Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
5780 MIDNIGHT PASS RD #210, SARASOTA, FL 34242
$999,000203 Days on yellowkey MLS ID: A4673708
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,269 (2025)Community: Gulf & Bay Club Ph 2Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,269
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: BEST VALUE AT SIESTA KEY BEACH GULF & BAY CLUB. Imagine living in Paradise…Welcome to your dream home on Siesta Key, where every day feels like a vacation. This beautiful beachfront corner unit in the prestigious GULF & BAY CLUB is located on the #1 Beach in America per Trip Advisor. Step into this stunning two-bedroom, two-bathroom unit, filled with natural light from expansive windows. Enjoy breathtaking sunrise and sunset views as part of your daily routine. The renovated interior features high ceilings, a gourmet kitchen with an office, modern bathrooms, smart storages and elegant details. Gulf & Bay Club is the gated resort community on the key. The serene property spans on 32 acres with 800 feet of private quartz sand beach, offering exceptional living. Beyond your home, Gulf & Bay Club offers world-class amenities, including scenic pathways to a freshwater lake with a rustic footbridge, a lush tropical courtyard with 3 heated pools, 6 pickleball courts, 4 tennis courts, 2 clubhouses and barbecue grills for social gatherings. Fitness enthusiasts can access a commercial gym, sauna, and media facility, while EV charging stations promote eco-friendliness. With an on-site rental management for one-month minimum rentals, this property is perfect for luxurious living and smart investment. Make this waterfront oasis your home where warm hospitality and serenity await.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Maurice Menager (941-238-8119)
3317 PINE VALLEY DR, SARASOTA, FL 34239
$550,000296 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
Elementary School: Wilkinson Elementary
High School: Sarasota High
Tax Year: 2024
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)
3229 BENEVA RD #203, SARASOTA, FL 34232
$190,00030 Days on yellowkey MLS ID: A4694705
REDUCED by $5,000 (2.6%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1978 Tax: $2,064 (2025)Community: Village Brooke Sec 3Condo
Taxes:$2,064
Remarks: Experience the perfect blend of modern style, privacy, and Sarasota convenience in this beautifully renovated second-floor condo at Village Brooke Condominium. Ideally positioned with no upstairs neighbors, this move-in-ready residence offers exceptional privacy and peaceful living just 6 miles from the world-famous Siesta Key Beach. Completely renovated from top to bottom, this beautiful condo features new flooring, fully updated bathrooms, modern recessed lighting, and a designer kitchen showcasing brand-new cabinetry, quartz countertops, and new stainless steel appliances. Every detail has been thoughtfully upgraded to create a fresh, contemporary feel rarely found in Village Brooke. Enjoy true maintenance-free living with the condo association covering exterior maintenance, grounds maintenance, private roads, cable TV, water, and sewer. Residents also enjoy resort-style amenities including two community pools, tennis courts, and shuffleboard courts — all within a beautifully maintained, centrally located Sarasota community close to shopping, dining, downtown Sarasota, and Florida’s Gulf Coast beaches. Whether you’re searching for a full-time residence or winter retreat, this fully updated condo delivers style, convenience, and value in one of Sarasota’s most desirable locations.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kathy Vandorne (941-275-3934)
3225 GULF WATCH CT, SARASOTA, FL 34231
$399,0005 Days on yellowkey MLS ID: TB8519650
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1216 Built: 1990Monthly Fee: $133 Tax: $3,345 (2025)Community: Gulf Gate GlenSingle Family
Taxes:$3,345
Elementary School: Gulf Gate Elementary
Remarks: Nestled within the desirable Gulf Gate Glen community, this location offers the perfect blend of convenience, recreation, and the laid-back Florida lifestyle that makes Sarasota so sought after. Residents enjoy being just minutes from the powder-soft sands of Siesta Key Beach, consistently ranked among the best beaches in the country. Whether you're spending the day boating on Sarasota Bay, exploring nearby waterfront parks, or taking in a breathtaking Gulf Coast sunset, this location places the very best of Sarasota right at your fingertips while remaining outside of a flood zone. Stepping inside, you'll immediately notice the soaring vaulted ceilings, abundant natural light, and luxury vinyl plank flooring that flows throughout the home. This well-designed floorplan offers 2 bedrooms, 2 bathrooms, and a spacious 2-car garage, creating the perfect balance of comfort and functionality. The kitchen features stainless steel appliances and overlooks a dining area, making everyday living and entertaining effortless. The owner's suite serves as a private retreat with a walk-in closet and an ensuite bathroom complete with dual sinks and a walk-in shower. French doors lead to the screened-in lanai, providing the ideal space to enjoy your morning coffee, unwind in the evenings, or entertain guests while enjoying Florida's year-round sunshine. One of the biggest advantages of living here is the everyday convenience. Gulf Gate Village is just around the corner, offering an eclectic mix of locally owned restaurants, coffee shops, bakeries, live music venues, and neighborhood bars that create a true sense of community. For shopping, dining, and entertainment, you're only a short drive from Downtown Sarasota, St. Armands Circle, and the countless cultural attractions that make Sarasota one of Florida's premier destinations. Outdoor enthusiasts will appreciate easy access to Legacy Trail, one of the area's most popular biking and walking trails stretching for miles throughout Sarasota County. Nearby parks, marinas, fishing spots, kayak launches, golf courses, tennis facilities, pickleball courts, and fitness centers provide endless opportunities to enjoy an active Florida lifestyle. Families will appreciate the proximity to highly regarded schools, while commuters benefit from quick access to US-41, making travel throughout Sarasota, Venice, and Lakewood Ranch simple and convenient. Sarasota Memorial Hospital, medical offices, grocery stores, and everyday necessities are all just minutes away. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional Sarasota location delivers the coastal lifestyle buyers dream about. Close to world-famous beaches, vibrant dining and entertainment, outdoor recreation, and everything that makes Florida's Gulf Coast so special, schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Bona Nedelkovska (727-238-6302)
1415 S SCHOOL AVE, SARASOTA, FL 34239
$619,90070 Days on yellowkey MLS ID: A4687920
REDUCED by $40,000 (6.1%) on 05/12/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1126 Built: 1955 Tax: $6,276 (2025)Community: Loma Linda Park ResubSingle Family
Taxes:$6,276
Elementary School: Alta Vista Elementary
Remarks: Sarasota midtown oasis in desirable Arlington Park Neighborhood. This 3 bedroom, 1 1/2 bath, TURNKEY FURNISHED (OPTIONAL) BLOCK home situated on a secluded corner lot, immaculately maintained and updated, could be yours as a primary residence or income producing rental property (7 DAY MINIMUM RENTAL). New AC with warranty. Roof: new APOC 585 silicone coating, newer double pane insulated windows with custom shades, tankless hot water heater, updated plumbing, new stainless steel appliances, granite countertops, IKEA kitchen cabinets and closet organizers. Terrazzo floors throughout with tile in both bathrooms. Property is fully FENCED with 2 gates providing access and parking for a small boat, camper or vehicle. Screened lanai overlooks hardwood deck and tropical plant landscaped yard. The city easement (a non build lot) on the east side of the property provides additional privacy. NO FLOOD INSURANCE REQUIRED. Located 2 blocks east of Sarasota Memorial Hospital, 4 miles to Siesta Beach (#1 beach in the USA), 5 miles to Lido Beach and 1 mile to Sarasota’s downtown world class shopping and entertainment. Short walk to Southside Village, Midtown Plaza, Legacy Trail and the Arlington Park & Aquatic Center hosting Live Music Events Alongside Pickleball, Tennis, Basketball Courts, Playgrounds, a Dog Park, Walking Trails, and Two Pools. Magical must see property!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Wendy Lewis (941-993-5708)
2037 and 2039 Jo an Dr JO AN DR, SARASOTA, FL 34231
$619,00052 Days on yellowkey MLS ID: A4692288
REDUCED by $10,000 (1.6%) on 06/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 1988 Built: 1955 Tax: $5,534 (2024)Community: High AcresSpa: YesHalf Duplex
Taxes:$5,534
Remarks: Live the Florida Dream for Free – Premier Sarasota Duplex with Income Potential Why choose between a luxury home and a smart investment? At 2037 & 2039 Jo An Drive, you can have both. This meticulously maintained side-by-side duplex offers a rare opportunity to occupy a beautiful 2BR/2BA residence while the identical neighboring unit generates significant rental income to offset your costs. The Lifestyle: Enjoy your own private oasis featuring a luxurious swim spa and a massive, deep-bay garage perfect for boat storage—all just 3 miles from the world-famous Siesta Key Public Beach. The Income: With RMF-1 zoning, this property is a turnkey powerhouse. Whether you prefer stable long-term tenants or want to capitalize on the high-demand short-term rental market, the numbers work in your favor. The Location: Tucked away on a quiet street but only minutes from Southside Village, premier dining, and top-rated schools. Ideal for: The "House Hacker": Live in one side and let the other pay your mortgage. The Seasonal Resident: Live here in the winter and rent both units during the peak vacation season. The Savvy Investor: Maximize your ROI with two updated units in a prime coastal location. Don’t just buy a home—buy an asset. Contact us today for a private tour and a full rental income projection.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Marcus Mumm (920-960-0413)
6139 HOLLYWOOD BLVD, SARASOTA, FL 34231
$999,90027 Days on yellowkey MLS ID: TB8512156
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 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)
611 TREMONT ST, SARASOTA, FL 34242
$3,399,000159 Days on yellowkey MLS ID: A4678455
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4194 Built: 2005 Tax: $21,457 (2025)Community: Siestas BaysideSpa: YesSingle Family
Taxes:$21,457
Remarks: A spectacular offering on one of Siesta Key’s most coveted streets, this stunning canal-front residence on Tremont Street represents a truly special opportunity to own a home that seamlessly blends boating, timeless island charm, and refined coastal living. Tucked beneath mature trees in a quiet, established enclave known for its old Siesta character, the property offers private canal frontage with a lift and a short, easy boat ride to the Intracoastal Waterway, all just minutes from Siesta Village and the world-renowned white sands of Siesta Beach. Homes of this caliber and setting are seldom available and must be experienced in person to be fully appreciated. Offering 4,194 square feet under air, the thoughtfully designed floor plan is both impressive and highly livable, ideal for full time residents and seasonal owners alike. Soaring ceilings, abundant natural light, and quality craftsmanship define the interior. The main floor primary suite is complemented by additional bedrooms on the main level, providing the ease of one level living, while the second floor offers a spacious guest suite and bonus room with peaceful views of the pool and canal. Exceptional indoor-outdoor living is at the heart of the home. Multiple pocketing sliding glass doors open wide to an expansive covered and fully screened lanai, creating a seamless connection between interior and exterior spaces. The outdoor living area is generous in scale and designed for entertaining, featuring a heated pool and spa, summer kitchen, gas fireplace, and multiple areas for dining and relaxation. The large screened layout allows you to comfortably enjoy outdoor living year round, regardless of the weather. Lush tropical landscaping enhances privacy and creates a tranquil island setting, while boating enthusiasts will appreciate the private lift and convenient access to open water. Impact-rated windows and doors, a generator, and a three-car garage provide peace of mind and everyday practicality. 611 Tremont Street combines location, boating, and lifestyle in a way few homes can. If you have been waiting for an exceptional Siesta Key property in one of the island’s most desirable neighborhoods, this is one you should see in person before it sells.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Mike Warm, Llc (941-525-2740)
5400 OCEAN BLVD #6-4, SARASOTA, FL 34242
$1,250,000294 Days on yellowkey MLS ID: A4663880
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $50,000 (3.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1970 Tax: $10,071 (2025)Community: TerraceCondo
Taxes:$10,071
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. Virtually Staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets convenience. Prepare to be captivated by panoramic vistas from your three spacious private balconies. Enjoy unobstructed views of pristine white sand beaches, sparkling aqua Gulf waters, downtown Sarasota's skyline, and even Longboat Key on clear days. Watch the twinkling lights of Siesta Key Village create an unforgettable backdrop as the sun sets—easily among the best views on Siesta Key. Enter through an inviting foyer with elegant tiled flooring leading into a beautifully updated kitchen featuring granite countertops & modern cabinetry. The spacious living area showcases dual sliding glass doors framing stunning Gulf views. The generous dining area provides ample space for entertaining. The primary bedroom features a private Gulf-view balcony with two full-size beds and an elegant ensuite bath with updated tile, modern cabinetry, and granite countertops. The guest bedroom offers a full bed and private sliding door to dazzling Gulf views, plus an updated full bathroom with modern finishes and tile shower. Elevated heated saltwater pool with sunset views, modern fitness center, community room, covered parking, and gated security with onsite management. Private beach access puts you steps from world-renowned Siesta Key Beach. Nestled at the end of the village, enjoy tranquility and convenient access to Siesta Key Village shops and restaurants—no car needed once you arrive. Beach Terrace represents the pinnacle of Gulf-front living. With the lowest pricing for a 2-bedroom in over 8 years, this move-in ready split-floor plan residence is your once-in-a-decade opportunity to own paradise where stunning views, luxury amenities, and coastal elegance unite.
Listing Agent: Mickey Kiernan (941-402-9115)
4078 GROVELAND AVE, SARASOTA, FL 34231
$335,000237 Days on yellowkey MLS ID: A4669478
REDUCED by $10,000 (2.9%) on 06/15/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1240 Built: 1981 Tax: $2,704 (2024)Community: Grove ParkSingle Family
Taxes:$2,704
Remarks: In a city where home prices often feel out of reach, this well-maintained three-bedroom, one-bath residence offers something increasingly rare: a real opportunity to plant roots in Sarasota without sacrificing location or potential. Set on a quiet, non-HOA neighborhood just minutes from the beach, downtown, shopping, and restaurants, this home proves that owning in Sarasota does not mean choosing between charm, location, and affordability. Inside, you will find an open layout with tile and laminate flooring, natural light throughout, and a warm, welcoming feel ready to be personalized. The kitchen has been thoughtfully updated with granite countertops and refreshed cabinetry that seamlessly blends function and simplicity, while unifying the living and dining areas. A cozy brick fireplace, featuring an above-mantel TV mount, anchors the living room, making it perfect for both quiet evenings with a book and hosting game day with friends. The primary bedroom features two closets and a dual-access ensuite bath that connects to the hallway leading to the home's two additional bedrooms. Step outside to a fully fenced backyard with a spacious deck, fire pit, and a large permitted shed that offers flexibility for storage or creative use, along with ample room for a home addition or pool, if desired. While it is not the biggest or flashiest house in town, it is real, it is ready, and it can be yours to shape. Whether you are a first-time buyer looking to stay in Sarasota on a budget, a seasonal visitor in need of a winter retreat, or someone who values authenticity, this is a home where you can begin to build not just equity, but a meaningful life. QUALIFIED BUYERS MAY HAVE THE OPPORTUNITY TO ASSUME THE EXISTING FHA LOAN AT A 2.9% INTEREST RATE. THIS RARE FINANCING OPTION COULD MEAN SIGNIFICANT MONTHLY SAVINGS COMPARED TO CURRENT MARKET RATES. ASSUMPTION IS SUBJECT TO LENDER APPROVAL AND BUYER QUALIFICATION. CONTACT THE LISTING AGENT FOR DETAILS.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
3618 MEDFORD LN #1538, SARASOTA, FL 34232
$255,00019 Days on yellowkey MLS ID: A4694975
0 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1651 Built: 1975 Tax: $2,660 (2025)Community: Village Green Sec 15Spa: NoVilla
Taxes:$2,660
Remarks: Under contract-accepting backup offers. Experience easy, low-maintenance living in this beautifully updated 2-bedroom, 2-bath residence located in the desirable 55+ Village Green community. Offering 1,651 square feet of comfortable living space, recent improvements include impact windows (2022), a new HVAC system (2022), roof replacement (2024), updated flooring, and a recently replaced dishwasher. Designed for both everyday comfort and entertaining, the spacious living and dining areas flow seamlessly into a bright Florida Room overlooking tranquil park-like green space just beyond your back door. Enjoy peaceful mornings, relaxing afternoons, and scenic views from this inviting retreat. Village Green residents enjoy access to a heated community pool, walking paths, mature oak trees, and beautifully maintained landscaping. Conveniently located near award-winning beaches, shopping, dining, medical facilities, and public transportation, this home combines comfort, convenience, and an active Florida lifestyle in one exceptional package.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)
Listing Agent: Jennifer Kenna (941-253-3003)
5917 OLIVE AVE, SARASOTA, FL 34231
$448,99925 Days on yellowkey MLS ID: O6411402
REDUCED by $24,001 (5.1%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1330 Built: 1957 Tax: $3,209 (2025)Community: Golden AcresSingle Family
Taxes:$3,209
Remarks: Virtually Staged. Located in the desirable coastal community of Sarasota, this inviting home offers a relaxed Florida lifestyle with a comfortable layout and bright, open living spaces. The interior features a functional flow designed for everyday living and easy entertaining, with well-sized bedrooms and versatile common areas. Outdoor space provides room to enjoy the warm weather year-round, whether relaxing, gardening, or hosting gatherings. Conveniently situated near Gulf beaches, shopping, dining, and cultural attractions, this property delivers both lifestyle and location in one of Sarasota’s most sought-after areas.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Raquel Littlejohn (470-279-6333)
2654 GRAND CAYMAN ST, SARASOTA, FL 34231
$357,00028 Days on yellowkey MLS ID: A4694859
REDUCED by $10,000 (2.7%) on 06/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1959 Tax: $2,737 (2025)Community: Bahama HeightsSingle Family
Taxes:$2,737
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!! Step into this move-in ready 2-bedroom, 2-bath home just minutes from world-famous Siesta Key and downtown Sarasota with no HOA restrictions! Enjoy the ultimate Florida lifestyle with top-rated schools and restaurants all within short distance, including Riverview High School and Phillippi Shores Elementary School. The open-concept living area features beautiful hand-painted ceiling details, abundant natural light, and a warm atmosphere perfect for relaxing. Major upgrades include a 50-year metal roof (2019), upgraded windows, new hot water heater (2025), upgraded kitchen and primary bathroom, and fresh interior paint (2026). High and Dry no flood insurance required! Schedule your private showing today! Move-in ready. List agent is owner.
Listing Agent: Mary Birkhold (941-266-8679)
3751 S SCHOOL AVE #11, SARASOTA, FL 34239
$145,000120 Days on yellowkey MLS ID: A4683405
1 Days Off yellowkey (back on 4/23/2026)
REDUCED by $4,900 (3.3%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972 Tax: $1,774 (2025)Community: Sunland AptsCondo
Taxes:$1,774
Remarks: Under contract-accepting backup offers. Stunning and move-in ready, this beautifully renovated and fully furnished 2-bedroom, 2-bath condo offers effortless living in an exceptionally convenient central Sarasota location. Perfectly positioned in the heart of the city, you are just minutes from Downtown Sarasota, Sarasota Memorial Hospital, and a straight drive to Siesta Key’s world-famous beaches. Enjoy the rare combination of accessibility and everyday walkability, with popular dining, cafés, and entertainment only a short stroll away. Inside, the condo has been updated to the nines, showcasing a bright, naturally light interior and a complete 2023 renovation including a modern kitchen with quartz countertops and breakfast bar, fully renovated bathrooms, updated flooring throughout, impact (hurricane-rated) windows, and custom window treatments. Offered fully furnished and move-in ready, this residence is ideal for seasonal living, downsizing, or anyone seeking a low-maintenance Sarasota retreat. Ground-floor convenience, a quiet private setting, parking directly outside the unit, and the added benefit of not being located in a flood zone further enhance the appeal. The community pool and laundry facilities are just steps away, adding to the ease of everyday living. Located within a desirable 55+ community, this condo delivers comfort, simplicity, and exceptional lifestyle appeal. Spend your time enjoying Sarasota’s favorite attractions while living in the heart of the city — mornings on Siesta Key’s world-renowned beaches, afternoons exploring local markets and boutiques, and evenings spent dining at the area’s exceptional restaurants. The property can be rented after 1 year of ownership with 4 month lease minimums - no pets allowed. Schedule your tour today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ryan Adamson, Pa (941-713-9234)
2224 BAHIA VISTA ST #E6, SARASOTA, FL 34239
$212,00019 Days on yellowkey MLS ID: A4695961
REDUCED by $3,000 (1.4%) on 06/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 982 Built: 1979 Tax: $2,936 (2025)Community: Cordova Gardens IiCondo
Taxes:$2,936
Remarks: Welcome to maintenance-free living the the heart of Sarasota! This beautifully maintained 2-bedroom, 2-bath condominium offers an ideal blend of comfort, convenience and location. The spacious floor plan is light filled and has a great split bedroom floor plan and an ideal blend of comfort, convenience and location. In addition to the bright living areas, a functional kitchen and generously sized bedrooms there is a private primary suite with en suite bath. Enjoy relaxing mornings on one of 2 private lanais and take advantage of the community pool. Located just minutes from downtown and minutes to world class Siesta Key Beach and Village as well as South Side Village with many restaurants and shops as well as Sarasota Memorial Hospital. Whether you're looking for a year-round residence, seasonal retreat, or investment opportunity, this move-in ready condo is a fantastic value in a highly desireable location. New AC
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lena Oberwetter (608-444-9009)
2242 CIRCLEWOOD DR #24, SARASOTA, FL 34231
$225,00011 Days on yellowkey MLS ID: TB8517647
1 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1176 Built: 1974Monthly Fee: $695 Tax: $1,028 (2025)Community: Woodside Village EastVilla
Taxes:$1,028
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 2242 Circle Wood Drive, a beautifully maintained 2-bedroom, 2-bath villa offering the perfect blend of comfort, convenience, and maintenance-free living in one of Sarasota’s most desirable locations. Inside, you'll find spacious living areas filled with natural light, an inviting floor plan, and a beautiful sunroom/den that provides the perfect space for a home office, reading room, or additional living area. Covered parking adds everyday convenience, while the lush tropical landscaping creates a peaceful setting you'll love coming home to. The community amenities elevate the lifestyle even further with a heated pool, tennis and pickleball courts, and beautifully maintained grounds. Location is everything, and this villa delivers. You're just minutes from Siesta Key Beach, St. Armands Circle, Downtown Sarasota, world-class dining, shopping, entertainment, and golf. Whether you're looking for a full-time residence, seasonal retreat, or low-maintenance Florida getaway, this villa offers the Sarasota lifestyle you've been dreaming of.
Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)
Listing Agent: Danielle Davis (813-526-5002)
1436 PINE BAY DR, SARASOTA, FL 34231
$4,698,00099 Days on yellowkey MLS ID: A4683228
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4128 Built: 2026Monthly Fee: $17 Tax: $7,062 (2025)Community: Johnson EstatesSpa: YesSingle Family
Taxes:$7,062
Remarks: Pre-Construction. To be built. Experience modern coastal living at its finest with the Coral Isle by Heritage Builders. Nestled on an expansive 20,000+ sq. ft. homesite in the highly coveted Oyster Bay neighborhood, this newly crafted ranch-style residence effortlessly blends contemporary design with timeless architectural elements. With 4,128 sq. ft. of air-conditioned living space all on one level, the home offers an ideal layout featuring four spacious bedrooms, a dedicated media room, private office, casual dining area, and an impressive four-car side-load garage. Inside, Heritage Builders’ signature high-end finishes take center stage. White oak flooring flows throughout the home, complemented by elegant arched entryways and thoughtfully designed details at every turn. The primary suite is a serene retreat, complete with an outdoor shower accessible directly from the luxurious primary bath—perfect for embracing the Florida lifestyle. The heart of the home is the expansive Great Room and open-concept kitchen, designed to bring family and friends together. A disappearing corner slider in the casual dining area blurs the lines between indoors and out, opening to the covered lanai, pool, and spa—an entertainer’s dream. The chef’s kitchen impresses with an oversized island, true walk-in butler’s pantry, and a full suite of Thermador appliances, offering ample space for prep, cooking, and hosting. Situated just 5 minutes from the world-famous Siesta Key Beach, a short walk to the exclusive Field Club, and mere minutes from the boutiques and dining of Southside Village, this location places you at the center of Sarasota’s most desirable amenities. Enjoy quick access to the arts and culture of downtown Sarasota, only 7 minutes away, all while residing in one of the area’s most charming and established neighborhoods. The Coral Isle brings modern luxury, thoughtful design, and unrivaled convenience together in one extraordinary home.
Listing is courtesy of: HB REALTY GROUP INC. (941-378-3983)
Listing Agent: Sara Boudarga (941-321-6352)
4003 BOOTH PL, SARASOTA, FL 34231
$355,90068 Days on yellowkey MLS ID: A4690238
REDUCED by $19,100 (5.1%) on 05/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1952 Tax: $2,979 (2025)Community: BrooksideSingle Family
Taxes:$2,979
Remarks: Under contract-accepting backup offers. Welcome to this FRESH and Bright centrally located home in Sarasota! It offers 3 bedrooms, 2 bathrooms, and valuable updates that provide both comfort and peace of mind. A BRAND NEW ROOF is scheduled for installation in mid-June 2026, while the freshly painted interior (May 2026), finished in a soft/neutral white, creates a light-filled and inviting atmosphere throughout the home. The beautifully updated kitchen features newer appliances, cabinetry, white quartz countertops, and fixtures, blending style and functionality for everyday living and entertaining. The spacious primary suite is complemented by a stunning bathroom renovation completed in March 2026, showcasing modern finishes and thoughtful design. The water softener is also new. UPDATED PHOTOS WILL BE TAKEN after the new roof is completed. Step outside and enjoy the spacious screened lanai, an ideal setting for morning coffee, evening relaxation, or gathering with family and friends. The large private backyard is shaded by mature trees, offering both beauty and privacy. A one-car carport under the main roofline adds convenience and enhances the property's overall value. Located within the highly sought-after Riverview School District, this home is just minutes from Siesta Key's world-famous beaches, vibrant downtown Sarasota, premier shopping and dining, parks, and major medical facilities. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional location offers enduring appeal. With many of the major improvements already completed—including the new roof, fresh interior paint, updated kitchen, renovated primary bathroom, and new water softener—this property presents an outstanding opportunity to enjoy the Sarasota lifestyle from day one. Combining desirable updates, a prime location, and room to make it your own, this home is ready to welcome its next owner.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Julie Shaw (941-408-4760)
3174 REGATTA CIR, SARASOTA, FL 34231
$428,90062 Days on yellowkey MLS ID: A4689148
REDUCED by $5,000 (1.2%) on 06/18/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1279 Built: 1963Monthly Fee: $6 Tax: $4,089 (2025)Community: Gulf GateSpa: NoSingle Family
Taxes:$4,089
Remarks: Bright and light, charming, nicely updated two bedroom, two bath home sold TURNKEY furnished in the lovely Gulf Gate community on a quiet circle street! Don’t miss this tropical oasis with a beautiful backyard and screened in patio ready for new owners – just bring your toothbrush! This community has an optional HOA and no CDD fees! This one car garage home includes the following updates: new exterior paint 2026, new interior paint in 2021, new wind rated sliding doors in 2021, new screened in patio 2021, new range and refrigerator in 2021, new garage exterior door in 2024, garage painted in 2023, new gas grill in 2026, new updated lighting in 2021, and new HVAC installed in 2020. Close to shopping, restaurants, and only 3.9 miles to the famous #1 Beach in the USA - Siesta Key! Enjoy as your personal home or as a great investment opportunity. Don't miss this home, make your appointment to see today!
Listing Agent: Alice Lewis (941-402-5564)
2135 DATURA ST, SARASOTA, FL 34239
$1,725,000101 Days on yellowkey MLS ID: A4685791
REDUCED by $75,000 (4.2%) on 05/08/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2539 Built: 2021 Tax: $7,357 (2025)Community: Grove Lawn RepSingle Family
Taxes:$7,357
Remarks: This exceptional custom-built residence seamlessly blends modern farmhouse design with superior craftsmanship and high-end finishes throughout. Offering 3 bedrooms, 2.5 baths, and an open-concept floor plan, the home delivers the perfect combination of style, comfort, and functionality in one of Sarasota’s most desirable locations. Striking curb appeal is highlighted by a custom cypress garage door, cypress porch accents, and a dramatic glass entry that welcomes you into a thoughtfully designed interior filled with natural light. European oak flooring, recessed lighting, and refined architectural details create a warm yet sophisticated atmosphere throughout the two-story home. At the heart of the residence, the spacious great room features soaring 12-foot vaulted ceilings accented by a decorative cypress beam and a sleek electric fireplace, creating an inviting space for both everyday living and entertaining. The chef-inspired kitchen is equally impressive, showcasing a Fulgor Milano dual-fuel range, Silestone quartz countertops, custom soft-close cabinetry, a waterfall-edge island, floating cypress shelving, designer brass fixtures, and a generous walk-in pantry. The luxurious primary suite serves as a private retreat, complete with a custom walk-in closet and a spa-like bath featuring dual showers, double vanities, and custom cypress shelving. Additional highlights include beautifully crafted wood staircases with wrought-iron railings leading to a versatile second-floor bonus room, as well as a spacious laundry and mudroom offering abundant storage and workspace. Outdoor living is equally appealing with a large, private backyard enclosed by a six-foot cypress shadowbox fence. With ample space for a future pool, the yard provides endless opportunities for entertaining, pets, and enjoying Florida’s year-round sunshine. Ideally located east of the Trail, this remarkable home is just minutes from Sarasota Memorial Hospital, Southside Village, and highly regarded Southside Elementary School. Downtown Sarasota’s vibrant dining, arts, cultural attractions, and world-renowned Gulf beaches are all within easy reach, making this a rare opportunity to enjoy modern luxury living in a premier Sarasota location.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
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