Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
2120 CRAFT LN, SARASOTA, FL 34239
$749,0008 Days on yellowkey MLS ID: A4696329
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1570 Built: 1956Monthly Fee: $17 Tax: $6,826 (2025)Community: Norwood ParkSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,826
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Beautifully remodeled coastal cottage in one of Sarasota’s most coveted locations—just minutes to Siesta Key, downtown Sarasota, and steps from Arlington Park and in the sought after Southside School District. Completely renovated late 2024, this move-in ready residence offers peace of mind with a substantial plumbing upgrade (37K) -with full repipe of all cast iron and all new hot and cold water lines. Additional all new IMPACT windows, beautiful new tile flooring throughout, and a fully transformed kitchen designed to impress. WOW that kitchen!! Quartz countertops, stylish cabinetry, designer lighting and backsplash, and effortless flow into the living spaces, the kitchen serves as the true heart of the home—perfect for everyday living and entertaining alike. All new appliances. Warm honey-toned wood-look tile creates a seamless, elevated feel throughout, while the desirable split floor plan offers both comfort and privacy. Tucked away from the guest bedrooms, the spacious primary suite feels like a private retreat and offers a rare feature for a home of this era—a generously sized closet along with a beautifully updated ensuite bath. Additional bedrooms provide flexibility for guests, family, or a stylish home office, including one space ideal for built-in workspace potential. The bright, welcoming living area invites relaxation, while the peaceful lanai, shaded beneath mature trees, creates the perfect backdrop for morning coffee, evening cocktails, or unwinding after a day at the beach. And then there is the location—truly exceptional. Just minutes to the world-famous Siesta Key, vibrant downtown Sarasota, waterfront dining, boutique shopping, arts, and entertainment. Even better, Arlington Park is only moments away, offering pools, pickleball, tennis courts, walking trails, playgrounds, and lush green space right in your neighborhood. Whether you are seeking a full-time residence, winter retreat, or investment opportunity, this home delivers the quintessential Sarasota lifestyle with style, convenience, and coastal charm.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Danelle Haag (941-806-9821)
7108 MIDNIGHT PASS RD, SARASOTA, FL 34242
$4,219,000102 Days on yellowkey MLS ID: A4685107
Bed: 7 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4697 Built: 1970Monthly Fee: $467 Tax: $10,150 (2025)Community: Siesta Properties IncSpa: NoSingle Family
Taxes:$10,150
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Remarks: A rare opportunity situated on an expansive 1.8 acres, this estate is located behind the gates of one of Siesta Key’s most exceptional estate settings. Surrounded by lush tropical foliage and serene lagoon-style water features, the property offers remarkable privacy and versatility with a 5-bedroom, 4-bath main residence and a separate 2-bedroom, 1-bath guest house—ideal for multi-generational living, hosting guests, or providing dedicated staff accommodations. The grounds evoke a secluded, natural sanctuary while remaining just minutes from Siesta Key’s vibrant dining, boutique shopping, and world-renowned coastline. Positioned within the prestigious Sanderling Club, the estate grants access to one of Sarasota’s most storied and sought-after communities. Celebrated for its historic bay-to-gulf setting and architectural significance, the Sanderling Club offers residents private beach access, 24-hour gated security, tennis and pickleball courts, a beach front clubhouse, and a members-only marina just steps from the property—delivering a refined coastal lifestyle unlike anywhere else. Located moments from the iconic, powder-soft sands of Siesta Beach, this property presents a rare chance to create a legacy residence in an extraordinary setting. Whether you choose to enhance the existing homes or envision an entirely new custom masterpiece, the possibilities are limitless. Properties of this scale within the Sanderling Club are exceptionally scarce, making this offering truly remarkable.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Maryana Zilinskiy (941-744-6065)
3137 BAY ST, SARASOTA, FL 34237
$529,99911 Days on yellowkey MLS ID: A4696080
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1672 Built: 1959 Tax: $7,057 (2025)Community: Bellevue TerraceSpa: NoSingle Family
Taxes:$7,057
Elementary School: Alta Vista Elementary
Remarks: Rare mid-century A-frame pool home in central Sarasota with no HOA and weekly rentals permitted. This block-construction home offers 4 bedrooms, 2 renovated baths, and a spacious primary suite with ensuite bath and private pool access. The kitchen features Corian countertops, under-cabinet lighting, and reverse osmosis connected to the refrigerator ice maker. Enjoy a fenced backyard with heated screened pool, excellent sun exposure, and a large paver patio for entertaining. Community park, Pompano Pickleball, and Legacy Trail access in neighborhood. Minutes to Downtown Sarasota, Pinecraft, Siesta Key, Lido Key, UTC, golf, dining, and SRQ Airport—ideal as a primary residence, vacation home, or investment property.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Sherry Rybczynski (303-325-1870)
8250 SANDERLING RD, SARASOTA, FL 34242
$18,900,000312 Days on yellowkey MLS ID: A4660281
Bed: 5 Bath: 6.0 Gar: 6 Liv Area Sq Ft: 7756 Built: 2000Monthly Fee: $450 Tax: $102,460 (2024)Community: Sanderling Club / Siesta KeySpa: YesSingle Family
Taxes:$102,460
Tax Year: 2024
Remarks: Guy Peterson's architectural masterpiece is located in Sarasota's most prestigious gated enclave. Positioned on the white sands of Siesta Key, 8250 Sanderling Road is more than a residence; it is a bold statement in modern architecture, masterfully envisioned by renowned architect Guy Peterson, FAIA. Set on 1.54 private acres with 150 feet of Gulf-front beach and 150 feet of lagoon frontage behind the gates of the exclusive Sanderling Club, this estate is a rare fusion of design innovation, artistic expression, and coastal tranquility. Widely recognized as one of Florida’s most iconic modern beach residences, the property has received top honors including the AIA Florida Test of Time Design Award, AIA Florida Gulf Coast Honor Award and the AIA Florida Excellence in Architecture Award, and has been featured in The Wall Street Journal, HGTV’s Homes Across America, Robb Report, Florida Design, Sarasota Magazine and more. It is also prominently included in Four Florida Moderns and 50 US Architects Residential and Planning, placing it among the most significant architectural achievements in the country. The home was designed as a series of four interconnected pavilions anchored in concrete and glass. It was reimagined in 2014 by the original architect, Guy Peterson, alongside Michael K. Walker and Richard Geary. The result is a striking architectural clarity that elevates the original design while introducing refined modern comforts. The sculptural façade is defined by bold horizontal lines, artful cutouts, and a seamless blend of poured concrete, steel, and sanded glass. A shell stone path leads to a dramatic entry, where the residence begins to unfold like a gallery of light and form. Inside, the interiors echo the clean geometry of the exterior. A soaring multi-level foyer acts as a central spine of the home, where light, shadow and structure interplay like a living installation. The custom-designed bar, lit by an onyx countertop, is functional and atmospheric. The dining room is framed by concrete columns and translucent glass, revealing a cinematic view of the Gulf beyond. The kitchen, anchored by warm teak millwork, features dual islands, Miele and Wolf appliances, and honed marble surfaces, creating a space as elegant as it is functional. The owner’s suite offers a peaceful retreat with a sitting area, private terrace, and coffee bar, while dual baths evoke spa-like tranquility with stone finishes and minimalist detailing. A private office with panoramic Gulf views inspires focus, while additional guest suites offer comfort and privacy with en-suite accommodations. Outside, a sprawling terrace connects indoor and outdoor living, ideal for intimate reflection or entertaining against the sound of waves. Residents of The Sanderling Club enjoy access to a private marina and beach plus 24-hour guard-gated enclave celebrated for its discretion and architectural legacy. With its distinguished pedigree and timeless design, 8250 Sanderling Road is a coastal sanctuary that honors the past, elevates the present, and secures its place among the most architecturally significant homes in on Florida’s Gulf Coast.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
6139 HOLLYWOOD BLVD, SARASOTA, FL 34231
$999,90020 Days on yellowkey MLS ID: TB8512156
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1810 Built: 1953 Tax: $9,362 (2025)Community: Pine Shores Estate 4Th SecSpa: YesSingle Family
Taxes:$9,362
Remarks: Offered below appraised value at $999,900, this truly one-of-a-kind Sarasota property presents a rare opportunity to own a private family compound just minutes from Siesta Key and located West of the Trail in the highly desirable Pine Shores neighborhood. Set on an oversized 0.34-acre gated, fenced, and walled homesite, this exceptional property offers two separate living residences, incredible flexibility, and resort-style outdoor living — all with NO HOA and NOT located in a flood zone. This property also represents an outstanding investment opportunity with a proven rental history and strong income-producing potential, making it ideal for seasonal rentals, multigenerational living, guest accommodations, or long-term investment strategies. The beautifully maintained main residence features 3 bedrooms and 3 baths with approximately 1,685 square feet of living space and is being offered fully turnkey furnished. ROOF (3 - 4 years old), HVAC 2025, TANKLESS WATER HEATER 2025. Pride of ownership is evident from the moment you arrive, with a long paver driveway leading to a charming, gated breezeway entrance and lush, low-maintenance tropical landscaping. The main home showcases polished terrazzo flooring, crown molding, remodeled kitchen and baths, granite countertops, impact-resistant windows and doors, and a state-of-the-art water filtration system. Outdoor living is exceptional with a heated saltwater pool, spa, summer kitchen, and expansive entertaining areas designed for the ultimate Florida lifestyle. Built in 2013, the detached oversized two-car garage structure adds tremendous value and versatility. Upstairs, guests or extended family will enjoy a spacious studio apartment complete with a full kitchen, breakfast bar, custom cabinetry, hardwood flooring, upgraded lighting and fans, built-in hideaway bed, full bath, and private laundry area. The garage also includes built-in storage shelving and an additional side carport. The oversized paver driveway and side access provide abundant room for boat, RV, or recreational vehicle parking. The expansive lot also offers future flexibility with room to potentially expand, add additional structures, or create a custom luxury estate environment. Located just minutes from Siesta Key Beach, Phillippi Estate Park, shopping, dining, and Sarasota’s vibrant cultural attractions, this is a truly special property combining location, privacy, flexibility, lifestyle, and investment value in one extraordinary offering.
Listing is courtesy of: MARZUCCO REAL ESTATE (239-776-5194)
Listing Agent: Lisa Kohan (239-272-5901)
6300 MIDNIGHT PASS RD #21, SARASOTA, FL 34242
$869,000144 Days on yellowkey MLS ID: A4678951
REDUCED by $30,000 (3.3%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1253 Built: 1969 Tax: $5,276 (2025)Community: Crystal Sands 1Villa
Taxes:$5,276
Remarks: Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
3324 THORNWOOD RD #3324, SARASOTA, FL 34231
$295,00090 Days on yellowkey MLS ID: A4686421
REDUCED by $12,000 (3.9%) on 06/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1981 Tax: $4,017 (2025)Community: Crooked Creek Sec 1Condo
Taxes:$4,017
Elementary School: Wilkinson Elementary
Remarks: Welcome to this beautifully updated ground-floor condo in the quiet, wooded community of Crooked Creek—locally referred to as “the hidden gem” of Sarasota. Surrounded by the 72-acre Red Bug Slough nature preserve, with private community access, this 2-bedroom, 2-bath residence offers the perfect blend of serenity and convenience, just minutes from everything Sarasota has to offer. Crooked Creek’s original two buildings, designed by Sarasota School of Architecture Modernist master architect Tim Siebert, FAIA, are constructed of CMU with stucco and reflect the clean, timeless lines of this iconic design movement. Inside, the home showcases a contemporary coastal aesthetic filled with natural light and thoughtful design. Hardwood floors flow throughout the main living spaces, complemented by stone flooring, built-ins, detailed molding, and plantation shutters, creating a refined and cohesive look. Four sets of French doors open to a stone-floored Florida room, allowing sunlight to pour into the home while offering peaceful views of the surrounding wooded landscape. Just off the kitchen, a private patio provides an additional outdoor space ideal for morning coffee or quiet relaxation. The kitchen features a recessed ceiling, granite countertops, stainless steel appliances, and a stone backsplash—blending both style and functionality. The spacious primary suite easily accommodates a sitting area or workspace and includes a beautifully appointed ensuite bath with double vanity sinks, stone basins and backsplash, tiled walls and floors, and a soaking tub with an overhead rainfall shower. The great room offers custom built-in shelving and a cozy electric fireplace, creating a warm and inviting space for relaxing or entertaining. This home also includes a security system for added peace of mind. Residents enjoy a range of community amenities including a pool, pool house with kitchen, gazebo, grills, tennis and pickleball courts, carport, storage room, and charming pedestrian bridge—all set within a lush, park-like environment. Located in a peaceful natural environment yet just minutes from world-renowned Siesta Key Beach, as well as shopping, dining, and entertainment, this Crooked Creek condo delivers the very best of Sarasota living.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
8501 MIDNIGHT PASS RD, SARASOTA, FL 34242
$29,995,00036 Days on yellowkey MLS ID: A4692839
Bed: 6 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 12000 Built: 2024 Tax: $141,465 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$141,465
Remarks: Set across nearly three acres of pristine waterfront on Siesta Key, Crystal Waters is the most significant private estate in Sarasota—a once-in-a-generation offering that redefines luxury living on Florida’s Gulf Coast. With extraordinary scale, architectural pedigree, and 217 feet of direct Sarasota Bay frontage, this landmark property represents a level of craftsmanship, beauty, and exclusivity rarely seen in the region. Designed by renowned architectural firm Stofft Cooney Architects and custom-built by Chris Jorgensen of Florida West Builders, the Palm Beach-inspired estate encompasses 10,267 square feet with five bedrooms, six full baths, and two half baths. Surrounded by lush tropical gardens and panoramic bay views, every aspect of the property has been conceived to deliver an unparalleled waterfront lifestyle. A dual-gated arrival along a Tabby seashell drive leads to a stately façade framed by towering palms and a grand porte cochère. Beyond solid mahogany doors, a magnificent foyer welcomes guests with travertine floors inlaid with cabochon stone and a sweeping staircase featuring hand-crafted Chippendale railings. Walls of impact glass dissolve the boundary between indoors and out, filling the residence with natural light and uninterrupted views of Sarasota Bay. Refined details include a natural gas fireplace with imported limestone hearth, hand-crafted Vitali European oak flooring in a warm Milano finish, custom millwork, and a serene palette of coastal hues. The kitchen is both a showpiece and gathering place, appointed with custom Campbell cabinetry, Cristallo quartzite surfaces, a custom La Cornue range, dual islands, and walk-in and butler’s pantries. A bayfront breakfast nook and formal dining room open seamlessly to expansive waterfront terraces. Nearby, the clubroom showcases hand-painted Gracie chinoiserie panels, vaulted cypress ceilings, and a wet bar. The first-floor primary suite serves as a private sanctuary overlooking the bay, with French doors opening to the pool terrace. Custom dressing rooms and spa-inspired baths surround a striking octagonal vestibule featuring New Ravenna mosaic floors, Calacatta Matarazzo quartzite, a soaking tub, and marble-clad shower. Upstairs, guest suites, a lounge, and an exercise room provide exceptional accommodations. An Old Florida-style guest residence above a four-car garage offers Pecky Cypress-lined interiors, vaulted ceilings, a full kitchen, covered balcony, and spacious bedroom suite. The main residence is further complemented by an oversized three-car garage. Outdoors, winding pathways lead through beautifully curated grounds to a spectacular 56-foot vanishing-edge saltwater pool that appears to merge with the bay beyond. A covered waterfront pavilion with fireplace, summer kitchen, and tongue-and-groove ceiling creates an elegant setting for entertaining. A private tennis court and lighted pavilion with lounge and fireplace complete the resort-caliber amenities. Along the shoreline, a 90-foot dock extends into Little Sarasota Bay and features a floating kayak launch and a 20,000-pound lift capable of accommodating a 34-foot vessel. Crystal Waters is more than a residence—it is Sarasota’s defining waterfront estate. Unmatched in scale, setting, craftsmanship, and provenance, it stands as one of the finest private properties ever created on Florida’s Gulf Coast. Available lot for sale directly across the street enjoys beach access.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
1966 WISTERIA ST, SARASOTA, FL 34239
$3,349,000244 Days on yellowkey MLS ID: A4668324
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $51,000 (1.5%) on 05/15/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3934 Built: 2026 Tax: $9,291 (2025)Community: Desota ParkSpa: YesSingle Family
Taxes:$9,291
Remarks: Under contract-accepting backup offers. Set within the coveted West of the Trail enclave, this newly constructed estate is a striking statement of contemporary design and quality craftsmanship. Thoughtfully designed with clean architectural lines and seamless indoor-outdoor flow. Exceptional attention to detail throughout the residence with 4-bedrooms + office/den + bonus loft and 6-bathrooms. European engineered hardwood and porcelain tile flooring, 9-foot interior doors, recessed ceilings and lighting, and a Level 5 wall finish. PGT impact-resistant, Low-E windows and expansive sliding glass doors flood the interiors with natural light. The open-concept great room is a dramatic focal point, featuring a soaring double-height ceiling and a striking slatted wood accent wall. State-of-the-art kitchen with premium Thermador appliance package, custom Studio Luxe cabinetry by Miralis, quartz countertops, and a waterfall island with designer breakfast bar seating. Opening seamlessly to the dining area and covered lanai, creating an ideal setting for entertaining. Large walk-in pantry, dedicated laundry room with Electrolux washer and dryer, elevator-ready storage space, and private office ensure everyday convenience is met with elegance. The main-level primary suite serves as a private retreat, featuring a spa-inspired bathroom and professionally designed, boutique-style custom closet. The second level offers three en-suite bedrooms, each with beautifully finished bathrooms and walk-in closets. Bathrooms are appointed with quartz countertops, LED mirrors, frameless glass shower enclosures, designer tilework, multiple shower heads, built-in niches, and integrated bench seating. A spacious loft lounge includes a wet bar with beverage refrigerator. Two expansive balconies provide additional space for relaxation or entertaining. Enjoy serene moments by the heated saltwater pool and integrated spa, covered lanai with summer kitchen, including grill, sink and refrigerator, and a dedicated poolside half bath. The backyard is fully enclosed with a six-foot privacy fence and includes green space suitable for pets or gardening. The pool area is screen-enclosure ready for year-round enjoyment. Ideally located just minutes from downtown Sarasota, top-rated schools, dining, shopping, and cultural attractions, this exceptional residence offers a rare opportunity to enjoy sophisticated West of Trail living with uncompromising design integrity and quality. Offering a one-year full developer warranty.
Listing Agent: Linda Driggs (941-374-2920)
5547 ASHTON LAKE DR #5547, SARASOTA, FL 34231
$299,50092 Days on yellowkey MLS ID: A4686214
3 Days Off yellowkey (back on 4/26/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1225 Built: 1990Monthly Fee: $550 Tax: $3,248 (2025)Community: Ashton Lakes 01 & 02Condo
Taxes:$3,248
Elementary School: Gulf Gate Elementary
Remarks: Location, Location, Location! Only 3.5 miles to the world-famous Siesta Key Beach. Close to I-75 and rte.41, shopping, hospital, schools and restaurants. A much sought after 2-bedroom, 2 bath, ground floor unit, garage, front porch, screened lanai with a captivating view of spring fed Sunnyside Lake and fountains can be yours. Bright & airy. Partially furnished. Ashton Lakes Community is located on 33 acres of luscious greenery, with 4 lakes, a combination of 2 tennis courts & 4 pickleball courts, 2 heated pools, one large with a lap lane, shuffleboard, clubhouse, grilling stations, and other amenities. we are connected to Merchants mart shopping center by a foot bridge. Shops include CVS, ACE hardware, liquor, Dollar store, restaurants and the famous Detwillers farm market for your shopping convenience. Come, make this slice of heaven your paradise in the sun. Disclosures attached. Roof 2010, Water heater 2015, Air handler 2022.
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Philip Abraham (941-441-6958)
2945 UPPER TANGELO DR, SARASOTA, FL 34239
$660,00050 Days on yellowkey MLS ID: A4690742
2 Days Off yellowkey (back on 6/9/2026)
REDUCED by $35,000 (5.0%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1439 Built: 1960 Tax: $6,132 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,132
Remarks: A rare offering within Sarasota’s desirable South Gate community, this meticulously restored Atomic Ranch embodies the essence of authentic Mid-Century Modern design. Revered as one of the foundational architectural styles of the 20th century, this residence has been thoughtfully preserved and elevated by discerning owners who understood the importance of honoring its original integrity. Ideally positioned in the heart of Sarasota, the home offers effortless access to world-class beaches, premier shopping and dining, top-rated schools, Sarasota Memorial Hospital, and the vibrant downtown district. The residence unfolds with a seamless, open-concept design, featuring three spacious bedrooms and two bathrooms, an inviting eat-in kitchen area, and expansive living areas designed for both comfort and entertaining. Walls of vintage sliding glass doors dissolve the boundary between indoors and out, opening to a generous pool terrace. Both covered and open-air, this creates a true indoor-outdoor lifestyle synonymous with classic Florida modernism. Authentic details remain beautifully intact, including original terrazzo flooring throughout, vintage architectural elements, and curated mid-century finishes that speak to the home’s heritage. An oversized garage, along with substantial fenced exterior space, provides flexibility for additional parking, including room for a boat or recreational vehicles. The home has been featured on Sarasota’s renowned “MOD Tour,” celebrated for its originality and preservation. As noted during the tour, the residence showcases vintage sliding glass walls, vibrant period kitchens and baths, and a fluid connection to the pool area. Carefully selected furnishings that reflect the era enhance the spirit of 1960s design. This is a truly special opportunity to own a piece of architectural history. Thoughtfully restored, exceptionally located, and ready to be experienced.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
2632 SUNNYSIDE ST, SARASOTA, FL 34239
$395,00054 Days on yellowkey MLS ID: A4690325
3 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1578 Built: 1957Monthly Fee: $17 Tax: $4,699 (2025)Community: South GateSingle Family
Taxes:$4,699
Remarks: Under contract-accepting backup offers. Charming mid-century modern 3 bedroom, 2 bathroom home with an oversized 2-car garage, located in the established, deed-restricted South Gate neighborhood of Sarasota. Offering classic Florida style, the home features original terrazzo flooring throughout the home with the exception of ceramic tile in the kitchen and a functional layout with a spacious primary bedroom that includes an en-suite bathroom and walk-in closet. The living room features a built-in bookshelf, and an enclosed sunroom offers flexible space for a home office or additional family area. The home retains original features and offers ample storage throughout, plus a bonus workshop suitable for hobbies or projects. Recent updates include AC replacement (2023) a new garage door (2023), and brand-new toilets. Home is connected to county sewer and comes with Hurricane shutters. The optional South Gate Community Association offers access to a community pool and community center, including the architecturally significant Victor Lundy-designed property with events and weekly classes. Located in the highly sought-after Southside Elementary school district and near Southside Village, Sarasota Memorial Hospital, and just minutes to Siesta Key Beach, with convenient access to shopping, dining, and everyday amenities.
Listing Agent: Rachel Harvey (941-726-9300)
1280 DOLPHIN BAY WAY #503, SARASOTA, FL 34242
$1,589,00087 Days on yellowkey MLS ID: A4687031
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2217 Built: 1998Monthly Fee: $1,985 Tax: $13,269 (2025)Community: Dolphin Bay-Siesta Key Sec ACondo
Taxes:$13,269
Remarks: Under contract-accepting backup offers. Experience endless panoramic views of downtown Sarasota and Sarasota Bay from the climate-controlled balcony of this newly renovated top-floor residence in the gated community of Dolphin Bay on Siesta Key. This spacious condo offers over 2,200 square feet of beautifully updated living space, featuring 2 bedrooms, 2 bathrooms, and a den, all enhanced by vaulted ceilings that create an open and airy coastal atmosphere. Enjoy stunning sunsets over Siesta Key Beach from the front entryway each evening, and wake to beautiful sunrises from the primary bedroom and lanai—an exceptional feature of this remarkable home. Residents of Dolphin Bay enjoy a true waterfront lifestyle with access to a private community dock, clubhouse, tennis courts, fitness center, and a resort-style pool. A private one-car garage, with epoxy flake floors, is conveniently located just steps from the elevator. Perfectly situated within minutes of the beach, shops, and restaurants, this residence combines luxury, convenience, and the best of Siesta Key living. Enjoy the waterfront lifestyle at its finest in this exceptional move-in-ready home. Contact me for a private showing today.
300 GARDEN LN, SARASOTA, FL 34242
$2,790,000284 Days on yellowkey MLS ID: A4662830
REDUCED by $209,000 (7.0%) on 05/21/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$12,545
Remarks: A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Holly Parry (941-809-8050)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000349 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
2304 RINGLING BLVD #101, SARASOTA, FL 34237
$139,000228 Days on yellowkey MLS ID: A4670262
REDUCED by $6,000 (4.1%) on 05/11/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 552 Built: 1965Monthly Fee: $577 Tax: $1,641 (2024)Community: Garden AptsSpa: NoCondo
Taxes:$1,641
Remarks: **!! SELLER SAYS……SELL !!** Seller will cover the remaining monthly fees for the rest of 2026 with an acceptable offer. THE BUYER WILL SAVE OVER $3,000.00!! Welcome to this charming ground floor, 1 bed 1bath condo within walking distance of all of Sarasota’s splendor! This unit is in excellent condition and boasts tile floors throughout. Newer kitchen appliances, counter tops and cabinets. This condo is light, spacious and accessible. This home also has its own reserved parking space and there is guest parking on site. The association has just updated the laundry facility with brand new washers and dryers. It is perfect as a weekend get-a-way, or as your primary residence. It is also in a rental friendly community and has an excellent long-term rental history. Whether you are an investor or an empty nester, this condo is ready for occupancy!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: David Dangelo (941-587-7268)
2110 MICHELE DR, SARASOTA, FL 34231
$2,525,000355 Days on yellowkey MLS ID: A4657130
REDUCED by $24,000 (0.9%) on 05/02/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4623 Built: 2025 Tax: $3,317 (2024)Community: MonticelloSpa: YesSingle Family
Taxes:$3,317
Remarks: OPEN, FLEXIBLE FLOOR PLAN designed to accommodate a variety of wishes and needs. New custom luxury home for sale in Sarasota Florida located on Coquina Island. This high-end Sarasota luxury estate features a private in-law suite, resort-style pool and spa, outdoor kitchen, and over 4,000 square feet of modern coastal living. One of a kind design to optimize the homesite, is located in the heart of Sarasota County offering luxury & timeless contemporary design. Just minutes from Phillippi Mansion Park, Siesta Key Beach, top-tier shopping, dining, Sarasota Memorial Hospital, Selby Gardens, and downtown Sarasota, this home enjoys a prime location. Key Features: 5 Bedrooms | 5 1/2 Bathrooms. 38' Wide Polyaspartic Garage with high ceilings, music speakers and 2 ceiling fans (space allows lifts in each bay). 13' High Ceilings in the great room. Gourmet Kitchen with sleek appliances, large island, cooktop hood, double wall ovens, coffee bar, and an expansive walk-in pantry with custom shelving and room for a full freezer or refrigerator. Truly a chef's delight! Spacious Master Suite with paver deck on main floor, his and hers huge walk-in custom closets, ensuite luxury bath. Private multiple decks and a large paver lanai overlooking the Pebble-Tec heated saltwater pool with spillover spa and outdoor kitchen Separate In Law Suite above the garage with a great room, full kitchen, bath, bedroom, laundry room, and balcony. Energy Efficient with Icynene insulation, soundproofed walls, and potential for solar power or generator. 3 HVAC units and zones. Instant hot water heater; separate water heater for in law suite, tankless hot water heater as well in main living spaces. Interior Highlights: High-end finishes and 2 custom-built open staircases. Wood and tile floors throughout. Floor-to-ceiling windows flood the home with natural light. Fully structured wiring for sound; 19 music speakers and 8 security cameras. Large laundry room with custom cabinetry, laundry sink, stone folding counter and hanging rod. Spacious pantry with custom shelves; electric dedicated circuit for additional freezer or refrigerator. Insulation in walls & ceiling for sound mitigation. WiFi mesh inside & out. Outdoor Oasis: Heated Saltwater Pool & Spa with spillover waterfall and floor clean system. 8 Security cameras. Outdoor Kitchen featuring marine-grade cabinets. Professionally designed tropical gardens with private well for the sprinkler system. LED Lit Circle Paver Driveway adds striking curb appeal. The home has been specifically designed for its setting, with eye appeal on all sides. Too many extra features to list! It is in a very quiet neighborhood, yet close to Sarasota. You will not be disappointed in this home!
Listing is courtesy of: FLORIDA HOME TEAM LLC (941-486-0012)
Listing Agent: John Ask (941-486-0012)
1794 CUNLIFF LN, SARASOTA, FL 34239
$2,997,00099 Days on yellowkey MLS ID: A4685523
REDUCED by $98,000 (3.2%) on 05/21/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3377 Built: 2015 Tax: $39,491 (2025)Community: Bay View Heights AddSpa: YesSingle Family
Taxes:$39,491
Remarks: Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed in natural light. Oversized 10-foot doors frame every room, while hurricane-impact sliding glass doors seamlessly connect the interior to a resort-style outdoor oasis. The expansive pool deck showcases a stunning lighted fountain spilling from the spa into the oversized pool, a rainfall pergola, and lush tropical landscaping surrounded by a six-foot privacy fence—creating the ultimate setting for both relaxation and entertaining. Built with the signature craftsmanship of Allegra Homes, the residence features exceptional custom millwork, striking feature walls, designer lighting, and distinctive ceiling details throughout. Spanning 3,582 square feet, this thoughtfully designed home offers four spacious bedrooms, three luxurious bathrooms, a private den/office with a turret ceiling, and a versatile bonus room. The gourmet kitchen—one of Allegra’s most beloved layouts—is a true culinary showpiece, appointed with Sub-Zero and Wolf professional-series stainless steel appliances, including a five-burner natural gas cooktop, a second Sub-Zero beverage refrigerator, custom luxury cabinetry, rich 3cm granite countertops, and a glass tile backsplash with hidden electrical outlets Adjacent to the kitchen, the elegant dining room features a dramatic aquarium glass window overlooking the pool and gardens, along with a built-in buffet accented by a mirrored feature wall. The home’s split floor plan provides exceptional privacy. The serene primary suite is a private retreat, offering a spa-inspired bath with a walk-through shower, dual vanities, and a private water closet. A custom walk-in closet features built-in shelving, drawers, and a hallway dressing mirror. The bedroom is highlighted by an intricate custom ceiling design, designer lighting, and private access to the pool deck. On the opposite side of the first floor, you’ll find a built-in desk alcove, a spacious laundry room, a secondary bedroom with a walk-in closet, a full hall bath, and the bonus room with disappearing sliding glass doors that open to the screened pool area. The first level features rich porcelain wood-style flooring, while the second level is comfortably carpeted and hosts the third and fourth bedrooms, along with a media closet and additional HVAC storage. Bahama shutters and custom blinds complete the bedrooms and bathrooms. Situated on a 0.28-acre elevated lot, built above the flood plain in 2015, this exceptional residence offers privacy, luxury, and an unbeatable central location. Just minutes away are Sarasota Memorial Hospital, Southside Village, and top-rated Southside Elementary, with Siesta Key Beach, downtown Sarasota, Westfield Siesta Key Mall, and St. Armands Circle only a short drive away. This remarkable property may be purchased turnkey furnished, including original artwork, bronze sculptures, designer furnishings, and custom rugs, available under a separate bill of sale. Schedule your private showing today. Proof of funds required with all offers.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Jill Berg (941-315-1199)
3117 JAMAICA ST, SARASOTA, FL 34231
$369,900126 Days on yellowkey MLS ID: A4681988
0 Days Off yellowkey (back on 6/8/2026)
REDUCED by $9,600 (2.5%) on 06/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1800 Built: 1980 Tax: $1,935 (2025)Community: The WlySpa: NoSingle Family
Taxes:$1,935
Remarks: Outstanding Sarasota location for this truly unique lakefront home, complete with a small private dock. Nestled on a wooded, private lot, the setting offers a peaceful retreat that feels worlds away—yet is just minutes from everything Sarasota has to offer. Inside, generous living areas and soaring ceilings create an open, airy atmosphere ideal for both everyday living and entertaining. There is ample space for gatherings, along with a versatile bonus area perfect for a study, den, or gallery. The main-floor primary suite features a walk-in closet for added comfort and convenience. The two-car garage is currently configured as a one-car garage with additional flex space that could serve as a bedroom or office and can easily be converted back to a full two-car garage. Two spacious upstairs bedrooms share a conveniently located bathroom. A large enclosed, air-conditioned lanai with French doors opens to a serene back patio, offering tranquil lake views and abundant wildlife. This home radiates warmth and character, reflecting years of cherished family and friend gatherings. Located just one block from Bee Ridge Park, which offers basketball, volleyball, softball fields, and a shaded playground, and within a highly sought-after school district for elementary, middle, and high school. Sarasota Memorial Hospital is only three miles away, downtown Sarasota just five miles, and world-famous Siesta Key Beach approximately seven miles away—featuring exceptional dining, shopping, and cultural attractions. This property has never flooded and sits well above sea level.
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
3246 MAIDEN LN, SARASOTA, FL 34231
$524,90075 Days on yellowkey MLS ID: A4688107
REDUCED by $24,600 (4.5%) on 06/05/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2170 Built: 1983 Tax: $4,622 (2025)Community: Kallas SubSingle Family
Taxes:$4,622
Remarks: **This is The One!** Prime Sarasota location just minutes to Siesta Key Beach, Downtown Sarasota, and more! This property offers strong potential as a primary residence, seasonal home, or investment opportunity. **NEW Roof in 2021** Functional layout with solid bones and opportunity to update or customize to maximize value. Private outdoor space and convenient access to shopping, dining, medical facilities, and I-75 add to the appeal. Ideal for buyers looking to capitalize on location and long-term upside in a highly desirable area. **NO HOA or Deed Restrictions** The Florida room provides the perfect spot to enjoy your morning coffee or unwind in the evening, and it opens to a spacious outdoor area—ideal for taking full advantage of Florida’s beautiful weather year-round. This property offers a versatile bonus space currently set up as a workshop **Potential to turn bonus space into living space/in-law suite with private entrance**, along with an additional climate-controlled room perfect for a home gym or flex space. Equipped with a 2-car attached garage PLUS an extra driveway on the side **Ample room for storing a Boat, Trailer, Lawn equipment, or other recreational vehicles.** Enjoy the freedom to truly make the space your own with endless possibilities. In addition, enjoy tons of storage space for all your holiday decorations and any additional items you may need to tuck away. Don't miss out on this incredible property - Reach out to schedule your private tour today! **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Ryan Miller (941-954-6925)
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