Location: Sarasota , 34239
Do Not Show Listings
1240 HILLVIEW DR, SARASOTA, FL 34239
$16,950,00017 Days on yellowkey MLS ID: A4688990
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4852 Built: 1992 Tax: $80,000 (2025)Community: Harbor AcresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$80,000
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’s most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood-paneled library, formal dining with 12-foot ceilings, and a wetbar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3700 S OSPREY AVE #205, SARASOTA, FL 34239
$225,00017 Days on yellowkey MLS ID: TB8494655
REDUCED by $12,000 (5.1%) on 04/23/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 991 Built: 1979 Tax: $2,548 (2025)Community: Plaza GardensCondo
Taxes:$2,548
Elementary School: None
High School: None
Middle School: None
Remarks: This fully renovated West-of-the-Trail condominium offers a rare opportunity to enjoy one of Sarasota’s most desirable locations at an approachable price point. Thoughtfully updated with custom imported Italian cabinetry and modern finishes, the residence features generous, well-proportioned living spaces that provide a level of comfort and openness not typically found in this price range. The building’s solid concrete construction ensures exceptionally quiet interiors, while elevator access and an in-unit washer and dryer add everyday convenience, complemented by additional shared laundry facilities. Residents are welcomed by a charming interior courtyard with mature tropical landscaping, creating a peaceful and inviting atmosphere. Ideally located just 10–15 minutes from Siesta Key Village and its world-renowned beaches, this condo is also minutes from Southside Village on Hillview Street, where you’ll find popular dining spots such as Libby’s Neighborhood Brasserie, Veronica Fish & Oyster, Morton’s Gourmet Market, and Pacific Rim. Everyday essentials are within easy reach, including Trader Joe's, Publix, and Sarasota Memorial Hospital, along with additional shopping and dining along US-41 near Bay Road. While the community offers a more relaxed lifestyle without resort-style amenities such as a pool or gym, it makes up for it with larger living spaces, quiet construction, and an unbeatable location. This is an outstanding opportunity to own a move-in-ready Sarasota condo near Siesta Key at a highly competitive price.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Roman Donato Ruiz (813-619-0792)
2421 PROSPECT ST, SARASOTA, FL 34239
$645,90096 Days on yellowkey MLS ID: A4677367
REDUCED by $1,600 (0.2%) on 04/23/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 972 Built: 1956 Tax: $4,592 (2025)Community: Arlington ParkSingle Family
Taxes:$4,592
Elementary School: Alta Vista Elementary
Middle School: Brookside Middle
Remarks: Now Offered at a Rare Value...Welcome to 2421 Prospect Street in Arlington Park’s Tightly Held RUSTIC LODGE…This Elegantly Refined Florida Mid-Century Retreat with Modern Coastal Finishes is Rooted in Sarasota’s Golden Era…the 1950s Marked a Time When Homes Were Designed & Built with Longevity & Craftsmanship—2421 is a Beautiful Reflection of That Legacy…Approached Not as a Renovation but as a Custom Crafted Rebuild...A Design-Conscious Builder Honored the Original Vision While Elevating the Residence to Meet Today’s Expectations for Style, Comfort, and Quality…the Integrity, Proportions, and Character Remain Intact, Now Enhanced by Refined Finishes, Seamlessly Integrated Contemporary Systems, Forward-Thinking Infrastructure, and Improvements Aligned with City of Sarasota Code…Sleek, Clean & Effortlessly Cool—As Though the 1950s Walked Into 2026 with Style…Expansive New PGT Impact Windows, Sliders & Doors Bathe the Home in Light While Preserving Tranquility…Every Detail Has Been Carefully Considered, Including All New Plumbing with Cast Iron Replacement Under the Slab, All New Electrical, HVAC Ductwork, and Engineered Structural Enhancements to Create an Open Floorplan...Insulated Interior Walls in Key Areas, Blown Attic Insulation, Tankless Water Heater, Fresh Paint, White Oak Style Plank Flooring with Four-Inch Baseboards, Frameless Glass Shower Doors, Custom Walk-In Closets, and Soft-Close Cabinetry Throughout…Curated Quartz Countertops Extend Across the Gourmet Chef’s Kitchen, Catering Pantry, Dry Bar, and Bathrooms…Recently Enhanced with a Brand-New Stainless Steel LG Dishwasher & New GE Profile Refrigerator…Additional Home Features Include Glass Tile Backsplashes, Substantial Kitchen Island with Tile Accent Lighting, and Vented Range Hood…Discreetly Integrated Throughout is a Fully Automated Smart Home System Offering Complete Flexibility—Including Remote Entry Keypads, Wireless Alarm, Ring Cameras, Motion Detectors, Panic Buttons, Remote-Control Ceiling Fans, USB & USB-C Outlets, Nest Thermostat, and Digitally Controlled Irrigation—Allowing the Home to Be Fully Automated or Enjoyed Traditionally at the Owner’s Preference…A Fully Screened Lanai with Custom Tongue & Groove Ceiling Extends the Living Space Outdoors, Complemented by New Epoxy Flooring Leading to the Paver Patio with Pool, Spa & Expansion Concepts Available…The Grounds Have Been Curated with a Six-Figure Landscape & Lighting Package, Fully Fenced, Double-Gated Privacy, Mature Junipers, Lush Clusia Hedges, Olive Trees, Bird of Paradise, and Fragrant Jasmine…A Three-Bedroom, One-and-a-Half-Bath Residence in the Heart & Soul of Arlington Park—Just Blocks to Legacy Trail and Arlington Park & Aquatic Center Hosting Live Music Events Alongside Pickleball, Tennis, Basketball Courts, Playgrounds, a Dog Park, Walking Trails, and Two Pools…Blocks to Sarasota Memorial Hospital, Minutes to Downtown Sarasota, Siesta Key, Longboat Key, Anna Maria Island, UTC Mall, and a Depth of Dining & Cultural Offerings Favored by Locals…Just a Fifteen-Minute Drive to Sarasota-Bradenton International Airport…Weekly Rentals Are Allowed, Not in a Flood Zone, No Storm Damage, No HOA, and Offered Turn-Key Furnished or Thoughtfully Curated to Buyer Preferences…Passed Down Through Only Two Owners Since the 1950s, This Home Represents Stewardship, Architectural Lineage, and Forward-Thinking Living…It’s Timeless, Intentional, and Unmistakably Rare…Schedule Your Private Tour Today & Live a Fuller Life!
Listing is courtesy of: FULLER GROUP (941-961-3100)
Listing Agent: Bo Fuller (941-961-3100)
2069 BOUGAINVILLEA ST, SARASOTA, FL 34239
$1,590,00075 Days on yellowkey MLS ID: A4681866
Bed: 6 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3249 Built: 1957 Tax: $13,058 (2025)Community: Long MeadowSingle Family
Taxes:$13,058
Remarks: Welcome to this fully furnished, newly updated Sarasota property situated on two combined lots totaling nearly half an acre, offering the flexibility and lifestyle potential in one of the area’s most popular areas of Sarasota. This multiple six-figure producing Airbnb is located just 1.5 miles to Siesta Key and approximately 2 miles to downtown Sarasota, this property provides quick access to world-class beaches, dining, shopping, and entertainment. The main residence features an open-concept floor plan designed for comfortable living and entertaining. A separate in-law suite offers ideal accommodations for guests or extended family, while the detached pool house provides additional flexible space suitable for a game room, private retreat, or entertainment area. At the center of the property is a private courtyard with a large pool, creating a resort-style setting perfect for gatherings and outdoor enjoyment. The oversized double lot allows for ample parking and generous outdoor space, a rare find this close to the beach. Significant upgrades have been completed throughout the property, including a new roof, new A/C units, new electrical, new electrical panels, new water lines to the road, a new irrigation system, and exterior landscape lighting, offering peace of mind for future owners. Whether you are seeking a primary residence, second home, or a versatile property with multiple living areas, this Sarasota residence stands out for its location, lot size, and turnkey condition.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Noah Ward (715-531-8021)
3631 SAN REMO TER, SARASOTA, FL 34239
$7,995,000173 Days on yellowkey MLS ID: A4669078
REDUCED by $250,000 (3.0%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4705 Built: 2021Monthly Fee: $13 Tax: $68,556 (2025)Community: San Remo EstatesSpa: YesSingle Family
Taxes:$68,556
Remarks: Anchored in one of Sarasota’s most coveted deep water waterfront communities, 3631 San Remo Terrace presents a rare opportunity to own a modern luxury home with direct boating access in San Remo Estates, just moments from Siesta Key, Downtown Sarasota, and Southside Village. Completed in 2021 by award-winning designer Stephen Chung and enhanced with thoughtful 2025 upgrades, this coastal contemporary residence blends clean architectural lines with warm, natural finishes, ideal for buyers seeking newer construction, move-in-ready condition, and hurricane-resilient design in a prime location. Positioned on protected sailboat water with no fixed bridges, the property offers seamless access to Sarasota Bay and a short, unobstructed ride to the Gulf, making it perfectly suited for avid boaters. Spanning approximately 4,750 square feet under air, with nearly 3,000 additional square feet of outdoor living space, the home is designed around the indoor-outdoor lifestyle today’s luxury buyers prioritize. The open-concept layout is anchored by a chef’s kitchen featuring a sculptural marble island and Sub-Zero and Wolf appliances, flowing effortlessly into a great light-filled room with a stone fireplace, custom built-ins, and floor-to-ceiling glass sliders that open to expansive terraces. A temperature-controlled wine room with 1,800-bottle capacity adds a refined touch, while the dining space creates a striking architectural focal point. The primary suite offers true resort-style living, with private access to both a tranquil courtyard with spa and sauna and the waterfront pool terrace. Inside, a custom walk-in closet and spa-inspired bath reflect the level of finish expected in a luxury retreat. The second level features three additional bedrooms, a flexible gym or office, and a loft-style workspace, providing versatility for modern living. Outdoors, the illuminated saltwater pool with a glass wall, newly enhanced outdoor kitchen, and expansive entertaining areas create a private waterfront oasis. The deep-water dock is equipped with a 20,000-pound boat lift, dual jet ski lifts, and a floating dock, delivering a true boating lifestyle. Additional highlights include a three-car garage with a lift, epoxy flooring, and custom storage. A fully integrated smart home system, featuring programmable lighting and shades, whole-home audio, Apple TV integration, a generator, and high-speed WiFi, meets the expectations of today’s tech-forward buyer. Furniture is available separately to create a more turnkey concept. Located within San Remo Estates, the home offers a rare balance of privacy and central convenience. Just minutes from Siesta Key via the nearby North Bridge, beach access becomes part of everyday life. Set on a deep-water basin seconds from Sarasota Bay, the property provides protected docking with immediate access to open water and a short ride to the Gulf. Southside Village and Downtown Sarasota are both a quick drive away without the need to cross any bridges, offering boutique shopping, cafés, acclaimed dining, and a vibrant arts and cultural scene. Everyday conveniences, including top-rated schools, Sarasota Memorial Hospital, and key corridors like US-41 and I-75, are all within close reach. This is a location that seamlessly connects protected waterfront living with the very best of Sarasota.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
1934 DATURA ST, SARASOTA, FL 34239
$1,600,00082 Days on yellowkey MLS ID: A4680304
REDUCED by $25,000 (1.5%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3091 Built: 2002 Tax: $9,130 (2025)Community: Desota ParkSingle Family
Taxes:$9,130
Remarks: A striking residence on one of Sarasota's treasured streets West of Trail, crowned with a NEW BARREL STYLE METAL ROOF, showcasing a raised front porch and grand double-door entry, all enveloped by a lush, resort-style tropical garden. This expansive home just freshly painted and professionally staged, offers four generously sized bedrooms, one boasting it's own large patio in the treetops. With over 3,000 square feet of thoughtfully designed living space, the home blends timeless elegance with comfort, creating an inviting setting for upscale entertaining and everyday living. Be welcomed by a grand two-story vaulted living and dining space, highlighted by an elegant curved staircase and open catwalk above. The spacious chef’s kitchen features a center island and breakfast bar, flowing seamlessly into the family room and through expansive sliding glass doors to a screened patio that evokes the feel of a private tropical paradise. The primary suite is conveniently on the main level, offering soaring ceilings and direct access to the patio. It includes a custom walk-in closet and a spa-inspired bath with dual vanities, a garden tub and a separate shower. Recent updates include NEW CARPETING IN ALL BEDROOMS, NEWER DUAL ZONED AIR CONDINTIONG SYSTEMS for optimal comfort, a NEW HOT WATER TANK and a COMPLETE WHOLE HOUSE RE-PLUMB, offering peace of mind and modern efficiency. ROOM FOR A POOL. Just steps away from Morton's Market, Veronica's, and other neighborhood favorites. Located in the highly regarded Southside Elementary School district, the home offers the very best of the West of Trail lifestyle, walkable to restaurants, boutiques shops, Sarasota Memorial Hospital, with easy access to downtown Sarasota and our world-famous beaches.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Christine Mazur (941-374-4015)
1876 MAGNOLIA ST, SARASOTA, FL 34239
$2,650,000138 Days on yellowkey MLS ID: A4674004
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3292 Built: 2025 Tax: $9,262 (2024)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$9,262
Tax Year: 2024
Remarks: Construction now complete! Move in to this stunning 2-story “Palonia IV Coastal” floor plan is one of the newest additions to the Allegra Homes collection of exquisite luxury residences and is located in the sought after West of Trail area near Siesta Drive, your direct pathway to Siesta Key. The cornerstone of the Allegra Homes’ vision is a dedication to excellence in custom home building and providing the very best in quality and design offered in today’s new home market. With 4 bedrooms, a den, a bonus room and 4 baths, the fabulous open living plan of 3,292 sq. ft. has been tastefully and thoughtfully designed with artistry, beauty and functionality. Upon entry into this upscale residence, you will first notice the great room with 16-ft. enhanced tray ceiling illuminated by natural light and a wall of pocketing sliders opening wide to a covered lanai. The full width of the back of the home has been dedicated to exceptional Florida living with a pool/spa, a covered dining area with detailed ceiling, and a fully-equipped outdoor kitchen … all screen enclosed and paver decking. Inside, the formal dining room features a wall of windows with fabulous views of your very own tropical oasis. The family chef will savor the ultimate kitchen set-up with large stone-topped island, abundant counter space and storage including a pantry, and premium appliance package such as Sub-Zero fridge and wine cooler, Wolf 36” gas cooktop and matching oven, drop-down microwave, ASKO quiet dishwasher, and even a Delta pot filler. The owner’s wing is a serene place of rest and rejuvenation. Bypassing the dual walk-in closets is the luxurious bath that’s absolutely delightful with its spacious glass shower and rain head, double vanities, large soaking tub and water closet. A den is also a part of the owner’s wing for added convenience for work or study. Guest accommodations are purposefully situated at the opposite end of the house for the utmost in privacy with access to a full bath and the gorgeous outdoor living area. Upstairs, there are 2 bedrooms, a bath and a bonus room for kid hangouts and family time. Additional amenities include a front porch, paver drive and entry, professionally landscaped and irrigation well, 2-car garage with epoxy finished floor, hurricane impact Low-E windows and sliding doors, crown molding, tray ceilings, natural gas water heater, and pool and house alarms. The prime location within Southside School District, celebrating 120 years of distinguished achievements awards, is ideal for families. And just about a mile from Southside Village and 2 miles south of downtown’s exciting smorgasbord of arts, entertainment, shopping, and dining is 1876 Magnolia Street, where people walk their dogs, neighbors greet one another, and families enjoy bike rides along tree-lined streets. This home creates a beautiful backdrop for a beautiful life.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1330 S JEFFERSON AVE, SARASOTA, FL 34239
$685,00044 Days on yellowkey MLS ID: A4685616
REDUCED by $100,000 (12.7%) on 04/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1716 Built: 1960 Tax: $7,730 (2025)Community: Rustic Lodge 2Single Family
Taxes:$7,730
Remarks: MAJOR PRICE REDUCTION - MUST SEE! This gorgeous home in the iconic Rustic Lodge enclave in Arlington Park was meticulously remodeled in 2020. The thoughtfully designed layout flows seamlessly from a central gathering space combining great room and kitchen—ideal for everyday living and entertaining. Highlights include soaring shiplap ceilings, engineered hardwood floors, premium lighting, and PGT impact doors and windows. The kitchen is anchored by a large island featuring granite countertops, high-end appliances, and custom cabinetry, while French doors open to the secluded outdoor spaces. This 3 bed 2 bath split floor plan features a Primary Suite with elegantly appointed walk-in closet and a spa-inspired bathroom complete with walk-in shower, soaking tub, and dual sinks. The north wing of the home includes two guest bedrooms and a full bath with shower/tub combination, offering separation and privacy from the primary suite. Conveniently located adjacent to the kitchen, the laundry room includes a top tier washer and dryer. An oversized garage affords a full wall of built-in storage space. Outdoor features include a newly landscaped garden, decorative awnings, delightful garden art, a driveway with inset river rock, and a walled "secret garden" oasis in the side yard, complete with shade umbrella and charming garden gate. Major systems/appliances replaced during the total renovation in 2020 include roof, air conditioning, water heater, electrical, plumbing, kitchen, bathrooms, flooring, and impact resistant doors and windows. Ideally situated on a corner lot near the Arlington Park complex, and just minutes from Downtown Sarasota, Southside Village, and award winning Siesta Key Beaches.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Carol-Ann Warr (941-780-0665)
2600 LOMA LINDA ST, SARASOTA, FL 34239
$375,00040 Days on yellowkey MLS ID: A4686114
1 Days Off yellowkey (back on 4/22/2026)
REDUCED by $25,000 (6.3%) on 04/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1166 Built: 1954 Tax: $4,430 (2025)Community: Arlington ParkSingle Family
Taxes:$4,430
Remarks: Under contract-accepting backup offers. Located on a large corner lot in the heart of Arlington Park, this classic Old Florida mid-century home offers an exceptional opportunity in one of Sarasota’s most desirable neighborhoods. Whether you’re looking to renovate and restore its charm or build a custom home, the property provides the ideal setting in a highly sought-after location. Enjoy true walkability with the YMCA just one block away and Arlington Park only two blocks away, featuring walking trails, tennis and pickleball courts, and a heated Olympic-size swimming pool. The neighborhood is known for its mature trees, quiet streets, and close proximity to everything Sarasota has to offer. Just five minutes to Sarasota Memorial Hospital and the vibrant shopping, dining, and cultural attractions of downtown Sarasota, and within easy reach of Sarasota’s world-renowned arts and entertainment scene, including the Van Wezel Performing Arts Hall and The Ringling Museum of Art.Only 15 minutes to the world-famous beaches of Siesta Key, as well as the waterfront dining, boutique shopping, and island lifestyle of St. Armands Circle and Lido Key. This property offers the rare opportunity to enjoy quick access to everyday conveniences, outdoor recreation, Sarasota’s celebrated arts and culture, and the Gulf Coast’s best beaches, all while creating the home or investment vision that fits your needs.
Listing is courtesy of: HARTMAN REAL ESTATE & COMPANY (941-500-4547)
Listing Agent: Zain Hartman (941-735-6415)
2215 DATURA ST, SARASOTA, FL 34239
$1,990,00077 Days on yellowkey MLS ID: A4681704
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2317 Built: 2018 Tax: $22,478 (2025)Community: GreenwichSpa: YesSingle Family
Taxes:$22,478
Remarks: Extraordinary Modern Sanctuary with Breathtaking Resort-Style Backyard Oasis on RARE Double Lot! Crafted by Majestik Homes—one of Sarasota's premier luxury homebuilders—this residence exemplifies innovative design, exceptional craftsmanship, and meticulous attention to detail. Known for redefining luxury living, Majestik Homes delivers bold, high-quality homes that prioritize safety, peace of mind, and timeless sophistication. This stunning home offers 4 bedrooms and 3 bathrooms with an open-concept layout featuring 10-foot ceilings, 8-foot doors, and abundant natural light through hurricane-rated impact-resistant windows, sliders, and doors. The chef’s kitchen stands out with quartz countertops, soft-close cabinetry, premium Sub-Zero refrigerator, induction cooktop, and high-end stainless-steel appliances, flowing seamlessly into the dining area and expansive great room with perfect sightlines to the front and rear yards. The luxurious primary suite is a serene escape with sliding glass doors to the patio, dual high-end custom walk-in closets, and a spa-like en-suite bath with dual vanities and open shower. The three additional bedrooms each feature beautiful high-end custom closets, with two separated by a stylish sliding barn door—ideal for guests, children, or a private home office. The two guest bathrooms are gorgeous and impeccably designed. One offers a sleek frameless glass walk-in shower with crisp white tilework, floating vanity, and tropical accents for a tranquil spa feel. The other provides a deep relaxing bathtub in sophisticated gray subway tile, paired with a pristine white vanity, bright natural light, and clean contemporary finishes—both showcase exceptional detail and timeless elegance. Premium upgrades include a new 16 SEER AC system, epoxy-coated garage floors, high-end built-in garage cabinetry, dedicated Tesla charging station, natural gas service with generator-ready hookup, hard-wired architectural uplighting for stunning evening ambiance, auto drapes throughout, and a private well for irrigation—a huge money saver on water costs. The backyard is the true centerpiece: a jaw-dropping saltwater infinity-edge pool with integrated hot tub, gas-heated for year-round use. This low-maintenance pool is self-cleaning and self-draining for effortless ownership. Surrounded by an expansive deck of premium Shellock pavers—renowned for durability, slip-resistance, and cool-to-the-touch feel—the oasis is fully enclosed by premium 6' white vinyl privacy fencing. Mature tropical landscaping, palms, and lush greenery frame the space. A dedicated kids’ play area along the north fence line adds family charm, complemented by a beautifully designed large chicken coop. The second lot offers a separate entrance from the north side road (Hyde Park) and abundant space for a 2nd garage, casita, home gym, pickleball court, RV/boat storage, or expanded outdoor living—truly endless possibilities. Smartly scaled for easy, low-maintenance living yet delivering an enormous resort-caliber backyard with unmatched privacy and versatility. No HOA restrictions. Just 1 minute to Sarasota Memorial Hospital—ideal for medical professionals. Downtown Sarasota (dining, arts, theater, shopping, entertainment) is 5 minutes away. Siesta Key is a quick 10-minute drive. Easy access to Van Wezel Performing Arts Hall, top-rated schools, Southside Village, Ringling College, USF Sarasota-Manatee, and I-75. Short drive to iconic St. Armands Circle and Lido Beach.
Listing is courtesy of: RONNIE DEWITT AND ASSOCIATES (941-755-0011)
Listing Agent: Ronnie Dewitt (941-650-2154)
1349 HARBOR DR, SARASOTA, FL 34239
$4,100,000110 Days on yellowkey MLS ID: A4676231
1 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4337 Built: 2012 Tax: $27,088 (2025)Community: Harbor AcresSpa: NoSingle Family
Taxes:$27,088
Remarks: Located in Harbor Acres, one of Sarasota’s most coveted neighborhoods, this coastal traditional residence enjoys an exceptional in-town setting just minutes from downtown and Southside Village, home to 14+ restaurants, Morton’s Gourmet Market, and Sarasota Memorial Hospital—truly the epicenter of city living. Poised on an elevated lot, this newly renovated 4-bedroom, 4-bath home offers a highly desirable and functional floor plan filled with natural light, high ceilings, and abundant windows throughout the main level. The thoughtfully designed first floor features a spacious primary suite with dual closets and a bath with soaking tub, along with an additional bedroom suite and a private office conveniently located near the living room and primary bedroom. The living room is anchored by a fireplace flanked with custom built-in bookcases and opens via sliding glass doors to the covered patio, creating seamless indoor-outdoor flow. A well-proportioned dining room sits just off the kitchen, ideal for both everyday living and entertaining. The open kitchen features new luxury appliances, quartzite countertops, a farmhouse-style sink, beverage refrigerator, custom pantry, breakfast bar overlooking the living room, and a sun-filled breakfast room. An oversized laundry room offers ample space for custom built-ins and includes a new washer and dryer. A full bath on the main level serves both the additional downstairs suite and functions as a pool bath. Recent updates include wide-plank oak flooring, quartzite kitchen countertops, new appliances, new light fixtures throughout, two new air conditioning systems, fresh interior and exterior paint, new vanities in the primary bath and one upstairs suite, and new tropical landscaping that creates a lush garden setting. Upstairs, a large family or game room is flanked by two bedroom suites and opens to a front terrace. Designed for indoor-outdoor living, the home features a screened pool, outdoor dining area, and summer kitchen. A 4-car garage with additional storage completes this exceptional offering. Harbor Acres is renowned for its voluntary homeowners association and strong sense of community, making it one of Sarasota’s most desirable neighborhoods.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
2940 BOUGAINVILLEA ST, SARASOTA, FL 34239
$650,00010 Days on yellowkey MLS ID: A4689977
2 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1710 Built: 1960Monthly Fee: $17 Tax: $6,279 (2025)Community: South GateSingle Family
Taxes:$6,279
Remarks: Stunning, mid-century modern home in highly desirable South Gate with views you must see to believe! If you could have picked one of the best lots in South Gate back in the 1960’s this may have been it. The two-bedroom plus office, two bath home sits on a bluff overlooking a wide portion of Philippi Creek including a large aquatic preserve. You’ll be mesmerized by long, unobstructed views in every direction. A nature lovers delight and absolutely intoxicating. But while location is important, there are many more features in this classic home to consider. Entering through the large foyer you’ll immediately notice beautiful terrazzo floors throughout and a great room with vaulted ceilings. There’s an adjacent dining area off the kitchen and all of these spaces look out through what appears to be a “wall of glass” dedicated to the world class view of flora and fauna. The primary bedroom also has views and access to the back yard and the primary bathroom has been upgraded with a separate tub and walk in shower. The den/office can be made more private with sliding pocket doors and function as a guest bedroom. It even has a dedicated, enclosed patio and garden space. There’s an attached, oversized garage with room for your workshop and a double wide driveway with plenty of parking. While this home has been appropriately updated and improved over the years you’ll find it’s all been done with a great sensibility to the original intent, quality and “hipness” so many are learning to appreciate, again.
Listing Agent: Barbara May (404-822-9264)
2612 BOTANY AVE, SARASOTA, FL 34239
$495,0004 Days on yellowkey MLS ID: A4688184
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1407 Built: 1962 Tax: $4,313 (2025)Community: South Gate ManorSingle Family
Taxes:$4,313
Elementary School: Wilkinson Elementary
Remarks: Welcome to 2612 Botany Ave, a true mid-century modern pool home offering comfort, privacy, and an unbeatable central Sarasota location. This 2-bedroom, 2.5-bath residence includes a flexible bonus room off the garage, ideal for a home office, gym, or future expansion. The home features high vaulted ceilings in the living and dining areas, creating a bright, open feel that reflects its classic mid-century design. Inside, you’ll also find a renovated kitchen (2025) with new appliances including a never-used oven, a Samsung Smart refrigerator, updated lighting, new flooring throughout the main living areas, and fresh interior and exterior paint. Step outside to a private screened lanai and pool, recently rescreened, with a fully fenced yard featuring new vinyl fencing (2024) and updated landscaping, perfect for relaxing or entertaining. The home is equipped with PVC/CPVC plumbing, and additional upgrades include a new AC (2024), offering peace of mind for years to come. Positioned in one of Sarasota’s more desirable pockets, this home offers convenient beach access while benefiting from a higher elevation than many surrounding areas. Ideally located just minutes from Morton’s Gourmet Market, downtown Sarasota’s dining, shopping, and cultural scene, and the waterfront, with Siesta Key Beach approximately 15 minutes away. A move-in ready home with thoughtful upgrades and a private pool in one of Sarasota’s most convenient locations.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Thomas Dupont (941-565-4029)
2410 PROSPECT ST, SARASOTA, FL 34239
$799,000299 Days on yellowkey MLS ID: A4656811
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1969 Built: 2017 Tax: $10,998 (2024)Community: Rustic Lodge 2Spa: NoSingle Family
Taxes:$10,998
Remarks: Welcome to this elegant 2017 constructed 'better than new' home that combines the convenience of easy access to Sarasota’s best parks, markets, restaurants, and top-rated schools, with a quiet, friendly neighborhood— plus just a short drive to world-famous sugar-sand beaches of Siesta Key and Lido Beach. Nestled on a lush corner lot in the heart of highly sought-after Arlington Park, this 3-bedroom, 2.5-bathroom residence offers 1,969 heated Sq Ft of beautifully finished craftsman style living and a spacious 2-car garage. The home has been meticulously maintained and thoughtfully upgraded to satisfy the comfort and conveniences required by today's modern lifestyle. You’ll be immediately impressed by the pristine curb appeal and the drama of the grand foyer showcasing soaring 20+ foot ceilings, adding to the home's modern style and open feel. Thoughtful details abound, including crown molding, gorgeous hardwood floors, and exquisite finishes throughout, accented by an abundance of natural light. The formal living and dining rooms create an ideal space for entertaining, while the well-appointed chef’s kitchen is a true showstopper—complete with quartz countertops, custom solid wood cabinetry, stainless steel appliances, a large island, pendant and recessed lighting, and a beautiful backsplash. The kitchen overlooks the bright and inviting combined family and dining area, seamlessly connecting the heart of the home. Upstairs, the huge master suite offers a peaceful retreat, featuring plush carpeting, a spacious walk-in closet, and a luxurious en-suite bathroom with dual vanities and a stunning dual-head walk-in shower. Two additional light-filled bedrooms provide plenty of space for family or guests. Outside is your expansive covered brick-paved patio, perfect for quiet evenings or entertainment, all within a fully fenced backyard with ample room to add a pool. Lush landscaping has been strategically positioned to provide the home with privacy while maintaining a sleek contemporary theme. Additional upgrades include a new A/C unit, new gutters, new washer & dryer, an alarm system, insulated garage door, EV charger, and a new refrigerator. This move-in ready charmer is truly better than new, and offers it all — style, space, and a prime Sarasota location!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
1714 WALDEMERE ST, SARASOTA, FL 34239
$1,800,00026 Days on yellowkey MLS ID: A4688029
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 2000 Tax: $4,256 (2025)Community: Hudson BayouSpa: NoSingle Family
Taxes:$4,256
Remarks: Rarely available 2001 built one story home on a 75 ft wide lot in the prime heart of West of Trail/ Southside Village area. One block to Sarasota Memorial Hospital and 3 blocks to the ever popular Southside Village shops and restaurants. A "true" neighborhood, Hudson Bayou is one of the most sought after areas to live in. This 4 bedroom (split bedroom plan) 3 full bath pool home has high ceilings and an oversized 2 car garage.
2440 VALENCIA DR, SARASOTA, FL 34239
$599,0004 Days on yellowkey MLS ID: A4690679
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1330 Built: 1956 Tax: $3,188 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,188
Remarks: Charming Sarasota home for sale with 2 bedrooms, 2 baths, over 1,300 square feet, a one-car garage, and a fully fenced backyard. Located in the highly sought-after Southside Elementary school district, this residence offers the perfect blend of charm, comfort, and convenience. Inside, beautiful terrazzo floors, integrated built-ins, and a light-filled Florida room create an inviting atmosphere with flexible space for relaxing, entertaining, or working from home. This home’s midcentury appeal and classic Florida style make it especially inviting. Ideally located near downtown Sarasota, Southside Village, Sarasota Memorial Hospital, restaurants, shopping, parks, and the beaches, this is an excellent opportunity for buyers seeking a primary residence, seasonal retreat, or investment property in Sarasota real estate, with its character, ease of living, and optimal location.
Listing Agent: Kelly Mooney (941-587-8430)
1394 HARBOR DR, SARASOTA, FL 34239
$7,750,00071 Days on yellowkey MLS ID: A4682309
REDUCED by $500,000 (6.1%) on 04/21/2026
Bed: 4 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5913 Built: 2004 Tax: $48,224 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$48,224
Remarks: Presenting a distinguished waterfront estate located in Sarasota’s premier bayfront community, Harbor Acres, widely regarded as the city’s most coveted neighborhood. Perfectly situated on a protected deep-water boat basin, this property offers immediate access to Sarasota Bay with the added benefit of a boat dock and lift on calm waters-ideal for larger vessels. With prized southern rear exposure, the home is bathed in natural light throughout the day, while capturing glowing sunsets across the water — a rare and highly desirable feature for waterfront living. The thoughtfully designed 4-bedroom, 6 bath floor plan offers exceptional flexibility and privacy, with distinct guest wings that function almost as private suites — ideal for hosting extended family, visiting friends, or even live-in arrangements without sacrificing personal space. The seamless flow between formal and casual living areas makes the home equally suited for elegant entertaining or relaxed everyday living. At the heart of the home, the chef’s kitchen features beautiful quartz countertops, island, abundant cabinetry, and premium appliances, opening effortlessly to the family room and outdoor living areas. A striking double-sided gas fireplace creates ambiance between key gathering spaces, enhancing both intimate evenings and larger gatherings. Enjoy the rare luxury of choosing between two primary suites. Both primary suites are serene retreats offering generous proportions, tranquil water views, and a spacious walk-in closets with custom built-ins designed for optimal organization. The spa-inspired baths provides a luxurious escape at the end of the day. Outdoor living is where this property truly shines. A fully equipped summer kitchen anchors the covered lanai, creating the perfect setting for waterfront dining and entertaining. The infinity edge pool, spa and outdoor lounge areas overlook the wide boat basin, where you can watch dolphins pass and boats glide by — all from the comfort of your own backyard.
1760 ARLINGTON ST, SARASOTA, FL 34239
$2,150,000254 Days on yellowkey MLS ID: A4661996
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2745 Built: 2012 Tax: $21,270 (2024)Community: Nichols Sarasota HeightsSpa: NoSingle Family
Taxes:$21,270
Remarks: One or more photo(s) has been virtually staged. Ideally positioned in Sarasota’s desired West of Trail, this 2012 custom-built three-bedroom, four-bath home blends timeless architecture with modern comfort—just a short stroll to Southside Village’s boutiques and cafés, Selby Gardens, the bay front, and Sarasota Memorial Hospital. Set on a fully fenced, 1/3-acre lot in the sought-after Southside Elementary district, the property offers a private oasis with a sun-soaked southern-exposure backyard—ideal for all-day light on the pool and covered patio. Outdoor living shines with a heated pool featuring a sun shelf, fire pit, landscaped lawn, and inviting front and back porches designed for effortless entertaining. Inside, nearly 2,800 square feet unfolds with a wood-burning fireplace, tile and luxury vinyl plank flooring, and a flexible layout suited for today’s lifestyle including a den/office that can easily be used as a fourth bedroom. The oversized laundry/mudroom streamlines daily life, while the two-car garage with extra storage adds convenience. The spacious primary suite opens directly to the pool and features dual walk-in closets and bath with double vanities, a walk-in shower, and soaking tub. Built with quality in mind—including block construction and a durable metal roof—this home offers peace of mind and enduring value. A rare opportunity to own newer construction West of Trail with accessibility, abundant natural light, and room to live the Sarasota lifestyle to its fullest—just minutes from downtown.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
3230 VILLAGE GREEN DR #1032, SARASOTA, FL 34239
$189,00064 Days on yellowkey MLS ID: A4683197
REDUCED by $6,000 (3.1%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1419 Built: 1971 Tax: $3,030 (2025)Community: South Gate Village Green 10Condo
Taxes:$3,030
Remarks: Welcome to a classic Florida home that perfectly blends comfort, style, and functionality. With its solid construction and timeless character, the home blends classic design with the potential for modern updates, making it perfect for buyers looking to personalize their space. Spacious living areas, abundant natural light, and a functional layout create an inviting atmosphere ideal for both relaxing and entertaining. The open-concept layout creates a seamless flow between the kitchen, dining, and living areas, making it all the more inviting. Village Green is a 55+ community that has a ton of amenities. Right on the other side of the neighborhood is even an executive golf course that can meet all your golfing needs.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: James Graves (678-817-8166)
3052 WEBBER ST, SARASOTA, FL 34239
$525,00038 Days on yellowkey MLS ID: A4685956
REDUCED by $10,000 (1.9%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2141 Built: 1964Monthly Fee: $17 Tax: $5,101 (2025)Community: South GateSingle Family
Taxes:$5,101
Remarks: One or more photo(s) has been virtually staged. Step into a piece of Sarasota charm where timeless character meets peace of mind. This lovingly maintained 1964 South Gate gem has been cared for by its original owner and is now ready to welcome its next chapter. Inside, you’ll find a functional split floor plan featuring three bedrooms and two full baths, offering both privacy and flexibility for everyday living. The home feels like a step back in time—in the best way—full of warmth, nostalgia, and the kind of solid construction you just don’t see anymore. Important updates provide confidence where it matters most, including a whole-house re-pipe in 2018, A/C replaced in 2020, and a roof from 2011. Connected to central sewer, this home combines classic appeal with essential modern improvements. Enjoy relaxing mornings or quiet evenings on the back porch, and take advantage of the oversized two-car garage with plenty of room for storage, hobbies, or extra space. Whether you’re looking to preserve its vintage charm or update it to your own style, this South Gate beauty is a rare opportunity to create something truly special in a centrally located, established neighborhood. Homes like this don’t come along often—schedule your private showing today and imagine the possibilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mary Jo Violett (941-928-8474)
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