile backsplash and ambient lighting and an expansive quartz island perfect for formal dining or casual entertaining. The living room flows effortlessly from the kitchen, opening onto a covered, tiled lanai—blurring the line between indoor and outdoor living. Floor-to-ceiling impact windows frame panoramic views of Sarasota Bay, the Ringling Bridge, and the city skyline, offering million-dollar scenery from the comfort of your home. Enter the generously sized and luxurious Primary Suite with custom built-ins and ample closet space. The ensuite bath is a spa-inspired bath with dual vanities, Hansgrohe Axor faucets, Toto washlet, walk-in shower with multiple heads and elegant finishes. The guest suite features custom cabinetry and an ensuite bathroom with a Victoria & Albert volcanic limestone bathtub. Other recent upgrades include Hurricane-impact windows and doors, tankless water heater, additional upper cabinetry in kitchen and utility room, ceiling fans and more. For your convenience & comfort there is easy elevator access, coveted garage parking space and private onsite storage. Fairway Bay residents enjoy the resort-Style amenities including Deeded beach access & exclusive beach club, 24-hour gated security, pool, spa, tennis courts, and fitness center plus all the perks of Bay Isles living. Whether you're soaking in the sun, enjoying vibrant Sarasota culture and nightlife, or relaxing in your private retreat, this home is a perfect sanctuary.

1932 Harbourside Drive Unit 244, Longboat Key

$975,000

3 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4686721 MLS ⋅ Active Status ⋅ Atrium BLDG.

Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.

2120 Harbourside Drive Unit 623, Longboat Key

$623,000

3 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4682869 MLS ⋅ Active Status ⋅ Fairway Bay BLDG.

Welcome to the Atrium—one of Longboat Key's most exceptional waterfront addresses. Perfectly positioned along the sparkling waters of Sarasota Bay, this stunning three-bedroom residence offers breathtaking panoramic views that will captivate you from sunrise to sunset. The spacious chef's kitchen is designed for both function and style, featuring abundant cabinetry, stainless steel appliances, and a double oven for the culinary enthusiast. Imagine preparing meals while gazing out at the endless blue waters of the bay—a view that never grows old. The thoughtfully designed split-bedroom floor plan provides privacy and comfort for family and guests. The expansive primary suite is a true retreat, surrounded by sliding glass doors that fill the room with natural light, welcome refreshing bay breezes, and provide direct access to the terrace where spectacular waterfront views await. This is coastal living at its finest. Ownership includes exclusive membership to the Bay Isles Beach Club, offering deeded beach access, social activities, scenic walking trails, heated pools, a state-of-the-art fitness center, tennis and pickleball courts, clubhouse amenities, and convenient kayak launches. For those seeking an even more elevated resort experience, optional membership to the Longboat Key Club provides access to championship golf, world-class Har-Tru tennis courts, a luxurious spa, waterfront dining, and a deep-water marina. Perfectly situated just minutes from St. Armand's Circle and downtown Sarasota's vibrant arts, shopping, and dining districts. Location, location, location is number one in Real Estate and this unit gets the award.

2110 Harbourside Drive Unit 523, Longboat Key

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