Downtown Homes for Sale

Rare Gillespie Park infill lot opportunity! 5,040 SF just steps from Downtown Sarasota in one of the city's most walkable neighborhoods (Walk Score 87). Existing 1941 cottage sold as-is — an ideal teardown/redevelopment infill lot for a builder, developer, or end-user ready to design a custom modern home. Surrounded by new construction, minutes to the Rosemary District, restaurants, and the Sarasota bayfront. Land value — bring your builder! Buyer to verify zoning/FAR with the City of Sarasota.

614 N Osprey Avenue, Downtown

$1,595,000

5 Beds ⋅ 5 Baths ⋅ A4702560 MLS

LOCATION, LOCATION, LOCATION! If you are seeking a premier home which is steps from the dining, culture, boutiques, and waterfront recreation of Downtown Sarasota/Main St, The Bay Park, the Rosemary District, Five Points Park, and Gillespie Park, this is the one! This beautifully renovated, Key West–inspired 5-bedroom, 2938 sf pool home welcomes you with a magnificent oak tree and gorgeous tropical landscaping. Inside, the chef-owner’s kitchen is a culinary dream complete with a professional Forno gas range, custom soft-close cabinetry, and sleek quartz countertops. High-end finishes elevate the open living areas, including rich hardwood floors, an electric fireplace, and a custom temperature-controlled wine room. A flexible downstairs bonus area with a half bath and closet can easily convert to a luxurious primary suite/5th bedroom. A 600 sf guest apartment, The Pineapple Loft, is consistently ranked 5 stars on Airbnb and features a vaulted ceiling, full kitchen, induction cooking, laundry, and a private balcony— fully qualifying for high-demand weekly rentals! The exterior features a screened courtyard lanai and a heated pool with a waterfall, while the local 10-acre park provides tennis, pickleball, walking trails, and a lively neighborhood scene. Don't miss this perfect blend of historic character, modern luxury, and ultimate flexibility in an incredible location.

1685 6th Street, Downtown

$2,595,000

3 Beds ⋅ 3 Baths ⋅ A4701211 MLS

Discover exceptional West of Trail living in Lincoln Park, an intimate waterfront enclave located along Hudson Bayou in Sarasota, Florida. This beautifully appointed residence offers the rare combination of privacy, boating access, and proximity to Downtown Sarasota, complete with a private deeded boat slip and 10,000 lb lift providing direct access to Sarasota Bay and the Gulf of Mexico. Situated on a quiet, tree-lined cul-de-sac shared by only eight residences, this distinctive 3-bedroom, 2.5-bath home offers 4,234 square feet of thoughtfully designed living space. Built in 2001, the residence blends timeless architectural details, refined craftsmanship, and comfortable everyday living in one of Sarasota’s most desirable West of Trail locations. The spacious floor plan features a private first-floor primary suite, soaring ceilings, crown molding, French doors, custom built-ins, hardwood and marble flooring, and a gas fireplace. Formal and casual living areas flow seamlessly throughout the home, creating an inviting setting for both entertaining and relaxation. At the heart of the residence, the chef’s kitchen features quality finishes, generous workspace, an eat-in dining area, and convenient access to the home’s main gathering spaces. Upstairs, two additional bedrooms share a Jack-and-Jill bathroom, with one bedroom offering a spacious adjoining sitting room and private terrace. A separate office provides a quiet and flexible space for working from home, reading, or managing daily tasks. The outdoor living spaces are equally impressive. Professionally landscaped gardens, bluestone terraces, ambient landscape lighting, and multiple seating and entertaining areas create a peaceful private sanctuary. An outdoor kitchen provides the perfect setting for alfresco dining, while the deeded dock and boat lift make it easy to enjoy boating, fishing, kayaking, and waterfront adventures throughout Sarasota Bay and the Gulf Coast. Tasteful updates completed over the years enhance the home’s comfort and enduring appeal while preserving its classic character. Whether enjoying quiet mornings in the garden, entertaining beneath the stars, or departing from your private boat slip for a day on the water, this Sarasota waterfront home offers an exceptional coastal lifestyle. Ideally located near Downtown Sarasota, Southside Village, Marie Selby Botanical Gardens, Sarasota Memorial Hospital, the Sarasota Bayfront, St. Armands Circle, and the renowned beaches of Siesta Key and Lido Key, this residence delivers an outstanding balance of privacy, convenience, and boating access.

1798 Lincoln Park Circle, Downtown

$1,749,990

3 Beds ⋅ 3 Baths ⋅ A4700595 MLS

Often desired but rarely found! Perfectly positioned in the heart of Laurel Park - one of Sarasota's most coveted neighborhoods - this exceptional 3-bedroom, 3-bath custom residence spanning 2,335 sqft offers the ultimate downtown Sarasota lifestyle. While Laurel Park is celebrated for its historic charm, opportunities to own a newer custom-built home with today's construction standards, modern design aesthetic, luxury finishes and a private pool are exceptionally rare. From your front door, enjoy a short stroll to award-winning restaurants, boutique shopping, the Bayfront, Marina Jack, Selby Gardens, theaters, art galleries, Payne Park and the weekly farmers market. Designed by acclaimed architect Mark Sultana of DSDG and built in 2019, this meticulously crafted residence offers the quality and peace of mind you'll appreciate - including concrete block construction, hurricane-impact windows and doors, a whole-house generator (2025), EV charger and energy-efficient systems. Inside, modern designed interiors with clean lines create a sophisticated yet welcoming atmosphere. The thoughtfully designed floor plan features light-filled living spaces with luxury vinyl plank flooring throughout, custom cabinetry, quartz countertops, pocketing sliders and spacious guest suites. The gourmet kitchen is equipped with a large split island with seating, premium LG appliances, Bosch dishwasher, walk-in pantry and a wine cooler. Living and dining spaces are open and light filled - perfect for entertaining or enjoying the tropical views and zen-like gardens. Step outside to the gas-heated saltwater pool and spa - the centerpiece of this private backyard retreat. Enjoy an outdoor kitchen with Artisan grill, multiple entertaining spaces, an expansive rooftop deck and professionally-designed landscaping that beautifully showcases the Selby-like botanical grounds. The result is a tranquil, resort-inspired setting that feels worlds away - yet is just blocks from downtown Sarasota. For buyers seeking the rare combination of downtown walkability, newer construction and contemporary architecture - 543 Columbia Court represents one of Laurel Park's finest offerings. A home of this caliber—with a pool, rooftop deck and today's build quality in one of Sarasota's most cherished neighborhoods — is an opportunity that seldom comes to market.

543 Columbia Court, Downtown

$2,749,000

5 Beds ⋅ 4 Baths ⋅ A4698379 MLS

A rare opportunity to own a one of a kind custom built residence in the heart of downtown Sarasota, 1680 Cherry Lane is tucked into one of Laurel Park's most charming streets while being just moments from everything that makes downtown so special. Blending timeless architecture with modern luxury, this brand new residence offers an exceptional lifestyle defined by thoughtful design, refined finishes, and one of Sarasota's most coveted locations. Spanning 3,128 square feet, this thoughtfully designed two story home features five bedrooms and four bathrooms, including a first floor primary suite and an additional main level bedroom that can easily function as a private office, guest suite, or den. Upstairs, three additional bedrooms provide flexibility for family, guests, or multigenerational living, creating a floor plan that is equally suited for everyday living and entertaining. At the heart of the home, the open concept living spaces are centered around a beautifully appointed chef's kitchen featuring premium Thermador appliances, custom cabinetry, quartzite countertops, and an oversized island that seamlessly connects the kitchen, dining, and living areas. Expansive PGT impact rated windows and doors flood the home with natural light while creating a seamless connection to the outdoor living spaces, while the private pool provide the perfect backdrop for year round entertaining and relaxation. Located within the highly sought after Southside Elementary School district, this exceptional residence is just minutes from downtown Sarasota's acclaimed restaurants, boutique shopping, Burns Court, Bayfront Park, Marina Jack, the city's vibrant arts and cultural scene, and Sarasota's world renowned Gulf beaches. Combining custom craftsmanship, luxury finishes, and an unbeatable location, 1680 Cherry Lane presents a rare opportunity to own a brand new custom home in one of Sarasota's most desirable neighborhoods.

1680 Cherry Lane, Downtown

$2,799,000

5 Beds ⋅ 5 Baths ⋅ A4697829 MLS

Virtually Staged. Rare brand-new construction in the heart of Laurel Park, 1681 Oak Street offers the ideal blend of modern luxury, thoughtful functionality, and an unbeatable downtown Sarasota lifestyle. Perfectly positioned in one of Sarasota’s most sought-after neighborhoods, this newly built residence places you just moments from downtown dining, shopping, Bayfront Park, Burns Court, Marina Jack, and Sarasota’s world-renowned Gulf beaches, while offering the charm and convenience of coveted downtown living. Spanning 3,128 square feet, the thoughtfully designed two-story floor plan features five bedrooms and four baths, including a first-floor primary suite and an additional main-level bedroom that can easily function as a private office, guest suite, or den. Upstairs, three additional bedrooms provide flexibility for family, guests, or multigenerational living, creating a layout that balances everyday comfort with long-term versatility. Designed for both elevated entertaining and daily living, the open-concept interior is centered around a beautifully appointed kitchen with premium Thermador appliances, custom cabinetry, quartzite surfaces, and seamless connection to the main living spaces. Expansive impact-rated PGT windows and doors fill the home with natural light while providing peace of mind and enhancing the home’s clean, modern aesthetic. Outside, a serene private pool creates a true backyard retreat and extends the living experience outdoors for year-round enjoyment. Whether hosting friends after dinner downtown or enjoying a quiet afternoon at home, the outdoor setting offers the perfect balance of privacy and relaxation. Located within the highly sought-after Southside Elementary School district and just minutes from Sarasota’s beaches, cultural amenities, restaurants, parks, and waterfront, 1681 Oak Street presents a rare opportunity to own a newly built home in Laurel Park, where quality construction, location, and lifestyle come together in one exceptional offering.

1681 Oak Street, Downtown

$875,000

3 Beds ⋅ 2 Baths ⋅ A4694679 MLS

A rare commercial-residential restoration opportunity for experienced rehabbers to revive a largely unaltered Mediterranean Revival bungalow in Burns Court—one of downtown Sarasota's most coveted historic neighborhoods. * Pre-listing home inspection report available upon request. Why restoration buyers will love this property: Prime Burns Court commercial/residential location — highly walkable, just steps from award- winning restaurants, boutiques, Burns Court Cinema, Five Points, and Bayfront Park. Original structural integrity — including hollow structural clay tile, lath and plaster construction, exceptionally durable and naturally resistant to moisture and termites. Largely unaltered original floor plan with hardwood floors, crown molding, plaster walls, decorative ironwork, and other preserved architectural details. One of the largest properties on Burns Court - 1,355 square feet of living space. Detached accessory building — the largest on Burns Court, with Pineapple Avenue frontage, ideal for guest quarters, artist’s studio, or an income-producing rental dwelling, retail or office space. Recent capital improvements — main house roof (2023), main house HVAC (2019), and under-main house pipe replacement (~2023). FEMA Flood Zone X while also being a short walk to the water Downtown Core (DTC) zoning with confirmed Transferable Development Rights (TDRs), providing additional investment potential. Also listed as Commercial under MLS# A471381.

411 Burns Court, Downtown

$1,895,000

5 Beds ⋅ 4 Baths ⋅ A4680261 MLS

Own a Sarasota Bay view home today. Introducing 1156 Cocoanut Avenue, a newly built modern residence that delivers bold architecture, refined finishes, and effortless urban living in the heart of Sarasota. Designed for today’s lifestyle, this striking home blends clean lines, open spaces, and elevated craftsmanship into a seamless expression of contemporary luxury. The home features five bedrooms and four bathrooms across 2,882 square feet. You are greeted by large-format, marble-look tile throughout the first floor for a seamless, elegant flow. From the moment you arrive, the home’s sleek exterior and architectural presence make a powerful first impression. Inside, light-filled interiors unfold with expansive open-concept living areas, high ceilings, and thoughtfully selected finishes that feel both high end and inviting. The Gourmet chef’s kitchen is equipped with top-of-the-line Café appliances featuring elegant gold accents, premium cabinetry, and seamless Calcutta quartz countertops throughout the home. The waterfall center island seats 6 comfortably, ideal for family meals, casual gatherings, or hosting large dinner parties. The layout is ideal for modern living—entertaining, everyday comfort, and stylish retreat. Having two spacious living rooms, one on each floor, offers versatile entertaining or relaxed family time. The primary suite is a true retreat with a spa-style bath, soaking tub, walk-in shower, and generous his-and-hers closets. Large-format tile flooring, energy-efficient construction, a two-car garage, and modern architectural details enhance both form and function. Outdoors, a private resort-style backyard awaits with a custom Pebble Tec pool, covered patio with tongue-and-groove ceiling plus stylish full summer kitchen, and a fully fenced lot with rear alley access for added privacy and ease. Additional features include a 2-car garage, energy-efficient design, and modern architectural finishes that emphasize comfort and style. Every element has been intentionally curated to reflect quality and design-forward living, creating a home that feels fresh, refined, and effortlessly functional. Ideally located in Sarasota’s sought-after downtown corridor, near Sarasota’s vibrant downtown, you’re just moments from the Rosemary District, world-class dining, art galleries, theaters, shopping, and the city’s renowned cultural scene. Enjoy quick access to the waterfront, marinas, and Sarasota’s award-winning beaches, all while being tucked into a rapidly growing and highly sought after neighborhood. You are just steps from the Bay and the Van Wezel through the beautiful Pioneer Park path. This is a rare opportunity to own a newly built modern home in one of Sarasota’s most dynamic locations. Schedule your private showing today and experience the lifestyle waiting for you! Would also make an excellent Airbnb. Call today for a showing!

1156 Cocoanut Avenue, Downtown

$14,900,000

4 Beds ⋅ 5 Baths ⋅ A4677001 MLS

Pre-Construction. To be built. Soon to be under construction. Located on the coveted waterfront of Bay Point Drive, this extraordinary custom residence represents a rare opportunity to own a truly bespoke new-build in one of Sarasota’s most desirable bayfront settings. Designed by the acclaimed DSDG Architects and expertly built by Dynan Construction, this home blends striking modern architecture with timeless coastal elegance. Showcasing open bay views, the residence features an expansive open floor plan anchored by a dramatic great room and living area with soaring ceilings, walls of windows, and floor-to-ceiling sliding glass doors that flood the interiors with natural light and seamlessly connect indoor and outdoor living. Entertain effortlessly with a sophisticated lounge and temperature-controlled wine cellar, complemented by a chef’s kitchen and oversized chef’s pantry. The home offers a six-car garage, ideal for collectors and car enthusiasts, and includes an elevator servicing all floors for ultimate convenience. The entire top floor is dedicated to a private primary suite retreat, complete with a serene sitting area and a private study, creating a peaceful sanctuary with elevated views. Outdoor living is equally impressive, featuring an expansive waterfront patio, tranquil koi pond, and multiple covered seating areas designed for year-round enjoyment and entertaining against the backdrop of Sarasota Bay. This exceptional new construction home is a statement of architectural excellence, craftsmanship, and luxury waterfront living—offering refined design, thoughtful amenities, and breathtaking views in a premier Sarasota location.

1521 Bay Point Drive, Downtown

$5,425,000

4 Beds ⋅ 5 Baths ⋅ A4669453 MLS

Under Construction. This exceptional, boater’s residence is ideally positioned on Hudson Bayou, designed to impress at every turn. Showcasing the very best of Sarasota’s waterfront lifestyle, the property features outstanding boating amenities, including 80 feet of new concrete seawall and cap, a private dock with lift and davit, and convenient bay and Gulf access beneath two fixed bridges. Spanning 3,906 square feet, the “Callie” model blends modern elegance with effortless livability. From the moment you arrive at 1821 Lincoln Drive, handcrafted iron doors open to a dramatic foyer with soaring ceilings and a striking open staircase. Beyond, captivating sightlines lead through the home to the sparkling pool, lush landscaping, and tranquil bayou. Light-filled interiors highlight refined finishes and distinctive architectural details. The great room, complete with an entertainment wall and formal dining area, is enhanced by a full wall of pocketing glass doors that seamlessly connect indoor and outdoor living spaces. The outdoor retreat is equally impressive, featuring a heated saltwater pool and spa, a covered cooking area, dining space, and additional screened seating—perfect for both lively gatherings and peaceful relaxation. At the heart of the home, the sleek island kitchen boasts high-end appliances, quartz countertops, solid wood cabinetry, and a butler’s pantry. The expansive primary suite occupies the full depth of the home, offering a private sanctuary with a dedicated study, oversized walk-in closet, and a luxurious bath with a freestanding soaking tub and glass-enclosed shower. Additional highlights include a downstairs bonus room with pool bath, a secluded guest suite with private bath, and a planned elevator shaft for easy access to the upper level, where additional ensuite bedrooms and a game room await. Located in the historic Avondale neighborhood, just south of downtown Sarasota, this home is surrounded by majestic, tree-lined streets and multi-million-dollar estates. It also lies within the highly regarded Southside School District, known for its exceptional academic offerings. Combining a prime waterfront location, state-of-the-art features, and impeccable design, this residence represents a rare opportunity. Crafted by the award-winning team at Allegra Homes, it stands as a statement of refined living and a lasting investment for the discerning buyer.

1821 Lincoln Drive, Downtown

$2,250,000

4 Beds ⋅ 4 Baths ⋅ A4668989 MLS

Welcome to your own private Spanish-Mediterranean-inspired sanctuary, perfectly nestled in the heart of Sarasota’s historical Laurel Park. This rare exquisitely updated 4-bedroom, 3.5-bath residence blends timeless charm with modern sophistication offering a dynamic combination of style, comfort, and versatility. This private gated home offers a separate guest or in-law suite with a full kitchen and en-suite bath ideal for extended family, visitors, or potential rental income. Step outside into a lush, resort-style backyard, where tropical landscaping frames a shimmering turquoise saltwater pool/spa and a retractable awning to enjoy your personal oasis for relaxing afternoons or elegant entertaining. Inside, the main home's fully renovated first level boasts European white oak flooring, a thoughtfully designed chef’s kitchen, and bespoke finishes throughout. Unique touches include a custom ventilated cat retreat tucked playfully beneath the staircase, blending charm and creativity. The newly crafted white oak staircase leads to the upper level, where the white oak floors continue and lime-washed plaster walls create a soft, elevated ambiance that’s both serene and stylish. All of this, just steps away from the vibrant lifestyle of downtown Sarasota; including Burns Court, Selby Gardens, and an abundance of dining, arts, and cultural attractions. There is also a kayak launch around the corner, so you're able to venture out via Hudson Bayou to the bay or to the neighborhood's "pocket park" on Laurel Street. With unmatched walkability and a one-of-a-kind design, this home offers a rare opportunity to live beautifully in one of Sarasota’s most beloved neighborhoods.

1724 Cherry Lane, Downtown

$5,495,000

4 Beds ⋅ 3 Baths ⋅ A4647998 MLS

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

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