Features & Amenities

Interior

  • Other Interior Features

    Built-in Features, Cathedral Ceiling(s), Crown Molding, Dry Bar, Eat-in Kitchen, Walk-In Closet(s)

  • Total Bedrooms

    3

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    NO

  • Heating YN

    YES

  • Heating

    Central

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Stucco

  • Other Exterior Features

    Lighting, Dock

  • Parking

    Driveway, Attached

  • Patio and Porch Features

    Deck, Patio

  • Pool

    Yes

  • Pool Features

    In Ground, Private

  • Waterfront YN

    NO

  • View

    Water, City

Area & Lot

  • Lot Features

    Corner Lot, Cul-De-Sac, Landscaped, Level, Near Golf Course

  • Lot Size(acres)

    0.36

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

Price

  • Sales Price

    $5,425,000

  • Tax Amount

    19595.71

  • Sq. Footage

    4, 733

  • Price/SqFt

    $1,146

HOA

  • Association

    YES

  • Association Fee

    $100

  • Association Fee Frequency

    Annually

  • Association Fee Includes

    N/A

School District

  • Elementary School

    Southside Elementary

  • Middle School

    Booker Middle

  • High School

    Booker High

Property Features

  • Stories

    3

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    1

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

Sarasota

Elementary School

Southside Elementary

Middle School

Booker Middle

High School

Booker High

Listing Courtesy of Peter Laughlin , PREMIER SOTHEBY'S INTERNATIONAL REALTY

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent AshleyBaillio

FOUNDER

AshleyBaillio

Call Ashley today to schedule a private showing.


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Welcome to 585 Gunwale Lane, a rare, full-bayfront offering in the desirable community of Country Club Shores on southern end of Longboat Key. On a .36-acre bayfront parcel with 117 feet on Sarasota Bay and 123 feet on a deepwater canal, this residence is a boater’s paradise. A newer seawall and 58-foot dock (2022) with a 24,000-pound boat lift assure easy access to Sarasota Bay and the Gulf of Mexico. On the bay side, Ghost Island sandbar emerges at low tide, creating a natural haven that attracts abundant wildlife and offers fantastic shelling. It also serves as a natural barrier, providing protection during storms. On the Gulf side, deeded access to an exclusive community beach is just a half-mile away. Whether you’re heading out for a day on the water or popping over to St. Armands Circle for dinner and shopping, this home puts you in the center of it all. The residence spans 4,733 square feet and includes three bedrooms and three-and-a-half baths. A soaring 20-foot ceiling defines the living room, where wall-to-wall built-ins create a refined focal point. The dining room opens to a remodeled kitchen outfitted with Graber wood cabinetry and professional-grade Frigidaire appliances. The primary bedroom is on the second floor, featuring a private bayfront balcony, dual walk-in closets, and an adjoining 270-square-foot bonus room ideal for a home office or wellness retreat. Outdoor amenities include a bayfront pool and spa for enjoying Florida sunsets. Additional highlights include impact-resistant windows and doors, and a two-car garage. For those who want to design and build their dream home, this property offers a spectacular location. Imagine a custom rooftop deck with breathtaking 360-degree views of the bay, Gulf, and downtown Sarasota. This is an opportunity to create something extraordinary. This exceptional property presents a rare opportunity to park your boat in the backyard and join the privileged few who call this well-established neighborhood home. By land or by sea, welcome to your fabulous Florida lifestyle!

585 GUNWALE LANE

Message successfully sent.

What would you like to know?

Related Properties

One or more photo(s) has been virtually staged. Looking for your own private Gulf Oasis? Enter your dream coastal retreat in the exclusive Aria community, located on the highly sought-after south end of Longboat Key. This area is especially desirable for its quiet, secluded atmosphere while still offering quick access to the world-class dining, arts, and cultural experiences of nearby Sarasota. This remarkable residence, surrounded by 300 feet of pristine private Gulf-front shoreline, offers a lifestyle unlike any other. As you approach through Aria's gated entrance, you are instantly embraced by thoughtful, timeless design, lush native landscaping, serene walking trails, and a lovingly preserved artesian well—a subtle yet meaningful tribute to the property's rich history. Step into your private elevator and discover nearly 4,000 square feet of exquisitely designed, light-filled living spaces. The expansive foyer welcomes you into an open-concept layout that seamlessly blends a chef's kitchen, spa-inspired bathrooms, and elegant living areas, all thoughtfully crafted for comfort and effortless entertaining. Towering 9+ foot ceilings, floor-to-ceiling glass windows, and wrap-around terraces ensure that the stunning Gulf views are yours to enjoy from every angle. Relax in the inviting family room or host unforgettable gatherings in the grand great room. The kitchen is a culinary masterpiece, showcasing luxurious quartz countertops, solid wood cabinetry for ample storage, and premier Wolf and Miele appliances. The primary suite offers a serene retreat designed for complete relaxation, with an opulent ensuite bathroom featuring two private baths connected by a spacious walk-in shower—an indulgent experience for everyday living. Two additional ensuite bedrooms provide ample space for guests, while a home office or optional fourth bedroom offers flexibility. A bonus room is perfect for hobbies, crafts, or additional storage. Living in Aria means immersing yourself in an unparalleled lifestyle. At the community's heart lies Villa am Meer, a beautifully restored 1935 seaside mansion that serves as the elegant residents' clubhouse. Whether you're entertaining guests or enjoying a quiet evening, you can unwind in the private wine cellar, selecting a bottle to savor on your terrace as the sun sets over the Gulf. Additional resort-style amenities include a beachfront pool and spa, yoga and fitness studios, a massage room, and a serene, service-oriented environment. A private, oversized two-car dehumidified garage offers additional convenience, while a resident caretaker ensures personal service is always just a phone call away. Aria is more than just a residence—it's a way of life. Make 2251 Gulf of Mexico Drive #301 your new home—a place where timeless elegance meets modern luxury. Live the extraordinary story by the sea at Aria.
#A4658325

LONGBOAT KEY

2251 GULF OF MEXICO DRIVE 301

4 Beds

4 Baths

5,022 Sq.Ft.

$6,250,000

MLS#: A4658325

Experience brand-new coastal luxury in this just-completed custom home, finished in June 2025 and located in the sought-after Emerald Harbor community on Longboat Key. Positioned on a spacious corner lot along a wide canal, this one-story residence offers the perfect blend of elegance, function, and laid-back Florida living. With direct beach access across the street and your own boat dock in the backyard, the location couldn’t be more ideal.
Inside, the home features beautiful hardwood floors throughout, soaring ceilings including twelve-foot heights in select rooms and a thoughtfully designed floor plan with three bedrooms, an office, a game room, fitness room, and a sitting area. The layout easily allows for conversion to five bedrooms if needed. Off the chef’s kitchen, custom wood beams add warmth and character, while the great room centers around a stunning fireplace, creating a space that feels both luxurious and inviting.
The kitchen is equipped with a full Thermador appliance package, high-end cabinetry, and expansive countertops perfect for entertaining or everyday living. The primary suite is a true retreat, offering two oversized walk-in closets and a luxurious his-and-her bathroom setup with dual vanities and a soaking tub.
Step outside to your private resort-style escape, complete with a gorgeous pool, elevated spa, and fully outfitted outdoor kitchen. The oversized four-car garage has high ceilings and is ready for multiple car lifts, ideal for car enthusiasts or extra storage.
Built to the latest codes and engineered for peace of mind, this home is just minutes from the Longboat Key Club, Anna Maria Island, and St. Armands Circle. Surrounded by nature, you’ll enjoy watching dolphins, manatees, and native birds right from your backyard.
This is Florida living elevated, effortless, and ready for you.
#A4657152

LONGBOAT KEY

670 OLD COMPASS ROAD

5 Beds

5 Baths

5,792 Sq.Ft.

$5,495,000

MLS#: A4657152

Step into a new era of coastal modern living with this breathtaking, newly constructed waterfront retreat, perfectly positioned on the exclusive north end of Longboat Key. Designed with intention and offered fully turnkey-furnished, this residence is a refined sanctuary where architectural elegance meets cutting-edge technology and relaxed sophistication.

The grand entry leads into a dramatic great room, showcasing driftwood-accented ceilings and expansive floor-to-ceiling windows that flood the space with natural light. From here, the home flows effortlessly into the open dining area and chef’s kitchen, where rich wood-tone custom cabinetry, premium appliances, and clean modern lines create an atmosphere of understated luxury.

Just off the dining space, you’ll find an expansive entertainer’s room with its own full bath—ideal for hosting dinner parties, events, or enjoying a night in with guests. Upstairs, the home’s private quarters await. Bedrooms two and three are located on the second level, while the third floor is reserved entirely for the primary suite, accessible by private elevator.

This executive-level retreat features multiple walk-in closets, serene private balconies overlooking the water, and a spa-inspired primary bathroom designed with curated finishes and timeless style.

Throughout the home, attention to detail is evident in every finish and feature—including a full Lutron lighting system, motorized shades, integrated surround sound, and a Brinks security system with CCTV monitoring.

Outside, the coastal lifestyle truly comes to life. Enjoy a resort-style pool, fire pit lounge, and a brand-new private dock just a few homes away from open water—offering easy access to the Gulf and endless boating adventures. This property was crafted to bring people together, whether relaxing with family or entertaining in style.
#A4655358

LONGBOAT KEY

590 DE NARVAEZ DRIVE

4 Beds

3 Baths

4,195 Sq.Ft.

$4,340,000

MLS#: A4655358

DISCOVER THE DIFFERENCE—A TRUE LUXURY CONDO IN A BUYER’S MARKET

Why This Longboat Key Residence Stands Above the Rest:

This isn’t just another beachfront condo—this is a thoughtfully curated, luxury retreat where every detail has been considered, and every upgrade already completed. Enjoy peace of mind with all updates required by Florida’s new condo legislation already done and paid for—no surprise assessments here. From new roofs in 2024 to updated elevator systems, fire alarms, and lush new landscaping, this is one of the few buildings on Longboat Key where the heavy lifting is complete.

Unmatched Perks You’ll Rarely Find Elsewhere:

Full-time, on-site staff provide concierge-level service whether you're in residence or away.
No size restrictions on two dogs—finally, bring your big dogs to the beach.
Private two-car garage with additional storage—a true rarity for beachfront condos.
Grill on your terrace—yes, it’s allowed here.
A SHOWCASE OF COASTAL SOPHISTICATION
Step into over 3,000 sq ft of fully renovated, elegantly appointed interior living space—complete with 3 bedrooms and 3 baths, designed for both upscale entertaining and serene daily living. The crown jewel? A 1,000 sq ft wraparound balcony with a built-in outdoor kitchen, where panoramic Gulf views set the scene for unforgettable evenings.

Interior Highlights:

Expansive open-concept floorplan with high-end finishes throughout
Chef’s kitchen with Wolf appliances and a custom eat-in island
Luxury primary suite with separate his-and-hers en-suite baths, private toilet rooms, and dual vanities
Private guest wing with sitting room, terrace, and separate entrance—perfect for long-term guests
Floor-to-ceiling hurricane-impact glass for maximum light and storm security (no damage from recent hurricanes)
Gas appliances, including outdoor grill permitted on your terrace
EXCLUSIVE COMMUNITY AMENITIES:

Only 32 residences ensure a quiet, boutique feel
Pet-friendly: 2 dogs allowed with no size restrictions
Beachfront pool, sundeck, and direct beach access
Fitness center, sauna, and steam room
Clubhouse for resident events
Private fishing pier
24-hour security and on-site management
Full-time maintenance, landscaping, and housekeeping staff ensure the grounds are always immaculate
Walkable to grocery, pharmacy, golf, and tennis
And yes... 365 sunsets a year
A UNIQUE AND PRIVATE COASTAL RETREAT—READY NOW
This is a rare opportunity to own a move-in ready, beachfront condo in a well-managed building with no looming assessments or headaches. Every detail has been handled—just bring your flip-flops and start living the Longboat lifestyle.

Schedule your private tour today.
#A4646994

LONGBOAT KEY

2333 GULF OF MEXICO DR 1A2

3 Beds

2 Baths

4,179 Sq.Ft.

$4,950,000

MLS#: A4646994

Embrace unparalleled modern elegance and coastal serenity at Infinity on Longboat Key, where refined architecture meets the timeless beauty of the Gulf of Mexico. This exclusive boutique condominium boasts only 11 meticulously designed residences, offering a private and luxurious retreat for those seeking a sophisticated island lifestyle. From your private elevator, enter a spacious foyer that flows into an expansive living area, where floor-to-ceiling glass sliders frame breathtaking Gulf views. Beyond, a large covered balcony with an outdoor kitchen and multiple seating areas beckons, perfect for alfresco dining amid endless ocean vistas. The open-concept kitchen exudes sophistication through its thoughtful design. Custom cabinetry in warm wood tones pairs beautifully with pristine stone countertops and Italian Britannium backsplash. Premium stainless steel appliances, including a gas cooktop and sleek hood, anchor the space. A central island provides both functionality and visual interest, while elegant pendant lighting and expansive Gulf views elevate the aesthetic, creating an inviting culinary environment that seamlessly blends style and practicality. The exquisite primary suite is a haven of calm, with sliders opening to a private balcony where you’ll awaken to the sound of waves and views of turquoise waters lapping sugar-white sands. The spa-inspired primary bath offers a tranquil escape, featuring dual vanities, a water closet, and a spacious walk-in shower. Thoughtfully designed guest suites ensure privacy and comfort. A versatile flex room provides endless possibilities, whether used as a home office, media room, or den. Additional conveniences include a well-equipped laundry room with ample counter space and storage. This condo comes with two private garages that can fit four cars. Resort-style amenities elevate the living experience with a beachfront heated pool, private spa overlooking the beach, large sun deck, beach access, an outdoor entertainment area, clubhouse with catering kitchen, fitness center, and pickleball/tennis courts. Infinity’s prime location on Longboat Key provides effortless access to St. Armands Circle’s world-class shopping and dining, as well as the vibrant cultural offerings of downtown Sarasota. Golf enthusiasts can enjoy nearby championship courses, while boating enthusiasts have easy access to marinas and coastal waterways.
#A4645607

LONGBOAT KEY

4765 GULF OF MEXICO DRIVE B202

3 Beds

3 Baths

4,808 Sq.Ft.

$5,995,000

MLS#: A4645607

Experience beachfront luxury in this spacious 3,800-square-foot 3-bedroom, 3.5-bath + den/office residence in the prestigious En Provence community on Longboat Key. A private elevator opens to a grand foyer with marble floors and tray ceilings. Expansive glass sliders in the living room frame stunning Gulf views and lead to an oversized terrace, perfect for seamless indoor-outdoor living. The expansive terrace is ideal for entertaining, featuring a built-in gas grill and outdoor cooking space overlooking the beach and lush grounds. The kitchen is both stylish and functional, featuring a center island, white cabinetry, and pristine white stone countertops. High-end appliances, including a natural gas cooktop, enhance the space, while a bold blue tile backsplash adds a striking contrast. The adjacent eat-in area, with Gulf views and a built-in desk, enhances both charm and practicality. The primary suite offers terrace access and a spa-like bath with a soaking tub, dual vanities, a makeup area, and a glass-enclosed shower. Two guest suites each include en-suite baths and scenic views. A large office provides flexibility and could easily convert into a fourth bedroom. Additional features include an in-residence laundry room and 2 car garage. Set on nearly six acres of pristine beachfront, En Provence blends elegance and convenience with a clubhouse, resort-style pool and spa, fitness center, and 24-hour guard gate. For those seeking additional amenities, optional membership to the nearby Longboat Key Club provides access to world-class golf, tennis, dining, a marina, and a spa.
#A4643048

LONGBOAT KEY

2161 GULF OF MEXICO DRIVE 3

3 Beds

3 Baths

4,600 Sq.Ft.

$4,995,000

MLS#: A4643048

From that very first moment you enter En Provence on Longboat Key, you realize you've entered a special and exclusive place. Private location on the Shimmering Gulf waters. Exquisitely taking advantage of all the views from almost every room and angle, but yet a level of comfort to just relax and take a breath. Stunning evening sunsets creating the backdrop in this direct Gulf-front, 3BR/3BA residence with private 2+ car air-conditioned garage. The ground level lobby entrance leads you to the private elevator. Exiting the elevator to your entry foyer, with its 11’ ceilings is when the true experience begins. The honed travertine marble floors lead you to the main foyer, where your potential new and rewarding lifestyle begins. This en Provence floor plan has the entire gulf front portion of your home open to the gulf waters. This area encompasses the grand saloon, dining room, kitchen and family room.  The kitchen boasts a center island with  warming drawers, abundance of drawers and cabinets in the Neff cabinetry, granite countertops, top-of-the-line Sub-Zero & Dacor appliances and a butler’s pantry. Meandering through these common areas you're drawn to the abundance of windows and glass. Through the sliding glass doors you enter the expansive terrace, which has a fully equipped summer kitchen with gas stove for your grilling enjoyment. The primary bedroom is entered through stately double-doors for the owner's ultimate escape. Of course, water views and an entrance to the terrace are also available. The primary bathroom has been completely renovated to a standard that only the photographs or a private viewing can describe. Every space is another adventure that must be visited to understand the exclusivity of this offering. Located in this intimate community of just 21 residences, En Provence provides the ultimate in beachfront living on Longboat Key, with its gorgeous pool and spa area, guard gate, community entertaining area with catering kitchen, fitness room and security monitored grounds.
#A4640254

LONGBOAT KEY

2141 GULF OF MEXICO DR UNIT 4

3 Beds

3 Baths

4,200 Sq.Ft.

$5,500,000

MLS#: A4640254

Spectacular unobstructed views of Sarasota Bay and the Intercoastal Waterway! This 4 bedroom, 4 bath, 4233 square foot home is in the sought-after Queens Harbour neighborhood behind the gates of Bay Isles. You enter the home through its unique entry centerpiece: the courtyard with a garden, pool, and spa. As you step through the gorgeous coastal French doors into the two-story foyer with a grand staircase to the upstairs, your eyes capture the wonderful, unobstructed views of the Bay and Intercoastal. You have arrived in your sanctuary on the fabulous Longboat Key. The open floor plan has two masters, one up and one down, each with fabulous baths and spacious closets with built-in cabinetry. The upstairs master even has its own washer and dryer! Architectural features include dome-tiered ceilings, crown molding, decorative columns, floor-to-ceiling windows, and abundant light. A chef's kitchen with a large family room and a Hemmingway private office overlooking the courtyard provide finishing touches to the downstairs. Outside is the covered rear deck, with a dining patio leading to the large dock. Upstairs is a true haven of spacious bedrooms, a master sitting room with built-in desk and cabinets, and two guest bedrooms with a roomy Jack and Jill bath with two sinks and a separate tub and shower. This well-maintained home has upgraded appliances, a 5-year-old roof, hardwood floors, complete impact-glass hurricane wind protection, and a new Generac generator. The home's outside attraction is complete with the tide-changing wildlife sanctuary at your bayfront back door, where dolphins cruise the bay, pelicans dive bomb for fish, and eagles and osprey hunt. Queens Harbour is a planned, semi-maintenance-free luxury community of 102 single-family homes. The Association provides turnkey landscaping services, including wells and irrigation, maintains the heated community pool, and is responsible for painting the exterior of each home every five years. Homeownership includes membership in the Bay Isles Beach Club, which provides private beach facilities including restrooms with showers, BBQ grills, volleyball, covered pavilion and various other covered eating areas, and, of course, the beautiful sands of Longboat Key's spectacular Gulf beach! Bay Isles offers easy access to Publix and CVS, plus a short drive to the famous St. Armands Circle. Memberships are available at The Longboat Key Club with access to 27 holes of pristine golf, 20 Har-Tru tennis courts at the renowned Tennis Gardens, 8 pickleball courts, a fantastic private marina with direct access to the intercostal, and 2 restaurants.
#A4639155

LONGBOAT KEY

3628 FAIR OAKS PLACE

4 Beds

4 Baths

5,226 Sq.Ft.

$4,850,000

MLS#: A4639155

DIRECT BEACH FRONT WALKOUT !!  Completely redone in 2024!!The west facing private terrace off the living room and master bedroom has the exclusive feature of a Gulf front terrace with a private staircase that leads directly to the sandy beach and azure waters of the Gulf of Mexico. This rarely available floor plan is a stunning residence with front and back terraces. The east private terrace captures vistas of the beautiful sunrises and the west terrace looks over the beach to the Gulf of Mexico plus spectacular evening sunsets. This home is both casual and elegant. The floor plan offers two bedrooms and a third room as an office or a bedroom with a full bath nearby. The Gulf front master has spectacular views plus a sliding door that leads to the large terrace. The master suite features ample closet space plus his and her private bath areas. L' Ambiance amenities include a concierge in the lobby, 24 hour guard gate for security and an Olympic size Gulf side pool surrounded by lush landscaping. Other amenities include two har-tru tennis courts, state-of-the-art fitness center with his and her locker rooms, game and billiard rooms, library, wine room and three private guest suites. This condo has two underground parking spaces plus a private storage locker. The location of L'Ambiance is minutes away from the shopping and dining on St.Armands Circle plus walking distance to Longboat Key Club restaurants and amenitie
#A4636316

LONGBOAT KEY

415 L AMBIANCE DRIVE C204

3 Beds

3 Baths

3,770 Sq.Ft.

$4,495,000

MLS#: A4636316

 - property

Send a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here