Sarasota Homes with Custom Architectural style

4 Beds ⋅ 4 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code

Set on nearly half an acre in the heart of Oyster Bay Estates, this beautifully maintained and remodeled residence enjoys one of Sarasota's most sought-after addresses. Perfectly positioned West of the Trail, just minutes from Siesta Key, The Field Club, Southside Village, and downtown Sarasota, it offers an enviable location in the epicenter of Sarasota. Designed entirely on one level, the home spans more than 3,600 square feet with a floor plan that feels just as relevant today as when it was built. A welcoming entrance opens beneath soaring cathedral ceilings, while the living room, family room, kitchen, and outdoor spaces connect effortlessly, creating a natural flow throughout the home. Large sliding glass doors open to the pool and spa, creating a seamless connection between the home's interior living spaces and its treed outdoor entertaining areas. Privately positioned, the primary suite serves as a peaceful retreat with a spacious walk-in closet and an oversized bath. Three additional bedrooms provide comfortable accommodations for family and guests, with one thoughtfully incorporating a built-in office, offering flexibility for those who work from home. Zoned for highly regarded Phillippi Shores Elementary, the home is equally well suited for growing families as it is for those seeking the convenience of single-story living. The open kitchen has been updated with stone countertops and stainless appliances. Equally appealing are the features that provide everyday confidence. Situated in a preferred X flood zone, the home is equipped with a metal roof with enhanced hurricane tie-downs, impact-rated windows and doors, and a private irrigation well. Practical improvements add lasting value while making ownership that much easier. Perhaps its greatest strength is the flexibility it offers. Move in and enjoy it exactly as is or gradually make it your own over time. The location, the lot, and the floor plan provide an exceptional foundation, allowing the next owner to personalize the home without ever compromising what makes it so special.

1511 N Lake Shore Drive, Sarasota

$299,000

2 Beds ⋅ 2 Baths ⋅ Mentone Court SubDv. ⋅ 34236 Zip Code

Discover exceptional value in the heart of Sarasota's vibrant Rosemary District. Offered furnished and move-in ready, this beautifully updated two-bedroom residence at Mentone Court combines modern finishes, low-maintenance living, and an unbeatable downtown location—all within an intimate community of just 16 residences. Whether you're searching for a seasonal retreat or investment opportunity, this inviting home offers an ideal blend of comfort, convenience, and city living. The thoughtfully designed open floor plan creates an airy, welcoming atmosphere where the living, dining, and kitchen areas flow effortlessly together. Luxury vinyl plank flooring extends throughout the main living spaces, complemented by fresh interior paint, abundant natural light, and a neutral palette ready for your personal style. Sliding glass doors open to a the screened lanai, creating the perfect setting for morning coffee, evening relaxation, or enjoying Sarasota's year-round sunshine. The galley-style kitchen features stainless steel appliances, solid-surface countertops, generous cabinetry, and an efficient layout that keeps you connected to the main living areas while entertaining. Both bathrooms have been tastefully renovated with clean, timeless finishes, while the spacious primary suite offers a walk-in closet and en-suite bath. A comfortable guest bedroom, interior laundry closet with washer and dryer hookups, and assigned parking complete this move-in-ready residence. Mentone Court is a charming boutique community known for its peaceful atmosphere, attractive landscaping, and exceptionally low monthly maintenance fees, which include exterior maintenance, professional management, and more—making ownership both affordable and worry-free. Perfectly positioned just blocks from Downtown Sarasota, residents enjoy one of the city's most walkable neighborhoods. Stroll to the boutiques, cafés, breweries, and acclaimed restaurants of the Rosemary District before exploring nearby Main Street, the Sarasota Farmers Market, Bay Park, Marina Jack, and Sarasota's renowned Cultural Coast, featuring theaters, museums, galleries, and live entertainment. St. Armands Circle, Lido Beach, and Siesta Key Beach are all just minutes away, offering the perfect balance of vibrant downtown living and Sarasota's celebrated coastal lifestyle. Beautifully updated, furnished, and ideally located, this residence presents an outstanding opportunity to own in one of downtown Sarasota's most desirable neighborhoods.

631 N Orange Avenue Unit 108, Sarasota

$17,650,000

4 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code

Four Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparalleled craftsmanship, and the restorative beauty of nature exist in perfect harmony. Offered fully furnished, the residence has been curated to provide an effortless, move-in-ready lifestyle, where every detail has been thoughtfully considered and every space evokes a sense of calm, balance, and understated luxury. Spanning more than 8,000 square feet, the home embraces the philosophy of seamless indoor-outdoor living. Expansive walls of glass dissolve the boundaries between the interiors and the surrounding tropical landscape, filling the home with natural light, gentle coastal breezes, and mesmerizing waterfront views. Rich exotic woods, natural stone, tranquil water features, and handcrafted architectural elements create an atmosphere reminiscent of an exclusive Balinese resort, where every room serves as a peaceful retreat. Designed as a private wellness oasis, the grounds are nothing short of breathtaking. Lush tropical gardens, mature specimen palms, fragrant flowering plants, and winding pathways lead through a series of serene outdoor spaces that inspire quiet reflection and effortless entertaining. A tranquil koi pond, crossed by picturesque footbridges, gently meanders alongside the residence, filling the air with the soothing sound of flowing water and creating a Zen-inspired tranquility throughout the estate. The resort-caliber outdoor living spaces are exceptional. An infinity-edge pool appears to merge effortlessly with the sparkling bay beyond and features a swim-up bar, spa, expansive sun shelves, and multiple terraces for lounging in the Florida sunshine. A dramatic sunken fire pit provides the perfect setting for evening gatherings beneath the stars, while the outdoor kitchen, covered dining pavilion, and numerous seating areas invite unforgettable alfresco entertaining against a backdrop of spectacular sunsets and panoramic waterfront vistas. With more than 700 feet of waterfront frontage, the property offers an extraordinary connection to the water that is rarely found. Whether setting out for a morning paddle through calm mangrove-lined waters or enjoying effortless boating from the private dock, every day begins and ends immersed in Sarasota's extraordinary coastal beauty. A dedicated waterfront garage, newer seawall, and abundant shoreline further enhance this exceptional waterfront lifestyle. Inside, every space has been thoughtfully designed to nurture both relaxation and recreation. A private theater, game room, fitness studio, and dedicated meditation room create an environment centered around wellness, entertainment, and everyday enjoyment. An oversized garage accommodating more than eight vehicles provides ample space for collectors and enthusiasts alike. Modern technology complements the home's timeless design with Crestron smart home automation, a three-stop elevator, whole-house generator, reverse osmosis water filtration system, and numerous additional upgrades that deliver effortless comfort, security, and peace of mind. This one-of-a-kind estate represents one of Siesta Key's most extraordinary luxury offerings and an exceptionally rare opportunity to own a true legacy property.

3799 Flamingo Avenue, Sarasota

$1,549,000

3 Beds ⋅ 4 Baths ⋅ Arlington Park SubDv. ⋅ 34239 Zip Code

Be the first to call this exceptional newly constructed home your own. Offering 3 bedrooms, 3.5 bathrooms, and a private office, this thoughtfully designed residence blends modern style, quality finishes, and seamless indoor-outdoor living in one of Sarasota's most desirable locations. Step inside to an open-concept floor plan filled with natural light, soaring ceilings, and large-format porcelain tile flooring throughout the main living areas. Just off the entry, the private office provides the perfect space to work from home, create a media room, or enjoy a quiet retreat. At the heart of the home, the chef's kitchen is designed to impress with quartz countertops, a full-height quartz backsplash, custom cabinetry extending to the ceiling, an oversized waterfall island, and a premium Thermador appliance package, including an induction cooktop, a 42-inch built-in French door refrigerator, and a combination wall oven. Sliding glass doors open to your own private backyard oasis, where a heated saltwater pool, spacious paver patio, and fully equipped outdoor kitchen with a built-in grill, granite countertops, and a mini fridge create the perfect setting for entertaining or simply enjoying Florida's year-round sunshine. Upstairs, each bedroom features its own en-suite bathroom and custom walk-in closet, offering comfort and privacy for family and guests alike. The spacious primary suite is a true retreat, complete with a spa-inspired bathroom designed for everyday relaxation. With no HOA and the ability to allow weekly rentals within the city limits, this property offers outstanding flexibility as a primary residence, vacation home, or investment opportunity. Ideally located just minutes from Downtown Sarasota, Siesta Key Beach, St. Armands Circle, Sarasota Memorial Hospital, The Legacy Trail, and top-rated schools, this home delivers the perfect combination of luxury, convenience, and the Florida lifestyle.

2590 Floyd Street, Sarasota

$2,800,000

4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Privately set on Palm Island in the heart of Siesta Key, this residence offers an exceptional combination of generous living space, thoughtful design and effortless access to the island’s most celebrated destinations. Just a short distance from the powdery, white quartz sands of Siesta Beach and the boutiques, dining and lively atmosphere of Siesta Village, this beautifully reimagined waterfront residence presents a rare opportunity to enjoy a relaxed coastal lifestyle without compromising comfort, privacy or quality. Nearly every aspect of the home was transformed, creating a fresh, modern interior, designed for both everyday living and gracious entertaining. Soaring ceilings, abundant natural light, a contemporary custom staircase and impact-rated windows and doors establish an open, airy atmosphere, while luxury vinyl and engineered hardwood flooring, recessed lighting and thoughtfully integrated storage add warmth and architectural interest. The expansive kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, upgraded stainless steel appliances, wine storage and an oversized quartz island with generous seating. Designed to accommodate everything from casual mornings to larger gatherings, the kitchen flows naturally into the surrounding living and dining spaces and continues outdoors to the pool, lawn and waterfront beyond. The main-level primary suite provides a serene private retreat with direct access to the pool area, a spacious custom-fitted closet and a beautifully appointed spa-inspired bathroom. Three additional bedrooms offer comfortable accommodations for family and guests, while an upstairs, separate flex space is ideally suited for a private office, exercise room or personalized retreat. A sunroom and conveniently positioned pool bath further enhance the home’s easy indoor-outdoor connection. Outside, the property reveals one of its most distinctive features: an unusually spacious backyard for Siesta Key. A broad lawn surrounds the heated pool, creating room for outdoor dining, recreation, pets and relaxed afternoons beneath the Florida sun. Beyond the pool, peaceful canal views and a private dock provide a tranquil waterfront setting with boating access. A well supplies the irrigation system, helping maintain the lush tropical landscape. A detached two-car garage offers valuable parking and additional storage for beach equipment, bicycles, paddleboards and other island essentials to enjoy the Siesta Key lifestyle. Morning walks along Siesta Beach, afternoons beside the pool and evenings dining in Siesta Village can all become part of everyday life. Spacious, extensively remodeled, and ideally positioned near the beach, Village and boating water, 430 Island Circle is a sophisticated yet wonderfully comfortable island retreat designed for those who want to experience the very best of Siesta Key.

430 Island Circle, Sarasota

$371,000

3 Beds ⋅ 2 Baths ⋅ Golf Club Estates SubDv. ⋅ 34240 Zip Code

Calling all dreamers with a paintbrush in one hand and a vision in the other—this three-bedroom, two-bath house is practically begging for a little love and a lot of imagination. Yes, it needs some tender care, but that's precisely where the fun begins. Think of it as a project with genuine payoff. The bones are here, the layout is ready, and there's no association looking over your shoulder dictating your every move. Renovate at your own pace, choose your own finishes, and shape a home that reflects exactly who you are. For investors, the story writes itself: a smart refresh could transform these walls into a dependable rental in a corner of Sarasota that is a desirable place to live. The surrounding neighborhood does plenty of the selling on its own. Lakeview Park sits just up the road, offering a breezy spot for morning outings or lazy weekend picnics. Grocery runs stay refreshingly simple with the Publix at Bee Ridge only minutes away, while a nearby bus stop along Cattlemen Road keeps commuting effortlessly connected. A well-regarded secondary school is within easy reach, too. Whether you're a first-time buyer eager to build sweat equity, a seasoned flipper hunting your next win, or an investor chasing steady returns, this one rewards a little effort with plenty of upside. Diamonds in the rough don't linger long around here. Come see the potential for yourself—schedule your private showing today.

3743 Wake Avenue, Sarasota

$504,900

2 Beds ⋅ 2 Baths ⋅ Hidden River SubDv. ⋅ 34240 Zip Code

At Hidden River, discover the ideal blend of country living and convenience on nearly five acres in this charming, well-maintained two-bedroom, two-bath home. In a unique fly-in community, this property is ideal for aviation enthusiasts, equestrians, gardeners or anyone seeking room to grow. A spacious hangar/workshop offers endless possibilities, including aircraft storage, hobbies or equipment. Greenhouse is ideal for growing your vegetables, and the expansive acreage provides ample space for horses, gardens or future expansion. Enjoy the privacy and peaceful surroundings while having access to the community airstrip and community center just moments away. A rare opportunity to own a versatile property with exceptional lifestyle options.

4498 Hidden River Road, Sarasota

$825,000

3 Beds ⋅ 3 Baths ⋅ The Villas On Laurel SubDv. ⋅ 34236 Zip Code

Virtually Staged. Located in the heart of downtown Sarasota, Villas on Laurel is a boutique community of only nine residences situated directly beside Laurel Park on a quiet one-way street. This location places you just a few blocks from Sarasota Bay, Marina Jack, Main Street dining, art galleries, theaters, shopping, and the Sarasota Farmers Market. This two-story townhome offers three bedrooms, three full bathrooms, and a versatile floor plan that includes a spacious first-floor living area along with a full guest bedroom and bath. Upstairs, a loft provides additional flexible living space, while two private bedroom suites create comfortable accommodations for owners and guests alike. Recent improvements include a new HVAC system (2025), luxury vinyl plank flooring (2025), and updated appliances. Community-wide capital improvements include a new membrane roof (2025), resurfaced parking area, refreshed landscaping, and additional maintenance projects that reflect a well-managed homeowners association. Impact-rated Andersen windows were installed throughout the community in 2004. Additional features include two reserved parking spaces, a community pool, community storage room, and classic Old Florida architecture updated in 2005. A rare opportunity to enjoy low-maintenance living in one of downtown Sarasota's most convenient locations- schedule your private showing today!

1685 Laurel Street Unit 3, Sarasota

$498,000

3 Beds ⋅ 2 Baths ⋅ Carlyle At Villages Of Palm Aire SubDv. ⋅ 34243 Zip Code

Welcome to Carlyle at The Villages of Palm-Aire, a highly sought-after, peaceful community in North Sarasota near Palm Aire Golf & Country Club. This beautifully updated 3-bedroom, 2-bath home is offering 1,807 square feet of open concept living space. The stunning kitchen is designed for chef-styled cooking. You’ll love the granite countertops, breakfast bar, spacious island with added storage, eat-in dining area, custom cabinetry, a five-burner GE GAS cooktop, GE Profile built-in convection and microwave ovens, a Broan range hood, and new KitchenAid stainless-steel refrigerator and dishwasher. The cabinets boast a Lazy Susan, glass front doors and a roll-out trash cabinet. Glass-paneled French doors lead to the formal dining room. The open concept floor plan of this home is enhanced by the 12 foot ceiling in the living room. Enjoy the split bedroom layout providing privacy for guests and families. The primary suite features dual vanities, modern lighting, a soaking tub, separate shower, and custom walk-in closet. The guest bathroom has access to the lanai for convenience. The spacious two-car garage is conveniently located just off the laundry room accessible from the kitchen. Laundry day will be stress free with the new LG ThinQ washer and dryer. And, there’s plenty of cabinetry in the laundry room to hide everything! Don’t miss the air conditioned bonus storage room accessible in the garage! When you’re all done at the end of the day, you’ll look forward to spending time on your quiet, peaceful and private covered lanai while listening to the fountain pond. The back yard is enclosed with a vinyl privacy fence which backs to a preserve area. Updates include a new 2026 gas water heater, 2025 roof, new stainless kitchen appliances, updated landscaping and new interior paint. Seller includes 3 flat screen televisions in this sale. Community amenities include a pool, pickleball and tennis courts, and a playground. Conveniently located near University Parkway and UTC Mall, the home is minutes from downtown Sarasota, St. Armands Circle, world-class Gulf Coast beaches, and Sarasota-Bradenton International Airport.

5122 Creekside Trail, Sarasota

$499,000

3 Beds ⋅ 2 Baths ⋅ South Haven SubDv. ⋅ 34231 Zip Code

WELCOME TO YOUR PRIVATE OASIS NESTLED IN THE HEART OF SARASOTA!! THIS IS A MUST SEE - TRULY ONE OF A KIND PROPERTY LOCATED ON AN OVERSIZED ALMOST 1/2 ACRE LOT WITH NO HOA RESTRICTIONS! You will be amazed when you pull up into your beautifully landscaped circular granite chip driveway. This area can be the new home for your RV, boat, work trucks and even another dwelling. This property is in a prime location and can be a family's OR an investors dream being minutes from everything that Sarasota has to offer-conveniently located less than 5 miles from famous Siesta Key Beach, premier shopping, coffee, and dining, including Trader Joes and Starbucks, US-41, I-75, top rated schools, and countless recreational opportunities. This property truly offers the best of both worlds - you can enjoy the tranquility of a secluded setting that offers the charm and serenity of country living, with super easy access to modern conveniences.-----------HOME DETAILS: •ON .45 ACRES-LESS THAN 5 MILES FROM THE WORLDS FAMOUS SIESTA KEY BEACH AND STEPS FROM US 41 •3 BEDROOM 2 BATH 1505 SQUARE FOOT UPDATED HOME •ROOF 9 YEARS OLD, AC, DUCT WORK, INSULATION AND WATER HEATER LESS THAN 5 YEARS OLD•PORCELAIN TILE AND LVP THROUGHOUT THE HOME•LARGE UTILITY ROOM THAT CAN ALSO BE USED AS A BONUS ROOM •STUNNING ENTERTAINMENT AREA THAT INCLUDES A 6-SEATER HOT TUB, FIRE PIT, EXTENSIVE SEATING AREA, AND NIGHTTIME LIGHTING •SPACIOUS FENCED IN BACKYARD THAT IS FULLY ARTIFICIALLY TURFED AND LANDSCAPED WITH AMPLE SPACE FOR OUTDOOR ACTIVITIES AND/OR FURRY FRIENDS TO PLAY SAFELY•NO HOA - ROOM FOR RV'S, BOAT, WORK TRUCKS, GARAGE, ADDITIONAL LIVING QUARTERS AND MORE•COUNTY WATER AND SEWER•EQUIPPED WITH NEW WHOLE HOME KOHLER GENERATOR•RESORT STYLE LANDSCAPING WITH FULL IRRIGATION SYSTEM AND NIGHTTIME LIGHTING SURROUNDING THE HOME•HOME IS NOT IN FLOOD ZONE•WELL REGARDED ZONED SCHOOLS INCLUDE PHILIPPI SHORES ELEMENTARY, SARASOTA MIDDLE AND RIVERVIEW HIGH•****This home will be available to view for the first time on SUNDAY -8/2/26 - 12:00pm-4pm****DO NOT MISS OUT ON THIS SPECTACULAR MUST SEE HOME! See YOU Sunday! GOOGLE MAPS DOES NOT TAKE YOU RIGHT TO THE HOME - From US 41 and Bee Ridge - Go south on 41 make a left on Worrington St right past Ace Hardware. Weave through the street down to the 5TH house on the left - make left right before FOR SALE SIGN there will be a small private road - make a left and house will on little private road. From Shade and Bee Ridge - Go south on Shade, make a right on Haley Ln. then right on Worrington St., go to end of street, make a left on School Ave then quick right to stay on Worrington St. After the first house on right, look for speed bump sign and the FOR SALE SIGN and make a right after onto the private road that takes you to the house.

2137 Worrington Street, Sarasota

$2,700,000

4 Beds ⋅ 4 Baths ⋅ Sarasota Heights SubDv. ⋅ 34239 Zip Code

Under Construction. Stunning new construction 4-bedroom, 4-bathroom modern farmhouse luxury home developed by Rustic Appeal LLC and built by EJM Custom Homes, situated on a prime corner lot in Arlington Park, one of Sarasota's most sought-after neighborhoods. Spanning 4,288 sq ft across two stories with a 4-car garage, this thoughtfully designed residence masterfully blends warm farmhouse character with contemporary finishes: natural stone, PVC cladding, and a striking standing seam metal roof on the exterior give way to an equally impressive interior. The grand foyer welcomes you with soaring double-height ceilings, floor-to-ceiling glazing windows, and a hand-crafted custom floating staircase. The gourmet chef's kitchen features a Calacatta marble waterfall island, custom cabinetry with extensive storage, professional-grade ZLINE appliances, built-in wine fridge, and separate bar area perfect for family gatherings and entertaining. The primary suite is a true retreat with a freestanding soaking tub, extended dual vanity with makeup area, heated floors, Delta dual shower system, brushed gold fixtures, and private balcony access. Three additional bedrooms include spa-inspired baths with unique color and design. Enjoy Florida living with a salt-water pool, spa, and outdoor kitchen. The oversized 4-car garage completes this one-of-a-kind offering. Just 5 minutes from Downtown Sarasota, 8 minutes from Siesta Key Beach, 10 minutes from St. Armands Circle, and walkable to Southside Village. Estimated delivery early 2027.

2082 Datura Street, Sarasota

$1,699,000

4 Beds ⋅ 3 Baths ⋅ Kenilworth Estates SubDv. ⋅ 34231 Zip Code

Welcome to 1711 Kenilworth Street, an exceptional opportunity to own a move-in-ready home in one of Sarasota’s most desirable West of the Trail neighborhoods. Located within the highly coveted corridor between Field Road and Mound Street, this home offers more than 3,700 square feet, four bedrooms, three full bathrooms, a first-floor office, and a rare three-car garage. At the time of listing, this is the lowest-priced move-in-ready home per square foot in this sought-after West of the Trail area, making it an outstanding value for buyers who want generous living space without sacrificing location, condition, or lifestyle. What truly sets this home apart is its peaceful lakefront setting. From the moment you enter, the open great room draws your attention through large sliding glass doors to the expansive water views beyond. The lake creates a beautiful backdrop throughout the home and offers a sense of privacy and tranquility that is incredibly difficult to find this close to downtown Sarasota. Over the past year, move-in-ready West of the Trail homes offering comparable water views have sold or been listed near the $4 million range, highlighting just how rare and valuable this setting is. Here, you can enjoy the same peaceful waterfront lifestyle at a substantially more approachable price. A welcoming front porch leads into the foyer and spacious great room, where beautiful oak flooring adds warmth and character. The fully screened lanai and travertine deck provide an ideal place to relax, entertain, dine outdoors, or simply enjoy the view. A private dock offers the perfect spot to fish, watch the turtles, and take in the abundant birdlife surrounding the lake. The expansive kitchen features a gas cooktop, abundant workspace, and a large gathering area designed for hosting family and friends. The primary suite feels like a true private retreat, with an oversized bedroom, two walk-in closets, a spacious bathroom with excellent storage, and a private owner’s office overlooking the water. The three additional bedrooms are also generously sized, giving family members and guests the space and privacy they need. A separate first-floor office adds even more flexibility for working from home, managing a busy household, or creating a quiet study. Upstairs, a large loft and oversized media, fitness, or recreation room provide additional space for entertaining and everyday living. This is a home that truly has everything you need from a space and functionality standpoint. There is room to spread out, work, host, relax, and move in comfortably without immediately needing to reconfigure the home or take on a major project. Outside, the clean, attractive landscaping complements the home without creating unnecessary upkeep. The property offers beautiful curb appeal while remaining relatively low maintenance, making it ideal for buyers who want to enjoy the Sarasota lifestyle without spending every weekend working on the house. Located just minutes from Sarasota Memorial Hospital, Southside Village, downtown Sarasota, Siesta Key, and some of the area’s best dining, shopping, and beaches, 1711 Kenilworth Street offers an increasingly rare combination of space, water views, a three-car garage, low-maintenance living, and an exceptional West of the Trail location. For buyers searching for a move-in-ready home in one of Sarasota’s most luxurious and established neighborhoods, this is a value that is difficult to duplicate.

1711 Kenilworth Street, Sarasota

Sarasota Homes with Custom Architectural style

Newest Sarasota Homes with Custom Architectural style