Location: Sarasota , 34234
Do Not Show Listings
3419 CHAPEL DR, SARASOTA, FL 34234
$549,9003 Days on yellowkey MLS ID: A4689270
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1032 Built: 1971 Tax: $5,337 (2025)Community: Desoto TerraceSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,337
Elementary School: Bay Haven Sch of Basics Plus Elementary
High School: Booker High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Don’t miss this adorable Florida home! You will fall in love with the neighborly front porch and the newly upgraded private landscaped courtyard. This updated 2 bed/2 bath home is tucked away on a quiet cul-de-sac at the end of Chapel Drive in the historical bayfront neighborhood of Indian Beach Sapphire Shores and is not in a flood zone. You could not find a better location blending city life with a friendly neighborhood vibe. Surprisingly, this tranquil abode is only 5-minutes to downtown Sarasota, less than 5 minutes to Sarasota Bradenton International Airport, 5-minutes to The John and Mable Ringling Museum of Art and 3-minutes to the Ringling College of Art and Design. This home is move-in ready with new AC in 2023, new water heater in 2022, new electrical panel in 2022, new roof in 2019, updated kitchen and bath, new impact resistant windows, and for the chef, your kitchen comes equipped with a gas stove. It is also equipped with fiber-optic internet. Not seen very often, enjoy off street parking for 5 or more cars. An air-conditioned garage with a new hurricane-proof garage door can be used for a variety of purposes. The front yard and the courtyard have been freshly landscaped, and a separate metered irrigation system installed. The fenced backyard offers a beautiful dining area under a screened gazebo as well as a fire pit for cool evenings. Enjoy the oak tree and the privacy of your backyard! If you choose to join the neighborhood HOA, you will share an annual picnic, yard sale and Easter Egg Hunt with neighbors, not to mention sunsets over Sarasota Bay at Indian Beach Park or Sapphire Shores Park. Don’t let this delightful home slip away - make it your seasonal getaway, your permanent residence or a vacation rental!
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
4946 BRYWILL CIR, SARASOTA, FL 34234
$1,595,000159 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
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
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)
1386 GRANTHAM DR, SARASOTA, FL 34234
$312,0006 Days on yellowkey MLS ID: A4689609
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1575 Built: 2008Monthly Fee: $299 Tax: $3,231 (2025)Community: Bradford Manor TwnhmsTownhouse
Taxes:$3,231
Remarks: Better than NEW! Renovated and Move-in ready! NEW ROOF, HVAC, Paint, Carpeting and Appliances! LOW HOA Fee of $299/month includes- Exterior Maintenance, Community Pool, Basic Cable/Internet & Trash Removal. Gated Community of Bradford Manor is located in a PRIME location! Close to a Downtown Sarasota, University Parkway, UTC, Sarasota Airport, Beaches, Shopping, Dining, Schools & MORE! Master Suite has a HUGE Walk in closet and attached Master Bathroom. Two Secondary Bedrooms share a hallway Full Bathroom. Spacious floorpan w/ a First Floor Half Bathroom, plenty of Guest Parking and a Screened in Lanai with no rear neighbors! Washer/Dryer located on the Second Floor for easy access!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Monica Desomma (202-427-4328)
1314 GRANTHAM DR, SARASOTA, FL 34234
$310,000147 Days on yellowkey MLS ID: A4672819
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1769 Built: 2020Monthly Fee: $299 Tax: $3,729 (2024)Community: Bradford Manor TwnhmsTownhouse
Taxes:$3,729
Elementary School: Emma E. Booker Elementary
Tax Year: 2024
Middle School: Booker Middle
Remarks: WOW - THIS PRICE IS IT!! NOW ONLY 310,000. While everyone else is settling for older outdated townhomes, this one just got even more affordable. A brand-new price on a 2020-built, move-in-ready townhome in a gated Sarasota community — modern finishes, contemporary construction, and a location that's only getting better. The home delivers everything you want: Bright open-concept living with tile floors, a granite kitchen with wood cabinetry, oversized breakfast bar, and a screened lanai that makes outdoor living effortless. Upstairs, three bedrooms, a smartly placed laundry area, and a primary suite with dual sinks, walk-in shower, and a serious walk-in closet. One-car garage, hurricane shutters, community pool and spa. Pet-friendly. No CDD fees. HOA that won't break the bank. The location is the real story. Minutes to SRQ Airport, Gulf beaches, and downtown Sarasota's restaurants and arts scene. And right next door? Gracewater — one of Sarasota's hottest new luxury developments — is already pushing values up in this corridor. You're not just buying a home, you're buying into a neighborhood on the rise. The window won't stay open long — call to schedule your private showing now.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Tina Clements (941-313-4175)
5019 STEVENS DR, SARASOTA, FL 34234
$669,90052 Days on yellowkey MLS ID: A4683765
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1592 Built: 1957 Tax: $5,172 (2025)Community: Sapphire HeightsSpa: NoSingle Family
Taxes:$5,172
Remarks: Fully renovated mid-century gem in the charming and highly coveted Indian Beach Sapphire Shores neighborhood of Sarasota. This exceptional three-bedroom, two-bathroom home has been lovingly preserved and thoughtfully restored with a strong emphasis on period-appropriate mid-century design and timeless style. Original terrazzo floors sparkle throughout the main living areas, honoring the home’s architectural roots. The fully renovated kitchen features new high-end appliances and blends seamlessly with the home’s classic aesthetic. The former Florida room has been transformed into comfortable year-round living space with permanent climate control, with the design anchored by an authentic vintage 1960s Preway wood-burning cone fireplace — a true statement piece. High-end mid-century light fixtures are showcased throughout, including multiple authentic Herman Miller pieces. Major updates provide peace of mind, including a new roof (2023), brand-new HVAC system and ductwork (2024), and a new solid wood privacy fence (2024). All bedrooms offer sizable closets, and the large zero-scaped front yard ensures beauty with minimal maintenance. The expansive backyard is a private retreat, featuring a generous paver patio and ample space for a pool or future additions. A newly installed barrel sauna and cold plunge create a spa-like sanctuary along the side yard, with convenient access from the principal suite. The true highlight of the home is the architect-designed principal bedroom and bathroom suite, completed in 2025 — an incredibly rare feature for this neighborhood and era. Designed as a private oasis, the light-filled bedroom includes a picture window and charming window seat, thoughtfully separated from the two guest bedrooms on the opposite wing of the home. The spacious en-suite bathroom is professionally interior designed and features high-end fixtures, a large walk-in shower, a freestanding spa tub, double vanity, and a walk-in closet. An exterior door provides direct access to the outdoor spa area for seamless indoor-outdoor living. Ideally located, this home is within a short distance to multiple beautiful waterfront parks and the renowned The John and Mable Ringling Museum of Art. Just five minutes to downtown Sarasota and ten minutes to the pristine beaches of Lido Key, you’ll enjoy the very best of Sarasota’s natural beauty and vibrant cultural scene — all from the comfort of your exquisitely restored mid-century home in one of the city’s most beloved neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Agnes Cameron (941-388-3966)
1709 N TAMIAMI TRL #522, SARASOTA, FL 34234
$530,00017 Days on yellowkey MLS ID: A4688048
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 855 Built: 2022 Tax: $6,479 (2025)Community: The Strand Of SarasotaSpa: YesCondo
Taxes:$6,479
Elementary School: Gocio Elementary
Remarks: Discover an exceptional waterfront penthouse at The Strand offering unobstructed, pristine views from Whitaker Bayou to Sarasota Bay right from your generously sized balcony. Built in 2022 and lightly used by the original owners, this immaculate, never-rented residence features impact-rated windows, sliders and doors, 9-foot ceilings, and thoughtful high-end upgrades throughout. The living area showcases a custom white wall unit with multiple shelving and a perfectly fitted 75" TV. The primary suite includes a walk-in closet with custom California Closet built-ins, while both the main bedroom and living room are equipped with motorized shades for effortless light control. The kitchen and both bathrooms feature custom installed stainless steel pullout cabinet organizers to maximize convenient storage. A versatile den with barn doors and a closet can function as an office or even a second bedroom. Modern conveniences include a smart A/C thermostat and programmable front-door lock, a programmable (from your phone) entry LED smart light fixture capable of altering brightness and displaying a rainbow of colors, wall light dimmers installed in kitchen, hallway and guest bath, front-loading full-size Samsung washer and dryer, garage parking beneath the building, and a private storage cage in an enclosed storage room. Enjoy resort-style amenities: heated pool and spa, fitness center, gas fire pit and grills, EV charging stations, dog park, and kayak launch with storage. Located mere minutes from vibrant downtown Sarasota — with fine dining, galleries, shopping, theater, bay front parks and The Bay community activities — this penthouse delivers refined waterfront living and easy access to coastal recreation.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Lisa Sebastian (941-544-5413)
2959 N LOCKWOOD MEADOWS BLVD, SARASOTA, FL 34234
$405,0004 Days on yellowkey MLS ID: TB8493921
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 924 Built: 1985 Tax: $3,867 (2025)Community: Lockwood MeadowsSpa: NoSingle Family
Taxes:$3,867
Remarks: Best single family offering in Sarasota at an affordable price—-Beach life? Siesta Key 10-15 min, Lido 7-10, Longboat 15-20. Schools 5 minutes! UTC Mall and Rt 75 are 10-12 minutes away. Downtown restaurants in 10 minutes. Want move in ready? 1 car garage, full shed in back yard. Want updates? Roof 2025, Water Heater 2025, AC and Ducts just replaced 2 months ago. Washer and dryer less than 3 yrs old. Full master bath and Walk in shower, new fridge and soft close cabinets. Want Florida living? Fire pit, Bermuda Cherry, Orange, Lime, Lemon, Tangelo, and Red Lime trees should bear fruit this year. 12 ftx 36 ft screened lanai for grilling and back yard lounging. Back yard is completely fenced. Room for a pool. No HOA! Established neighborhood NEVER WET! No storm damage history.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Leah King (813-957-8924)
1063 40TH ST, SARASOTA, FL 34234
$260,00011 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
$480,0004 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)
5214 BEECHMONT AVE, SARASOTA, FL 34234
$180,00047 Days on yellowkey MLS ID: A4684037
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1060 Built: 1973 Tax: $2,497 (2025)Community: Tri-Par EstatesSpa: YesMobile Home
Taxes:$2,497
Remarks: Tri-par Estates in an active, vibrant 55+ community where each property is individually owned with a deed and title to the home. This large corner lot is NOT in the flood zone, but IS in the pet-friendly area and the homes comes furnished. The open living/dining combo is spacious and bright with updated windows, mostly 2025- low-e/double-pane. Other updates include vinyl planking floor throughout, kitchen, bathrooms, all appliances newer including water heater, and freshly painted throughout. The main washroom features a step-in shower, and the primary ensuite has a tub with shower. The laundry is located inside the home for your easy convenience. Public records indicate 880 sq ft for the main house; a mini-split unit has been added to the all-season Florida room for a total of 1,060 sq ft. Outside updates include: TPO roof- 2025, aluminum carport - 2026, pavers -2025, electrical box, garden sprinkler system, and addition of a 10' x 14' shed which provides tons of space for all your storage needs. Tri-par provides a wealth of amenities: enjoy the heated/cooled Olympic-sized for year round swimming, newly constructed large hot tub, palapa tiki hut, pickleball courts, fitness center, shuffleboard courts, miniature golf, horseshoes, game rooms for ping-pong, billiards and more. The clubhouse is host to events such as dinners, dances, and celebrations of all kinds. Situated only minutes from downtown Sarasota, museums, shopping, eateries, the airport and of course the world-renowned Siesta Key and Lido key beaches! You own your own land in this special parks and recreation district, and pay no HOA fee directly to the association. The annual amount of $1,648 is included in your property taxes, and includes such items as fiber-optic internet and direct TV- many channels. Golf cart-friendly community with optional storage for your R/V or boat.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Ivy Neyedly, Pllc (941-914-1994)
4928 DESERT INN AVE, SARASOTA, FL 34234
$85,00087 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
$172,4009 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 Agent: Angelo Sammarco (941-284-5673)
1363 23RD ST, SARASOTA, FL 34234
$284,90018 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
$525,00015 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
$1,500,00045 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Angela Adams (941-809-9760)
320 S SHORE DR, SARASOTA, FL 34234
$4,149,00073 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)
428 SAPPHIRE DR, SARASOTA, FL 34234
$1,195,00073 Days on yellowkey MLS ID: A4679800
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2174 Built: 1990 Tax: $7,492 (2025)Community: Sapphire ShoresSpa: NoSingle Family
Taxes:$7,492
Remarks: Discover the ultimate coastal retreat at 428 Sapphire Drive, a stunning block-construction residence situated on a rare and expansive double lot in the prestigious Sapphire Shores area. A long driveway and winding sidewalk lead you through a beautifully landscaped front yard to this secluded haven, which is set back from the street for maximum privacy. Inside, the home exudes a modern, industrial-chic aesthetic featuring sleek polished concrete floors, soaring vaulted ceilings, and a fresh interior paint palette. The open-concept gourmet kitchen is a focal point, illuminated by a bright skylight and appointed with premium Quartz countertops, abundant cabinetry, and a high-end stainless appliance suite including a Bosch cooktop and refrigerator alongside a KitchenAid double oven. The thoughtful layout offers exceptional flexibility; the current library, featuring a recently replaced north-facing impact window, was originally a third bedroom and can easily be restored to its original configuration. Seamlessly connecting the interior to the outdoor oasis are sliding pocket glass doors that retreat to open the living area to the lanai, offering both an elegant architectural feature and an added layer of protection for the block-construction core. The master suite serves as a private sanctuary with its own bay-facing impact window, a spacious walk-around closet, and a luxurious ensuite bathroom featuring a deep soaker tub and a separate walk-in shower. Significant structural upgrades provide peace of mind, including a new metal roof installed in 2023 and brand-new hurricane-rated garage doors added in 2025. The epoxy-finished garage also comes equipped with a Tesla charging station, catering to modern efficiency. The outdoor living space is a true oasis, fully enclosed by a vinyl privacy fence. Relax in the heated saltwater pool surrounded by elegant Shellock pavers, or enjoy the convenience of the lanai’s solar shower. The sprawling backyard is a nature lover’s dream, boasting a dedicated butterfly garden, a cozy fire pit, and an irrigation system powered by well water. A versatile detached storage building, currently utilized as a home gym, is equipped with its own air conditioning unit and dedicated kayak storage. Perfectly positioned just minutes from Downtown Sarasota, this home is also a short stroll from the Ringling Museum and the scenic bayfront paths of Sapphire Shores Park.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
5308 TRI PAR DR, SARASOTA, FL 34234
$179,0009 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
$675,00010 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)
940 ALAMEDA WAY, SARASOTA, FL 34234
$3,360,00047 Days on yellowkey MLS ID: A4683727
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2689 Built: 1956 Tax: $23,384 (2025)Community: Owens Alan TSingle Family
Taxes:$23,384
Remarks: Introducing a perfectly positioned waterfront gem on Whitaker Bayou where the inlet opens up to Sarasota Bay. This charming 4BR/4BA is in the sought-after Indian Beach/Sapphire Shores community an exclusive location that captures both tranquility and convenience. The home is gated and, has been completely updated and offers stunning Bay and/or Bayou views from virtually every room. You will love the light and bright interior. A wall of windows spans through the living/dining area, opening up to the elegant pool and the large covered and screened patio area. 3 of the 4BR are ensuite, which is ideal for privacy. All of them in accordance with the theme of this property: Perfect & Seamless indoor /outdoor living! The master on the ground floor opens to the pool area, the 2nd suite opens to a large deck overlooking the Bayou and Bay and the 3rd suite (2nd floor) has a balcony that captures wonderful sunset views. Perfect for maritime enthusiasts, a beautiful extended dock, 120 foot of seawall, boatlift and immediate access to the bay. This waterfront property is also ideal for vacation rentals if your goal is to generate lucrative income. Upgrades include: new HVAC, newer roof and new water heater. A waterfront haven only steps away from cultural attractions, fine dining, and boutique shopping. Coastal living in one of Sarasota’s most desired downtown neighborhoods. Call for a private showing.
Listing is courtesy of: CHARITY & WEISS INTERNATIONAL LLC (941-365-0022)
Listing Agent: Annabel Serio (941-894-7929)
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