AgentLogo

Florida

3331 OLD OAK DRIVE

SARASOTA , FL 34239

MLS#: A4675449

$1,995,000

Status: Active
Listing number: A4675449
Listing provided by: COMPASS FLORIDA LLC
Listing agent phone: None
Last update: 3 days ago
New on site 4 days ago
Browse Properties
SHORELAND WOODS SUB - Residential

Property

Beds

4

Full Baths

3

1/2 Baths

1

Year Built

1950

Sq.Footage

2,483

A private, gated masterpiece where Old Florida romance meets modern coastal luxury. Tucked within the coveted West of the Trail enclave, this exquisitely reimagined estate delivers a rare blend of architectural heritage, refined craftsmanship, and elevated contemporary living. Beyond the stately motorized wrought-iron gate, a sweeping brick-paver drive meanders beneath towering live oaks, setting an unforgettable first impression of timeless elegance and privacy. Wrapped in a freshly painted pecky cypress façade and crowned by a newer standing-seam metal roof, the residence honors classic Florida design while embracing today’s luxury standards. Inside, a welcoming foyer unfolds into an airy, open-concept living space anchored by rich natural wood floors and impeccable finishes throughout. A dramatic dual-sided stone fireplace creates a striking focal point between the living and dining areas, while a sophisticated dry bar sets the stage for effortless entertaining. A private office—thoughtfully positioned away from the main living areas—offers flexibility as a refined workspace or guest retreat, complete with an adjacent half bath. At the heart of the home, the chef’s kitchen is nothing short of spectacular, featuring premium stainless steel appliances, a natural gas range, custom cabinetry, designer backsplash, and an oversized marble island that commands attention. A built-in coffee bar adds a touch of indulgence, while French doors invite the outdoors in. Step into a resort-inspired sanctuary where a heated saltwater pool and spa shimmer beneath a newly installed panoramic screen enclosure. Entertain with ease in the fully equipped summer kitchen, complete with stainless gas grill, vent hood, and prep station, or gather around the gas fire pit for evenings under the palms. A newly updated outdoor shower with hot and cold water enhances the spa-like ambiance, while the expansive, lushly landscaped yard offers exceptional privacy and room to relax, play, or unwind. The primary suite is a true retreat, featuring three generous closets, a cozy fireplace, and French doors opening directly to the lanai for seamless indoor-outdoor living. The spa-inspired en-suite bath showcases luxurious finishes, custom vanities, and a walk-in shower designed for pure relaxation. Additional highlights include a spacious laundry room, oversized two-car garage, and curated architectural lighting that bathes the estate in a warm, elegant glow at dusk. Perfectly located just minutes from the Siesta Key North Bridge and the boutiques and dining of Southside Village, this property offers the rare balance of serene seclusion and coastal convenience. Situated outside of a flood zone—with flood insurance optional—this estate represents both luxury and peace of mind.

Features & Amenities

Interior

  • Other Interior Features

    Dry Bar, Open Floorplan, Walk-In Closet(s)

  • Total Bedrooms

    4

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air, Zoned

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central, Electric, Natural Gas, Zoned

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Frame

  • Other Exterior Features

    Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters

  • Parking

    Boat, Driveway, Garage Door Opener, Guest, Oversized, Workshop in Garage, Attached

  • Patio and Porch Features

    Deck, Enclosed, Patio, Porch, Screened

  • Pool

    Yes

  • Pool Features

    Heated, In Ground, Salt Water, Private

  • Waterfront YN

    NO

  • View

    Trees/Woods

Area & Lot

  • Lot Features

    Landscaped, Private

  • Lot Size(acres)

    0.36

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Florida

Price

  • Sales Price

    $1,995,000

  • Tax Amount

    18715.0

  • Sq. Footage

    2, 483

  • Price/SqFt

    $803

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    34

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


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

Middle School

High School

Listing Courtesy of Adnan Dedic , COMPASS FLORIDA LLC

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 Ashley Baillio

FOUNDER

Ashley Baillio

Call Ashley today to schedule a private showing.

(561) 609-2391

franko+southflorida@init.hr


* 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.
A private, gated masterpiece where Old Florida romance meets modern coastal luxury. Tucked within the coveted West of the Trail enclave, this exquisitely reimagined estate delivers a rare blend of architectural heritage, refined craftsmanship, and elevated contemporary living. Beyond the stately motorized wrought-iron gate, a sweeping brick-paver drive meanders beneath towering live oaks, setting an unforgettable first impression of timeless elegance and privacy. Wrapped in a freshly painted pecky cypress façade and crowned by a newer standing-seam metal roof, the residence honors classic Florida design while embracing today’s luxury standards. Inside, a welcoming foyer unfolds into an airy, open-concept living space anchored by rich natural wood floors and impeccable finishes throughout. A dramatic dual-sided stone fireplace creates a striking focal point between the living and dining areas, while a sophisticated dry bar sets the stage for effortless entertaining. A private office—thoughtfully positioned away from the main living areas—offers flexibility as a refined workspace or guest retreat, complete with an adjacent half bath. At the heart of the home, the chef’s kitchen is nothing short of spectacular, featuring premium stainless steel appliances, a natural gas range, custom cabinetry, designer backsplash, and an oversized marble island that commands attention. A built-in coffee bar adds a touch of indulgence, while French doors invite the outdoors in. Step into a resort-inspired sanctuary where a heated saltwater pool and spa shimmer beneath a newly installed panoramic screen enclosure. Entertain with ease in the fully equipped summer kitchen, complete with stainless gas grill, vent hood, and prep station, or gather around the gas fire pit for evenings under the palms. A newly updated outdoor shower with hot and cold water enhances the spa-like ambiance, while the expansive, lushly landscaped yard offers exceptional privacy and room to relax, play, or unwind. The primary suite is a true retreat, featuring three generous closets, a cozy fireplace, and French doors opening directly to the lanai for seamless indoor-outdoor living. The spa-inspired en-suite bath showcases luxurious finishes, custom vanities, and a walk-in shower designed for pure relaxation. Additional highlights include a spacious laundry room, oversized two-car garage, and curated architectural lighting that bathes the estate in a warm, elegant glow at dusk. Perfectly located just minutes from the Siesta Key North Bridge and the boutiques and dining of Southside Village, this property offers the rare balance of serene seclusion and coastal convenience. Situated outside of a flood zone—with flood insurance optional—this estate represents both luxury and peace of mind.

3331 OLD OAK DRIVE

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

Price reduced
Located in the highly sought-after Avondale neighborhood, this beautiful “Old Florida” home has been extensively and tastefully updated while maintaining its timeless charm. The split floor plan includes three oversized ensuite bedrooms, an additional powder room, and a separate study/den conveniently positioned adjacent to the primary suite. Floor-to-ceiling windows and an open floor plan allow for abundant natural light and views of the heated saltwater pool, travertine deck, and generously sized backyard. Significant renovations in 2022 and 2023 include a new primary suite addition, an extensive kitchen remodel with updated electrical and plumbing, and new flooring throughout. Exterior improvements are equally impressive, featuring impact-rated doors and windows throughout, enhanced landscaping with drainage systems, irrigation, front yard fencing, and updated lighting. Additional features include a 2-car garage with epoxy flooring, metal roof (2007/2021), and newer A/C (2021). Perfectly situated between Southside Village and the vibrant Downtown Sarasota Bayfront, the property is also located within the highly sought-after Southside Elementary School District, making it a premier choice for those seeking convenience, style, and location.
#A4666374

SARASOTA

1846 LINCOLN DRIVE

3 Beds

3 Baths

2,618 Sq.Ft.

$2,195,000

MLS#: A4666374

New on site today
Welcome to this thoughtfully curated home nestled within the gated serenity of The Landings. Designed for both beauty and purpose, this residence features a well-planned layout that offers a harmonious blend of openness and privacy. With four bedrooms and three full baths, the accommodations are generous, highlighted by a primary suite that includes a Master Bath uniquely designed with two private toilet rooms. The expansive second bathroom has a TUB and is ideally and centrally located for family and visiting guests. The heart of the home is the updated kitchen, showcasing Caesarstone countertops, custom built-in cabinetry, and top-of-the-line appliances, including a Wolf gas cooktop, Miele dishwasher, and a EuroCave wine fridge with a capacity for over 200 bottles. The attention to detail is evident in the unique storage solutions found throughout the home, such as the secret storage cabinet in the kitchen, modernized closets with built-in systems, and a floor-to-ceiling pull-out medicine cabinet in the Primary Bath fashioned like an oversized spice rack. In this home, everything has a place, and nothing is without intent. Peace of mind and modern convenience are paramount here. The property is fortified with hurricane-impact windows installed throughout and a full-house Kohler generator. In 2025, important updates were completed including a complete pool renovation, new air-conditioner and tankless water heater. The garage is equally well-equipped, featuring a dedicated plug-in outlet for hybrid or electric vehicles and a mini-split AC system. Outside, the private grounds are serene and well-maintained; a large, fenced-in, and shaded yard surrounds a completely redone pool and spa. Additional exterior features include a turf dog run and an extended driveway that provides ample off-street parking. This residence is located in The Landings, a prestigious gated community of 702 residences bordering the Intracoastal Waterway in south Sarasota. Spanning 280 acres with a mix of stand-alone houses, townhouses, and villas, the neighborhood offers a rich array of amenities, including a USTA-recognized Racquet Club and two nature preserves. Residents enjoy access to a walking trail, gazebo, kayak launch, and a butterfly garden, all nestled amidst 75 acres of mangroves that provide natural beauty and storm mitigation.
#A4671323

SARASOTA

1690 PINE HARRIER CIRCLE

4 Beds

3 Baths

3,017 Sq.Ft.

$1,600,000

MLS#: A4671323

New on site 1 day ago
Welcome to 12016 Legacy Estates Blvd, a meticulously maintained 3-bedroom, 3.5-bath home offering 3,639 sq. ft. of living space in a sought-after resort-style community. This spacious residence features beautiful porcelain tile floors, abundant natural light, and an open layout designed for both comfortable living and entertaining. The home provides plenty of space for family and guests and includes an oversized bonus room that can be easily converted into a fourth bedroom or media room. Pride of ownership is evident throughout. Step outside to your private outdoor retreat featuring an oversized lanai, outdoor kitchen, and a serene pool overlooking a peaceful pond, perfect for relaxing or hosting gatherings while enjoying Florida’s indoor-outdoor lifestyle. Residents enjoy access to an impressive resort-style clubhouse offering a fitness center, spa, game room, and large common areas ideal for social events. The community pool is complemented by the popular Bahama Bar, serving great food and drinks in a relaxed setting. For outdoor enthusiasts, the community offers two convenient access points to the famous Legacy Trail, perfect for running, walking, or biking. This exceptional property combines luxury, space, and outstanding amenities in an unbeatable location.
#A4676570

SARASOTA

12016 LEGACY ESTATES BOULEVARD

3 Beds

3 Baths

3,639 Sq.Ft.

$2,150,000

MLS#: A4676570

New on site 2 days ago
NEW construction with IMPACT RESISTANT WINDOWS & SLIDERS...welcome to the Grand Santa Maria by Medallion Home! This 3-bedroom plus den, 3-bath home with pool and spa is perfectly positioned on 4 pristine acres. The property offers privacy, modern luxury, and an abundance of natural beauty with an opportunity to indulge in a lifestyle that caters to both relaxation and entertainment. Upon entering, experience luxury at its finest with high ceilings adorned with intricate details in every room. The heart of this home is the gourmet kitchen, with white cabinetry, stainless steel appliances, and an expansive island, overlooking the great room and out to the pool. The spacious den/office presents a versatile space that can serve as a home office, playroom, exercise room, or even a guest room as needed. Your retreat awaits in the owner’s suite…the en-suite bathroom featuring separate sinks, a zero-entry, walk-through shower, two separate walk-in closets, as well as private water closet. Two guest bedrooms ensure that everyone has their own private space with two closets in each room. Design elements include the inviting great room with a 12' peak ceiling that seamlessly connects to the rest of the home's 10' ceilings and 8' doors. Natural wood flooring is throughout the entire home...no carpet! The extended covered patio area is pre-plumbed and prewired for your future outdoor kitchen. Enjoy a refreshing swim or a soothing soak in your pool and spa, or just relax with a cool drink as you enjoy the serene privacy. Located in FEMA flood zone X, 56 feet above sea level—offering the lowest flood risk—this exceptional property is the perfect balance of luxury, function, and nature and NO CDD FEES. Just 20 minutes from Sarasota’s award-winning Beaches, Dining, Hospitals, and Cultural Attractions and 15 minutes from Lakewood Ranch’s Downtown Dining and Shops. Schedule your private tour today and experience the unmatched lifestyle this home provides.
#A4676553

SARASOTA

3499 QUIVER COURT

3 Beds

3 Baths

3,537 Sq.Ft.

$2,091,600

MLS#: A4676553

New on site 3 days ago
If you’re looking for a home that combines modern luxury in an away-from-it-all setting with easy access to wonderful Sarasota, 3586 Recurve Circle is the property for you.  This nearly new 5 bedroom, 4 bathroom Grand Cayman estate is situated on an expansive, private 8 acre lot in the gated Hampton Lakes community with no rear neighbors and a serene conservation view.  Built with an extended lanai and graced with an additional bonus room/5th bedroom, this home is perfectly designed for indoor-outdoor living. Whether you’re looking for a spacious property to connect with family and friends or just want room to breathe, this property checks these boxes and more.  Soaring ceilings greet you at the front door with an easy flowing floor plan that leads you past the den, living room, dining room, and butler pantry to your beautiful kitchen with impressive quartz countertops and on to the bright, inviting family room.  The capacious primary suite encompasses the entire east side of the home and includes a generous 15x18 walk-in closet, soaker tub, and walk-in shower with waterfall showerhead.  On the western side of the home are 3 more bedrooms with full ensuite bathrooms and a bonus room with a large closet that can be used however you see fit.  The home has thoughtful options above the base model including an additional bedroom, double driveway, and generous screened and covered outdoor space perfect for entertaining or taking in the peaceful view.  Your cavernous garage (1,325 sq ft) has room for four vehicles and more.  Situated away from it all but close to everything - just minutes from Lakewood Ranch and Waterside Place.  Come embrace all this estate home has to offer and imagine yourself in this unique opportunity.
#TB8459416

SARASOTA

3586 RECURVE CIRCLE

5 Beds

4 Baths

4,452 Sq.Ft.

$2,200,000

MLS#: TB8459416

New on site 2 days ago
Welcome to this stunning 5-bedroom, 5-bathroom home ideally located near the Hillview District, downtown Sarasota, and just minutes from to Southside Elementary School. Enjoy the best of “West of the Trail” living in this beautifully updated residence that blends timeless architectural charm with modern luxury. The home features a brand-new gourmet kitchen highlighted by a striking double island with quartz waterfall countertops, stainless steel appliances including a gas cooktop and hood, a wine refrigerator, and a custom buffet offering abundant storage. A true formal dining room provides the perfect setting for entertaining. Original travertine tile floors flow throughout the expansive first floor, leading to the primary suite with a large walk-in closet and a spa-inspired ensuite with direct access to the pool deck. The split floor plan also includes a private guest suite with its own ensuite bath. Floor-to-ceiling windows fill the home with natural light and showcase views of the exceptional backyard. Upstairs, you’ll find three additional bedrooms and two fully updated bathrooms. The backyard is truly a rare find—a private oasis featuring a spacious pool, covered lanai, pergola, outdoor shower, storage shed, and full fencing. With its generous size and proximity to downtown, this outdoor space is perfect for relaxing, entertaining, or creating lasting memories. This exceptional home offers comfort, elegance, and an unbeatable location—an opportunity not to be missed.
#TB8459204

SARASOTA

1826 BOYCE STREET

5 Beds

5 Baths

3,270 Sq.Ft.

$2,150,000

MLS#: TB8459204

New on site 3 days ago
In the well-established Loma Linda Park neighborhood in Sarasota, this new construction, Divald Homes custom-built two-story home offers a blend of modern design and traditional elements. The home is ideally near downtown Sarasota, Siesta Key and Sarasota Memorial Hospital, with no deed restrictions or HOA fees. The home features four bedrooms and three baths, including a spacious primary suite on the main floor. The open-concept floor plan featuring a 24-by-48-inch modern floor tile throughout, large sliding doors and windows offers a light-filled welcoming space ideal for entertaining. The main floor includes a gourmet kitchen, dining area, living room, private den/bedroom 4, primary suite with an ensuite bath and a dedicated laundry room. The chef’s kitchen is a centerpiece, showcasing Bosch appliances, an oversized island with waterfall quartz countertop, and custom floor-to-ceiling full-overlay cabinetry in a beautiful honey-stained wood tone. The living room is highlighted by a striking marble tile accent wall with custom wood shelving and modern designed 42-inch linear electric fireplace. The living room opens seamlessly to the lanai, complete with an outdoor kitchen, including a gas grill, refrigerator and sink. You will also enjoy the pool with sundeck, oversized outdoor patio and a beautiful backyard with lush native plantings. A convenient pool bath offers direct access from the lanai and the private den. The dining area is elegant and inviting, featuring a statement iron chandelier and a wall of windows overlooking the backyard. Just off the kitchen, the main-floor primary suite serves as a private retreat with a luxurious en-suite bath featuring a marble stone accent wall, a large walk-in shower with seamless glass enclosure, a sculptural slipper tub, double vanity with quartz countertops, natural wood cabinetry, LED mirrors and a spacious walk-in closet with custom built-ins. The laundry room is conveniently near the oversized two-car garage with 12-foot ceilings, large windows for natural light and direct access to the side yard. Upstairs, an ornate wrought-iron and hardwood staircase leads to two additional bedrooms, a beautifully finished guest bath and a versatile flex room ideal for a game room, study or guest accommodations. This thoughtfully designed home offers refined finishes, flexible living spaces and an exceptional location, ideal for enjoying the Sarasota lifestyle.
#A4676235

SARASOTA

2303 LOMA LINDA STREET

4 Beds

3 Baths

2,708 Sq.Ft.

$1,999,000

MLS#: A4676235

Fantastic opportunity to own a unique home on Palm Island, in this exceptional Siesta Key residence, ideally located at 5334 Calle Florida. Situated on a large lot and elevated approximately 10 feet above sea level, the main home has never flooded during any storms, offering peace of mind along with island luxury. This 4-bedroom, 3-bathroom home features 2,838 square feet of thoughtfully designed living space highlighted by a dramatic great room with soaring 20-foot ceilings, creating an open and airy coastal feel. The large primary suite has a custom built window seat, 2 walk in closets and an oversized primary bathroom. The entire home features built in speakers including teh back porch. Designed for comfort and efficiency, the home is equipped with a three-zone air conditioning system and hurricane-rated Kevlar screens, hurricane rated garage and front door for added protection. The spacious two-car garage provides ample storage, perfect for island living. The exterior is landscaped with outdoor lights and power in soffits for seasonal or all year round lighting. Outdoor living is elevated—literally—with an elevated, heated pool and hot tub, an outdoor shower, and plenty of space to relax or entertain in true Florida style. Located on Palm Island, just moments from the world-renowned Siesta Key Beach, this property offers the perfect blend of privacy, elevation, and coastal charm. Whether as a primary residence or luxury retreat, this home is a rare opportunity to own a high-and-dry island property in one of Sarasota’s most sought-after neighborhoods. Roof replaced 2021, Pool resurfaced 2024, Pool cage re painted and re screened 2025, Water heater 2025.
#A4676260

SARASOTA

5334 CALLE FLORIDA

4 Beds

3 Baths

2,838 Sq.Ft.

$2,170,000

MLS#: A4676260

Escape to the ultimate Siesta Key lifestyle with this rarely available, coastal contemporary condo—offering the perfect blend of luxury, privacy, and convenience with direct access to the sugar-white sands of world-renowned Siesta Key Beach and Crescent Beach. Known for its quartz-crystal sand and turquoise waters, this top-rated beach offers stunning sunsets, gentle waves, and vibrant coastal charm, all just a short stroll from your door. Nestled in a boutique enclave of only five residences, this exclusive unit has fresh interior paint, lives like a single-family home and is one of only two in its building. this unit encompasses the entire floor and shares no walls with other units. With five private patios, a built-in outdoor grill, tall ceilings and windows, and plantation shutters throughout, the light-filled layout offers an open flow between living, dining, and kitchen spaces—accented by custom cabinetry, upscale finishes throughout. The spacious primary suite provides a private retreat, while the entire home is thoughtfully designed on one level for effortless living. A private elevator offers direct access from your oversized ground-level garage, which is nearly 1,000 square feet and accommodates three vehicles plus storage, along with a private driveway for guest parking — a rare find on the Key. This property is zoned for short-term, weekly rentals and boasts a strong rental history, making it an exceptional opportunity for both personal enjoyment and possibility to earn over $120,000 in investment income. Enjoy walkable access to beachside boutiques, island restaurants, and boat rentals, plus quick and easy access on and off the island, making it ideal for both full-time living and a low-maintenance vacation home. Shared amenities include a serene pool, private owner's clubhouse, and common area used by only five residences, ensuring a peaceful and private setting. Whether you're searching for a serene retreat or a stylish beach escape with income potential, this home offers a unique opportunity to live in the heart of Siesta Key’s coastal paradise. Furnishings optional - not included in list price.
#A4676253

SARASOTA

1021 CRESCENT STREET 1

3 Beds

3 Baths

2,780 Sq.Ft.

$1,935,000

MLS#: A4676253

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

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

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service