Location: Sarasota
Do Not Show Listings
2507 BENEVA RD #10, SARASOTA, FL 34232
$159,900148 Days on yellowkey MLS ID: A4679145
REDUCED by $5,100 (3.1%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1964 Tax: $2,318 (2025)Community: Forest Lakes Country Club EstateCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,318
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to your Sarasota retreat in a highly desirable central location close to everything. This charming 2 bedroom, 2 bath corner condo on the second floor offers an ideal blend of comfort, convenience, and opportunity. The spacious layout provides a bright, open feel. Enjoy Florida living year-round from your enclosed private balcony, perfect for morning coffee, quiet afternoons, or relaxed evenings with friends. The well-maintained community features a sparkling pool, making it easy to unwind and enjoy the sunshine just steps from your door. For golf enthusiasts, The Palms Golf Club at Forest Lakes is nearby, offering a picturesque setting to practice your swing. Downtown Sarasota is just a short drive away, where you'll find a wonderful array of shops, restaurants, and cultural attractions, while the Legacy Trail, just around the corner, is perfect for biking, walking, jogging, and enjoying the natural beauty of the area. Plus, the pristine beaches of Siesta Key and Lido Key are within easy reach as well. Rentals are allowed, making this an excellent option for investors. Whether you’re looking for a primary residence, a second home, or an income-producing property, this condo offers endless potential in one of Sarasota’s most convenient locations. Schedule your private showing today and envision the possibilities!
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Ellen Gesell (941-320-3432)
2551 WILKINSON RD, SARASOTA, FL 34231
$399,9009 Days on yellowkey MLS ID: A4696791
Bed: 3 Bath: 0.0 Liv Area Sq Ft: 1469 Built: 1955 Tax: $3,559 (2025)Community: Forest HillsApartment
Taxes:$3,559
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Virtually Staged. A Piece of Sarasota History Meets Modern Opportunity: The "Siesta Key Style" Duplex with TWO separate electrical panels! Own a landmark piece of Sarasota history. Nestled on an expansive, wooded double lot at the western end of Wilkinson Road, this "Siesta Key style" bungalow offers a rare blend of timeless character and modern updates. Surrounded by a lush, quarter-acre canopy of mature bamboo, majestic oaks, and tropical palms, this property is a private sanctuary just minutes from the best of the Gulf Coast. Two units, endless potential and fully remodeled between 2023 and 2024, this versatile duplex is an ideal setup for savvy investors, multi-generational families, or those looking to "house-hack". Unit 1: A spacious 2-bedroom, 2-bathroom layout. Unit 2: A charming 1-bedroom, 1-bathroom retreat. Modern Upgrades & Peace of Mind: Every major system has been addressed so you can enjoy "turn-key" living or immediate rental income. Roof: New commercial-grade TPO membrane roof (2022) with a 30-year life. Climate: Brand new, energy-efficient mini-split AC systems in both units. Infrastructure: New plumbing throughout and separate electrical panels for each side. Interior: A fresh mix of new and restored flooring, newer appliances in unit 1, and stylish finishes. Exterior: Extra storage in the outdoor shed and plenty of room to roam & garden on the oversized lot. Location is Everything!!! Whether you’re heading to the beach, to work or to the city, you are perfectly positioned: 5 Minutes to the North Siesta Key Bridge. 12 Minutes to the vibrant culture and dining in Downtown Sarasota. 11 Minutes to the freeway for easy commuting. Don't miss this rare chance to own a functional, fully updated landmark in one of Sarasota’s most convenient locations. Some photos are visually staged. Schedule your private tour today!
Listing is courtesy of: BOUDRIE REAL ESTATE GROUP INC (941-730-5674)
Listing Agent: Rebekah Boudrie (941-730-5674)
5546 MODENA PL, SARASOTA, FL 34238
$429,000156 Days on yellowkey MLS ID: A4677319
REDUCED by $10,000 (2.3%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1693 Built: 2003Monthly Fee: $490 Tax: $4,920 (2025)Community: Villagewalk Unit 2AVilla
Taxes:$4,920
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: MAJOR PRICE REDUCTION! Recent price improvement positions this tastefully updated home competitively with less-updated recent sales in the community. The seller has authorized a substantial price adjustment and is considering alternative plans for the property should it not sell. Live the Florida lifestyle in this tastefully RENOVATED two-bedroom, two-bath villa in Sarasota’s sought-after Village Walk community. This home has the OPTIONAL EXTENDED LIVING ROOM with a larger open living area. Much more desirable in contrast to the smaller standard size offered in this model according to long time residents. the vaulted ceilings and an open layout highlight the RENOVATED KITCHEN APPLIANCES and CERAMIC PLANK-STYLE FLOORING throughout the main living areas. Major systems recently replaced, including a NEWER AC SYSTEM and WATER HEATER. Both bedrooms feature en-suite baths and WALK-IN CLOSETS. The BATHROOMS HAVE BEEN UPDATED, The primary bathroom has ALL-NEW CERAMIC TILE, COUNTERTOPS, CABINETRY, SINKS, SHOWER AND FIXTURES, while NEWER PLUSH CARPETING adds comfort to both bedrooms. Enjoy peaceful lake views from the EXPANDED AND RENOVATED LANAI, featuring PAVER FLOORING, A LARGE SCREENED ENCLOSURE, AND A REMOTE-CONTROL POWER CANOPY FOR ADDED SHADE—perfect for year-round outdoor living. Additional highlights include an interior utility room and a TWO-CAR GARAGE WITH A DURABLE, STAIN-RESISTANT FLOOR FINISH. Village Walk has a very active gated community with an event planning staff and offers high-end, resort-style amenities including extra large pools, modern complete fitness center, multiple tennis and pickleball courts, scenic walking paths, and on-site conveniences, stores, restaurants, a tiki hut bar and gas station. Ideally located in Palmer Ranch, just minutes from shopping, dining, the Legacy Trail, and Siesta Key beaches.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dan Lussier (941-900-7122)
1807 UNIVERSITY PL #151, SARASOTA, FL 34235
$199,00089 Days on yellowkey MLS ID: A4686953
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1964 Tax: $2,296 (2025)Community: Strathmore Villa Sec 09Villa
Taxes:$2,296
Remarks: Welcome to maintenance-free Florida living in the highly desirable 55+ community of Strathmore Villas! This rare beauty offers the privacy of a single-family home with only the carport and storage area attached, perfect for buyers seeking low-maintenance, and easy living in a convenient location. This 2 bedroom, 2 bathroom home features a spacious airy layout with a large living room, a separate dining area, and abundant natural light throughout, ideal for both relaxing and entertaining. The fully equipped kitchen is designed to impress with ample cabinetry, matching appliances, a butcher block center island, and unique backsplash and countertops that create a charming coastal, beach-inspired feel. The primary suite is a true retreat, complete with a private en-suite bathroom featuring a relaxing walk-in shower. The second bedroom and full guest bathroom offers flexible space, perfect for overnight guests, a home office, or hobby room. Enjoy your own tropical backyard oasis with lush landscaping, making it the prime spot for morning coffee, gardening, or soaking up the Florida sunshine in peace. Residents of Strathmore Villas enjoy resort-style, maintenance-free amenities, with HOA fees covering roof, exterior maintenance, grounds care, pest control, water, sewer, trash, basic cable, escrow reserves, plus access to a community pool and clubhouse, making this an excellent option for snowbirds or full-time residents. Location is everything, and this home delivers! You’re just minutes from UTC Mall, downtown Sarasota, St. Armands Circle, championship golf courses, top-rated restaurants, shopping, and world-famous Gulf beaches. If you’re searching for a move-in ready villa, this is the one. Don’t miss your chance to own a piece of paradise, call today to learn more!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joey Lamielle (941-350-0016)
5313 SAN JUAN DR, SARASOTA, FL 34235
$295,000136 Days on yellowkey MLS ID: N6142648
1 Days Off yellowkey (back on 6/16/2026)
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 1258 Built: 1972 Tax: $3,039 (2025)Community: De Soto LakesSpa: NoSingle Family
Taxes:$3,039
Elementary School: Emma E. Booker Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Custom Built -Great starter home with Water Views in DeSota Lakes community located in highly desirable Sarasota FL. Expansive water views from Living Room - Kitchen- Dining and both bedrooms. Sliding glass doors lead out to the covered patio with a large backyard. Wood burning fireplace will take the nip out of the air on that rare occasion. Plenty of parking for your boat/RV. This home has a lot of potential to make your very own. NO HOA or CDD fees here.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Tammy Kitt (941-284-7274)
7815 GENEVA LN, SARASOTA, FL 34243
$350,000130 Days on yellowkey MLS ID: W7882865
REDUCED by $25,000 (6.7%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1533 Built: 1990Monthly Fee: $200 Tax: $5,093 (2024)Community: Treetops At North 40 - St CharlesSingle Family
Taxes:$5,093
Elementary School: Kinnan Elementary
High School: Southeast High
Tax Year: 2024
Middle School: Braden River Middle
Remarks: Short Sale. FULLY LOADED—and FLAWLESSLY DONE! Tucked inside the boutique, tree-canopied ENCLAVE of Treetops at North Forty, this 3-bedroom, 2-bath single-family home delivers the rare combination of refined upgrades, peaceful surroundings, and an unbeatable central Sarasota location. Homes in this intimate community don’t come along often—especially not ones that have been this thoughtfully and thoroughly improved. Every inch of this home has been elevated with intention. Starting at the top, a BRAND-NEW ROOF and BRAND-NEW WATER HEATER take care of the big-ticket items buyers value most, while fresh interior and exterior paint create a crisp, cohesive look that feels both modern and timeless. The FULLY REMODELED KITCHEN is a true showpiece, featuring STONE countertops, all-new custom-style cabinetry, and a complete suite of BRAND-NEW APPLIANCES, designed to be as functional as it is beautiful. Whether you’re hosting friends or enjoying a quiet morning coffee, this space simply works. Step outside the breezeway, or plant an herb garden here, with tons of square footage for all of your plants. Both bathrooms have been COMPLETELY RENNOVATED with updated finishes, fixtures, showers and tubs, and a spa-inspired feel that turns everyday routines into small luxuries. Plush new carpet in the bedrooms creates a soft, comfortable retreat at the end of the day! A brand-new washer and dryer adds convenience, while the WHOLE HOME WATER PURIFICATION system quietly enhances daily living with cleaner, better-tasting water throughout the house. This home truly stands apart when it comes to storm preparedness. With a new roof already in place and a MANUAL-CAPABLE ELECTRIC AWNING that remains functional even during power outages, the home is thoughtfully equipped for Florida’s weather realities. Adding to its appeal, the property sits above the flood plain, offering increased confidence, reduced flood risk, and potentially lower insurance considerations—an increasingly important factor for today’s buyers. It’s a home designed not just to look good, but to perform well when it matters most. Outside, the lifestyle upgrades continue. The property is positioned on one of the largest lots in the community, backing up to protected CONSERVATION LAND for rare privacy and peaceful views with no rear neighbors. The brand-new electric awning with integrated lighting creates a shaded, flexible outdoor living space—perfect for relaxed evenings, weekend gatherings, or quiet moments surrounded by nature. Treetops at North Forty is a boutique community prized for its quiet charm, mature landscaping, and sense of retreat—yet it offers a COMMUNITY POOL, no age restrictions, no CDD fees, and a welcoming, neighborly atmosphere. All of this is just minutes from UTC Mall, SRQ Airport, New College, and the endless dining, shopping, and cultural experiences that make Sarasota so desirable. This home isn’t just updated—it’s curated, offering a polished, low-maintenance lifestyle in a community that feels private, established, and special! Opportunities like this don’t linger, so schedule your showing and experience it for yourself.
Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
Listing Agent: Brooke Overton (315-439-3013)
1315 WESTPORT LN #1412, SARASOTA, FL 34232
$289,0008 Days on yellowkey MLS ID: A4696836
0 Days Off yellowkey (back on 6/16/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1861 Built: 1972Monthly Fee: $620 Tax: $3,694 (2025)Community: Village Green Forest Lake 14Villa
Taxes:$3,694
Remarks: Experience carefree Florida living in this beautifully updated contemporary villa located in a desirable 55+ community. This elegant two-bedroom, two-bath residence with a one-car garage showcases an open-concept design enhanced by designer porcelain tile flooring throughout, custom cabinetry, quartz countertops, and premium Wolf appliances. Smart home features, LED lighting, Hunter Douglas blinds, and impact windows provide both style and peace of mind. The spacious floor plan flows effortlessly to a private setting overlooking some of the community's most lush and picturesque Florida foliage. Just steps away, residents enjoy easy access to the sparkling community pool and shuffleboard courts, creating the perfect backdrop for an active and social lifestyle. Major updates create exceptional value, including a new A/C system (2022) with Nest thermostat, water heater (2020), and both tile and flat roofs replaced in 2017. Lawn care is included, allowing more time to enjoy everything Florida has to showcase. Whether relaxing among the tropical landscaping or gathering with friends at the pool, this villa delivers the ideal combination of sophistication, comfort, and low-maintenance living. Close by are several Sarasota famous restaurants. In 1972 the construction of these villas was superior and sound. Built to last!
Listing is courtesy of: DENISE OYLER PA (941-914-6526)
Listing Agent: Denise Oyler (941-914-6526)
3537 S SCHOOL AVE, SARASOTA, FL 34239
$690,00044 Days on yellowkey MLS ID: A4691686
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1988 Built: 1961Monthly Fee: $17 Tax: $3,895 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,895
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: PRICE ADJUSTMENT of $25k. Private Oasis Awaits! This home is perfect for year round living, a Florida get away or an income generating property. It offers 3 bedrooms and 2 bathrooms and just under 2,000 square feet of comfortable living. The layout is thoughtfully designed, with 3 separate sitting areas with an abundant natural light through the large windows. The tiled flooring provides a clean, modern aesthetic, complemented by the neutral color palette. The updated kitchen is spacious, with ample wood cabinetry and a quartz countertop, providing plenty of storage and preparation space. The primary bedroom is generously sized with a bathroom, offering a comfortable retreat and a door to walk out onto covered lanai. Additional features include an inside laundry room, newer appliances, energy-efficient double-pane windows, tile roof only 10 years old and plantation shutters throughout for added charm. The outdoor space is perfect private oasis for relaxation while enjoying the sparkling resurfaced pool with a screened enclosure. The oversized lot features lush landscaping and spacious paved driveway, creating a welcoming outdoor atmosphere. In addition, the backyard is fenced in for pets with plenty of room to store watercraft. If desired, the property is Airbnb-ready and is within city limits so weekly rentals are approved. The city location makes for an ideal choice to call home to escape and relax on Siesta Key beaches or explore downtown Sarasota and all it has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kimberly Mcmahon (941-812-5092)
4476 DEER TRAIL BLVD, SARASOTA, FL 34238
$479,000127 Days on yellowkey MLS ID: A4682511
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1848 Built: 1994Monthly Fee: $285 Tax: $4,716 (2025)Community: Villas At Deer CreekSingle Family
Taxes:$4,716
Elementary School: Gulf Gate Elementary
Remarks: Beautifully updated home in Villas at Deer Creek. This home is located in one of Palmer Ranch's most beautiful mature neighborhoods. The home has many nice features. All rooms are spacious with a great open plan kitchen, dining and living areas. Adjacent to the kitchen is a beautiful built-in executive desk. Cabinets are solid wood. There are two very large bedrooms and an ofiice/den that also has a murphy bed for guests Wrap-around windows and recessed lighting keep all of the living areas light and bright. From the screened lanai you can enjoy long views of the green belt and the lake. There is an inside utility room and a large 2 car garage. The AC was replaced in 2020, This home has a touch of elegance which is seldom found in modern homes. Deer Creek is a maintenance -free community. There is a private neighborhood pool. This location allows for easy access to Lowes, Costco, Target, Publix, banks and numerous restaurants. The Legacy Bike Trail is nearby. Siesta Key is a quick 15 minute drive.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Carolyn Francis (941-400-0083)
6144 MIDNIGHT PASS RD #3N, SARASOTA, FL 34242
$1,385,00011 Days on yellowkey MLS ID: A4696434
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1967 Tax: $16,658 (2025)Community: Island HouseCondo
Taxes:$16,658
Remarks: Island House Dream Condo on Siesta Key! Experience the best of beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, unbeatable location, and effortless island living come together. Perfectly positioned in one of the most desirable beachfront buildings in the community, this second-floor condo offers truly unobstructed beach and water views with no other condo or building standing in your way. From the moment you arrive, the view takes center stage. Enjoy stunning beach views from all living areas, including the living room, guest bedroom, and master bedroom. New hurricane-impact windows and expansive glass bring the beauty of Siesta Key inside, creating a bright, open, coastal retreat from every angle. This is as close to the sand as it gets—literally beachfront and just steps from the world-famous powdery sand and warm Gulf waters. The elevated second-floor setting gives you the privacy and peace of mind you want, with no past water intrusion or storm damage to the unit, while still offering easy access to the beach and a convenient ramp for luggage. Inside, the condo is move-in ready and designed for easy beach living, featuring tile flooring throughout, an updated kitchen with solid-surface/granite counters, and beautifully updated bathrooms with elegant tiled showers. Whether you are looking for your own Siesta Key escape or an income-producing investment, the flexible 3-night minimum rental policy makes this an outstanding opportunity. Island House offers everything you need for the perfect beach lifestyle, including on-site management, refreshed landscaping, outdoor dining and game areas, beach chairs, chaise lounges, shaded beach cabanas, shuffleboard, cornhole, a heated community pool, and a clubhouse with billiards, foosball, board games, and puzzles. When you are ready to explore, hop on the free trolley or local ride-share vans to Siesta Key Village for shopping, dining, and nightlife, or venture to Turtle Beach, downtown Sarasota, restaurants, boating, fishing charters, performing arts, museums, parks, and the Legacy Trail. This is more than a condo—it is your front-row seat to Siesta Key’s legendary beach lifestyle. Bring your toothbrush, swimsuit, and love for sunsets, because this one is ready to enjoy!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Christine Walker (941-779-4342)
5610 MIDDLE AVE, SARASOTA, FL 34243
$373,90024 Days on yellowkey MLS ID: A4694925
REDUCED by $10,000 (2.6%) on 06/16/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2430 Built: 2004 Tax: $5,506 (2025)Community: Desoto AcresSingle Family
Taxes:$5,506
Remarks: INVESTOR SPECIAL / VALUE-ADD OPPORTUNITY IN DESOTO ACRES! Situated on OVER 1/2 ACRE in the desirable Desoto Acres area of Sarasota, this 2004-built 3 bedroom, 3 bathroom home offers 2,430 sq ft of living space with tremendous upside potential. Spacious layout, attached garage, and large lot create an excellent canvas for renovation, modernization, or long-term hold. Property needs TLC and updates but has strong bones and plenty of potential for the right buyer. Ideal opportunity for investors, rehabbers, contractors, or buyers looking to customize a larger home on acreage in a highly sought-after Sarasota location. Rare chance to secure a newer-built home on .59 acres with room to add value. Conveniently located near University Pkwy, shopping, dining, SRQ Airport, and downtown Sarasota. Property being sold AS-IS. Cash or hard money financing preferred. Bring your vision and unlock the potential!
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
1817 6 TH ST, SARASOTA, FL 34236
$999,99929 Days on yellowkey MLS ID: A4694609
REDUCED by $95,001 (8.7%) on 06/12/2026
Bed: 8 Bath: 3.0 Liv Area Sq Ft: 2211 Built: 1932 Tax: $12,519 (2025)Community: Gillespie Park SubSpa: NoSingle Family
Taxes:$12,519
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. Build your downtown Sarasota legacy on one of the largest and most strategically positioned parcels to come to market in Gillespie Park in years. This rare ±19,400 SF double lot (100' x 194') sits in the heart of one of Sarasota's most actively transforming neighborhoods, offering a blank canvas for contractors, custom builders, developers, and end users ready to capitalize on the city's most compelling infill corridor. DTN (Downtown Neighborhood) zoning allows for this ±0.45-acre site the potential to support approximately 5 residential units, a luxury single-family estate, a multi-generational compound, or a boutique townhome project (buyer to verify all uses with the City of Sarasota). The two combined lots create a 100-foot-wide buildable footprint that is extraordinarily rare at this proximity to downtown. Located in Flood Zone X, the property carries no mandatory flood insurance requirement and faces none of the elevation and construction cost burdens that affect so much of coastal Sarasota — a significant competitive advantage for any development pro forma. The site is clean and ready for permitting. Gillespie Park is not an emerging neighborhood — it has arrived. Adjacent to the Rosemary District (Sarasota's most walkable neighborhood with a Walk Score of 88), the area is surrounded by completed and ongoing new construction. Residents walk to Main Street dining, the Sarasota Farmers Market, Whole Foods, Sprouts, Regal Cinema, the Van Wezel Performing Arts Hall, and The Bay — Sarasota's transformative 53-acre waterfront park. Siesta Key Beach is approximately 20 minutes away. Opportunities to acquire nearly half an acre with this zoning flexibility, this location, and this lot dimension do not come along often. Whether you are a developer looking for your next high-margin project or a buyer ready to build a custom urban oasis, this is the site.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Vincent Lamaida (941-416-5654)
3927 DESOTO RD, SARASOTA, FL 34235
$725,00075 Days on yellowkey MLS ID: A4689010
REDUCED by $24,000 (3.2%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1782 Built: 1983Monthly Fee: $13 Tax: $3,686 (2025)Community: Desoto PinesSingle Family
Taxes:$3,686
Remarks: Under contract-accepting backup offers. PRICE REDUCED!!!!Set on an expansive 1.06-acre lot, 3927 DeSoto Road in Sarasota offers a rare combination of space, privacy, and versatility. The oversized parcel provides endless possibilities—whether you envision lush landscaping, additional structures, or simply enjoying the open room to spread out. At the heart of the outdoor space is a huge pool, perfect for entertaining, relaxing, or creating a true backyard retreat. With this much land surrounding it, the pool area feels private and resort-like, offering plenty of room for outdoor seating, dining, and recreation. Inside, the home features a spacious interior layout with generous living areas designed for comfort and functionality. Large rooms, open flow, and abundant natural light create an inviting atmosphere that’s ideal for both everyday living and hosting guests. This property stands out for its rare lot size, impressive outdoor amenities, and roomy interior, making it a unique opportunity in Sarasota for anyone looking for space without sacrificing convenience. Home is located very close to UTC, Benderson Park and all local beaches and downtown Sarasota.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Gabe Gadah (941-376-4229)
3988 LOSILLIAS DR, SARASOTA, FL 34238
$1,575,00025 Days on yellowkey MLS ID: OM725373
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4840 Built: 1988Monthly Fee: $323 Tax: $13,005 (2025)Community: PrestanciaSpa: YesSingle Family
Taxes:$13,005
Remarks: Nestled behind the gates of one of Sarasota’s most established neighborhoods, this Prestancia home offers quiet luxury and golf course views, where expansive indoor and outdoor living spaces epitomize Florida-living. The thoughtfully designed layout boasts a private master wing on one side, and casual living areas and additional bedrooms on the opposite. Joining the two wings are a formal dining and living room, distinguished by high ceilings, transom windows, and sliding doors which lead to an inviting outdoor retreat. The grand, master suite includes a dressing area, large walk-in closets, and a convenient, wall-enclosed dog yard for pets to safely enjoy. The adjoining master bath hosts separate custom vanities, a Roman walk-in shower, and a water-closet equipped with a hands-free electronic toilet/bidet. Just beyond the spa tub, double French doors open onto a secluded outdoor gathering space complete with a fireplace, perfect for unwinding on cozy evenings. The spacious kitchen is well suited for preparing both gourmet meals and quick refreshments served through the pass-through sliding windows that open to the outdoor eating area. Adjacent the kitchen is a large family room with soaring ceilings, a stone fireplace, and full wet bar. The outdoor oasis is bordered by the home on three sides and the 3rd hole of TPC Prestancia on the fourth, and includes a sparkling pool and spa, integrated grill, shaded area for dining and plenty of space to enjoy Florida sunshine. Residents of this Audubon Cooperative Sanctuary community enjoy watching families of sandhill cranes while bald eagles soar overhead. Just minutes from Siesta Key Beach and downtown Sarasota, the home’s new roof, pull down storm shutters, and a whole home generator provide worry-free living. Optional membership is available at TPC Prestancia Golf Club featuring two 18-hole courses, dining, and social activities.
Listing is courtesy of: BLUE MAGNOLIA REAL ESTATE LLC (352-441-0743)
Listing Agent: Heidi Jasper (352-441-0743)
7524 WESTMORELAND DR, SARASOTA, FL 34243
$5,500,00010 Days on yellowkey MLS ID: A4695898
Bed: 6 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 6215 Built: 2001 Tax: $15,233 (2025)Community: Whitfield Estates Unit 1Spa: NoSingle Family
Taxes:$15,233
Elementary School: Florine J. Abel Elementary
High School: Bayshore High
Middle School: Electa Arcotte Lee Magnet
Remarks: Set on a premier waterfront lot in the Sarasota/Bradenton area, this single-family estate offers panoramic water views, a separate guest house, and the kind of indoor-outdoor living buyers expect at the luxury level. The main residence (3806 sq ft) is designed for entertaining and everyday comfort, with expansive living spaces, a well-appointed kitchen, and seamless access to the pool and outdoor areas, while the guest house (2409 sq ft) provides ideal accommodations for visitors, extended family, or a private office retreat. Comfortable luxury living on a combined 1+ acre lot (there are 2 parcels included in this offering) with a spectacular panoramic water view. Beautifully kept grounds accented by Royal palms create the feel of a family compound that elegantly states, "You've made it!" The three-story main house has a twin grand winding staircase and an elevator to the second-floor main level. Tall double-trey ceilings w/ uplighting and massive impact glass windows and doors provide an absolutely breathtaking view of the swimming pool and the Sarasota Bay. Built on 38 concrete and steel reinforced pilings, the main house was constructed in 2001, and the windows and doors were upgraded to hurricane standards. In fact, the owner has a flood policy on the main house for just $1,200 per year. There is an oversized 3 car garage with an expanded work area and 220V power if you have an electric car. Plus, a massive unfinished storage and fun area with non-conforming pool bath below the main living area elevated approximately 18' above. The completely separate guest house also with views of the bay includes an additional 3 bedrooms, great room, dining room, full kitchen, office and attached 2 car garage. The guest house was built in 1950 and remodeled to mimic the Coastal Mediterranean style of the main house. The pool ranges from 3' to 7' in depth and includes remote control lighting and a water feature. The pool and outdoor area create the perfect setting for parties or special events. The pool is surrounded by a huge concrete deck that extends as a patio under the cover of the massive main observation and entertainment deck above. There are rough ins for an outdoor kitchen on the ground floor patio. There is also an additional observation deck off the 3rd floor living room that, with a slight zoom on your camera, provides a nice view of John Ringling bridge. Longboat Key provides night lights beyond the bay, and your own private Osprey nest adds to the natural symphony of life on the water. Boaters, you are less than a mile away from Sara Bay Marina. Commuters, you are less than 3 miles away from SRQ. Beach goers, you are less than 10 miles from Lido Beach and St Armands Circle. Professionals, you are less than 7 miles from downtown Sarasota. Kayakers, walk to the Riprap and launch! Be sure to watch the individual videos showing each interior. They are not just slideshows. This is the first time this property has been offered for sale since the builder owned it. An acre of mainland bayfront land is rare in the Sarasota/Manatee waterfront community. Don't Daydream and miss out on your Dream home. The main home is being sold partially furnished with a few exclusions. The guest house is unfurnished. Capture the Zen of waterfront living for yourself and future generations now.
Listing is courtesy of: FLORIDA INTERNET REALTY LLC (941-961-4983)
Listing Agent: Steve Rider (941-504-5163)
411 BURNS COURT, SARASOTA, FL 34236
$1,075,00029 Days on yellowkey MLS ID: A4694679
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1345 Built: 1926 Tax: $4,644 (2025)Community: Burns Court Sub OfSingle Family
Taxes:$4,644
Remarks: Under contract-accepting backup offers. This iconic commercial/residential Burns Court bungalow, the ultimate live/work space, offers a rare opportunity to restore and personalize a truly unique downtown property in one of Sarasota's most coveted historic neighborhoods. The Burns Ct. facing 2-bedroom, 1-bath main residence features a private masonry-walled back courtyard leading to a large 1-bedroom, 1-bath detached unit. This unit, with frontage on Pineapple Avenue, is ideal for commercial or residential use, a guest apartment, private office/studio, small shop... Located in the heart of nationally designated Historic Burns Court, one of downtown Sarasota’s most walkable neighborhoods, the property is just steps from an award-winning cinema, restaurants, boutiques, and the Bayfront, yet notably outside of a flood zone. Many original architectural details remain intact, including decorative ironwork, moisture-resistant plaster walls, crown molding, and original hardwood floors. A beautiful, mature oak tree provides valuable shade and enhances the home’s historic charm. The home has excellent bones for a dream restoration project, the main house featuring a 2023 roof and 2019 HVAC. Built-in equity: Zoned Downtown Core (DTC), the property includes confirmed transferable development rights (TDRs), which may be sold to a developer or investor thanks to a new historic preservation ordinance effective as of December 2025. Whether you envision creating a stunning live/work environment, generating income from a detached apartment, or designing an elegant commercial space, this charming property offers exceptional flexibility and historic character.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Erin Difazio (941-870-8060)
8340 WINGATE DR #1023, SARASOTA, FL 34238
$335,00031 Days on yellowkey MLS ID: A4694124
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1999 Tax: $4,083 (2025)Community: Pinestone At Palmer RanchCondo
Taxes:$4,083
Remarks: Light-filled, spacious, and perfectly positioned to enjoy tranquil lake views, this beautifully refreshed 3-bedroom, 2-bath condo offers 1,604 square feet of effortless Florida living. Vaulted ceilings create an airy sense of space, while the lanai and two lakeview bedrooms invite you to relax and unwind in a peaceful setting. What truly sets this property apart is the exceptional lifestyle offered by the community—where impressively low HOA fees unlock an amenity package rarely found at this price point. Enjoy a resort-style pool, full fitness center, clubhouse, movie room, tennis, pickleball, shuffleboard, library, and a vibrant social atmosphere with regular resident events. This is low-maintenance living without compromise.
Listing Agent: Daria Fairchild (941-650-7207)
7861 PINE TRACE DR #7861, SARASOTA, FL 34243
$330,000589 Days on yellowkey MLS ID: A4625460
REDUCED by $15,500 (4.5%) on 06/04/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1731 Built: 1988 Tax: $2,936 (2023)Community: Pine TraceCondo
Taxes:$2,936
Tax Year: 2023
Remarks: Virtually Staged. Find your FOREVER home in Pine Trace in Palm Aire. This community is charming and close to Palm Aire Country club which offers a variety of membership. Golf,tennis,pickleball,swimming, dinning and social are all part of this excellent facility. UTC Mall, Sarasota Airpot, St. Armands,downtown Sarasota (with cultural events and venues) unparalleled beaches, and tourist attractions are all close by. This home is updated with new flooring and paint and a fenced in yard with lush tropical foliage. The kitchen is large with stainless steal appliances and lots of storage. Two outdoor seating areas are just right for entertaining.IT IS A PERFECT HOME IN A PERFECT LOCATION TO LIVE THE FLORIDA LIFESTYLE. EASY TO SHOW
Listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE (941-921-1000)
Listing Agent: Suzanne Van Gundy (941-545-3470)
1356 POINT CRISP RD, SARASOTA, FL 34242
$4,495,00045 Days on yellowkey MLS ID: A4692551
2 Days Off yellowkey (back on 5/12/2026)
Bed: 5 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 7443 Built: 2005 Tax: $61,095 (2025)Community: Point Crisp AddSpa: YesSingle Family
Taxes:$61,095
Remarks: Virtually Staged. Ideally positioned on the exclusive Point Crisp Peninsula of Siesta Key, this waterfront estate offers a rare blend of privacy, scale, and direct boating access, with sweeping views spanning both Little Sarasota Bay and the Intracoastal Waterway. Set on over 230 feet of water frontage, the property features a newly constructed T-shaped dock (2025) and allows for effortless arrival by land or water, all complemented by the rare advantage of nearby beach access. Spanning more than 7,400 square feet of interior living space, the five-bedroom residence is designed for elevated coastal living, where expansive entertaining areas and walls of glass frame panoramic water views throughout. Freshly painted and ready for personal customization, the two-story interior is defined by high coffered and tray ceilings, crown molding, solid-core doors, and a blend of marble and wood flooring. A grand double-door entry opens to a soaring living area with a cathedral ceiling and statement fireplace, while floor-to-ceiling sliding glass doors create a seamless connection to the outdoor living spaces. The multi-level outdoor setting is designed for both gathering and relaxation, featuring an extended travertine deck, covered lounge areas, an outdoor gas fireplace, a summer kitchen with built-in grill and wraparound bar, an additional grilling station, and a heated pool and spa—all overlooking the tranquil waterfront. At the center of the home, the gourmet kitchen was redesigned in 2022 with quartzite countertops, custom cabinetry, professional-grade appliances, and an oversized island with seating. The adjacent family room offers built-in features and direct access to the outdoor entertaining areas, creating a natural flow for everyday living. The primary suite, located on the main level, serves as a private retreat with expansive water views, a custom walk-in closet, and a spacious en-suite bath. An additional guest suite on this level provides flexibility for a study, fitness room, or nursery. The second level is dedicated to guest accommodations and recreation, offering a home theater, an oversized game room with wraparound bar, multiple terraces, and three additional bedroom suites—one of which is generously scaled to function as a second primary suite—each with access to outdoor living spaces. The ground level includes a six-car split garage with multiple storage and utility rooms, supporting both functionality and flexibility. Located within one of Siesta Key’s most sought-after enclaves, this residence offers the unique combination of close beach access and protected boating waters. Just minutes away, Siesta Key Village provides dining and boutique shopping, while downtown Sarasota offers a vibrant cultural scene with theaters, galleries, waterfront parks, and marinas—delivering a lifestyle that balances coastal tranquility with everyday convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
3711 HIDDEN RIVER RD, SARASOTA, FL 34240
$750,00064 Days on yellowkey MLS ID: A4690484
1 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2164 Built: 1973 Tax: $5,521 (2025)Community: Hidden RiverSingle Family
Taxes:$5,521
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. A rare opportunity to own nearly 10 acres in one of Sarasota’s most unique aviation communities, offering the ultimate blend of privacy, space, and lifestyle. With direct access to a private airstrip, this property is ideal for aviation enthusiasts seeking the convenience of keeping their aircraft just steps from home. Set on expansive, picturesque land, the property features a private hangar, allowing for seamless fly-in, fly-out access, along with a tennis court and a variety of existing structures including a barn, stable, greenhouse, and additional outbuildings—creating endless possibilities for recreation, storage, or hobby use. The existing 3-bedroom, 2-bathroom block home offers over 2,100 square feet of living space and presents a prime opportunity for a buyer to update, renovate, or reimagine the space to their vision. Being sold as-is, the home provides a strong foundation with solid construction, making it an ideal option for investors or those looking to create a custom estate without starting from scratch. Surrounded by mature trees, natural landscape, and peaceful water views, the setting feels like a private retreat while still being conveniently located to town. Whether you’re looking to restore and personalize the existing home, build your dream estate, or create a private aviation retreat, this property offers a rare combination of land, flexibility, and lifestyle in a highly sought-after location.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Katie Cobb (913-744-0248)
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