Location: Sarasota , 34234
Do Not Show Listings
5310 N TUTTLE AVE, SARASOTA, FL 34234
$850,00025 Days on yellowkey MLS ID: A4685035
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2408 Built: 1956 Tax: $7,598 (2025)Community: Desoto AcresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,598
Elementary School: Emma E. Booker Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Invest in one of central Sarasota’s most versatile acreage opportunities with this gated 2.23-acre RE1-zoned estate in the historic Desoto Acres community, offering rare land-use flexibility with no active HOA and no enforced deed restrictions. Positioned for future growth, the property is fully secured with perimeter fencing and an electronic security gate at the 53rd Street entrance, with dual asphalt driveways already installed to support expanded use. A cleared and prepped secondary build site provides immediate potential for a detached guest house, ADU, or professional-grade workshop. Approximately $106,000 in recent capital improvements—including a 2023 roof, 2019 HVAC, new water heater, heavy-duty double septic system with lift station, and a deep-drilled 251-ft well recently rejetted with a brand-new submersible pump—significantly reduce future infrastructure costs and strengthen development readiness. While the existing residence is dated, it is fully functional and refreshed with a brand-new mini-split system in the owner’s suite, providing immediate climate-controlled comfort for a primary resident or a phased renovation project. A four-car garage configuration includes an oversized attached two-car garage and a detached air-conditioned workshop, plus 50-amp RV hookups to accommodate specialty storage needs. Located just minutes from UTC and downtown Sarasota, this property represents a strategic land-bank or custom compound opportunity with substantial upside potential. This is a rare find for the buyer who values independence, infrastructure, and a blank canvas for their Florida lifestyle. Schedule your private tour and evaluate the possibilities today.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Tory Uccello, Jr (941-504-8052)
1137 40TH ST, SARASOTA, FL 34234
$310,00062 Days on yellowkey MLS ID: TB8476870
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1237 Built: 1957 Tax: $3,871 (2025)Community: BraeburnSingle Family
Taxes:$3,871
Elementary School: None
High School: None
Middle School: None
Remarks: Located just 10 minutes from Downtown Sarasota and 10 minutes to SRQ Airport, this beautifully updated 2-bedroom, 1-bath home offers comfort, style, and convenience in one ideal package. Remodeled in 2022, the home features luxury vinyl plank flooring throughout and a neutral interior that still shows beautifully. The kitchen and bathroom were upgraded with quartz countertops and modern finishes, complemented by updated appliances. Major improvements include impact windows throughout, a 2022 A/C system, and a 2018 roof — giving buyers added confidence in the home’s key components. A versatile bonus room provides flexible space for a home office, den, or guest area. The utility room includes a water heater and washer/dryer hookup for everyday convenience. Move-in ready and thoughtfully updated, this Sarasota home is perfectly positioned near shopping, dining, and the vibrant downtown scene. Schedule your showing today.
Listing is courtesy of: JULIAO REAL ESTATE, LLC (954-459-0147)
Listing Agent: Olivia Costa (585-727-5428)
355 S SHORE DR, SARASOTA, FL 34234
$2,295,000158 Days on yellowkey MLS ID: A4671767
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 3276 Built: 1954 Tax: $9,362 (2024)Community: Sapphire Shores Resub Blk MSpa: NoSingle Family
Taxes:$9,362
Tax Year: 2024
Remarks: Build Your Dream Home on Sarasota Bay in Sapphire Shores! Set on an expansive 0.34-acre (14,665-sq.-ft.) waterfront lot, this property presents a rare opportunity to create a custom Sarasota residence in one of the city’s most desirable West-of-Trail neighborhoods. Perfectly positioned on a protected inlet that opens directly to Sarasota Bay, this oversized homesite offers stunning water views and the ideal setting for a modern coastal estate with private dockage and outdoor living space. Nestled among multi-million-dollar properties in the sought-after Sapphire Shores community, the location captures both tranquility and convenience. Just minutes from downtown Sarasota, residents enjoy easy access to world-class dining, boutique shopping, cultural landmarks, and vibrant nightlife. Nearby attractions include The Ringling Museum of Art, Sarasota Jungle Gardens, and the Van Wezel Performing Arts Hall, while Lido Beach, Longboat Key, and St. Armands Circle are only a short drive away. Offering a coveted combination of bay proximity, generous lot size, and prime positioning within Sarasota’s prestigious museum district, this property is ready for new vision—whether you imagine a coastal contemporary retreat or timeless Sarasota modern. Opportunities of this caliber are increasingly rare in today’s market—seize the chance to build your dream home in one of Sarasota’s most storied waterfront enclaves.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
919 47TH ST, SARASOTA, FL 34234
$299,80046 Days on yellowkey MLS ID: A4684905
REDUCED by $9,100 (2.9%) on 04/16/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1352 Built: 1925 Tax: $4,150 (2025)Community: Broadway Court Of Indian BeachSingle Family
Taxes:$4,150
Elementary School: Bay Haven Sch of Basics Plus Elementary
Remarks: This unique Sarasota bungalow and detached studio are ideally situated on an oversized 125 x 135 lot (over 0.38 acres), offering exceptional space and privacy just under two miles from downtown Sarasota. Enjoy convenient access to Lido Beach, St. Armands Circle, Marina Jack’s, City Island, and O’Leary’s Tiki Bar, with Siesta Beach only a short 20-minute drive away. Located within walking distance to the Ringling Museum and Sarasota Bayfront—perfect for taking in breathtaking sunsets—as well as Asolo Theater, local breakfast spots, and neighborhood favorites like Riccio’s Pizzeria. Nearby conveniences include Publix, Whole Foods, Walmart, SRQ Airport, New College, USF Sarasota-Manatee, and Ringling College of Art and Design. Set on a picturesque street lined with towering, mature Washingtonia Robusta palms, the property offers a tranquil, Old Florida feel. Priced near land value, this is a rare opportunity for developers, preservationists, or homeowners seeking a private retreat with room to expand. The fully fenced lot is lushly landscaped with mature palms, oaks, and bamboo, attracting a variety of birdlife. An outdoor shower and deck provide the perfect space to unwind after a day at the beach. Inside, the home features a spacious foyer—ideal for an office, yoga, or music space—a Florida room with its own AC unit, and two vintage ceramic tile bathrooms. Additional highlights include seven Hunter ceiling fans, a 2013 Trane AC heat pump, and a 2019 roof by Singleton Roofing with a transferable warranty. Original architectural charm shines through with true plaster walls, knotty pine paneling, built-ins, solid five-panel wood doors, crystal doorknobs, picture rails, and wood flooring beneath Berber carpeting. An oversized carport adds convenience. The detached studio, under its own roof, offers a full bath with pedestal sink, cathedral ceilings with exposed wood beams, a private deck, and outdoor shower—ideal for guests, rental income, or a creative workspace. This non-deed restricted property provides ample room for a boat, RV, pool, hot tub, or future expansion. The home is equipped with GE and Whirlpool appliances, and Kohler and Moen fixtures. Stove can be converted to gas, line is present. Easy to show with notice. Motivated seller—unlock immediate equity and more value with your personal updates
Listing is courtesy of: CLUB REALTY (941-726-2677)
Listing Agent: Brooke O'Malley (941-726-2677)
835 INDIANA LN, SARASOTA, FL 34234
$450,000388 Days on yellowkey MLS ID: A4646238
0 Days Off yellowkey (back on 3/12/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1373 Built: 1957 Tax: $5,793 (2024)Community: Bay HavenSingle Family
Taxes:$5,793
Remarks: Under contract-accepting backup offers. DESIRABLE 3 BEDROOM/2BATH HOME LOCATED WEST OF THE TRAIL. ONLY 2 STREETS AWAY FROM THE SARASOTA BAY, CLOSE TO RINGLING ART MUSEUM, SRQ AIRPORT, NEW COLLEGE, USF, DOWNTOWN SARASOTA SHOPPING, RESTURANTS AND MORE. REPLACED NEW ROOF IN 2024.
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mike Horner (941-544-3315)
1709 N TAMIAMI TRL #502, SARASOTA, FL 34234
$599,00088 Days on yellowkey MLS ID: A4679227
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1050 Built: 2022 Tax: $7,354 (2025)Community: The StrandSpa: NoCondo
Taxes:$7,354
Elementary School: Gocio Elementary
Remarks: PRICE IMPROVEMENT AND GREAT VALUE! Experience this coveted top floor and closest to the Bay location and the fantastic water views, beautiful sunsets, five-star amenities, gated access, and incredible proximity to Downtown Sarasota, the Bay Park, and the area's spectacular beaches. PLUS option to purchase a boat slip with 16,000 lb. lift and 2nd parking space with sunshade! Built in 2022, this residence affords a second-to-none waterfront lifestyle. The 1050 sf, 1 bedroom + office/den, 2 full bath unit features upgraded finishes, sizable living area, designated dining space, serene primary bedroom with luxe owner's bath, expansive custom closet, and private open-air terrace overlooking the water. Perfect as a primary or secondary home, or investment property where weekly rentals are welcome. Entertain in your chef's kitchen with stainless Samsung appliances, upgraded white subway tile backsplash, soft close cabinetry, statement quartz countertops and a generously sized peninsula. The main living space is filled with natural light and affords stunning water views through 9' hurricane-rated sliding glass doors. The office/den is perfect for all of your organizational needs. Additional noteworthy features include custom designed closets, in-unit laundry with Samsung washer and dryer, pendant lighting, designer ceiling fans and custom window treatments. This unit includes 1 under-building parking space and private secure storage. The Strand, brought to life by renowned architectural firm HOYT, and award-winning interior design firm JKL Design features fantastic resort style amenities including heated swimming pool/spa, fitness center, gas fire pit and grills, electric car charging stations, dog park, 1000' boardwalk, kayak and paddleboard launch, and ample guest parking. In addition to the fabulous surroundings and culture of Downtown Sarasota, you can enjoy the restaurants, cafes and bars that are just a stone throw away from The Strand. Make the most of the azure water and explore the top-rated beaches and bays and make this exceptional residence, community and city your home today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1709 N TAMIAMI TRL #503, SARASOTA, FL 34234
$550,000159 Days on yellowkey MLS ID: A4671066
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 958 Built: 2022 Tax: $7,016 (2025)Community: The StrandSpa: NoCondo
Taxes:$7,016
Remarks: Experience this breathtaking penthouse waterfront condominium with sunset views in the resort style gated complex, The Strand. With direct boating access to the Bay and Gulf of Mexico, serene water views, option to purchase a deeded boat slip with 16,000# lift, five-star amenities and fantastic proximity to Downtown Sarasota and area beaches, this residence affords a second-to-none waterfront lifestyle. This unit features a prime location in the Strand in the building closest to the bay and on the 5th floor providing incredible views! The 1 bedroom + office/den, 2 full bath open floor plan features upgraded finishes, custom closets, sizable living area, dining area and open-air terrace. Perfect as a primary or secondary home, or investment property where weekly rentals are welcome. Entertain in your chef's kitchen with stainless Samsung appliances, upgraded white subway tile backsplash, soft close cabinetry, statement quartz countertops and 2 generously sized peninsulas with room for seating. The main living space has incredible natural light and affords stunning water views through 9' hurricane-rated sliding glass doors. This smartly designed home boasts a serene primary bedroom with custom closet, luxe owner's bath with quartz vanity, and laundry area with stackable Samsung washer and dryer. Office/den with closet perfect for all of your organizational needs and an additional full bath with tub. Other noteworthy features: custom designed closets, pendant lighting, and designer ceiling fans. Includes 1 deeded under building parking space, and private secure storage. Welcome to The Strand, brought to life by renowned architectural firm HOYT, and award-winning interior design firm JKL Design Group. Fantastic resort style amenities including heated swimming pool/spa, fitness center, gas fire pit and grills, electric car charging stations, dog park, boardwalk, and kayak launch & storage. In addition to the fabulous surroundings and culture of Downtown Sarasota, you can enjoy the restaurants, cafes and bars that are just a stone throw away from The Strand. Live THE lifestyle exploring top-rated beaches and bays. Make this exceptional residence, community and city your home today!
4946 BRYWILL CIR, SARASOTA, FL 34234
$1,595,000162 Days on yellowkey MLS ID: A4670935
REDUCED by $54,000 (3.3%) on 04/15/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2534 Built: 2004 Tax: $10,069 (2023)Community: Sapphire ShoresSingle Family
Taxes:$10,069
Tax Year: 2023
Remarks: Discover an exquisite blend of Old-World charm and modern luxury in this custom Mediterranean jewel located in Sapphire Shores, the heart of Sarasota’s Historic Museum Area. This property is NOT IN A FLOOD ZONE but just a short walk to Sun Circle, a scenic bayfront park on Sarasota Bay. The neighborhood is surrounded by the city’s most renowned cultural institutions, including The John and Mabel Ringling Museum of Art, Sarasota Ballet, and Florida Studio Theater. Spanning 2,534 square feet under air, this elegant residence features three bedrooms and three baths, with two luxurious en-suites for ultimate privacy and comfort. High-end finishes such as travertine floors, granite countertops, and tray ceilings elevate the home’s timeless sophistication. The open floor plan beautifully balances both leisure and formal areas. A gracious foyer flows seamlessly into the living room and open-concept kitchen creating an ideal setting for entertaining. You will also find both a casual dining area and a formal dining room for those special occasions. Designed for Florida’s indoor-outdoor lifestyle, the home’s salt water pool and exotic sunken fire pit make the backyard a true retreat. When hosting gatherings, you'll find plenty of room for parking in the unique motor court framed by a decorative block wall accented with Frank Lloyd Wright styled vases. Whether you're drawn to the rich history of Sapphire Shores, the vibrant arts scene, or simply desire a refined retreat near the water, this home offers a rare opportunity to own a piece of Sarasota’s finest. 2 miles north of downtown Sarasota and a short drive to St. Armands Circle and the beaches of Lido and Longboat Key. Conveniently located near University Parkway anchored by Sarasota Bradenton Airport on the west and University Town Square shopping and dining district on the east.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Jennings (941-650-7354)
1063 40TH ST, SARASOTA, FL 34234
$260,00014 Days on yellowkey MLS ID: A4688949
REDUCED by $20,000 (7.1%) on 04/14/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1030 Built: 1959 Tax: $3,023 (2025)Community: BraeburnSingle Family
Taxes:$3,023
Remarks: Cute 2br-1 bath on double lot.
Listing is courtesy of: ONE STEP AHEAD REALTY INC (561-951-7332)
Listing Agent: Joseph Stephens (941-400-9084)
1339 22ND ST, SARASOTA, FL 34234
$480,0007 Days on yellowkey MLS ID: TB8497340
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1681 Built: 1959 Tax: $3,260 (2025)Community: Cocoanut HeightsSingle Family
Taxes:$3,260
High School: Riverview High
Remarks: Charming Updated 3BR/2.5BA Home in Sarasota – Move-In Ready! Discover this beautifully renovated gem at 1339 22nd St, Sarasota, FL 34234 (1,681 sq ft living space on an 8,871 sq ft lot). Perfect blend of modern updates and classic Florida charm! Key Features: Prime Corner Lot with Double Street Access: Unique lot connecting to two streets (22nd & adjacent), offering exceptional curb appeal and flexibility. Ample Parking + 2-Car Attached Garage: Wide driveway spaces multiple vehicles easily – no parking hassles! Brand New Luxury Vinyl/Porcelain Tile Flooring Throughout: Sleek, durable, and easy-care for coastal living. Fully Updated Bathrooms: 2.5 modern baths with contemporary finishes. New AC System: Efficient, quiet cooling for year-round comfort. All-New Electrical & Plumbing: Complete modern rewiring and piping for safety and peace of mind. Gourmet Kitchen Shines: White shaker cabinets, stunning gray granite counters, blue subway tile backsplash, stainless steel appliances (fridge, dishwasher, range, microwave), and spacious breakfast bar open to the living/dining area. No HOA! Walk to Ringling College, minutes to Siesta Key beaches, downtown Sarasota dining/shopping, and SRQ airport. Built 1959, feels brand new inside. Zoned RSF3 – ideal for families, investors, or downsizers.
Listing is courtesy of: RADIUS REALTY GROUP LLC (407-541-0779)
Listing Agent: Guillermo Gomez (407-497-9846)
4928 DESERT INN AVE, SARASOTA, FL 34234
$85,00090 Days on yellowkey MLS ID: A4679124
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 672 Built: 1967Monthly Fee: $137 Tax: $2,301 (2025)Community: Tri-Par EstatesMobile Home
Taxes:$2,301
Remarks: Well-maintained single-wide manufactured home offering a bright and functional layout with comfortable living spaces throughout. The home features an open living and dining area with abundant natural light, neutral finishes, and durable flooring. The kitchen offers ample cabinet storage, granite style countertops, and convenient access to the main living areas. Bedrooms are generously sized with built-in closets, and the bathroom includes tiled walls, a tub/shower combination, and updated vanity. Additional features include an enclosed Florida room, covered carport, and ample storage space. The exterior offers a wide driveway and low-maintenance landscaping. Conveniently located near shopping, dining, medical facilities, and major roadways, with easy access to downtown Sarasota and surrounding areas. A great opportunity for affordable Florida living.
Listing is courtesy of: FIDATA REAL ESTATE LLC (941-705-2818)
Listing Agent: Jose Ramirez Hernandez (941-527-9290)
5001 OAKLAND HILLS AVE, SARASOTA, FL 34234
$172,40012 Days on yellowkey MLS ID: A4687593
0 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 860 Built: 1961Monthly Fee: $137 Tax: $2,143 (2025)Community: Tri-Par EstatesSpa: YesMobile Home
Taxes:$2,143
Remarks: This extensively renovated two-bedroom, two-bath residence offers a range of recent upgrades, including newer windows with faux blinds, a TPO roof completed in December 2025, an upgraded AC system (2023), vapor barrier (2024) and a newly constructed carport (2025). The modernized kitchen is equipped with stainless steel appliances less than three years old, soft-close all wood cabinetry featuring a lazy Susan, granite countertops, and garbage disposal. Most walls have been drywalled, complemented by textured finishes on both walls and ceiling. Ceiling fans are installed throughout the home, while both bathrooms have undergone comprehensive remodeling. Additional enhancements include updated PEX plumbing, a washer and dryer positioned in an interior shed, and meticulously maintained landscaping. This move-in-ready home boasts high-quality upgrades and stands prepared for its next owner. Tri-par Estates is a 55+ community that provides a wealth of amenities: enjoy a heated and cooled large pool for year-round swimming, a brand-new spa, tiki hut, pickleball courts, fitness center, shuffleboard, miniature golf, horseshoes, and various recreation hall rooms equipped with ping-pong, billiards, card tables, a kitchenette, sewing areas, and more. The expansive clubhouse regularly hosts dinners, dances, and other events. Situated only minutes from downtown Sarasota, you’ll have easy access to marinas, shopping, restaurants, museums, the world-renowned Siesta Key and Lido Key beaches, and Sarasota airport. In this special park and recreation district, residents own their land directly, with no separate HOA fees—an annual fee of $1,648 is included in your property taxes. Internet and TV included in the annual fee This is also a golf cart-friendly community with optional RV or boat storage when available. Don’t miss the opportunity to join this lively, well-established neighborhood in paradise.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Angelo Sammarco (941-284-5673)
1363 23RD ST, SARASOTA, FL 34234
$284,90021 Days on yellowkey MLS ID: A4687997
REDUCED by $15,000 (5.0%) on 04/13/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1100 Built: 1956 Tax: $2,253 (2025)Community: Central HeightsSingle Family
Taxes:$2,253
Remarks: Located in Central Heights within Sarasota city limits, this 1,100 sq ft single-family home sits on a spacious .19 acre lot and offers a great central location. You’re just minutes to downtown Sarasota, Sarasota Airport, shopping, restaurants, and about 10 minutes to Lido Beach. Inside features tile flooring throughout for easy maintenance, along with fresh interior and exterior paint. The kitchen offers shaker-style cabinets and stainless steel appliances with plenty of space to work with. The home includes 3 bedrooms all split, one full bathroom with a shower/tub combo and ceiling fans in the bedrooms and main living areas. Major updates include a 2021 A/C system and a new hot water heater, with a 2013 roof already in place. The large yard provides room to expand, entertain, or store toys—lots of potential depending on your needs. Solid option for a primary residence, rental, or a simple Florida getaway in a convenient location. Property is vacant and easy to show!
Listing is courtesy of: RELAX PROPERTY GROUP, LLC (941-923-7200)
Listing Agent: Dane Peterson (239-357-5692)
1621 DR MARTIN LUTHER KING WAY, SARASOTA, FL 34234
$525,00018 Days on yellowkey MLS ID: O6395721
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2075 Built: 2009 Tax: $1,424 (2026)Community: Newtown Heights First Add ToSingle Family
Taxes:$1,424
Tax Year: 2026
Remarks: This multi-tribe property at 1621 Dr Martin Luther King Way is a fantastic investment opportunity. Open concept layout with an elegant fireplace in the living room and a kitchen design for entertaining with stainless steel appliances and granite countertops. Conveniently located near shopping, dining, and public transportation. This home is 10 minutes from Sarasota's nearest award winning sugar sand beach, the library, Van Wenzel performing Art Hall, restaurants, walking distance to downtown Sarasota, hospital, major shopping Mall, Ringling Museum and Ringling Art school, five minutes from Sarasota - Bradenton airport. The property provides easy access to everything the area has to accord. The exterior boasts well-maintained landscaping, providing a welcoming first impression. Don't miss the chance to own this versatile income-producing property. The home has two bedrooms with attached bathrooms, one on the first floor, and the other on the second floor.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
941 VIRGINIA DR, SARASOTA, FL 34234
$1,500,00048 Days on yellowkey MLS ID: A4684540
Bed: 6 Bath: 4.5 Liv Area Sq Ft: 3492 Built: 1945 Tax: $9,217 (2025)Community: Bay HavenSpa: YesSingle Family
Taxes:$9,217
Remarks: A Rare Piece of Sarasota History with current income of over 167,000 / yr. Four turn-key furnished residences. Three City Lots. One Extraordinary Piece of Sarasota History. Welcome to 941 Virginia Drive, a truly unique historic property originally built by John Ringling Jr., offering vintage Sarasota charm paired with modern flexibility and lucrative income. Set on three city lots, this 125-foot-long masonry residence creates an extraordinary private compound with four distinct living spaces. The main residence features two bedrooms, one and a half bathrooms, and an office or den, highlighted by timeless architectural details including stone porches, arched doorways, pecky cypress paneling, tall vaulted beamed ceilings and a wood-burning fireplace. Modern updates complement the historic character with stainless steel appliances, granite countertops, and updated fixtures. The property is designed for lifestyle, opportunity and flexibility for extended family, guests or continued successful short-term rental business. In addition to the main home, the estate includes three separate guest residences providing privacy and versatility. There are two in-law suites that feature full kitchens, a private pool, hot tub, outdoor shower, patio access and a private bathroom; one offers one bedroom and the other two bedrooms. There is an additional one-bedroom dwelling with a convenient kitchenette, private bathroom and laundry. Located just two miles north of downtown Sarasota, the property offers easy access to Lido Key, Longboat Key, St. Armands Circle, and the vibrant dining, arts, and cultural scene of downtown Sarasota. Whether you envision a private historic estate, a multi-generational compound or a unique established vacation rental business, this rare property offers exceptional character, privacy and opportunity in one of Sarasota’s most desirable locations. Don’t miss this opportunity to Own a Piece of Ringling History — A Private Sarasota Compound with Vintage Charm and Resort-Style Living.
Listing Agent: Angela Adams (941-809-9760)
320 S SHORE DR, SARASOTA, FL 34234
$4,149,00076 Days on yellowkey MLS ID: A4680700
2 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2978 Built: 1966 Tax: $48,104 (2025)Community: Sapphire ShoresSingle Family
Taxes:$48,104
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Positioned at the tip of Stephens Point, where Sarasota Bay opens wide and the sky feels endless, 320 South Shore Drive commands what many consider the finest views in the city. With sweeping 180-degree panoramas across North Sarasota Bay, glowing downtown lights and elegant arc of the Ringling Bridge, this is a setting that delivers unforgettable sunsets, constant water activity, and a front row seat to dolphins and wildlife passing by daily. The home’s clean lines, open layout, and extensive use of glass create a seamless connection between indoors and out, allowing the surrounding water and sky to become part of everyday life. From the moment you arrive through the gated entry and enter into the all-glass foyer, the experience is unmistakable. Light pours in, sightlines extend in every direction, and the bay immediately takes center stage. Set on nearly half an acre with expansive direct frontage on Sarasota Bay, the property offers a sense of privacy and an exceptional relationship to the water. Boating enthusiasts will appreciate direct access to the bay, while those drawn to quieter moments will enjoy watching the colors of sunset shift across the horizon and the calm rhythm of the water below. The interior spaces are well-suited for everyday living and entertaining. The living and dining areas are wrapped in glass and flow seamlessly to the outdoor areas, creating an easy indoor-outdoor lifestyle. The kitchen is functional and well-positioned, offering generous workspace, quality finishes and uninterrupted bay views. The primary suite serves as a private retreat, positioned to capture long water views and enhanced by a spa-inspired bath that blends indoor and outdoor living. Additional guest accommodations are thoughtfully arranged, offering comfort and privacy for family and friends while maintaining the home’s cohesive modern aesthetic. Outdoors, the full width lanai and lap pool overlook Sarasota Bay, offering an inviting space to relax, entertain and take in the sunsets that define this location. Mature landscaping, including a striking banyan tree, adds character and a sense of place to the property. 320 South Shore Drive is more than a waterfront home. It is a legacy property that brings together architectural significance, extraordinary views and one of Sarasota’s desired locations. A modern masterpiece designed for those who value design, setting and simple luxury of living on the water at its best.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Mike Warm, Llc (941-525-2740)
5308 TRI PAR DR, SARASOTA, FL 34234
$179,00012 Days on yellowkey MLS ID: A4689063
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 800 Built: 1969Monthly Fee: $137 Tax: $3,385 (2025)Community: Tri-Par EstatesSpa: YesMobile Home
Taxes:$3,385
Remarks: This residence showcases high-quality craftsmanship and includes multiple recent upgrades. Key replacements within the past few years feature a gas water heater (2022), air conditioning unit (2022), and TPO roof. Interior enhancements comprise barn doors, freshly installed drywall, modernized bathrooms and kitchen with new cabinetry, stainless steel appliances, and granite countertops. The property is fitted with single-hung, double-pane windows incorporating a tilt-in design for convenient maintenance. Exterior features include palm trees and vinyl siding. A generous 9x8 wood-framed shed equipped with electrical service offers additional storage space and houses the washer and dryer. Tri-par Estates is a 55+ community that provides a wealth of amenities: enjoy a heated and cooled large pool for year-round swimming, a brand-new spa, tiki hut, pickleball courts, fitness center, shuffleboard, miniature golf, horseshoes, and various recreation hall rooms equipped with ping-pong, billiards, card tables, a kitchenette, sewing areas, and more. The expansive clubhouse regularly hosts dinners, dances, and other events. Situated only minutes from downtown Sarasota, you’ll have easy access to marinas, shopping, restaurants, museums, the world-renowned Siesta Key and Lido Key beaches, and Sarasota airport. In this special park and recreation district, residents own their land directly, with no separate HOA fees—an annual fee of $1,648 is included in your property taxes. Internet and TV included in the annual fee This is also a golf cart-friendly community with optional RV or boat storage when available. Don’t miss the opportunity to join this lively, well-established neighborhood in paradise.
4925 REMINGTON DR, SARASOTA, FL 34234
$675,00013 Days on yellowkey MLS ID: A4685614
Bed: 3 Bath: 0.0 Liv Area Sq Ft: 1605 Built: 1958 Tax: $5,532 (2025)Community: Sapphire HeightsApartment
Taxes:$5,532
Remarks: Excellent investment opportunity or perfect personal retreat in beautiful Sarasota! This single family home well-maintained property at 4925 Remington Dr is currently operating as a successful short-term rental/Airbnb, offering immediate income potential for investors or flexibility for part-time use. The home features a bright and comfortable layout with inviting living spaces, making it ideal for both guests and full-time residents. The property offers a relaxed Florida lifestyle with outdoor areas perfect for entertaining or enjoying the warm Sarasota weather. Conveniently located near world-class beaches, shopping, dining, and entertainment, this property attracts vacationers year-round. Its desirable location and established rental use make it a rare opportunity for buyers seeking income-producing real estate in Sarasota. Whether you’re looking for a turnkey investment, seasonal getaway, or full-time residence, this property offers versatility, location, and excellent potential.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Mariele Hoffman (941-225-0800)
$675,00068 Days on yellowkey MLS ID: A4682036
REDUCED by $10,000 (1.5%) on 04/07/2026
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1605 Built: 1958 Tax: $5,532 (2025)Community: Sapphire HeightsSingle Family
Remarks: Welcome to 9425 Remington Drive — where privacy, freedom, and prime Sarasota living converge in one exceptional offering. Within walking distance of a stunning Sapphire Shore Park, where you can relish in breathtaking sunsets. Located in one of Sarasota’s most desirable West of Trail enclaves, just moments from the water, this property represents a rare opportunity in a location where land value and long-term appreciation consistently outperform broader market trends. In this coveted pocket, lifestyle, proximity, and scarcity drive demand — making opportunities like this increasingly limited for those seeking to secure a premier address in a timeless coastal setting.This refined 3-bedroom, 3.5-bath residence spans 1,605 square feet of thoughtfully designed space, delivering both sophistication and comfort — all without HOA fees or deed restrictions, a rarity that elevates both lifestyle and investment value. Each bedroom serves as a private retreat, complete with its own en-suite bath, creating an ideal layout for guests, multigenerational living, or a seamless work-from-home setup. A beautifully positioned powder room enhances convenience for entertaining. The open-concept design flows effortlessly, filled with natural light and understated elegance. The living spaces are designed for connection yet maintain a sense of calm and separation, offering both intimacy and versatility. Outdoors, the true luxury reveals itself — absolute freedom. Park your boat or RV, design your outdoor sanctuary, or tailor the property to your vision without restriction or approval. Located just minutes from downtown Sarasota, SRQ Airport, St. Armands Circle, and the Gulf Coast’s renowned beaches, this address delivers the ultimate balance of accessibility and coastal sophistication. This is more than a home — it’s an opportunity to live unrestricted in one of Sarasota’s most desirable and convenient locations.
2731 17TH ST, SARASOTA, FL 34234
$225,00014 Days on yellowkey MLS ID: A4688863
0 Days Off yellowkey (back on 4/12/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 801 Built: 1984 Tax: $2,294 (2026)Community: Lenray HeightsSingle Family
Taxes:$2,294
Remarks: Under contract-accepting backup offers. Don’t miss this great property featuring 2 bedrooms and 1bathroom. This property is perfect for investors looking for a hassle-free addition to their portfolio. Convenient layout, strong rental potential, and stable occupancy make this a smart buy.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Larisa Trexler (941-928-1347)
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