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$4,299,999
4 Beds 5 Baths Midwood Manor SubDv. 34239 Zip Code A4666725 MLS Active Status
Virtually Staged. West of Trail luxury meets modern innovation at 1759 Waldemere Street. This brand-new, custom-built residence embodies timeless design, contemporary craftsmanship, and intentional indoor–outdoor living. Set on a .33-acre lot just steps from Southside Village and Sarasota Memorial, the home delivers sophistication, convenience, and exceptional attention to detail in one of Sarasota’s most sought-after neighborhoods — a rare opportunity in the coveted West of Trail community. Spanning 4,513 square feet, the two-story floor plan features four bedrooms, five baths, an office with private entry, and a media room that opens to a 480-square-foot balcony overlooking the property. Designed for both everyday living and elegant entertaining, the home showcases expansive sliding glass doors that blur the line between indoors and out, opening to a heated saltwater pool, spa, and lush landscaped backyard for year-round enjoyment. The designer kitchen serves as the heart of the home, featuring Sub-Zero and Wolf appliances, custom cabinetry, imported stone, and a hidden butler’s pantry. The first-floor primary suite epitomizes luxury with zero-corner sliders that open directly to the pool and outdoor living area. Inside, a spa-inspired bath includes a freestanding tub, walk-in shower, and a custom built-in walk-in closet. Upstairs, two en suite bedrooms and a second-floor primary suite give privacy for family or guests. A versatile media room and expansive outdoor terrace complete the level, overlooking the serene backyard oasis. Every detail has been thoughtfully curated — from the bespoke, locally handcrafted Sapele wood entry door to hurricane-impact windows and doors, a three-car garage with epoxy flooring, and professional landscaping surrounding the fenced backyard. Ideally located in the highly regarded Southside Elementary School district, near Sarasota Memorial Hospital and the shops and dining of Southside Village, with downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle just minutes away. This is more than a home — it’s a statement of Sarasota luxury living.

1759 Waldemere Street, Central Sarasota

$3,700,000
4 Beds 5 Baths Seminole Heights SubDv. 34239 Zip Code A4667508 MLS Active Status
Stunning New Construction by Award-Winning Architect Dan Lear in coveted West of Trail Neighborhood** This meticulously designed luxury home offers the perfect blend of modern elegance and timeless sophistication. Near Selby Gardens, Morton's Market, and Sarasota Memorial Hospital, this exceptional property provides both convenience and style. Spanning over 3,800sqft of living area, this expansive residence boasts four spacious bedrooms, five full bathrooms, a enormous den with terrace, and a dedicated office space, all thoughtfully crafted for contemporary living. The grand, open-concept great room is the heart of the home, seamlessly floating over the pool area with a stunning large corner pocketing glass door that connects the interior to the beautifully landscaped outdoor oasis. The second floor features three guest suites, each with its own private terrace, offering tropical views and tranquility. The home's striking exterior showcases luxurious vein-cut travertine, creating a refined, sophisticated look. This is an extraordinary opportunity to move right in to a worry free one-of-a-kind masterpiece.

1642 Bahia Vista Street, Central Sarasota

$2,250,000
5 Beds 6 Baths Terrace Gardens SubDv. 34237 Zip Code A4666533 MLS Active Status
Pre-Construction. To be built. Welcome to this stunning 3,434 sq. ft. single-story residence, where modern luxury meets timeless Italian craftsmanship. Ideally located within Sarasota city limits, this property qualifies for weekly rentals—a rare and highly desirable feature that opens the door to significant income opportunities in one of the area’s most sought-after vacation rental markets. This 5-bedroom, 5.5-bathroom residence is designed with both style and functionality in mind. Showcasing imported Italian fixtures, custom cabinetry, and premium flooring throughout, every detail reflects Milano Homes’ signature quality and sophistication. The expansive open-concept kitchen and living area are perfect for entertaining, while floor-to-ceiling hurricane-rated windows and sliding glass doors bathe the space in natural light and create a seamless connection to the outdoors. Step outside to your private retreat featuring a sparkling pool, sun-soaked deck, and ample space for relaxation or entertaining under the Florida sky. Perfectly positioned just minutes from downtown Sarasota, residents and guests will enjoy easy access to boutique shopping, fine dining, award-winning beaches, the scenic Legacy Trail, and local parks with tennis and pickleball courts. Whether you’re looking for a full-time residence, seasonal escape, or an income-producing short-term rental, this home offers a rare opportunity to enjoy the Sarasota lifestyle while capitalizing on high-demand weekly rental potential. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.

440 S Lime Avenue, Mid Town Sarasota

$209,000
2 Beds 2 Baths Cordova Gardens SubDv. 34239 Zip Code A4666617 MLS Active Status A6 BLDG.
Welcome to this beautifully maintained end-unit condominium ideally situated in one of Sarasota’s most sought-after neighborhoods. Just minutes to vibrant downtown Sarasota’s arts district, offering fine dining, boutique shopping, theaters, and cultural venues. Close to the scenic Bayfront Park and Marina Jack, perfect for waterfront dining, walking trails, and watching sunsets over Sarasota Bay. Easy access to Sarasota Memorial Hospital, world-class beaches (including Siesta Key and Lido Beach), and premier golf courses. This spacious 2-bedroom, 2-bath split-plan layout offers privacy and comfort, ideal for both seasonal or year-round living. As an end unit, this home features extra privacy and natural light, enhanced by soaring vaulted Pecky Cypress ceilings and large transom windows that fill the open-concept living area with abundant light, while adding warmth and architectural character. The open floor plan includes a spacious kitchen, perfect for entertaining, and flows into the main living and dining areas. Enjoy a bonus loft perfect for a home office, guest space, or creative studio, and relax on two private, screened-in lanais—ideal for morning coffee or evening cocktails. Additional features include updated bathrooms, in-unit laundry, and plenty of storage throughout. Whether you're looking for a primary residence, seasonal retreat, or an income-producing property (with 6-month rental capability), this home offers the best of Sarasota living in an unbeatable location.

2232 Bahia Vista Street Unit A6, Central Sarasota

$1,999,000
4 Beds 4 Baths Alta Vista Heights SubDv. 34237 Zip Code A4666469 MLS Active Status
This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for a strong six figure range income annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.

2231 Wood Street, Mid Town Sarasota

$595,000
Towles Sub SubDv. 34236 Zip Code A4664844 MLS Active Status
Prime Development Opportunity in Downtown Sarasota or build your dream home here! Discover the possibilities with this vacant parcel at 1930 Adams Lane, perfectly positioned in the heart of Sarasota. Zoned Downtown Edge (DTE), this property offers exceptional flexibility for future development in one of the city’s most desirable and walkable locations. Situated just steps from Main Street, Payne Park, shopping, dining, and Sarasota’s vibrant cultural scene, this site provides endless potential—whether for residential, mixed-use, or commercial projects. An added advantage: adjacent parcels are also available, creating a rare opportunity for potential assemblage to expand your footprint and maximize development density. With Sarasota’s continued growth and demand for urban living, this property is ideal for investors, builders, and visionaries seeking a prime downtown project. Don’t miss your chance to secure land in one of Sarasota’s fastest-growing corridors.

1930 Adams Lane, Sarasota

$795,000
1 Beds 1 Baths Towles Sub SubDv. 34236 Zip Code A4664827 MLS Active Status
Prime investment and redevelopment opportunity in Sarasota’s sought-after Towles Court Arts District! This mixed-use property offers approx. 750 sq. ft. of commercial/gallery or studio space plus 363 sq. ft. of residential use, making it ideal for live/work tenants, creative professionals, or small businesses. Historic details and metal roof—blend with flexible layouts to attract both renters and end users. With zero side setbacks and DTE (Downtown Edge) zoning, the property offers significant redevelopment upside. Surrounded by other commercial and residential parcels, 1950 Adams Lane also presents excellent assemblage potential for investors or developers looking to create a larger mixed-use or residential project. Located just steps from downtown Sarasota’s restaurants, shops, galleries, and cultural amenities, this property combines immediate income potential with long-term growth. A rare chance to secure a prime footprint in one of Sarasota’s most dynamic districts!

1950 Adams Lane, Sarasota

$949,000
2 Beds 3 Baths Premier On Main SubDv. 34237 Zip Code A4657909 MLS Active Status Building 2 BLDG.
Are you dreaming of the ideal uptown location close to everything Sarasota? Discover modern Sarasota living with outdoor style at Premier on Main in the Park District at the east end of Main Street, downtown Sarasota. Ready to live your best Sarasota life? Welcome to Premier on Main, a just-completed collection of contemporary townhomes designed for those who crave outdoor living, accessible culture and modern style in the heart of Uptown as we call it. Near Main Street’s bustling arts and cultural district, farmers market, buzzworthy restaurants, live music venues and the new 53-acre bayfront park, this is your gateway to the ultimate Florida lifestyle. Morning runs over John Ringling Bridge. Sunset drinks on the rooftop. Bike to brunch or kayak the bay. This is the Sarasota experience elevated. Designed for your active, social life. Over 2,395 total square feet including 1,950 air-conditioned living space. Incredible 396-square-foot rooftop entertainment deck with optional hot tub and outdoor kitchen, ideal for sunny lounging or hosting friends under the stars. Spacious, light-filled living areas with soaring ceilings and designer finishes. Chef-inspired kitchen with oversized island and premium stainless appliances. Private elevator for easy living across all levels. Two bedrooms with en-suite baths and walk-in closets—room for guests, roommates or that home office you’ve always wanted. Urban convenient, Sarasota cool. Just blocks from the bayfront and downtown nightlife. Close to local cafes, restaurants, arts venues and farmers market. Bike-friendly location with easy access to parks and beaches. Sleek, contemporary architecture with high-end details. Energy-efficient systems and impact-rated windows and doors for safety and peace of mind. Practical perks for modern buyers. Private two-car garage with bonus flex space, ideal for gym, studio or gear storage. Low maintenance living with HOA covering landscaping, road upkeep and more. Move-in ready with special developer financing incentives available for a limited time. See why Sarasota millennials and modern buyers are choosing Premier on Main for their next-level urban lifestyle. Visit this fully furnished model or our 3 bedroom model next door at 2170 Fruitville Road. Open weekends noon-3 p.m. or by appointment. Contracts are being accepted now so grab your slice of downtown Sarasota before it’s gone!

152 Audubon Place, Mid Town Sarasota

$3,200,000
5 Beds 6 Baths Avondale SubDv. 34236 Zip Code A4657794 MLS Active Status
Ensconced in the heart of the highly esteemed West-of-Trail Avondale neighborhood, this stunning 5-bedroom, 4.5-bath, 4400 square foot residence seamlessly blends timeless charm with modern luxury. Situated on a rare 14,750 sq ft oversized lot, the original 1952 home was extensively renovated and thoughtfully expanded in 2022, more than doubling its original square footage—all on a single level. Step inside to discover an open-concept layout designed for both comfort and entertaining, featuring a state-of-the-art kitchen with custom cabinetry, high-end appliances, a spacious eating area, and an impressive full butler’s pantry. The kitchen flows effortlessly into the elegant dining room and the great room, all bathed in natural light and finished with premium materials throughout. The home offers a separate formal living room and a versatile bonus room overlooking the pool—ideal for a home office, library, or sunlit sitting room. The owner's suite features sliding glass doors to access the pool, transom windows that filter in natural light, two walk-in closets, and top of the line finishes in the spa-like bath. The guest wing offers an over-sized bedroom, perfect for a home gym or private in-law suite, and provides privacy and flexibility for guests or multigenerational living. Every detail has been meticulously curated, from designer finishes to thoughtful storage solutions. Outside, enjoy lush landscaping, generous green space, and the perfect setting for outdoor entertaining. The lap pool and spa offer privacy and access to indoor-outdoor living spaces. All of this is located in the highly sought after Southside Elementary School district, and within walking distance to downtown Sarasota and Southside Village, placing dining, shopping, and cultural attractions just steps from your door.

1838 Alta Vista Street, Downtown

$3,750,000
3 Beds 4 Baths Demarcay SubDv. 34236 Zip Code A4657527 MLS Active Status Demarcay BLDG.
In the heart of Downtown Sarasota, at the coveted corner of Main Street and Palm Avenue, this Penthouse Collection residence on the 15th floor of the newly built DeMarcay rises above the city with sweeping views of downtown, Sarasota Bay, Big Pass, and onward to the Gulf of Mexico. Step outside and walk to art galleries, acclaimed restaurants, boutiques, theaters, the farmers’ market, the city marina, wellness studios and live music. When the beach calls, St. Armands Circle and Lido Beach are just three miles over the Ringling Bridge. DeMarcay elevates downtown living with resort-style amenities crowned by an 18th-floor bi-level terrace featuring 360-degree vistas. Residents enjoy a state-of-the-art fitness center, an owners’ lounge, outdoor kitchen, and an impressive pool terrace designed for sunset gatherings and entertaining, supported by 24/7 on-site staff for personalized service. This is the only condominium in downtown Sarasota with 24/7 valet parking service, offering a distinctive, space-saving parking configuration and the ease of round-the-clock attended vehicle access. Bayside on the 15th floor, this 3,407-square-foot residence offers three private bedroom suites, a separate office/den, powder room, open living and dining, laundry, and a private bayfront balcony. Volume ceilings and expansive windows bring in natural light and frame the water-and-sky backdrop throughout. The chef’s kitchen pairs imported Italian cabinetry with quartz countertops, a Miele five-burner gas cooktop, and integrated Miele appliances. The primary suite is a serene retreat with a spa-inspired bath featuring designer Italian cabinetry, porcelain undermount sinks, a soaking tub, and a generous walk-in shower. An 18-story boutique community of only 39 residences, DeMarcay blends contemporary architecture with Sarasota’s heritage, thoughtfully preserving and restoring the historic facades of the original DeMarcay Hotel (1922) and the Roth Cigar Factory (1923–1938). A rare opportunity to live at Sarasota’s most walkable crossroads—elevated, effortless and distinctly downtown.

33 S Palm Avenue Unit 1501, Sarasota

$1,870,000
4 Beds 4 Baths Harbor Acres SubDv. 34239 Zip Code A4656365 MLS Active Status
This unique home is in the desirable neighborhood of Harbor Acres. World renowned Selby Botanical Gardens is less than a mile from your new home. This mid-century jewel was built in 1956 and was originally a 2/2. The original bathrooms are still in their original state and are in good condition providing a cool retro vibe. The original hardwood floors and fireplace exude warmth and sophisticated charm. The current owner purchased the home in 1989 and remodeled the kitchen and added a new wing on the house with 2 additional large bedrooms ensuite with baths. Copious amounts of storage in all 4 bedrooms and a huge laundry room with lots of closet space as well. The garage is oversize and there is a picturesque circular driveway for ample parking. There is plenty of room to put in a pool of your own design. The house was re-roofed in 2018. Some of the most beautiful homes in Sarasota are your neighbors in Harbor Acres. And Flower Drive is a special address with the highly sought after Southside Elementary School just 1-mile away, you can’t beat this property. In real estate it is all about Location, Location, Location. This home has plenty of room for the family, so, come on home!

1541 Flower Drive, Central Sarasota

$3,270,000
3 Beds 4 Baths The Edge Sarasota SubDv. 34236 Zip Code A4655024 MLS Active Status The Edge Sarasota BLDG.
Pre-Construction. To be built. Discover a rare opportunity at The Edge Sarasota—where boutique living meets vibrant city life. Residence A is a premier 3-bedroom, 3-bathroom corner residence offering over 3,200 square feet of open, modern living in one of Sarasota’s most in-demand downtown locations. From the 6th floor, this light-filled residence wraps the northwest side of the building offers exceptional natural light with floor-to-ceiling walls of glass. Step out onto your generous wraparound terrace and watch the sunset over the city. Designed to be as unique as you, the home features a great room and separate living room that connects to a chef’s kitchen with Italian cabinetry, Wolf and Sub-Zero appliances including a gas cooktop, a large island with waterfall edge and a butler’s pantry for easy entertaining. A thoughtfully designed owners’ suite provides a true retreat with a gracious foyer, midnight bar, walk-in closet and en suite bathroom featuring dual vanities, private water closets, glass enclosed shower and soaking tub. Beyond your residence, enjoy a curated collection of luxury amenities including a resort-style pool deck with hot and cold plunge pools, cabanas and two outdoor kitchens. The owners’ club focuses on wellness and entertainment with a fully equipped fitness center complete with a yoga room and infrared sauna. Two treatments rooms afford plenty of space for your personal massage therapist or a physical therapy session. The social room includes a lounge, bar, game room and catering kitchen. For more intimate gatherings, reserve the private dining room featuring resident wine lockers and a separate bar area. The building’s boutique size—only 27 residences—creates a community feel in the heart of Sarasota’s vibrant Arts District. Walk to acclaimed restaurants, galleries, boutiques, and the Bayfront, embracing a lifestyle that combines culture, convenience, and sophistication. Construction is progressing with limited opportunities to customize your finishes—secure your place at The Edge today and invest in a rare downtown Sarasota address with lasting appeal. Images shown are artist renderings intended to illustrate the interior finishes and design concepts for this community.

290 Cocoanut Avenue Unit 601, Downtown

$5,495,000
4 Beds 3 Baths Bay Point Park SubDv. 34236 Zip Code A4647998 MLS Active Status
Being in the same family for 75 years, this is a rare opportunity to own a stunning, nearly half-acre waterfront lot in the highly desirable Bay Point Park neighborhood of Sarasota. Situated on protected sailboat water with no bridges to the Gulf of Mexico, this unique property offers unparalleled access to the serene waters of Sarasota Bay, with breathtaking views of the iconic Ringling Bridge and the vibrant downtown Sarasota skyline. Enjoy a truly walkable lifestyle with the best of Sarasota at your doorstep. Stroll to Marie Selby Botanical Gardens, the charming shops and gourmet restaurants of downtown, the quaint Southside Village, and the renowned Morton's Gourmet Market—all just moments away. Tucked away in a tropical oasis, this secluded lot offers privacy, tranquility and convenience, providing the perfect setting for a custom-built home with sweeping waterfront views. Located in one of the most sought-after West of the Trail neighborhoods, this large waterfront parcel presents a unique opportunity to create a luxurious sanctuary in one of Sarasota's most coveted locations. Whether you’re an avid sailor or simply appreciate the beauty of coastal living, this property is your perfect canvas. Don’t miss the chance build your dream home on this exceptional slice of Sarasota paradise—where the natural beauty, luxury, and lifestyle you’ve always dreamed of can finally become a reality.

1479 Bay Point Drive, Downtown

$1,745,000
3 Beds 4 Baths Hudson Bayou SubDv. 34236 Zip Code A4629855 MLS Active Status Na BLDG.
Virtually Staged. Discover Laurel on the Water — a rare waterfront enclave of seven canal-front townhomes at 1720 Alderman St, Sarasota. Priced at $1,745,000, this newly constructed three-story residence with elevator blends striking contemporary design with effortless coastal living just blocks from downtown. Thoughtfully oriented to maximize light and water views, the home showcases expansive impact glazing, multiple balconies, and a dramatic waterfall-edge kitchen island with premium appliances and custom cabinetry. A versatile first-floor great room with a private entrance functions perfectly as an office, guest suite, or media space. The open plan flows seamlessly to outdoor living and water-facing vistas—ideal for entertaining or quiet relaxation. A private slip is available; the property sits off Hudson Bayou with direct access leading to Sarasota Bay for easy waterfront recreation (kayak, paddleboarding). Laurel on the Water delivers maintenance-free living with a resort-style pool, lush landscaping, and a spacious two-car garage for secure parking and storage. Live moments from Sarasota’s cultural core: the Ringling Museum, theaters, ballet and opera, and an exceptional dining scene featuring numerous Zagat-rated restaurants. Marina Jack, world-class beaches, including Siesta Key, are just minutes away, and multiple golf courses are within a short drive. 1720 Alderman St is more than a home—it's a refined waterfront lifestyle in one of Sarasota’s most coveted neighborhoods. Schedule your private showing today.

1720 Alderman Street, Sarasota

$1,999,000
5 Beds 3 Baths Terrace Gardens SubDv. 34237 Zip Code A4562867 MLS Active Status
Pre-Construction. To be built. A custom ranch home with a high pitched metal roof and attached guest house on a 12,000 sq ft fully fenced lot on a quiet cul-de-sac, close to Sarasota downtown restaurants, shops and the Legacy Trail, an 18 1/2 mile recreational trail connecting Sarasota and the city of Venice. The trail is popoular for biking, walking and running with amenities like restrooms, playgrounds and bike repair stations. A short walk to Payne Park and the free Bay Runner trolly service that connects downtown, St. Armands Circle and Lido Beach. The home has an open floor plan with ceilings that tray up to 11'4". Sliding glass doors brining in the morning sunlight and overlooking the pool and extensive covered outdoor living space with grill area. The main house has 3 bedrooms, 2 full baths, foyer, dining room and great room. The fabulous kitchen with Viking appliancaes, custom cabinets, a large island, quartize countertops, walk-in pantry with a sink. Laundry room with washer, dryer and sink along with built in storage for hanging clothes. 2 Instant Hot water hearters (one in guest house). The attahed guest house has a living room, kitchenette, 2 bedroms, full bathroomm with 10'8" ceilings throghout and laundry with washer and dryer. and sliding glass doors overlooking the heated pool. there is also an outdoor shower.. The attached oversized 2 car garage with sink and EV charging station

263 Lime Circle, Mid Town Sarasota

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