Longboat Key Homes with Street Lights Community Features

Longboat Key Homes with Street Lights Community Features

Welcome to Longboat Key, Florida—a hidden gem nestled along the stunning Gulf Coast, where pristine beaches meet a vibrant community. Known for its luxurious lifestyle, this charming barrier island boasts an array of outdoor activities, from sunbathing on its soft sandy shores to indulging in water sports like kayaking and paddleboarding. With its lush landscapes and breathtaking sunsets, Longboat Key is a paradise for nature lovers and beach enthusiasts alike.

One of the standout features of Longboat Key is its welcoming neighborhoods, particularly those within the Homes with Street Lights community. This community not only enhances the aesthetic appeal of the area but also ensures safety and convenience for residents. Picture evening strolls under the glow of streetlights, where neighbors greet each other warmly, fostering a sense of camaraderie and belonging.

The Homes with Street Lights community is designed with families and individuals in mind, offering a tranquil environment that encourages outdoor living. With well-maintained streets and beautifully landscaped properties, this community is perfect for those seeking a peaceful retreat while remaining close to the vibrant culture and amenities Longboat Key has to offer.

Residents can enjoy a plethora of nearby dining options, boutique shopping, and recreational activities, all while being just moments away from the shimmering waters of the Gulf. In Longboat Key, every day feels like a vacation, and the Homes with Street Lights community is the perfect place to call home. Come discover your slice of paradise today!

Newest Longboat Key Homes with Street Lights Community Features

2800 Harbourside Drive Unit E06, Longboat Key
$275,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Embrace effortless coastal living with this prime 55-foot boat slip in an elite deep-water harbor on scenic Longboat Key, perfectly positioned just off Sarasota Bay. Sized to fit vessels up to 50 feet with a 19-foot beam total length, the slip comes fully equipped with water, high-speed Wi-Fi, and a private metered power pedestal. Marina residents enjoy exceptional conveniences including a full-service fuel station, flexible pump-out service, a complimentary shuttle to St. Armands, and a 24-hour bathhouse with laundry and a ship store. Tailor your coastal lifestyle further with optional upgrades: join the Bay Isle Beach Club for exclusive beachfront sunset access, or secure a membership at the prestigious Longboat Key Club for resort pools and fine dining. Situated only half a mile from Publix, CVS, and local conveniences, this is your ultimate island headquarters.

2800 Harbourside Drive Unit E06, Longboat Key
2600 Harbourside Dr Unit N-09, Longboat Key
$225,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Only slip available on N-dock! Slip N-09 is a 45 x 20 Boat Slip at Longboat Key Moorings Marina for sale. The slip is located on the north side of the pier. Exceptional views of Sarasota Bay and the city skyline, mid-pier for easy access. LBK Club membership is optional. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 40 LOA.

2600 Harbourside Dr Unit N-09, Longboat Key
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
3070 Grand Bay Boulevard Unit 645, Longboat Key
$925,000
2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code
Fully renovated 2BR/2BA Grand Bay condo with 2 parking spaces and Sarasota Bay and downtown views. Bright interiors feature easy-care tile floors and a kitchen with quartz counters, breakfast bar, and high-end appliances. Partially furnished with Robb & Stuckey pieces. A large wraparound balcony overlooks the Longboat Key Club golf course, Sarasota Bay, and downtown Sarasota. This gated community offers 24/7 guards, on-site management, and a clubhouse with fitness center and party room with bar and chef’s kitchen. Outside, enjoy the pool, spa, wading pool, grill area, and tennis courts. Bay Isles’ private beach club offers a pavilion, grills, and beach volleyball. Sidewalks throughout. Walk to Publix, CVS Pharmacy, a nail salon, and other shops. Optional Longboat Key Club membership (separate fee): 45 holes of golf, marina, beach club, spa, Har-Tru tennis courts, pickleball courts, and 5 restaurants. Resort-style living, ready to enjoy.

3070 Grand Bay Boulevard Unit 645, Longboat Key
1591 Gulf Of Mexico Drive Unit 515, Longboat Key
$2,670,000
1 Beds ⋅ 2 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Exceptional opportunity to be a resident at The St. Regis Longboat Key for under $3,000,000. Enter your private elevator into a dramatic living area with high ceilings and expansive glass featuring spectacular views of Sarasota Bay. The living area opens to a large outdoor terrace with a Wolf gas grill for easy entertainment. The chef’s kitchen is equipped Poggenpohl cabinetry, top-of-the-line Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, large refrigerator and beverage center. If you don’t feel like cooking, just order room service from one of The St. Regis’s esteemed dining venues. The Earth finishes were curated by Marc Michaels Interior Design and were selected to remain timeless. The owner’s suite is luxurious and opens to the outdoor terrace for your morning coffee. Relax after a day at the beach or saltwater lagoon in the spa like bathroom boasting double vanities, water closet with Toto bidet toilet, soaking tub and oversize shower with seamless glass enclosure. The floor plan was altered to include two full bathrooms and is large enough to graciously accommodate overnight guests. A custom built owner’s suite closet and motorized blinds complete this beautiful residence. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!

1591 Gulf Of Mexico Drive Unit 515, Longboat Key
1241 Gulf Of Mexico Drive Unit PH1102, Longboat Key
$5,995,000
3 Beds ⋅ 5 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code
Experience an exceptional expression of Gulf-front living in this impeccably maintained penthouse at The Water Club on Longboat Key. Occupying the coveted northwest penthouse position on the 11th floor of Building One, this pristine residence encompasses approximately 3,400 square feet with three bedrooms and four-and-a-half baths. Three separate balconies capture sweeping views of the Gulf of America, providing inviting settings for morning coffee, alfresco relaxation, and spectacular sunsets. An under-building parking space and an additional semi-private garage complement this distinguished waterfront offering. Set within 16 acres of magnificent beachfront grounds, The Water Club offers an extraordinary collection of amenities that extends the comforts of home well beyond your residence. The beautifully renovated, 18,000-square-foot clubhouse provides elegant spaces for relaxation, recreation, and entertaining, including a club room with billiards, a library with fireplace, and a ballroom with catering kitchen. Four lighted Har-Tru tennis courts, a heated junior Olympic pool, hot tub, spa, and fitness center create a resort experience, while a firepit, grills, and direct access to a beautiful stretch of beach invite you to embrace the coastal lifestyle. Gated security, concierge services, on-site management, and climate-controlled storage add everyday comfort and convenience. Ideally situated at the southern end of Longboat Key, this residence places you minutes from the boutiques and dining of St. Armands Circle, downtown Sarasota’s vibrant waterfront and cultural attractions, and an array of exceptional restaurants. Nearby conveniences include Publix and CVS, with the Longboat Key Club’s golf, tennis, and dining offerings close at hand. The neighboring St. Regis further enhances this desirable coastal setting, and Sarasota Bradenton International Airport is approximately 20 minutes away. Welcoming up to two pets, The Water Club is equally appealing as a full-time residence or a refined seasonal retreat. Discover the rare combination of penthouse privacy, generous living spaces, captivating Gulf views, and an exceptional beachfront lifestyle. Schedule your private showing today.

1241 Gulf Of Mexico Drive Unit PH1102, Longboat Key
455 Longboat Club Road Unit 402, Longboat Key
$2,000,000
3 Beds ⋅ 4 Baths ⋅ Pierre SubDv. ⋅ 34228 Zip Code
Beachfront mornings begin with dazzling Gulf views on your oversized terrace, above the palms and close enough to see and hear the surf. Spacious, bright and airy, this renovated waterfront three-bedroom condominium lives much larger than its 2,400-plus square feet. Behind the guarded gates of the Longboat Key Club on the island’s southern tip, this peaceful enclave offers an enchanting beach with a rare feeling of privacy. Only minutes from St. Armands Circle, Bay Isles Publix shopping center, the St. Regis and downtown Sarasota’s celebrated arts and culture scene, yet it feels worlds away. The Pierre strikes a rare balance, intimate yet spacious, just 66 residences on nearly seven lush acres. The heated pool, spa, Har-Tru tennis courts, fitness center and beach feel surprisingly uncrowded, even at the height of season. Gulf views fill nearly every room. Evenings bring unforgettable sunsets, then twinkling views of the golf course, Sarasota Bay and city lights to the east. Two expansive balconies make indoor/outdoor living and entertaining easy. The guest room has beach views and its terrace access. A kitchen designed by a serious cook flows beautifully into the living areas, and the dual-aspect dining area offers Gulf and city views with direct access to both balconies, ideal for dinner parties. The flexible layout lets the 3rd bedroom serve as an office or formal dining room, and some owners have added a fourth bedroom! The Pierre’s spacious floor plans stand apart on Longboat Key, where most condominiums are smaller two-bedroom units as few offer this much space at this price. Three guest suites (two one-bedroom, one two-bedroom with large living room and kitchen) welcome overflow guests. Concierge, garage parking, deeded beach access and pet-friendly. Optional Longboat Key Club membership adds 45 holes of golf, tennis, pickleball, spa, fitness, dining, marina and private beach service. Year-round or lock-and-leave, this is so much more than a beach house. It feels like home.

455 Longboat Club Road Unit 402, Longboat Key
4330 Falmouth Drive Unit 107, Longboat Key
$399,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
First time on the market in 25 years with OWNER FINANCING AVAILABLE, 40% down, 5.5% interest on balloon note or amortization, all negotiable. This turnkey, first-floor, two-bedroom, two-full-bath condominium in gated Longboat Harbour has hosted a lifetime of memories and is ready for its next chapter. Freshly painted and move-in ready, it opens through a glass-enclosed lanai straight onto the lawn and harbor, with boats docked a short distance away and Sarasota Bay beyond. Tile floors, plantation shutters and a bright kitchen with a pass-through to the dining area keep life easy. Being on the ground floor, you skip the elevator and stairs and enter right out to the pool, your covered parking and the path to the beach. Owners report no flood damage in their 25 years of ownership. Amenities include heated pools, a fitness center, a sauna, billiards and game rooms, a clubhouse, a putting green, shuffleboard, a fishing pier, grills, kayak storage and a private Gulf-side beach house across Gulf of Mexico Drive with parking, restrooms, showers and gear storage. Bayside sunrises, Gulf sunsets, Publix and dining nearby and SRQ about 13 miles. Owner financing is available; ask for the terms. Quick close is possible. Approximately $15,000 in 2027 rental bookings are already in place, according to the current owner.

4330 Falmouth Drive Unit 107, Longboat Key
3060 Grand Bay Boulevard Unit 124, Longboat Key
$1,699,000
2 Beds ⋅ 3 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code
Discover an exceptional opportunity to embrace the refined waterfront lifestyle at Grand Bay, one of Longboat Key’s most prestigious gated communities within Bay Isles. This beautifully updated 2-bedroom, 2.5-bath residence offers approximately 2,550 square feet of elegant living space, framed by sweeping views of Sarasota Bay, the manicured golf course, and the Sarasota skyline. From the moment you enter, warm wood floors, expansive living areas, and floor-to-ceiling windows create a sense of effortless sophistication. The living room opens through a wall of sliders to a private terrace, inviting morning coffee, sunset entertaining, and quiet moments above the water. A formal dining room with wet bar and wine refrigerator, along with a striking gourmet kitchen featuring stone countertops, an extended island, glass-panel cabinetry, pendant lighting, and premium stainless appliances, makes entertaining as seamless as it is memorable. The primary suite is a true sanctuary, opening to the terrace with panoramic bay views and featuring a spa-inspired bath with soaking tub, walk-in glass shower, dual vanities, and separate water closet. The guest suite offers its own terrace access and private en-suite bath, providing comfort and privacy for family and visitors. Life at Grand Bay extends well beyond the residence. Residents enjoy resort-caliber amenities including a clubhouse, two heated pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Membership to the Bay Isles Beach Club provides private Gulf-front access, complete with gated entry, pavilion, restrooms, showers, picnic areas, BBQ grills, and beach chair storage. The pet-friendly community also welcomes large dogs, making it easy to bring the whole family into this exceptional coastal setting. Ideally positioned behind the gates of the Longboat Key Club in Bay Isles, this residence places you minutes from celebrated dining, boutique shopping, golf, boating, and the cultural attractions of Sarasota. It is more than a home; it is a rare opportunity to live the quintessential Longboat Key lifestyle, where luxury, privacy, and waterfront beauty come together every day.

3060 Grand Bay Boulevard Unit 124, 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
554 Spanish Drive S, Longboat Key
$425,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.

554 Spanish Drive S, Longboat Key
2550 Harbourside Drive Unit 333, Longboat Key
$1,395,000
3 Beds ⋅ 3 Baths ⋅ Marina Bay SubDv. ⋅ 34228 Zip Code
Set within the gated BAY ISLES community, this MARINA BAY residence offers a rare combination on Longboat Key: the scale and privacy of a single-family BAYFRONT home with the ease of condominium living. Spanning approximately 3,000 square feet with three bedrooms and two-and-a-half baths, the residence feels expansive and closely connected to Sarasota Bay. Floor-to-ceiling glass across the main living areas and primary suite frames mature mangroves and coastal trees, creating a peaceful, park-like setting with filtered morning light and bay views. Nearly 400 square feet of screened lanai space extends the living area outdoors, while a second west-facing balcony serves the guest bedrooms and captures afternoon light and evening skies. The primary suite offers bay views from bed, terrace access, dual walk-in closets and a spacious bath with soaking tub, dual vanities and glass-enclosed shower. The kitchen features quartz countertops, Sub-Zero refrigeration, generous prep space, a wet bar with beverage refrigerator and a built-in desk nook. A large walk-in laundry room adds substantial workspace and storage. Freshly painted with new carpeting, the residence also features two-zone air conditioning with new condensers installed in 2025, two hot-water tanks with flood-stop protection, air-conditioned storage, assigned garage parking and exceptional closet space. Marina Bay is known for attentive management and a well-run homeowners association, with an experienced on-site manager and amenities including a fitness center, tennis and pickleball courts, heated resort-style pool, EV charging and car-washing facilities. The building's new roof was completed in 2025, and the community is pet-friendly. Longboat Key Club Marina is immediately adjacent, while Publix, CVS, banking and the post office are just blocks away, creating a genuinely walkable daily rhythm uncommon on Longboat Key. Ownership also includes access to the private Bay Isles Beach Club, a gated Gulf-front retreat with parking, pavilions, grilling areas, restrooms and sunset seating. Optional membership at the nearby Longboat Key Club offers golf, tennis, spa and wellness amenities, and waterfront dining. For buyers seeking the comfort and proportions of a home without the maintenance of one, this Marina Bay residence offers an uncommon balance of space, privacy, nature and convenience.

2550 Harbourside Drive Unit 333, Longboat Key
Start Your Search

How much is your home worth?

Get instant property value now!