Location: Sarasota
Do Not Show Listings
1045 FOX CREEK DR, SARASOTA, FL 34240
$3,400,00032 Days on yellowkey MLS ID: A4694380
Bed: 4 Bath: 5.0 Gar: 5 Liv Area Sq Ft: 6721 Built: 2007Monthly Fee: $25 Tax: $12,620 (2025)Community: Fox Creek AcresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,620
Elementary School: Tatum Ridge Elementary
High School: Booker High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Exclusively situated on 5.1 expansive acres, this custom-built Sarasota estate is masterfully designed as a fully self-contained private family enclave. Completely insulated from the outside world, the property is introduced by a long, palm-lined approach and a sweeping circular paver driveway, where total privacy and the Florida lifestyle are immediately evident. The primary residence spans 6,721 square feet of luxurious living space, making a grand architectural statement the moment you enter a foyer flanked by towering 24-foot ceilings. The estate showcases abundant natural light, French doors and rich maple built-ins throughout. At the heart of the home, the epicurean kitchen features elite millwork by Campbell Cabinetry, a spacious L-shaped island, a butler's pantry, and professional-grade Wolf and Sub-Zero appliances—including dual ovens and a specialized warming drawer. The fluid floor plan offers unmatched versatility, hosting a formal dining room with custom tray ceilings, a magnificent Great Room with fireplace under a 22-foot ceiling, two separate private offices, one of which has a wood-beamed cedar ceiling, and a spectacular, approximately 1,000-square-foot recreation wing outfitted with its own full kitchen and bath. Retreat to the first-floor owner’s suite, an elegant sanctuary featuring a private sitting area, a spa-inspired bath, and peaceful views overlooking the estate and pool. Outdoor living captures the estate-style relaxation, with a vast screened lanai and a sparkling saltwater pool overlooking open lawns and mature perimeter landscaping that naturally buffers the property. Recreational amenities are premier, featuring an integrated basketball court and a dedicated section of the driveway already marked for pickleball. The sprawling grounds serve as a grand retreat, anchored by an exceptional detached multi-car garage pavilion. Perfect for collectors or specialized hobbyists, this secondary structure features oversized 11-foot doors, a dedicated RV and boat storage area, carport, and a versatile, fully plumbed auxiliary suite with a full shower, ideal as a detached executive workspace or private retreat. Unequaled in structural integrity, the home functions as a fortified private fortress engineered with poured-concrete construction, comprehensive rebar reinforcement, elevated foundation, standby generator, salt-and-carbon water filtration system, separate sprinkler well, and advanced 13-camera security system. Providing space perfectly zoned to accommodate equestrian pursuits, miniature horses, alpacas, or exotic hobby collections, the OUE1 acreage offers absolute lifestyle freedom, all while being securely situated in Flood Zone X, with an exceptionally low annual HOA fee and no CDD. Positioned at the absolute center of convenience, the estate sits just 3.5 miles from Waterside Place, 4 miles from the University Town Center district, and 4.5 miles from Main Street Lakewood Ranch—placing championship golf courses, premier dining, luxury shopping, and active community calendars right at your fingertips. Surrounded by the tranquility of your private sanctuary, allure of downtown Sarasota and world-renowned Gulf Coast beaches await just moments beyond your gates.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Judi Taulbee (941-544-6227)
5365 BARTOLOMEO ST, SARASOTA, FL 34238
$725,00017 Days on yellowkey MLS ID: A4696542
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1918 Built: 2019Monthly Fee: $520 Tax: $3,651 (2025)Community: Esplanade On Palmer RanchSingle Family
Taxes:$3,651
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: Virtually Staged. One or more photo(s) has been virtually staged. Built in 2019, this meticulously maintained 3-bedroom, 2-bath residence offers 1,918 sq.ft. of thoughtfully upgraded living space designed for both comfort and functionality. The home features a spacious extended lanai complete with a Hot Springs hot tub, creating the perfect setting for outdoor relaxation and entertaining. Interior upgrades include custom California Closets in the primary suite, custom cabinetry in the laundry room, and elegant plantation shutters throughout. Additional enhancements include a 240-volt hookup for a home generator, whole-house surge protector, Culligan whole-home water filtration system, lanai hurricane shade, plantation shutters, and an extended driveway for added convenience and parking flexibility. This property combines modern construction with quality upgrades and attention to detail throughout. Esplanade on Palmer Ranch delivers a true resort lifestyle with the on-site Bahama Bar restaurant, resort pools and spa, fitness center with studio classes, 8 pickle ball courts, 2 tennis courts, 3 dog parks, scenic nature trails, and direct Legacy Trail access. Oscar Scherer State Park is just one mile away. More than a home, this is a private luxury retreat offering the ultimate blend of elegance, recreation, wellness, and Gulf Coast living. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mark Quire (941-993-5706)
708 42ND ST, SARASOTA, FL 34234
$649,00085 Days on yellowkey MLS ID: A4688855
REDUCED by $26,000 (3.9%) on 06/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1210 Built: 1936 Tax: $5,492 (2025)Community: Indian Beach Map OfSingle Family
Taxes:$5,492
Elementary School: None
High School: None
Middle School: None
Remarks: Come see this charming and peaceful Old Florida gem with detached cottage ideally situated in the desirable Indian Beach/Sapphire Shores neighborhood located west of the trail. Here is a rare opportunity to own two meticulously maintained homes within the city limits in Indian Beach/Sapphire Shores, a community rich with art, culture, and history. Picture tree-lined streets, character-filled homes, and being just moments from the shimmering Sarasota Bay. You are in for a treat as you enter the main home through a central air-conditioned enclosed front porch into a home with all of its original, timeless character including glass doorknobs, lovely baseboards and trim, vintage light fixtures, painted heart of pine floors, and functional double-hung windows. This original 1930s home (732 sf) features two bedrooms (freestanding wardrobes), one bath, and a spacious combination dining/living area. An additional wonderful highlight is the central air conditioned detached guest cottage (478 sf) with kitchen, living area, one bathroom and bedroom alcove along with a screened porch and patio, and attached one-car garage. This cottage is ideal for multi-generational living or Airbnb or full-time lease opportunities. All furnishings and fixtures convey: the front unit is partially furnished; the back unit is turn-key furnished. The property includes a very nice new 12x16 Tuff Shed ideal for an artist’s studio, workshop, or just additional storage. Set on a lush 12,000+ square foot lot, the property is spacious with plenty of room for parking, entertainment and other possibilities. You are sure to enjoy the established vegetable and flower gardens. Adding to the charm, you may catch sight of the neighborhood's colorful wild peacocks who love to display their feathers. Excellent location just minutes from the Ringling Museum, SRQ Airport, and downtown Sarasota as well as close proximity to Lido Key Beach, St. Armands Circle, and Siesta Key. Two high-end homes are currently under construction on the block. This sweet property is waiting to fit your needs whether as live-in residences, a rental investment, multi-generational living, or any combination thereof. This peaceful neighborhood in "Turks Cap" (sometimes referred to as the Museum District) has a rural feel with narrow, tree-lined streets and roaming peacocks. This is a no through street with no traffic. If you want quiet and relaxed, you have found the neighborhood.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Helen Magill (941-320-7166)
7505 WEEPING WILLOW BLVD, SARASOTA, FL 34241
$860,000277 Days on yellowkey MLS ID: O6346384
REDUCED by $15,000 (1.7%) on 06/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3141 Built: 1987Monthly Fee: $119 Tax: $8,342 (2024)Community: Bent Tree VillageSingle Family
Taxes:$8,342
Elementary School: Lakeview Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: Virtually Staged. Luxurious Lakefront Living in The Woodlands of Bent Tree! This beautiful home offers a private setting on over half an acre, backing onto a spring-fed lake in the gated Woodlands of Bent Tree. Nestled in an A-rated school district and surrounded by lush landscaping, this property combines elegance, comfort, and convenience in one perfect package. Featuring 4 bedrooms, 3 baths, a 2-car side-entry garage, and a brand new roof, the split plan design showcases both functionality and style. Enjoy formal living and dining rooms, a spacious family room with soaring ceilings, a fireplace, and a stylish wet bar. The chef’s eat-in kitchen is a showstopper with quartz countertops, stainless steel appliances, and direct access to the family room—ideal for gatherings and entertaining. Your expansive primary suite includes a spa-inspired bath with dual sinks, a jetted garden tub, large walk-in shower, and generous walk-in closet. Secondary bedrooms are equally spacious, offering flexibility for guests, family, or office space. Step outside to your private oasis: a screened pool and spa overlooking breathtaking lake views, with plenty of room to relax or entertain. The expansive backyard provides additional space to enjoy the outdoors. Just a short golf cart ride to Bent Tree Country Club or Laurel Oak Country Club, and minutes from Siesta Key Beach, UTC Mall, downtown Sarasota, shopping, and dining—this home has it all. Don’t miss this rare opportunity to own in The Woodlands of Bent Tree—schedule your private showing today and fall in love with the perfect blend of luxury, privacy, and natural beauty!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Christine Landrau (407-949-1421)
1595 PINYON PINE DR, SARASOTA, FL 34240
$649,90016 Days on yellowkey MLS ID: A4696972
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2359 Built: 2004Monthly Fee: $80 Tax: $3,631 (2025)Community: Villages At Pinetree Spruce PiSpa: NoSingle Family
Taxes:$3,631
Remarks: WELCOME TO YOUR DREAM HOME! Situated in a highly sought-after community with low HOA fees and no CDD fees, this beautifully maintained 3 bedroom, 3 bathroom single-family home delivers the perfect blend of comfort, functionality, and modern Florida living. Prepare to fall in love with this stunning, turnkey residence that perfectly blends modern luxury with everyday comfort. Every major detail has been meticulously updated, offering your total peace of mind and a true “move-in-ready” experience. THE HEART Of the HOME - Step in to a bright, expansive open-concept layout featuring a very large living room, a spacious dining room and seperate cozy den - perfect for a family movie nights or a quiet reading nook. The entire home boasts brand- new luxury vinyl plank flooring (2024), freshly painted walls in a crisp, modern palette, and beautiful designer light fixtures that add a tough of elegance to every room. MODERN CHEF’S KITCHEN - The show stoping new kitchen (2024)features contemporary cabinets, sleek countertops, ample space for meal prep and entertaining. WORK FROM HOME - The private home office is a standout feature, complete with stylish functional barn doors that adds the perfect balance of privacy and architectural charm. OUTDOOR OASIS - Step outside into your personal paradise. The sparkling swimming pool is surrounded by brand new pavers (2024), creating a pristine, resort-style setting for summer BBQs, sunbathing or evening cocktails under the stars. KEY UPGRADES - HVAC System 2024, Flooring durable luxury vinyl 2024, Paint 2024, Pool Pavers 2024, Kitchen 2024 Schedule your tour Today! This Immaculate home combines top- tier2024 renovations and won’t stay long on the market!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Basia Lenczowski (941-779-5571)
4060 WEBBER ST, SARASOTA, FL 34232
$329,50067 Days on yellowkey MLS ID: A4691042
REDUCED by $19,500 (5.6%) on 06/04/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1546 Built: 1960 Tax: $3,916 (2025)Community: Southern ViewSpa: NoSingle Family
Taxes:$3,916
Elementary School: Brentwood Elementary
Remarks: Virtually Staged. Welcome to 4060 Webber Street—an ideally located Sarasota home offering convenience, flexibility, and access to some of the area’s most sought-after outdoor amenities. Just moments from the Legacy Trail, the Sarasota Springs Trailhead, Downtown Sarasota, UTC, and world renowned beaches. This property is perfect for those looking to enjoy all that the Florida lifestyle has to offer. The home features a comfortable layout with inviting living spaces and plenty of natural light, enhanced by luxury vinyl plank flooring throughout the main living areas and primary bedroom for a clean, modern feel. The living room is anchored by a cozy wood-burning fireplace, creating a warm focal point for relaxing or entertaining. The spacious, open kitchen offers ample room for cooking, gathering, and hosting, making it the true heart of the home. The property features a fully fenced yard with a double gate on the side, providing direct access to a concrete pad—ideal for storing a boat, trailer, or additional vehicles. With no HOA restrictions, you’ll enjoy the freedom to make the most of your property without added limitations—whether for personal use or investment purposes. Located just a short drive to Siesta Key, downtown Sarasota, shopping, dining, and major roadways, this home combines accessibility with lifestyle appeal. Don’t miss this opportunity to own a versatile property in a prime central Sarasota location
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Derek Robbins (941-356-4906)
2374 ARLINGTON ST, SARASOTA, FL 34239
$579,000152 Days on yellowkey MLS ID: A4680088
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1126 Built: 1961 Tax: $6,734 (2025)Community: Arlington ParkSpa: NoSingle Family
Taxes:$6,734
Elementary School: Alta Vista Elementary
Middle School: Brookside Middle
Remarks: Virtually Staged. Located in Sarasota’s highly sought-after Arlington Park neighborhood, this thoughtfully updated residence delivers a compelling combination of comfort, functionality, and proximity to the city’s most popular destinations. With a renovated three-bedroom layout, the home is move-in ready and ideally positioned just minutes from downtown Sarasota and the area’s renowned Gulf beaches. The interior features an open-concept design that connects the living, dining, and kitchen areas, creating an easy flow for everyday living and entertaining. Luxury vinyl plank flooring extends throughout the main living spaces, while freshly painted walls in a neutral color palette enhance the light-filled atmosphere. Two updated bathrooms provide modern convenience and a cohesive finish. The kitchen serves as the heart of the home, offering granite countertops, a full-height tile backsplash, ample cabinetry, and a central island that adds workspace and casual seating. Sliding doors open to a spacious, fully fenced backyard—an inviting outdoor setting with room to relax, garden, or create a customized outdoor retreat. Additional exterior storage adds everyday practicality. Residents enjoy immediate access to Arlington Park, known for its playground, fountains, walking paths, picnic areas, basketball courts, and tennis facilities—just moments from the front door. The nearby Southside Village offers popular dining spots, local boutiques, and everyday conveniences, while downtown Sarasota’s arts, dining, and waterfront attractions are only a short drive away. World-famous beaches including Siesta Key Beach and Lido Key are easily accessible, providing endless opportunities for coastal recreation. This Arlington Park home offers an ideal balance of neighborhood charm, city convenience, and access to Sarasota’s best lifestyle amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
2660 DICK WILSON DR, SARASOTA, FL 34240
$1,299,00072 Days on yellowkey MLS ID: A4690365
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $50,000 (3.7%) on 06/05/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3166 Built: 1997Monthly Fee: $369 Tax: $6,823 (2025)Community: Laurel Oak Estates Sec 10Single Family
Taxes:$6,823
Remarks: Under contract-accepting backup offers. Laurel Oak Estates, beautifully on a private .91-acre lot with mature landscaping, this spacious four-bedroom home with office/den offers 3,166 square feet of comfortable living. Thoughtfully designed with custom window treatments, crown molding, and a deluxe lighting system throughout, the home blends elegance with everyday functionality. Kitchen features a large island, Corian countertops, white cabinetry and opens to the main living areas. Sliding glass doors lead to an expansive outdoor space with a large pool and spa, creating an indoor-outdoor lifestyle. Additional highlights include impact windows, a newer tile roof, and a three-car garage providing ample storage. In the guard-gated community, this private property offers security and serenity in a beautiful setting. Membership in Laurel Oak Country Club is optional. Two championship golf courses, 12 Tru-Har tennis courts, pickleball and an active social calendar. Come live the lifestyle!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Linda Dooley (941-400-7359)
4304 MIDLAND RD, SARASOTA, FL 34231
$340,00060 Days on yellowkey MLS ID: TB8502989
REDUCED by $34,900 (9.3%) on 05/26/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1447 Built: 1952 Tax: $3,143 (2025)Community: Floral Park HomesteadsSpa: YesSingle Family
Taxes:$3,143
Elementary School: Wilkinson Elementary
High School: Riverview High
Remarks: This meticulously maintained 3-bedroom residence offers the ideal blend of vintage Florida character and high-quality contemporary improvements—all in a prime Sarasota location. Metal roof (2011), new HVAC system (2023), and tankless water heater (2020). Original wall planking replaced with new Sheetrock and insulation to improve energy efficiency. New flooring installed in 2020 flows throughout the open-concept living areas. Private fenced backyard with a sparkling pool (2019) and an above-ground heated spa—perfect for year-round enjoyment. Conveniently situated near Sarasota’s most desirable destinations. Approximately 5 miles to the world-renowned Siesta Key Beach; it is also close to Lido Key Beach. Minutes to St. Armands Circle and Downtown Sarasota’s vibrant restaurant and cultural scene. Near major retailers, grocery stores, and the shops along Bee Ridge Road and Southside Village. Just around the corner from Bee Ridge Park with green space, playgrounds, and community activities.
Listing Agent: Brenda Olivas (407-280-0208)
8420 WEBBER RD, SARASOTA, FL 34240
$1,399,00096 Days on yellowkey MLS ID: A4687127
REDUCED by $101,000 (6.7%) on 05/06/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3104 Built: 2010Monthly Fee: $133 Tax: $5,532 (2025)Community: Regent LakeSpa: NoSingle Family
Taxes:$5,532
Remarks: One or more photo(s) has been virtually staged. LUXURY,LAND & 24 ACRE LAKE VIEW THE ULTIMATE FLORIDA LIFESTYLE Exclusive 13-Home Community- A True Hidden Gem Experience the pinnacle of Sarasota luxury living in this exceptional lakefront pool home estate set on over one plus private acre in the exclusive Regent Lake community. Showcasing the highly desirable Osprey floor plan, this expansive residence with 3104 sq ft of living space offers 4-bedrooms, office /library 3-bath offers refined living with an oversized 3-car garage and a thoughtfully designed split floor plan ideal for both entertaining and everyday comfort. From the moment you arrive, you are greeted with breathtaking panoramic views of a 25-acre spring-fed lake, delivering stunning sunsets and a peaceful, no-through-traffic setting that is truly rare to find. Inside, elegance meets functionality with formal living and dining rooms, a spacious family room, and a gourmet kitchen designed to impress. Featuring stainless steel appliances, granite countertops, upgraded wood cabinetry, built in oven microwave combination, cooktop, custom wood vent hood, walk-in pantry, breakfast bar, center island, and a bright morning room — this kitchen is truly the heart of the home. The luxurious primary suite is a private retreat, offering direct access to the pool and lanai along with serene lake views. The spa-style bath includes a garden tub, walk-in shower, dual vanities, and dual closets, including an oversized walk-in. Step outside to your screened lanai and pool area where indoor and outdoor living blend seamlessly. Enjoy tranquil lakefront views, breathtaking sunsets, and a private fenced area perfect for pets. Recent upgrades provide peace of mind and modern efficiency, including: ** Bahama hurricane shutters throughout ** New A/C (2025) ** New water heater (2025) ** Whole-house generator with buried 500-gallon propane tank ** Reinforced garage door (150 mph rated) ** Added attic insulation ** All Bedrooms have brand new Laminate flooring just installed last week Regent Lake is an intimate community of just 13 homes, offering low HOA fees, no CDD, and a lifestyle centered around privacy and nature. The spring-fed lake is navigable by canoe or kayak, adding to the unique charm of this one-of-a-kind property. Conveniently located near shopping and top-rated Tatum Ridge Elementary School, this home offers the perfect blend of luxury, location, and lifestyle. This is more than a home — it’s a rare opportunity to own a private waterfront estate in one of Sarasota’s most exclusive settings.
Listing is courtesy of: REAL ESTATE BOUTIQUE LLC (941-726-8061)
Listing Agent: Maria Atkins (941-726-8061)
5146 COTE DU RHONE WAY, SARASOTA, FL 34238
$699,90017 Days on yellowkey MLS ID: A4696420
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2578 Built: 2003Monthly Fee: $684 Tax: $5,216 (2025)Community: Silver OakSingle Family
Taxes:$5,216
Remarks: Under contract-accepting backup offers. Beautifully upgraded& expanded Tuscan style maintenance free home located in The Vineyards of Silver Oak on Palmer Ranch. Custom built by Gibralter builders & expanded to nearly 2600 sq. ft. under air. Recent upgrades include: New tile roof in 2019,replumbed in 2023, new stainless appliances in kitchen & new washer & dryer. 3 bedrooms (hidden office closet), 3 baths 2 full & 1 half bath. Upgraded Travertine look tiles, custom wood look floors in the primary & second bedrooms. Very open, light & bright great room floor plan. Kitchen has wood cabinets & granite counters. Large extended screened lanai overlooking very private preserve views ( no road noise). This boutique community of 72 homes providing maintenance for complete landscaping & irrigation maintenance. A private community center available only to The Vineyards offers a pool, fitness & cozy clubhouse with kitchen for special events. The Vineyards is located in this Executive community of Silver Oak on Palmer Ranch close to shopping, restaurants, The Legacy bike trail & just minutes from world famous Siesta Key Beach.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Cynthia Bowers (941-650-4808)
3799 COUNTRYSIDE RD, SARASOTA, FL 34233
$549,00039 Days on yellowkey MLS ID: A4694295
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1849 Built: 1982Monthly Fee: $50 Tax: $3,054 (2025)Community: Country PlaceSpa: NoSingle Family
Taxes:$3,054
Remarks: Discover Country Place a highly sought-after neighborhood of 173 homes in the heart of Sarasota, Florida. Super LOW HOA of $600 a year. Nearby School Districts including Riverview High, This 3-bedroom, 2-bathroom single-family pool home is easy to maintain with carpeted bedrooms and ceramic tile flooring throughout. ADA accessible ramps throughout. Step outside to your private screened in pool. The covered lanai at 17x35 provides great entertaining to relax with family. Inside, the home features spacious living areas and a layout brimming with potential. With its generous size, prime location, oversized fenced yard and a family-friendly neighborhood, this property is an ideal canvas to create your dream home. Whether you're looking for a quiet haven or vibrant family space near top beaches, schools and amenities, this home offers it all. Don't miss this rare opportunity, schedule your showing today! New A/C May 2025, New Pool Pump and light 2024, Pool Refinished June 2026. Pool cage and tile work upgraded in 2024, Qualifies for Hurricane Insurance Discounts, Impact Windows and Lexan Panels for the Sliders throughout give you peace of mind during Hurricane season. Fresh Paint, GE Refrigerator, Dishwasher, Pool Cage, Screening in 2025 Just a short drive to the world-renowned Siesta Key Beach, The two car garage with plenty of storage up in the attic. All this in a friendly, low HOA community ($600/year). A dog friendly neighborhood - and they have their own HOA page! Just minutes from top rated schools, area parks, the scenic Red Bug Slough and the Legacy Trail. Siesta Key’s world famous beaches and the shops and restaurants of downtown Sarasota, St Armand's Circle. SRQ, TPA RSW PGD airports all readily accessible.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
5974 SAN MICHELLE DR, SARASOTA, FL 34243
$353,900156 Days on yellowkey MLS ID: N6142540
REDUCED by $16,000 (4.3%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1531 Built: 1987Monthly Fee: $87 Tax: $2,850 (2024)Community: Longwood Run Ph 3 Pt ASpa: NoSingle Family
Taxes:$2,850
Elementary School: Emma E. Booker Elementary
Middle School: Booker Middle
Remarks: Experience serene lakefront living in this beautifully maintained 3-bedroom, 2-bath residence, thoughtfully designed as either a true three-bedroom home or a two-bedroom plus den to suit your lifestyle. Set on a tranquil lake, this home offers captivating water views and a peaceful backdrop where native wildlife and dreamy Florida afternoons take center stage. A screened front entry welcomes cooling breezes throughout the home, creating an effortless indoor-outdoor flow without the nuisance of insects. Inside, the open, airy floor plan is filled with natural light and designed for both relaxation and entertaining, perfectly capturing the essence of Florida living. Located on a quiet cul-de-sac along San Michele in the desirable Longwood Run community, this home enjoys a prime position along the University Parkway corridor—minutes from Sarasota’s world-class beaches, SRQ International Airport, downtown Sarasota, and Main Street Lakewood Ranch. Additional highlights include low annual HOA fees and a flexible rental policy allowing a minimum six-month lease once per year with no waiting period. Offered as the owners relocate to be closer to family, this is a rare opportunity to own a stunning lakefront home in an exceptional Sarasota location.
Listing Agent: Vince Fuda (941-615-8000)
7303 MANATEE ST, SARASOTA, FL 34243
$536,25069 Days on yellowkey MLS ID: A4690664
REDUCED by $28,750 (5.1%) on 05/21/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2740 Built: 1985 Tax: $4,976 (2025)Community: Whitfield Estates Blks 55-63Spa: NoSingle Family
Taxes:$4,976
Remarks: NO FLOOD * NO CDD * VOLUNTARY $35/YEAR HOA PROVIDES FINE DINING ACCESS AT Sara Bay Country Club. AVIATION ENTHUSIASTS TAKE NOTE! This bright and spacious 4 bedroom, 3 bathroom + den + bonus room contemporary home sits on an oversized fenced corner lot and offers soaring ceilings, abundant natural light, and move-in-ready peace of mind. RECENT UPGRADES INCLUDE: Hurricane impact windows (2024) Solar panels (2024) Roof (2016) Hot water heater (2025) Refrigerator (2024) Dishwasher (2019) Garbage disposal (2021) Washer (2019) Dryer (2020) HVAC (2017) Irrigation pump (2023) Located in sought-after Whitfield Estates, this unique neighborhood is in Manatee County while maintaining a Sarasota address. Conveniently positioned near Sarasota-Bradenton International Airport, residents enjoy exceptional access to everything the area has to offer. Neighborhood highlights include: 5-minute Uber to the airport 5-minute drive to multiple colleges and universities 12-minute drive to downtown Sarasota 20-minute drive to the white sands of Lido Key Beach Not a golfer but love upscale dining? Whitfield Estates residents may choose to pay the optional $35/year HOA fee, granting eligibility for a culinary membership at the exclusive Sara Bay Country Club. With its size, location, and convenience, this property also presents a strong opportunity for short-term rental income, Airbnb potential, or student housing investment.
Listing Agent: Amanda Reichert (603-377-0281)
3317 PINE VALLEY DR, SARASOTA, FL 34239
$550,000301 Days on yellowkey MLS ID: A4663718
REDUCED by $15,656 (2.8%) on 06/19/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 1964 Tax: $4,160 (2024)Community: Frst Lakes Country Club EstatesSingle Family
Taxes:$4,160
Remarks: REMODELED SPACIOUS OPEN FLOOR PLAN IN FOREST LAKES COUNTRY CLUB CLOSE TO GOLF COURSE THIS CLASSIC FEATURES A NEW KITCHEN WITH A TON OF SHAKER CABINETS AND QUARTZ COUNTER TOPS. ALL NEW STAINLESS APPLIANCES INCLUDING A KITCHENAIDE FRENCH DRAWER REFRIGERATOR.THE REMODEL INCLUDED NEW HURRICANE RATED WINDOWS THROUGHOUT AND A NEW BARREL TILE ROOF. THE INTERIOR IS FRESHLY PAINTED AND HAS ALL NEW DOORS. THE FLOORS FEATURE A MODERN WOODLIKE LAMINATE WHICH GIVES THE INTERIOR A WARM COZY FEEL. BATHROOMS WERE UPDATED WITHOUT NEW VANITIES SHOWER TILE AND STYLISH ARMITAGE AQUA FIXTURES. THE INTERIOR HAS MANY 54" CASA SALERNO CEILING FANS. HUGE FAMILY ROOM WITH FIVE PICTURES WINDOWS OVER LOOKING A SHADY BACKYARD BRINGS A TOUCH OF NATURE INSIDE.THIS EKEGANT HOME ALSO FEATURES A NEW TANKLESS HOT WATER HEATER, NEW LANDSCAPING BEDS, MYRAID OF CLOSET SPACE AND FRESHLY PAINTED EXTERIOR. THE ONLY THING MISSING IS YOU AND YOUR FRUNITURE!!
Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)
Listing Agent: Karl Helbig (941-376-7653)
8008 MIDNIGHT PASS RD, SARASOTA, FL 34242
$3,750,000220 Days on yellowkey MLS ID: A4672889
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4190 Built: 2015 Tax: $25,117 (2024)Community: Mira Mar SubSpa: YesSingle Family
Taxes:$25,117
Remarks: Welcome to the side of Siesta Key most visitors never discover — and many locals refuse to leave. Located on the peaceful southern stretch of Midnight Pass Road, 8008 Midnight Pass sits far enough from the congestion of the Village and Beach Road traffic, yet only minutes from Crescent Beach and waterfront dining. Here, mornings start with bike rides under a canopy of palms, neighbors walk dogs along quiet streets, and evenings end with sunsets reflecting across Heron Lagoon. This is the residential, laid-back Siesta Key lifestyle buyers search for but rarely find available. Behind a newly installed private gate, fresh coastal landscaping and a new perimeter wall create a true sense of arrival and privacy. The 2015-built waterfront home has been extensively improved, offering the feel of a newer construction property without the wait, cost, or uncertainty of building on the island. Inside, the home has been refreshed with new flooring throughout, fresh interior paint, updated stair railings, and designer lighting. A full Sonos surround sound system, Brilliant smart switches, Philips Hue lighting, and an upgraded security system provide modern convenience, while spray-foam attic insulation improves comfort and efficiency year-round. The completely reimagined kitchen serves as the centerpiece of the home, featuring Viking appliances, quartzite countertops and backsplash, custom cabinetry with under-cabinet lighting, a custom hood, dedicated bar area, and Viking ice maker. The open living space flows directly to expansive sliders overlooking the calm waters of Heron Lagoon — a view that immediately explains why owners love this side of the island. A flexible den with a custom Murphy bed provides additional guest accommodations, and upstairs guest bedrooms have been enhanced with wainscoting and designer wallpaper. One guest bathroom has been fully remodeled and all bathrooms have been updated with new fixtures and lighting. Outdoor living is where the property truly shines. The lagoon-front setting offers a kayak and paddleboard launch from your backyard, an IPE dock for fishing or sunset watching, and a revitalized pool area with new equipment and LED lighting. A newly screened upper balcony lanai creates a peaceful retreat above the water, while the private basketball court adds a rare amenity not commonly found on Siesta Key. This is a home designed for those who want Siesta Key without the crowds — boating, biking, paddleboarding, and quiet evenings just minutes from the beach. 8008 Midnight Pass is not just a waterfront property; it’s an opportunity to experience the calmer, residential side of island living while still being close to everything that makes Siesta Key world-famous. Schedule your private showing and experience the difference in person.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Jeff Lauer (941-441-6555)
2806 BUTTERFLY JASMINE TRL, SARASOTA, FL 34240
$948,00058 Days on yellowkey MLS ID: A4692014
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3019 Built: 2022Monthly Fee: $358 Tax: $11,880 (2025)Community: Windward At Lakewood RanchSingle Family
Taxes:$11,880
Remarks: Envision the Florida lifestyle in Lakewood Ranch at 2806 Butterfly Jasmine Trail, set on a private preserve lot within the gated community of Windward. This popular two-story Triumph model by Neal Homes features a first-floor primary suite, four bedrooms plus an office, and four full baths—each bedroom with its own ensuite—along with a convenient half bath for guests, offering a thoughtful and functional layout throughout. From the moment you enter, soaring ceilings and stunning sightlines lead straight to the saltwater pool and peaceful preserve beyond. The chef’s kitchen is the centerpiece, complete with stainless steel appliances, gas range, a large island with pendant lighting, soft-close solid wood cabinetry, under-cabinet lighting, a large pantry, and a walk-in pantry. The primary suite and two more bedrooms are located on the first floor, while upstairs offers a private guest retreat with a bedroom and full bath, along with a spacious bonus room ideal for a playroom or family room. Located just minutes from UTC, Waterside, downtown Sarasota, and the Gulf beaches including Siesta Key, Lido, and Anna Maria Island, the location is exceptional. The 9,600 sq. ft. clubhouse, two gyms, playground, tennis and pickleball courts, two dog parks, and two resort style pools making it the perfect place to reconnect with your family and neighbors. Don’t wait years to build when your dream home is awaiting you at 2806 Butterfly Jasmine Trail.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
6223 DONNINGTON CT, SARASOTA, FL 34238
$675,00036 Days on yellowkey MLS ID: A4694589
REDUCED by $10,000 (1.5%) on 06/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2081 Built: 1999Monthly Fee: $120 Tax: $4,210 (2025)Community: The HamptonsSingle Family
Taxes:$4,210
Elementary School: Ashton Elementary
Remarks: Experience Open, Modern Living in The Hamptons! Enjoy high ceilings and an airy layout with a completely remodeled kitchen and pool area. Enjoy the stunning pool views from the updated dining and living rooms. The spacious master suite features direct pool access, a luxurious en suite bath with dual sinks, and a large walk-in closet. Two additional bedrooms and one completely remodeled guest bath—while the den is perfect as a nursery, office, or gym. Cook in style in the newly remodeled eat-in kitchen with white Shaker cabinets, matte-black hardware, a trendy backsplash, and sleek white and black granite counters. The separate laundry room includes a newer washer, dryer, and wood-slab countertop. An oversized garage provides ample space for two cars, bikes, and storage. Relax or entertain in the enclosed lanai with covered outdoor dining and an inviting in-ground pool, and a paver patio deck. Located just 2 minutes from the Legacy Bike Trail, 10 minutes to Siesta Key, and close to top schools, shopping, and downtown Sarasota, this home offers unbeatable quality of life and investment value. If you're in Palmer Ranch or anywhere in 34238, you've probably noticed the big changes at US-41 and Beneva. The new vision for Sarasota Square includes curated retail, chef-driven dining, wellness and fitness concepts, modern residences, landscaped gathering areas, and a walkable, pedestrian-friendly layout. Early renderings suggest an experience-driven destination, similar to Waterside Place or Downtown Wellen-designed around how people want to live, shop, dine, and connect. For Palmer Ranch, it could become the closest thing to a true town center, bringing new energy and lifestyle appeal right to the community. Don’t miss your chance—schedule a private showing today! You will not be disappointed.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Ed Martinez (941-504-2995)
2550 WILD CHERRY PATH, SARASOTA, FL 34240
$749,00082 Days on yellowkey MLS ID: A4689137
REDUCED by $20,000 (2.6%) on 06/15/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2334 Built: 2023Monthly Fee: $370 Tax: $8,605 (2025)Community: Windward At Lakewood RanchSingle Family
Taxes:$8,605
Remarks: The best one-story value in Windward under $1M - on a coveted corner lot with room to add a pool— Welcome to 2550 Wild Cherry Path, a 3 bedroom, 3 bath + den Triumph model with 2,334 square feet of thoughtfully designed living space in one of Lakewood Ranch’s most sought-after and amenity-rich gated communities. From the moment you arrive, the tile roof, paver driveway, and mature landscaping create a warm, inviting first impression. Inside, the open layout is bright and functional, featuring 9-10 ft tray ceilings, wood-look tile flooring, and a seamless flow between the great room, kitchen, and dining area. The kitchen is well-appointed with gas appliances, a large island, generous cabinetry, and a walk-in pantry. The primary suite is spacious and private, with room for a sitting area, two large walk-in closets, and a well-designed bath with dual vanities and a walk-in shower. Two additional bedrooms and bathrooms provide flexibility for guests or family. The screened and covered lanai is built for Florida living, complete with an outdoor kitchen and additional remote electric screen for comfort and protection. Windward offers a true resort lifestyle with two pools, fitness center, pickleball, dog parks, playground, and a full-time lifestyle director. Just minutes to Waterside, top-rated schools, and everything Sarasota has to offer.
10192 MILKY WAY CIR, SARASOTA, FL 34241
$1,279,99853 Days on yellowkey MLS ID: A4692094
REDUCED by $20,001 (1.5%) on 06/17/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3847 Built: 2023Monthly Fee: $220 Tax: $13,654 (2025)Community: Skye Ranch - CassiaSpa: YesSingle Family
Taxes:$13,654
Remarks: PRICE REDUCED! Enjoy the Florida life under glowing sunset skies and serene lake views in this luxury 5 bedroom plus office, 4.5 bath, 3-car garage, HEATED SALTWATER POOL home with 3,847 square feet of interior living space and a stunning outdoor pool area that your friends and family will envy. * High-end touches include wood-look luxury laminate flooring, picture-frame and crown molding, designer lighting, and a spacious great room with a coffered ceiling. The gourmet kitchen features a large island with quartz counters, 5 burner gas cooktop with a pot filler and vented hood, French door refrigerator, double ovens (including one with an easy-open French door), a scullery/butler's pantry with wine fridge, and a walk-in pantry. The main-floor primary suite offers a custom dream closet that brilliantly connects to the laundry room and a spa-like bathroom with enormous walk-in shower and dual vanities. There is a beautiful powder room for guests, and the floorplan is both open while still having zones for privacy, including an office with French doors, a formal dining room/library, and a breakfast nook. * Upstairs, you'll enjoy a LARGE LOFT that makes for a perfect playroom, workout space, gaming lounge, or man cave. It's surrounded by four additional bedrooms (including two en suites) to create flexible space for guests and family, work, and play, with no carpet in common areas and brand-new carpet in upstairs bedrooms for comfort. * Outside, the heated saltwater pool and pavered patio are straight out of a magazine, with a dramatic 360-degree cascading spa, sunshelf, a water feature, bubblers, and umbrella holder. The shaded area features a full outdoor kitchen with a Napoleon grill, vented hood, and gorgeous backsplash, and it is enhanced by pocketing sliders for seamless indoor-outdoor living. * THIS HOME FEATURES A THREE CAR GARAGE, AND A LARGE DRIVEWAY TO ACCOMMODATE YOUR FRIENDS AND FAMILY! ** The Skye Ranch community is gated and has one of the nicest amenity centers (The HUB) in the area, featuring a resort style pool, a lap pool, fitness center, climbing wall, numerous social spaces (including a kids' lounge), an air-conditioned gymnasium, and a coffee bar. This home and neighborhood are just a quick bike or golf cart ride to the brand new districted K-8 school, Skye Ranch School; and Sarasota Suncoast Academy, The Classical Academy, and Out of Door Academy Lower Campus are also just minutes away. This community is wonderful for all ages and the house is completely move-in ready, so schedule your showing before this one gets away!
Listing Agent: Alison Stottlemyer (941-504-7260)
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