Homes for Sale Near Booker High in Sarasota - 416 homes

Remarks: Not every home is simply built to be lived in; the most exceptional are crafted to be experienced. We invite you to discover this prestigious custom-built Lee Wetherington architectural masterpiece in LakeHouse Cove at Waterside. This home offers a floor plan that celebrates both scale and intimacy, set against the rare privacy of a protected preserve. Crafted with precision and curated with intention, it reflects the sensibilities of owners who value refinement at every turn. Step through the glass entry into soaring twelve-to-fourteen-foot ceilings, framed by expansive niches, custom lighting, and wide crown detailing. Walls of pocketing glass disappear and blend the interior with the outdoors in a way that feels effortless yet striking. Engineered wood floors flow through open living spaces, while an Arhaus Dandelion chandelier anchors the main gathering room with quiet drama. The kitchen is designed as both a showpiece and a place of purpose. Café Platinum appliances, including a five-in-one Advantium oven, and the custom wood hood and mantle elevate the space. A Ruvati forty-five-inch workstation sink takes functionality to a new level with the Dual-Tier collection that converts your sink into a full workspace. Heavy-duty cookware drawers and a walk-in pantry with custom carpentry ensure beauty and function remain in balance. The designer backsplash is an opulent luster that rivals mother-of-pearl, infused with flare straight from the sea and extending from counter to ceiling, complemented by under-cabinet lighting and discreet outlets that preserve clean lines. The primary suite is a retreat defined by thoughtful scale and elegant finishes. Two oversized walk-in closets with mirrored dressing space adjoin a bath featuring dual vanities, a deep soaking tub, and a triple-head shower with dedicated lines for comfort and performance. Two additional ensuite bedrooms, an office framed by solid core double pocket doors, and a versatile bonus room complete the interior. Beyond its beauty, this home is engineered for lasting comfort. PGT Low-E impact glass, whole-house water filtration with salt-free conditioning, a Navien tankless system with rapid hot water, dual HVAC air handlers, climate-controlled storage, and exterior security cameras with NVR reflect a commitment to quality. The outdoor living environment enhances the sense of privacy with its preserve backdrop. The lanai becomes a destination of its own with a summer kitchen featuring an oversized grill, a fire table lounge, and generous dining space that invites gatherings of every scale. The custom pool, complete with waterfall, sun shelf, and programmable lighting, transforms the setting into a resort-inspired centerpiece. Professional landscaping with dramatic uplighting frames the residence, ensuring it shines just as brightly at night. LakeHouse Cove is a lifestyle shaped by thoughtful amenities and natural surroundings. Residents enjoy a resort-style pool, fitness center, and clubhouse, along with kayaking, pickleball, and bocce. Hop on the community water taxi to Waterside Place or head to the boathouse to use the community kayaks. Acres of preserve and miles of shoreline create a natural rhythm, while Waterside’s vibrant lakefront town center offers dining, culture, and convenience within moments of home. This residence is a rare opportunity to own a home where architectural artistry, meticulous craftsmanship, and an extraordinary lifestyle come together in harmony.

Listing is courtesy of: KW SUNCOAST (941-792-2000)

Listing Agent: Mike Polachek (941-524-0241)

Remarks: One or more photo(s) has been virtually staged. Nestled in the quiet, pet friendly community of Village Oaks features this Immaculate updated 2-bedroom, 2 bathroom Condo/Villa that offers a move-in-ready retreat. This fully updated unit features a new hot water heater installed in January 2026 and boasts a freshly repainted interior throughout. The modernized kitchen offers a pass-through to the dining area. Updated Master Bath with dual sinks, and walk in shower. Enjoy the look of luxury vinyl that flows seamlessly through every room. The open-concept living room boasts of high ceilings, while an enclosed Florida room (lanai) provides a private space to enjoy the lush surroundings. The villa features a convenient in unit laundry area with a washer and dryer tucked into a dedicated laundry closet.Enjoy the convenience of a private one car garage with remote access, plus two dedicated exterior parking spots right outside your villa. Community pool overlooking lake along with tennis/pickleball court for outdoor activities. Ideally situated between I-75 and downtown Sarasota, offering quick access to the University Town Center Mall (UTC), local dining and world-class beaches.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Laura Flood (941-725-2500)

Remarks: Refined downtown living with a modern, urban edge in Sarasota’s Rosemary District. This stylish 2-bedroom, 1-bath residence features soaring 10-foot ceilings, porcelain tile throughout, upgraded kitchen island, generous closet space, and exposed concrete accents that create a sleek architectural aesthetic. A covered terrace extends the living space, while assigned covered parking and a rare 60-ft temperature-controlled storage unit provide exceptional value and convenience. Built in 2021, this boutique building offers low HOA fees and a third-floor amenity level with pool, BBQ area, and outdoor shower. Ideally positioned among some of downtown’s most established and emerging luxury residences, the location offers effortless walkability to shops, galleries, restaurants, and the cultural heart of the city. A unique purchase opportunity—perfect as a chic pied-à-terre, stylish first condominium, or guest suite complementing a larger primary home.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Dave Hall (646-256-6524)

Remarks: PRICE IMPROVEMENT & MOTIVATED SELLER! Location, Location, Location! I know that saying is real estate cliche, but in this instance, it's absolutely true! This beautiful 3 bedroom, 2 1/2 bath, 2 car garage home with heated pool is nestled against a preserve and located in the popular and highly sought after Longwood Run subdivision. You're just minutes away from world famous beaches, first class shopping at UTC, medical facilities and a myriad of restaurants covering just about everyone's favorite dish. Easy access to I-75, US 41 and just minutes to Sarasota Bradenton International Airport (SRQ). Home updates worth noting include a new tile roof in 2020, kitchen cabinets & quartz countertops in 2025, primary, guest and pool baths all updated within the last 2 years and the pool was resurfaced in 2024. The generous room sizes and easy flow of this home will draw you in, but the peace and tranquility found enjoying your pool area/outdoor living with gorgeous preserve views will make you want to stay! One bedroom is currently being used as a den/office, but could easily have a closet added, if needed. Primary bedroom offers sliders to the pool area along with 2 walk-in closets (hers and hers, LOL), ensuite bathroom with quartz countertops, soaking tub and stand alone shower stall. An affordable HOA, superb location and a fabulous home. . . . what more could you ask for? Schedule your private viewing today and make this home yours - before someone else does!

Listing is courtesy of: SETTLES REAL ESTATE LLC (941-685-3600)

Listing Agent: Cherie De Hay (941-809-6828)

Remarks: Positioned on one of the most coveted lakefront homesites within Artistry Sarasota, this impeccably enhanced Monet residence embodies a refined, tranquil lifestyle with a thoughtful balance of privacy, elegance, and modern comfort. Lush, mature landscaping lines both sides of the backyard, creating a secluded sanctuary while preserving sweeping water views and generous space for a future pool—an ideal backdrop for quiet mornings and effortless outdoor living. The residence offers a sophisticated and functional layout with three ensuite bedrooms, a dedicated den, and a well-appointed powder room for guests. The primary suite with wood effect Porcelain tile flooring is a serene retreat, oriented to capture long lake vistas and soft natural light enhancing the home’s calming atmosphere. Inside, the interiors present a crisp, luminous aesthetic complemented by carefully curated upgrades, including large format high gloss tile. The great room is anchored by a custom-designed fireplace feature, framed by solid white oak built-in shelving and cabinetry with integrated lighting—delivering both architectural presence and warmth. Over $130,000 in builder and owner enhancements elevate the home throughout, including whole-house plantation shutters, bespoke drapery, custom office built-ins, and a redesigned laundry room with added cabinetry and workspace. Further refinements include large-format polished tile flooring across the main living areas, quartz surfaces in the kitchen, soft-close cabinetry with crown detailing, designer lighting, and spa-inspired bathrooms with tile extending to the ceiling. The outdoor living experience is equally considered, with a screened patio enclosure, professionally reimagined landscaping, and sealed paver driveway completing the home’s polished presentation. As one of the most extensively upgraded Monet residences currently available, this property offers a rare level of completion and move-in readiness within the community. Residents of Artistry Sarasota enjoy a gated, maintenance-free environment complemented by resort-style amenities, including a clubhouse, pool, pickleball and basketball courts, playground, and scenic walking trails. With no CDD fees and a location outside of a flood zone, the home also provides peace of mind. Ideally situated, this residence offers convenient access to The Mall at University Town Center, championship golf courses, acclaimed dining, and the renowned cultural and waterfront destinations of Sarasota—including its world-class beaches and vibrant arts scene. Furnishings may be available separately.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: Welcome to BLVD Sarasota, a stunning downtown sanctuary in the sky where luxury living meets extraordinary views from every room. Perched in the desired corner stack of the building, this exclusive residence offers uninterrupted, floor-to-ceiling panoramas of Sarasota Bay and the vibrant city skyline — all from the comfort of each space in the home. Whether you're waking up in the primary suite, preparing a meal in the chef’s kitchen, or hosting guests in the expansive living and dining areas, you're surrounded by natural beauty at every turn. Exit your private elevator into over 5,000 square feet of exquisitely designed indoor-outdoor living. The open floor plan is drenched in natural light from walls of PGT impact-rated glass, ensuring every room becomes a front-row seat to Sarasota’s spectacular sunsets, coastal waters and sparkling city lights. The oversized, wrap-around terrace extends your living experience outdoors, offering multiple seating, lounging and dining areas — all designed to showcase the unrivaled, wrap-around water and city views. Offered turnkey furnished, this residence includes three spacious bedrooms with en-suite baths, a private office and two additional half baths, blending the space and comfort of a single-family home with the ease of elevated condominium living. Interior features include soaring 11-foot ceilings, Lutron-controlled lighting, motorized window shades, premium finishes, and designer-selected furnishings that elevate the elegance throughout. The gourmet kitchen is a showpiece with custom gray Irpinia cabinetry, quartz countertops and top-of-the-line appliances — all positioned to ensure you never miss a moment of the view. Entertain effortlessly with two oversized pantries, dual sinks and generous storage. The primary suite is a retreat, offering breathtaking vistas right from bed, along with dual custom walk-in closets and a spa-inspired bath with a soaking tub, frameless glass shower, and refined Kohler fixtures. BLVD Sarasota is a lifestyle unlike any other, offering residents top-tier amenities such as a rooftop infinity-edge pool, outdoor kitchen, wine cellar, state-of-the-art fitness center, golf simulator and a fifth-floor pet lawn with a grooming station. Enjoy two premium parking spaces, a private elevator entrance and a humidity-controlled storage locker. Just a short distance from the 53-acre Bay Park and Sarasota’s world-class dining, arts and marina scene, this is more than a home — it’s your front-row seat to the best of the Gulf Coast. Residence 1201 is not just a place to live — it’s a window to the world, where every room frames an unforgettable view.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Katy Mcbrayer (941-400-2406)

Remarks: Welcome to Lakehouse Cove at Waterside where maintenance- free living meets vibrant resort style amenities in the heart of Lakewood Ranch. Move right in to this cozy, coastal craftsman fully furnished Halyard model from Homes by Towne with 2 bedrooms, a den, and a light drenched bonus room on a conservation lot. This spacious and well-designed home has a sense of openness from the moment you walk into the warm and dramatic foyer. The heart of the home features a gourmet kitchen with Cambria quartz countertops, beautiful cabinetry, under-cabinet lighting, a large walk-in pantry, and eat-in dining area. The kitchen blends seamlessly with the expansive Great Room that boasts striking volume tray ceilings, built-ins, and shiplap detailing. A thoughtful split floor plan offers privacy for guests or family members and the modified 330 square foot bonus room provides an additional spot to relax and unwind separate from the Great Room. Newer construction provides peace of mind as the home is equipped with impact windows, sliders, and doors. Additional features include a 20,000 watt Kohler generator and an Aquasana 5 stage water filtration system. Life at Lakehouse Cove means more than just a beautiful home- it’s a lifestyle. Enjoy 6 pickleball courts, a resort-style pool and spa overlooking Lake Kingfisher, a state-of-the-art fitness center, boathouse with kayak launch, 2 dog parks, community club house and fire pits where neighbors gather for breathtaking sunsets. Just a short stroll brings you to Waterside Place where you can enjoy shopping, dining, a weekly farmers market and other year round events. Don’t miss the opportunity to make your dream Florida lifestyle a reality.

Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)

Listing Agent: Sasha Rosin (941-323-0261)

Remarks: Welcome to Renaissance residence 314, a blend of charm and modern luxury in this fully renovated condominium offering over 1,000 square feet of thoughtfully designed living space. This beautifully updated unit features an expansive family and dining room, an oversized primary bedroom, and a versatile den that can easily serve as a second bedroom. Completely renovated in 2024, this home is move-in ready with every detail meticulously updated for your convenience. The sleek kitchen boasts matching GE Profile appliances, an LG washer and dryer, and new cabinetry with built-in storage solutions, offering ample space for all your needs. Freshly repainted in a neutral palette and paired with new luxury vinyl flooring throughout, the space provides a timeless foundation for any design style you choose. The spacious primary bedroom includes custom built-in closets and offers plenty of room to craft your ideal Sarasota retreat, while the remodeled en-suite bath features elegant quartz countertops, new cabinetry and a stunning shower with dual showerheads, exuding style and comfort. Renaissance is more than just a residence, it’s a lifestyle. This 16-story condominium high-rise offers an impressive array of resort-style amenities, including beautifully landscaped plazas and fountains, 24-hour front desk service and keycard secured entry. The building’s proactive maintenance ensures peace of mind, with recent updates including a new roof and cleaned piping systems in 2024. Designed with durability in mind, Renaissance features reinforced concrete beams, fireproof materials, and elevated guest parking and lobby spaces, providing stability and security. Residents enjoy world-class amenities such as a clubroom, business center, fitness center, resident theater and concierge services. For hosting guests, the building offers two fully equipped guest suites available by reservation. This unit comes with two assigned parking spaces conveniently on the third floor of the secured garage, ensuring your vehicles are protected and elevated over 50 feet above sea level. In the heart of Sarasota’s vibrant cultural district, Renaissance places you near The Bay Park and the city’s dynamic social scene. Designed in the style of an Italian villa, the building's charm is matched by its prime location, where water views are preserved thanks to Renaissance's ownership of aerial rights over the park. Embrace the luxury, convenience and unmatched beauty of living in Renaissance Unit 314. Your Sarasota dream home awaits!

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Moriah Taliaferro (941-504-9910)

Remarks: Welcome to 3696 Quiet Pond Lane, a warm and inviting two story home tucked into one of the prettiest, tree filled neighborhoods around. The layout just makes sense. The primary suite is on the main floor, giving you privacy and convenience, while two additional bedrooms are upstairs, perfect for family, guests, or a home office setup. The primary bedroom is truly oversized, with plenty of room for a sitting area, reading nook, or whatever retreat space you have been dreaming about. Downstairs features durable and stylish LVP flooring, ideal for everyday living. The kitchen has been thoughtfully updated with a newer dishwasher, and the home also includes a newer washer and dryer. Big ticket items have already been taken care of, including a roof replaced in 2022, AC in 2021, and a water heater in 2024. Even the screens and gutters have been updated, so you can move in without a long to do list. Step outside and you will find a backyard that feels like your own private escape. The pool overlooks a peaceful pond through a canopy of trees, creating a serene and private setting that is hard to find. Whether you are hosting friends or enjoying a quiet morning coffee, this space delivers. The neighborhood itself is lush and beautifully landscaped, filled with mature trees and plantings that give it character and charm. You are centrally located, just a short drive to downtown and the beaches, so you can enjoy the best of everything without sacrificing tranquility at home. If you are looking for space, updates, and a backyard that feels special, 3696 Quiet Pond Lane is one you will want to see in person.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Beth Helvey Pa (941-330-3600)

Remarks: NEW PRICE!! LUXURY, LOCATION, AND LIFESTYLE - Sarasota living at its finest. Located in Hidden Creek, residents enjoy NO CDD fees, lower HOA dues, and a prime location with easy access to UTC, restaurants, shopping, airports and Sarasota’s renowned Gulf Coast beaches. Just moments from the vibrant energy of Waterside Place and Lakewood Ranch Main Street, this impeccably designed residence delivers a refined blend of comfort, functionality, and elevated style. Thoughtfully upgraded and beautifully maintained, the home is perfectly suited for both relaxed everyday living and effortless entertaining. At the heart of the home, the open-concept gourmet kitchen features a spacious center island, quartz countertops, stainless steel appliances, and upgraded cabinetry, seamlessly flowing into the great room, dining area, and outdoor living space. Step outside to your private backyard retreat, where a heated resort-style pool, fully equipped outdoor kitchen, mature landscaping, and fencing create an inviting oasis - ENHANCED BY SOLAR ENERGY EFFICIENCY for forward-thinking living. The flexible floor plan offers 4 bedrooms, 3.5 bathrooms, a private office on the main level, and an upstairs loft. The first-floor primary suite provides a peaceful escape with a spa-inspired bath, dual vanities, glass-enclosed shower, and custom walk-in closet. Three upstairs bedrooms and a spacious upstairs loft room/area are ideal for guests or multi-generational living. Enjoy tranquil water views from the upstairs balcony overlooking the pond, with no rear neighbors for added privacy. Additional highlights include abundant storage throughout, built-in upper laundry cabinetry, designer closets in select bedrooms, and a newly replaced dishwasher (2025). This custom residence showcases timeless finishes, thoughtful craftsmanship, and a layout designed for modern lifestyles. Easy install Kevlar hurricane shutters! Residents enjoy a sports lot with a soccer field, picnic tables, playground, covered pavilion with restrooms and endless walking/bike trails. Schedule your private showing today and experience the perfect balance of luxury, convenience, and Florida living!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Tracy Seider (941-356-2057)

Remarks: Welcome to your dream home in the highly sought-after Lakehouse Cove at Lakewood Ranch. This exceptional Tideland floor plan by Homes by Towne offers the perfect blend of luxury, comfort, and true waterfront living, highlighted by expansive panoramic lake views. This thoughtfully designed 3-bedroom, 4-bathroom residence features a spacious open-concept layout accented by high-end finishes and quality upgrades throughout. The main level includes a dedicated office, ideal for working from home or creating a private retreat, as well as a generous primary suite with a spa-inspired bathroom and large walk-in closet. Step outside to the oversized screened lanai and take in tranquil mornings and breathtaking sunset views over the lake—an ideal setting for relaxation and entertaining. The upper level offers a versatile bonus living area, perfect for a media room, guest suite, or additional gathering space. Each bedroom is designed for privacy and comfort, with its own en-suite bathroom, making this home well-suited for family and guests alike. Situated within the amenity-rich Lakehouse Cove community, residents enjoy access to a resort-style clubhouse, fitness center, pool, kayak launch, and miles of scenic walking trails. Conveniently located near shopping, dining, and all that Lakewood Ranch has to offer, this lakefront home presents a rare opportunity to enjoy refined Florida living at its best.

Listing is courtesy of: RANCH REALTY (941-228-1229)

Listing Agent: Kevin Bryceland (941-228-1229)

Remarks: Welcome to 2280 Midnight Pearl Dr, a beautifully designed and maintained one-story home offering comfort, functionality and modern style. Built with durable all-concrete block construction, this residence features a truly open-concept layout perfect for both everyday living and entertaining. At the heart of the home, a spacious kitchen with a large island overlooks the dining area, great room and cozy breakfast nook, creating a seamless flow of living space. From here, step out onto the covered lanai and enjoy the screened back porch—ideal for relaxing or hosting guests year-round. A sun tunnel skylight fills the home with natural light, helping reduce the need for artificial lighting during the day and contributing to lower power bills. The owner’s suite is thoughtfully positioned at the rear of the home, providing optimal privacy along with an ensuite bath. Two additional bedrooms are located at the front and share a full bathroom, making this layout ideal for families or guests. Convenience meets practicality with a laundry room just off the garage, functioning perfectly as a mudroom entry into the kitchen. The home also comes equipped with stainless steel appliances, including a dishwasher, range, refrigerator and microwave. Residents enjoy a low HOA fee of just $124 per month, which includes access to a beautiful heated community pool and fitness room. Additional updates include a newly replaced roof in September 2025, offering peace of mind for years to come. Ideally located with easy access to I-75, this home is just a short drive from Sarasota’s world-famous beaches, shopping, dining and top-rated schools. This well-maintained home combines modern features with a smart layout in a spectacular and convenient location—ready for you to move in and enjoy.

Listing is courtesy of: PELICAN REALTY CORP (941-270-2650)

Listing Agent: Anna Bridinger, Pa (941-544-8195)

Remarks: Welcome to Chandlers Forde in The Meadows—a neighborhood surrounded by mature trees and the peaceful feel of an enchanted forest. This beautifully renovated villa-style condo with 2 car garage offers ultimate privacy with a wooded view and a glimpse of the golf course beyond. This 2-bedroom, 2.5-bath home with a den (which can easily be converted into a third bedroom) has been tastefully updated from top to bottom. The home has a cozy yet elegant feel, with soaring ceilings and a grand double-sided stone fireplace that serves as the centerpiece of both the living and dining rooms. The living room is extra spacious, with tranquil views of the trees—an ideal space for hosting or simply relaxing by the fire. The kitchen was completely UPDATED in 2023–2024, featuring leathered granite countertops, custom cabinetry, premium appliances including Bosch, and an oversized chef’s prep sink. A custom coffee counter and the addition of a dry bar with wine fridge between the dining room and living room make the space perfect for entertaining. Just off the living room and primary suite is a Florida room—perfect for al fresco dining, morning coffee, or relaxing after a long day. With electric already in place, it’s ready for your new hot tub. The main-floor primary bedroom is expansive and elegant, featuring a walk-in closet crafted by CLOSETS BY DESIGN for maximum organization. The ensuite bath feels like a private spa, offering quartz countertops, a walk-in shower with custom glass door, and serene finishes throughout. The main floor also includes a RENOVATED half bath (2024) and a laundry area with washer and dryer hookups for convenience. Upstairs is illuminated by an elegant mid-century modern chandelier and large hurricane-impact windows that invite in an abundance of natural light. The open den/office space w/ built-in closet can easily serve as a third bedroom. A guest bedroom with vaulted ceilings overlooks the trees, an updated guest bath with quartz countertops, a tub-shower combination, and extra closet space rounds out the second floor. Beyond the beauty, this home offers peace of mind. All windows and exterior sliders are HURRICANE-IMPACT RATED The cast iron waste pipes have been replaced with PVC, electrical hookups have been added for the included generator, AND EV CHARGER. Additional upgrades include, reverse osmosis system at the kitchen sink and refrigerator, whole-house water softener, two new AC units (2018) with duct cleaning in 2024, and GE front-loader washer and dryer (2023) and the ROOF was replaced in 2022. In Chandlers Forde, residents enjoy two private pools, while The Meadows offers a lifestyle unlike any other in Sarasota with 14 miles of walking and biking trails winding through over 1,650 acres of mature landscaping, ponds, and natural preserves. For a small fee there is access to a state-of-the-art fitness center, JR Olympic pool, golf, tennis, and 10 pickleball courts. The community also includes a dog park and an active social calendar hosted by the community center. Ideally located between downtown Sarasota and University Town Center, The Meadows places you 5 minutes from UTC, Benderson Park, the new Mote Marine campus, fine dining, and shopping, 15 Minutes to Sarasota’s downtown cultural offerings—including the symphony, opera, ballet, and locally owned restaurants and 20 minutes to St Armands circle and award winning beaches. This stunning home combines luxury, comfort, and nature—truly a place to call home.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Lee Brewer (941-724-3448)

Remarks: A Rare Piece of Sarasota History with current income of over 167,000 / yr. Four turn-key furnished residences. Three City Lots. One Extraordinary Piece of Sarasota History. Welcome to 941 Virginia Drive, a truly unique historic property originally built by John Ringling Jr., offering vintage Sarasota charm paired with modern flexibility and lucrative income. Set on three city lots, this 125-foot-long masonry residence creates an extraordinary private compound with four distinct living spaces. The main residence features two bedrooms, one and a half bathrooms, and an office or den, highlighted by timeless architectural details including stone porches, arched doorways, pecky cypress paneling, tall vaulted beamed ceilings and a wood-burning fireplace. Modern updates complement the historic character with stainless steel appliances, granite countertops, and updated fixtures. The property is designed for lifestyle, opportunity and flexibility for extended family, guests or continued successful short-term rental business. In addition to the main home, the estate includes three separate guest residences providing privacy and versatility. There are two in-law suites that feature full kitchens, a private pool, hot tub, outdoor shower, patio access and a private bathroom; one offers one bedroom and the other two bedrooms. There is an additional one-bedroom dwelling with a convenient kitchenette, private bathroom and laundry. Located just two miles north of downtown Sarasota, the property offers easy access to Lido Key, Longboat Key, St. Armands Circle, and the vibrant dining, arts, and cultural scene of downtown Sarasota. Whether you envision a private historic estate, a multi-generational compound or a unique established vacation rental business, this rare property offers exceptional character, privacy and opportunity in one of Sarasota’s most desirable locations. Don’t miss this opportunity to Own a Piece of Ringling History — A Private Sarasota Compound with Vintage Charm and Resort-Style Living.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Angela Adams (941-809-9760)

Remarks: Why wait for a new build when the craftsmanship, elegance, and over $180,000 in premium upgrades have already been meticulously completed? Located in Shoreview community of Waterside at Lakewood Ranch, this residence offers a sophisticated blend of three bedrooms, three bathrooms, a private office, and a spacious three-car garage. Architectural Excellence & Unrivaled Security. From the moment you arrive, the home captivates with striking curb appeal. The custom glass front entry and enhanced garage doors set a new standard for luxury and safety. These are no ordinary doors—featuring 0.5-inch thick hurricane-rated glass, they are four times thicker than standard builder-grade doors, providing peace of mind without compromising on style. Grand Interiors Step inside to an atmosphere of light and volume, defined by soaring 12-foot ceilings and a seamless open-concept design. The Heart of the Home: Designed for effortless entertaining, the living spaces flow intuitively from one room to the next. Work & Rest: A quiet, beautifully appointed office offers a retreat for creativity, while the spacious bedrooms and spa-inspired bathrooms provide ultimate serenity for family and guests. An Outdoor Oasis The lifestyle extends outdoors into a backyard designed for recreation and relaxation: Gourmet Outdoor Kitchen: Perfect for al fresco dining. Personal Putting Green: Hone your game in the privacy of your own backyard. Pet Paradise: A dedicated dog run is ready for your pups. Plus, with the community dog park directly across the street, daily social time with neighborhood friends is effortless. Every detail of this home has been thoughtfully curated, allowing you to move right in and begin living the lifestyle you’ve been imagining. In a community that truly has it all, there is nowhere else you’ll want to be.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Tina Hannaford (941-465-1765)

Remarks: Welcome to Tivoli Village—an exclusive, private community of just 100 residences nestled among mature trees and lush landscaping. This beautifully maintained 2-bedroom, 2-bath villa with a den/office and 2-car garage offers the perfect blend of tranquility and convenience, ideally located near UTC shopping and dining, I-75, Nathan Benderson Park, Sarasota-Bradenton International Airport (SRQ), and just a short drive to downtown Sarasota and Gulf Coast beaches. Step inside to an open-concept floor plan featuring soaring cathedral ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The updated kitchen showcases newer stainless steel appliances, ample cabinetry with slide-out shelving, a breakfast nook, and an extended breakfast bar overlooking the main living space. Sliding glass doors lead to an enclosed lanai, with additional paver patio space extending into a private, tropical outdoor retreat complete with native Florida landscaping and a custom tiled table and seating area. The spacious primary suite is privately situated at the rear of the home and features an updated en-suite bath with dual vanities, granite countertops, and a walk-in shower with built-in bench. A split-bedroom layout ensures privacy for guests, with a secondary bedroom and full bath located at the front of the villa. The versatile den/office includes a skylight and closet, making it ideal for a home office or potential third bedroom. Recent upgrades include exterior painting (2023) and a new HVAC system (2023), offering peace of mind for years to come. Tivoli Village residents enjoy a scenic setting with four spring-fed lakes, fishing opportunities, majestic oak trees, and a tranquil nature trail. The HOA provides exceptional value, covering major expenses such as property insurance, exterior maintenance (including power washing and painting), roof replacement and repairs, as well as lawn care and irrigation—delivering low-maintenance, worry-free living. Don’t miss this opportunity to own a move-in-ready villa in one of Sarasota’s most charming and conveniently located communities!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Diane Goodwin (941-706-6620)

Remarks: Nestled in the sought-after community of Lakewood Ranch Waterside, this exceptional two-story home offers a harmonious blend of comfort and functionality in a picturesque setting. The main floor features a thoughtfully designed great room floor plan with volume ceilings showcasing custom coffered details, along with a private office ideal for working from home. The kitchen is a centerpiece of style and efficiency, boasting a large center island with seating, quartz countertops, stainless steel appliances, a gas cooktop, and a spacious walk-in pantry. The primary suite is a private retreat, complete with a walk-in shower, private water closet, and an expansive custom-organized dressing room. Two additional bedrooms and bathrooms on the main floor provide ample space for family or guests. Upstairs, a generous bonus room, along with a fourth bedroom and full bath, creates an ideal space for visitors. Enjoy a private pool and outdoor kitchen, perfectly positioned to take in serene lake views and a rare backdrop of a prestigious polo farm, where the sight of grazing horses enhances the setting. Shoreview residents enjoy a wide array of amenities, including a fitness center, resort-style pool, tennis and pickleball courts, and more. Located just minutes to Waterside Place, with convenient access to Lakewood Main Street, University Town Center, downtown Sarasota, I-75, beaches, top-rated schools, and medical facilities.

Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)

Listing Agent: Katina Shanahan (941-702-0437)

Remarks: Lavish boutique living in the heart of Downtown Sarasota awaits at the Plaza at Five Points. This tastefully updated, turnkey 2-bedroom, 2-bath condo residence, with a covered lanai/balcony, offers city living with refined style and comfort. A spacious entry foyer with a dedicated office nook provides a practical and welcoming first impression—ideal for year-round living or a stress-free seasonal retreat. The kitchen features sleek quartz countertops and newer, high-quality appliances. The primary en-suite bedroom showcases beautiful city views, a California-style walk-in closet, and access to the private lanai. The guest bedroom is generously sized and offers equally charming downtown vistas. The lanai is accessible from both the living room and the primary bedroom, providing a seamless indoor-outdoor flow. Additional features include two deeded garage parking spaces conveniently located near the lobby, and a private storage room. Building security includes controlled access at all entry points and elevators, ensuring peace of mind. Enjoy an elevated lifestyle with luxurious amenities including front desk concierge service, front desk steward, valet parking, rooftop heated pool and spa, outdoor grilling area, cabana with gazebo, a well-equipped fitness center, community room with catering kitchen and fireplace, conference room, and a guest suite available for weekly reservations. Step out of your lobby into Sarasota’s vibrant arts and entertainment district. Just a short stroll to the Sarasota Opera House, theaters, live music venues, art galleries, eclectic shopping, and top-rated dining. Whole Foods is around the corner for added convenience. The Bayfront and Marina Jack are just minutes away, offering a variety of boating and waterfront activities. Easy access St. Armands Circle, Lido Beach, Longboat Key, and world-renowned Siesta Key Beach. The Sarasota-Bradenton International Airport, Selby Botanical Gardens, Van Wezel Performing Arts Center, and the Asolo Repertory Theatre are all within a short drive. The building performs like a champ during hurricanes and storms. Residences with this floor plan in ‘The Plaza at Five Points’ are rarely available—schedule your private or virtual showing today. Vacant and easy to show.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)

Listing Agent: Ronald Greene (941-445-2985)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Positioned at the tip of Stephens Point, where Sarasota Bay opens wide and the sky feels endless, 320 South Shore Drive commands what many consider the finest views in the city. With sweeping 180-degree panoramas across North Sarasota Bay, glowing downtown lights and elegant arc of the Ringling Bridge, this is a setting that delivers unforgettable sunsets, constant water activity, and a front row seat to dolphins and wildlife passing by daily. The home’s clean lines, open layout, and extensive use of glass create a seamless connection between indoors and out, allowing the surrounding water and sky to become part of everyday life. From the moment you arrive through the gated entry and enter into the all-glass foyer, the experience is unmistakable. Light pours in, sightlines extend in every direction, and the bay immediately takes center stage. Set on nearly half an acre with expansive direct frontage on Sarasota Bay, the property offers a sense of privacy and an exceptional relationship to the water. Boating enthusiasts will appreciate direct access to the bay, while those drawn to quieter moments will enjoy watching the colors of sunset shift across the horizon and the calm rhythm of the water below. The interior spaces are well-suited for everyday living and entertaining. The living and dining areas are wrapped in glass and flow seamlessly to the outdoor areas, creating an easy indoor-outdoor lifestyle. The kitchen is functional and well-positioned, offering generous workspace, quality finishes and uninterrupted bay views. The primary suite serves as a private retreat, positioned to capture long water views and enhanced by a spa-inspired bath that blends indoor and outdoor living. Additional guest accommodations are thoughtfully arranged, offering comfort and privacy for family and friends while maintaining the home’s cohesive modern aesthetic. Outdoors, the full width lanai and lap pool overlook Sarasota Bay, offering an inviting space to relax, entertain and take in the sunsets that define this location. Mature landscaping, including a striking banyan tree, adds character and a sense of place to the property. 320 South Shore Drive is more than a waterfront home. It is a legacy property that brings together architectural significance, extraordinary views and one of Sarasota’s desired locations. A modern masterpiece designed for those who value design, setting and simple luxury of living on the water at its best.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Mike Warm, Llc (941-525-2740)

Remarks: Located in the desirable Longwood Run – Del Sol Village community, this beautifully maintained 3-bedroom, 2-bath residence offers privacy and peaceful preserve views. Soaring ceilings and abundant natural light enhance the open-concept layout, designed for both comfortable daily living and entertaining. Plantation shutters add character, and the spacious lanai overlooks a lush natural backdrop. Major updates include a new HVAC system (2026) with a 10-year warranty, a newer roof (2018), a whole-house water softener, a triple-filter kitchen water system, and an upgraded 50-gallon water heater. The extra-long garage accommodates larger vehicles. Situated in Flood Zone X with a low HOA, the community is bike-friendly and pet-friendly, and conveniently located near Sarasota’s beaches, upscale shopping, dining, and cultural attractions. Move-in ready and thoughtfully updated, this home offers privacy, comfort, and convenience in a serene setting.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Louis Wery (941-232-3001)