Location: Sarasota , 34233
Do Not Show Listings
4606 TIPPECANOE TRL #119, SARASOTA, FL 34233
$160,000222 Days on yellowkey MLS ID: A4671371
1 Days Off yellowkey (back on 5/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1258 Built: 1973Monthly Fee: $437 Tax: $882 (2024)Community: Lake TippecanoeCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$882
Elementary School: Ashton Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Riverview Middle
Remarks: Under contract-accepting backup offers. Brand New Price!! Welcome to Lake Tippecanoe — Sarasota’s Premier 55+ Community! This beautifully maintained 2-bedroom, 2-bath ground-floor condo offers 1,258 sq. ft. of comfortable, maintenance-free living in the heart of Sarasota. Step inside to an inviting open floor plan where the kitchen seamlessly flows into the great room—perfect for entertaining or relaxing. Natural light fills the spacious Florida room/dining area, overlooking a peaceful backyard setting. MOTIVATED SELLER Enjoy the convenience of indoor laundry and the ease of community living, with the association taking care of lawn maintenance, exterior upkeep (including the roof), pest control, cable, water, and trash pickup—so you can focus on enjoying the Florida lifestyle. Lake Tippecanoe is a well-established and friendly 55+ community featuring a clubhouse, social activities, and a serene lakefront setting. Ideally located near Sarasota’s world-famous beaches, top-rated golf courses, shopping, and dining, this condo offers the perfect blend of comfort, convenience, and community. Come experience the relaxed Sarasota lifestyle you’ve been dreaming of at Lake Tippecanoe!
Listing is courtesy of: JOHN HARDING REALTY (941-777-3007)
Listing Agent: Josh Mott (941-780-3063)
5520 ROSEHILL RD #203, SARASOTA, FL 34233
$199,900155 Days on yellowkey MLS ID: A4677482
REDUCED by $20,000 (9.1%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1141 Built: 2002 Tax: $2,812 (2025)Community: Admirals WalkCondo
Taxes:$2,812
High School: Riverview High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: $20,000 PRICE IMPROVEMENT! Live in a TREE HOUSE and park your car in a GARAGE. Lowest priced 2-bedroom in Admiral’s Walk with a garage! This second-floor corner condo has everything you are looking for: impact glass hurricane windows, newer roof & hardiboard siding, newer A/C system and newer washer/dryer! Plus, a 1-car oversized garage (12’ X 26’ long) for extra storage. The light and bright interior space has a great room floor plan featuring a vaulted ceiling with clerestory window and windows on two walls with water views. The open kitchen has a breakfast bar overlooking the dining area and a pantry. The two bedrooms have ensuite bathrooms with large walk-in closets. Admiral’s Walk is a New England style community with ponds, fountains and mature trees. There are plenty of amenities to suit everyone’s taste. Relax by the pool or soak in the spa, work out at the fitness center, visit the clubhouse and play pool, or cook dinner on the community grill. Your pets will be happy here too. Two pets up to 65 pounds each are allowed. Siesta Key beaches are a short drive away and there are plenty of shopping, dining and cultural destinations nearby. You’ll find easy access to I-75 for a quick drive to UTC Mall and Benderson Park. Come live the Florida lifestyle!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Barb Standish (941-504-9458)
4860 CEDAR OAK WAY, SARASOTA, FL 34233
$725,0006 Days on yellowkey MLS ID: A4696764
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2527 Built: 2000Monthly Fee: $48 Tax: $5,264 (2025)Community: Three OaksSpa: NoSingle Family
Taxes:$5,264
Remarks: Some homes are well-built, some have vibrant personalities. This stunning four-bedroom-plus-office retreat in Three Oaks has both; a quality-built home with warmth, and interiors that carry an energy that's vivid, layered, and genuinely inviting. The heart of the home is a spacious chef's kitchen that would turn heads in any price range. Paneled SubZero refrigerator, a touch cooktop with double ovens, and granite counters with breakfast bar set the stage. The kitchen opens to both the living room and the pool beyond; conversation flows naturally here. A split floor plan gives the primary suite its own quiet wing, complete with a generous walk-in closet, and ensuite bath with jetted garden tub and generously sized shower. Three additional bedrooms and a full bath, plus pool bath extend along the other side. An office, family room, foyer, and dining room provide plenty of space for work, reading, and hobbies. This home was purposefully designed with outdoor living in mind with direct access to the screened pool enclosure from the primary suite, dining room, living room and pool bath. Open the expansive sliding glass doors for a seamless transition to the pool deck where you’ll enjoy a heated saltwater swimming pool and an outdoor kitchen with Wolf grill, refrigerator, and sink. The setting is beautifully framed by mature tropical landscaping that creates a sense of calm and privacy. Among the flourishing foliage are papaya and banana trees, hibiscus, agave, bougainvillea and desert rose. A koi pond with waterfall adds a quiet, meditative note to the backyard setting, and the neighborhood lake view stretches beyond, with stunning sunrises visible from throughout the home. Insurance is a breeze with a brand-new tile roof in June 2026 and no flood insurance required. Ideally located in an A-rated school corridor (Ashton Elementary, Sarasota Middle, Riverview High), and just minutes from the white quartz sands of Siesta Key. Three Oaks is a neighborhood of 280 homes with low HOA fees of just $575 per year. Three Oaks is located west of I-75 near the corner of Proctor Road and Honore Avenue. Three Oaks. 2,527 square feet. One of a kind. Schedule your private showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
5560 ROSEHILL RD #201, SARASOTA, FL 34233
$229,90068 Days on yellowkey MLS ID: A4689325
REDUCED by $20,000 (8.0%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 2002 Tax: $2,965 (2025)Community: Admirals WalkCondo
Taxes:$2,965
Remarks: Bright and spacious loft-style condo in the gated community of Admirals Walk. This two-story layout features cathedral ceilings, an open living area, and a flexible loft space suitable for an office, guest area, or media room. The kitchen includes a breakfast bar and pantry, and the split-bedroom design provides privacy for both bedrooms. Each bedroom offers a walk-in closet, and the interior laundry room provides additional storage. Community amenities include a resort-style pool, spa, fitness center, clubhouse, and on-site management. HOA fees include cable, internet, water, sewer, and trash. Conveniently located near I-75, shopping, dining, UTC, downtown Sarasota, and area beaches.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Greg Dudley (240-461-7460)
5005 BEE RIDGE RD, SARASOTA, FL 34233
$369,0007 Days on yellowkey MLS ID: TB8517363
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1151 Built: 1960 Tax: $3,418 (2025)Community: Ridgewood Estates 01St AddSingle Family
Taxes:$3,418
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: This delightful 3-bedroom, 2-bathroom single-story home offers the perfect slice of the Florida lifestyle, boasting an established vacation rental income history for savvy buyers. Centrally located for ultimate convenience, you are a quick drive from both vibrant Downtown Sarasota and the world-famous Siesta Key Beach. You will absolutely love the expansive backyard and the peaceful view across the street. Plus, you enjoy unbeatable walkability right across the street from the 55-acre Urfer Family Park, giving you instant access to nature trails, playgrounds, and fitness paths. From the street, mature landscaping creates immediate curb appeal. Step inside to a bright, open-concept floor plan, controlled by a modern Google Smart Home thermostat. The chef-ready kitchen comes fully equipped with gorgeous granite countertops, a large island, and updated appliances, including a new microwave and dishwasher (both installed in 2023). Down the hall, the layout features a spacious primary suite with a dedicated workstation, a flexible second bedroom, and a comfortable third bedroom—along with a newly added washer/dryer combo (2023) for ultimate convenience. Step outside into your private backyard to find a brand-new 500+ square foot concrete patio, providing the perfect blank canvas for alfresco dining, entertaining, and soaking up the Florida sunshine. Whether you are looking for a profitable investment or your own private haven, this exceptional property is a must-see!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Krisztina Juhasz (571-423-8772)
4338 MADEIRA CT #3346, SARASOTA, FL 34233
$190,00041 Days on yellowkey MLS ID: A4692389
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $5,000 (2.6%) on 06/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1988 Tax: $2,516 (2025)Community: Casa Del Sol Sec ICondo
Taxes:$2,516
Remarks: Under contract-accepting backup offers. Enjoy peaceful lake views from this move-in ready 2-bedroom, 2-bath condo—perfect for full-time living or a seasonal retreat. Located on the second floor, you’ll love the cathedral ceilings and the added privacy of having no one above, creating a bright and airy feel throughout. Gently used by part-time owners, this thoughtfully cared for condo offers an ideal Sarasota lifestyle with easy access to beaches, shopping, dining, and more. Recent updates include a 2024 HVAC system and hot water heater, along with newer appliances for added peace of mind. Some furnishings are available for convenience, making this an easy transition whether you’re looking for a primary residence or a “lock-and-leave” getaway. Low condo fees and an active community at Casa Del Sol complete the package—offering the perfect blend of comfort, location, and value.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Janice Melzer Langa (941-404-0802)
4165 ROSAS AVE #3088, SARASOTA, FL 34233
$319,99013 Days on yellowkey MLS ID: A4695896
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1532 Built: 1989Monthly Fee: $669 Tax: $2,081 (2025)Community: Casa Del Sol Sec IvCondo
Taxes:$2,081
Elementary School: None
High School: None
Middle School: None
Remarks: Virtually Staged. Welcome to 4165 Rosas Avenue, a rare opportunity to own one of the few detached residences within the desirable maintenance-free community, Casa Del Sol. Offering the privacy and feel of a single-family home, this beautifully maintained 3-bedroom, 2-bath residence combines spacious living with thoughtful updates throughout. Step inside to discover soaring ceilings, abundant natural light, and an open, inviting floor plan designed for both everyday living and entertaining. The updated kitchen features modern finishes, ample cabinetry, and generous counter space, seamlessly connecting to the main living areas. A unique wet bar adds character and functionality, creating the perfect space for hosting guests or enjoying a quiet evening at home. The spacious primary suite serves as a private retreat, while two additional bedrooms provide flexibility for family, guests, or a home office. Large sliding glass doors open to outdoor living spaces that bring the beauty of Florida living indoors. The detached design offers added privacy rarely found within condominium communities, making this home truly stand out from the competition. Residents enjoy the convenience of low-maintenance living while benefiting from the comfort, space, and independence typically associated with a single-family residence. Conveniently located near shopping, dining, golf, beaches, and all that Sarasota is known for, this is an exceptional opportunity to enjoy the Florida lifestyle. HVAC-2021 - Tile Roof- 2011 - Water Heater - 2024. Schedule your private tour today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Heather Palo (941-374-2154)
7919 LIMESTONE LN #13-204, SARASOTA, FL 34233
$330,000104 Days on yellowkey MLS ID: A4684105
INCREASED by $35,000 (11.9%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1346 Built: 2007 Tax: $3,643 (2025)Community: Stonehaven Ph 4, 5, 6, 7 & 25Condo
Taxes:$3,643
Remarks: Virtually Staged. Enjoy comfortable, low-maintenance living at 7919 Limestone Lane #13-204, an end-unit, stylish walk-up residence in Sarasota featuring three bedrooms, two bathrooms, and an attached one-car garage. Guests are greeted by a paver walkway, an inviting side entry, and lush landscaping, while owners enjoy direct access from the garage. Inside, a tiled foyer leads to an open-concept floor plan, where the bright, spacious great room with crown molding, ceiling fan, designated dining area, and diagonal tile flooring flows seamlessly into the kitchen. Here, cherry wood cabinetry, granite countertops with a breakfast bar, and all-new stainless-steel appliances—including a microwave, refrigerator, range, and dishwasher—replaced at the end of 2024—are complemented by recessed lighting, pantry, and above-cabinet display space. Each bedroom features built-in closets, ceiling fans, laminate flooring, and access to a full bath with tub and shower. The laundry closet has a washer and dryer, less than two months old, and never used. The primary suite offers direct balcony access, a walk-in closet, and an en-suite bath with tiled shower, glass doors, and solid-surface counters. The covered and screened balcony overlooks a private park. All fans, lights, sockets, and switches were recently updated. The AC and water heater are brand new, and the garage door motor was replaced a year and a half ago. Blending functional design with tasteful finishes and extensive updates, this home is ideally situated for Sarasota living in Stonehaven. This beautifully maintained, gated, pet-friendly community delivers an impressive array of amenities and lifestyle features at an affordable price. Residents appreciate concrete-block construction, hurricane-impact windows and doors, and tranquil surroundings. The maintenance-free setting boasts lush landscaping, a year-round heated pool, playground, scenic lake for appreciating wildlife and tranquil views, and low monthly fees that cover exterior upkeep and irrigation. Ideally positioned just a mile from I-75 and a short drive from the world-renowned beaches of Siesta Key, Stonehaven is in a desirable A-rated school district. Convenient access to public transportation enhances connectivity throughout Sarasota, while nearby trailheads make it easy to explore the Legacy Trail and enjoy the outdoor lifestyle. You'll also find plenty of shopping, dining, and parks in the area. The neighborhood offers guest parking and a welcoming atmosphere for a variety of lifestyles. Reasonable leasing restrictions make this an excellent investment option. With its combination of comfort, convenience, and resort-inspired amenities—at a value rarely found in Sarasota—Stonehaven stands out as a premier choice for those seeking a relaxed yet active Florida experience.
Listing is courtesy of: CANDY SWICK & COMPANY (941-954-9000)
Listing Agent: Candy Swick (941-376-9000)
3927 COUNTRY VIEW LN, SARASOTA, FL 34233
$585,00062 Days on yellowkey MLS ID: A4690240
REDUCED by $24,900 (4.1%) on 06/11/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2319 Built: 1979Monthly Fee: $50 Tax: $5,477 (2025)Community: Country PlaceSingle Family
Taxes:$5,477
Remarks: Price improvement! This is the one, best priced home in the neighborhood. One of Sarasota's rarest locations is available! Featuring one of the more popular layouts the neighborhood has to offer. Plenty of space, split floor plan, and natural light. This spacious pool home sits on one of the only dead-end cul-de-sacs in Country Place. This home has all the important updates; Roof Summer of 2017, the A/C and the water heater replaced in the Summer of 2021. Country Place boasts large lots, ensuring privacy and neighbors who take pride in their homes. In addition to the 3 bedrooms and adjacent 3 baths, there is a bonus room/den. As well as plenty of space for entertaining with two family rooms and 2 dining rooms. You'll have to see this one for yourself and imagine all the possibilities this endless space has to offer.
Listing is courtesy of: TREND REALTY (941-928-3449)
Listing Agent: Baily Block (941-961-3772)
3761 COUNTRYSIDE RD, SARASOTA, FL 34233
$749,00089 Days on yellowkey MLS ID: A4685476
REDUCED by $10,000 (1.3%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2399 Built: 1981Monthly Fee: $50 Tax: $3,438 (2025)Community: Country PlaceSingle Family
Taxes:$3,438
Elementary School: Wilkinson Elementary
Remarks: Virtually Staged. NEW PRICE...Home is where our story begins...come see this beautifully remodeled 3 bedroom, 2/1 bath home in the rarely available and desirable COUNTRY PLACE neighborhood. From the moment you step through the front door into the welcoming foyer, you’ll fall in love. This move-in ready home features an open living room that looks out to the lanai and sparkling pool, creating the perfect space for relaxing or entertaining. The beautifully updated kitchen showcases granite countertops with a peninsula breakfast bar, wood cabinetry, all stainless steel appliances, and a bright breakfast nook overlooking a serene screened outdoor sanctuary. The spacious primary suite offers a generous walk-in closet, while the primary bathroom features an extra-large shower and convenient access to the pool area. The two guest bedrooms are bright and welcoming; each enhanced with large windows and built-in closets. Additional highlights include polished Porcelain Tile and Modern Plank Ceramic Tile flooring throughout and fully updated bathrooms. Major updates include, Roof (June 2024), Garage Door (2023), Exterior Paint (2024), Interior Paint (2026), all Stainless Steel Appliances (2026), Granite Counter Tops (2026), Tankless/Instant Hot Water Heater (2026), 10 ft privacy fence in backyard and a Deep well. You’ll also enjoy an oversized deep garage (26’x22’). For families relocating to Sarasota, this home is located in an “A” rated school district, an important factor for many buyers. Country Place is a centrally located deed-restricted community of approximately 170 homes with no CDD fees, known for its large lots, lush landscaping, and private in-ground pools. This prime location is walking distance to Red Bug Slough Preserve, a 72-acre nature preserve offering miles of hiking trails, a playground, picnic shelters, and a fishing dock—perfect for wildlife and bird watching. Just minutes away you’ll find Siesta Key Beach, local restaurants, Westfield Siesta Key Mall, Detwiler’s Farm Market, Publix, and much more. Enjoy nearby activities including boating, fishing, parasailing, kayaking, swimming, and snorkeling. Be sure to view the 3D Interactive Panoramic Tour to fully appreciate the elegance and charm of this exceptional home.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Linda Scheller, Llc (941-806-7981)
4242 MADEIRA CT #3315, SARASOTA, FL 34233
$279,00071 Days on yellowkey MLS ID: A4685842
REDUCED by $10,000 (3.5%) on 06/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1063 Built: 1989Monthly Fee: $458 Tax: $1,180 (2025)Community: Casa Del Sol Sec ViiCondo
Taxes:$1,180
Remarks: Move-in ready and thoughtfully updated, this beautiful 2-bedroom, 2-bathroom end-unit home offers the perfect combination of comfort, style, and scenic surroundings. The inviting interior features an open and airy layout, enhanced by hurricane-impact windows and a hurricane-rated sliding glass door for both safety and peace of mind. Elegant plantation shutters add a refined touch, while a built-in TV with an electric fireplace creates a warm and cozy living area. The eat-in kitchen is ideal for casual dining offering ample space and functionality. The primary suite serves as a private retreat, complete with a walk in closet and a beautifully updated ensuite bath featuring high-end finishes, including a custom-made vanity sourced from North Carolina. The primary bathroom has been tastefully renovated within the last two years. Additional major upgrades include a full plumbing repipe, along with a water heater, washer, and dryer all replaced just two years ago—ensuring modern efficiency and reliability. One of the standout features of this home is the converted, air-conditioned back patio, perfect for use as a sunroom, home office, or additional living space to enjoy year-round comfort while taking in the tranquil lake views. Located in the desirable Casa Del Sol community, residents enjoy a vibrant lifestyle with amenities including tennis and pickleball courts, shuffleboard, bocce ball, a heated pool for cooler months, and a clubhouse with a pool, poker tables, a gym, books and endless ongoing activities. Conveniently situated near I-75, this home is just a short drive to Siesta Beach, University Town Center, Waterside, and downtown Sarasota—offering easy access to shopping, dining, and the world-renowned Gulf Coast beaches. This exceptional home truly offers the best of Florida living—schedule your showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Carey Hibbs (941-915-9235)
5531 ROSEHILL RD #203, SARASOTA, FL 34233
$179,900190 Days on yellowkey MLS ID: A4674707
4 Days Off yellowkey (back on 5/18/2026)
REDUCED by $20,000 (10.0%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 2002 Tax: $2,572 (2025)Community: Admirals WalkCondo
Taxes:$2,572
Remarks: Under contract-accepting backup offers. Discover the perfect blend of style, comfort, and convenience in this refreshed 2-bedroom, 2-bath corner-unit condo in the gated community of Admirals Walk. Featuring a versatile loft space—ideal for a home office, guest room, playroom, or extra lounge—this layout offers the flexibility today’s lifestyle demands. Step inside to an open floor plan with vaulted ceilings and plenty of natural light. The kitchen, flows effortlessly into the spacious living and dining area—perfect for hosting friends, relaxing after work, or enjoying family time. Both bedrooms include walk-in closets and en-suite bathrooms, and the conveniently placed laundry room sits between them for easy everyday living. Located just 6 miles from Siesta Key Beach and minutes from Clark Road and I-75, this home puts you close to schools, hospitals, shopping, dining, and everything Sarasota has to offer. Admirals Walk is a pet-friendly, maintenance-free community featuring resort-style amenities: a beautiful clubhouse with a pool and jacuzzi, modern fitness center, game room, and meeting spaces. Your association fee even includes internet, cable, water, sewer, trash, and security, offering excellent value and peace of mind. This condo delivers the Florida lifestyle you’ve been searching for. Schedule your showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Brett Keyser, Jr (941-957-8425)
4576 BLISS RD, SARASOTA, FL 34233
$385,00092 Days on yellowkey MLS ID: A4685762
1 Days Off yellowkey (back on 6/10/2026)
REDUCED by $10,000 (2.5%) on 06/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1475 Built: 1978 Tax: $3,533 (2025)Community: Sarasota HighlandsSpa: NoSingle Family
Taxes:$3,533
Remarks: Welcome to 4576 Bliss Road, a beautifully updated family home nestled in one of Sarasota’s most desirable neighborhoods, renowned for its top-rated schools and friendly community atmosphere. This spacious 3-bedroom, 2-bathroom residence is thoughtfully designed with a smart split floor plan that provides both privacy and comfort for every member of your family. Step inside to discover brand-new plumbing and elegant, durable luxury vinyl plank flooring that flows seamlessly throughout the home, combining style with practicality for busy family life. The bathrooms have been meticulously remodeled to create spa-like retreats, blending modern elegance with functionality, ensuring a relaxing and rejuvenating space for your family to unwind. Additional upgrades include impact-resistant windows that offer peace of mind and energy efficiency, along with a complete home repipe to ensure long-lasting reliability. Outside, you’ll find a fully fenced yard that offers a safe, private oasis for children and pets to play freely or for hosting unforgettable family gatherings and celebrations. Whether it’s a quiet evening on the patio or a lively weekend BBQ, this outdoor space is designed to accommodate all your family’s needs. This home perfectly marries the timeless charm of classic Sarasota updates that buyers desire—all within a highly sought-after school district that prioritizes education and community values. Don’t miss this rare opportunity to secure a comfortable, stylish, and welcoming home at 4576 Bliss Road, where your family’s new chapter awaits.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Robert Krasow (941-363-6507)
346 ANDROS DR, SARASOTA, FL 34233
$170,00055 Days on yellowkey MLS ID: A4691142
REDUCED by $29,000 (14.6%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 2003Monthly Fee: $178 Tax: $2,425 (2025)Community: Windward IslesManufactured Home
Taxes:$2,425
Remarks: WELCOME TO WINDWARD ISLES – ONE OF SARASOTA’S MOST DESIRABLE RESIDENT-OWNED 55+ COMMUNITIES! This WELL-MAINTAINED 2 BEDROOM, 2 BATH DOUBLE-WIDE HOME offers the perfect blend of comfort, convenience, and FLORIDA LIFESTYLE LIVING. Built in 2003 and featuring APPROXIMATELY 930 SQ FT OF HEATED SPACE, this home sits on a nicely sized lot with COVERED PARKING, A PRIVATE DRIVEWAY, AND ADDITIONAL STORAGE SHED. Step inside to find a LIGHT AND BRIGHT FLOOR PLAN with LAMINATE FLOORING THROUGHOUT MAIN LIVING AREAS, a SPACIOUS LIVING ROOM, and a FUNCTIONAL KITCHEN equipped with CONVECTION OVEN, REFRIGERATOR, MICROWAVE, and more. The PRIMARY SUITE includes a WALK-IN CLOSET and EN-SUITE BATH, while the SPLIT BEDROOM DESIGN offers privacy for guests. Enjoy your morning coffee or evening relaxation from MULTIPLE OUTDOOR SPACES INCLUDING A SCREENED PORCH, FRONT PORCH, AND REAR PATIO—perfect for taking in Sarasota’s year-round sunshine. WINDWARD ISLES IS A LAND-OWNED CO-OP COMMUNITY offering residents access to a HEATED COMMUNITY POOL, RECREATIONAL FACILITIES, AND A FULL CALENDAR OF SOCIAL ACTIVITIES. The LOW HOA FEE (APPROX. $178/MONTH) INCLUDES WATER, TRASH, LAWN MAINTENANCE, AND COMMUNITY AMENITIES, making this an EXCEPTIONAL VALUE. Ideally located just minutes from SHOPPING, DINING, MEDICAL FACILITIES, AND WORLD-FAMOUS GULF BEACHES, this property offers both PEACEFUL COMMUNITY LIVING and EASY ACCESS TO EVERYTHING SARASOTA HAS TO OFFER. Whether you're looking for a SEASONAL RETREAT or a FULL-TIME RESIDENCE, this home is a fantastic opportunity to own in a HIGHLY SOUGHT-AFTER COMMUNITY. SCHEDULE YOUR PRIVATE SHOWING TODAY.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Jeff Simpson (941-504-5552)
4306 MADEIRA CT #3335, SARASOTA, FL 34233
$269,00041 Days on yellowkey MLS ID: TB8506253
REDUCED by $20,999 (7.2%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1998Monthly Fee: $418 Tax: $2,555 (2025)Community: Casa Del Sol SarasotaSpa: NoCondo
Taxes:$2,555
Middle School: Oak Park School South
Remarks: AMAZING AND RARE OPPORTUNITY TO OWN A FIRST FLOOR END UNIT WITH NO STAIRS!!! THIS APARTMENT AT 4306 MADEIRA CT UNIT 3335 SARASOTA FL 34233, FEATURES 2 BEDROOMS 2 BATHROOMS AND 1083 SQFT, FULLY RENOVATED WITH MARBLE COUNTERTOPS, CALACATTA FLOORS, SPACIOUS CLOSETS. LAUNDRY WITH BRAND NEW APPLIANCES. JUST 10 MINUTES AWAY FORM FLORIDA FINEST BEACHES AND NATIONWIDE FAMOUS SIESTA KEY BEACH, CLOSE TO SHOPPING, RESTAURANTS, GOLF COURSES, THE HOSPITAL, DOWNTOWN, SARASOTA AIRPORT, AND 5 MINUTES AWAY FROM UTC MALL. ONLY ONE MILE AWAY FROM EXIT 207 OF I 75, THE ASSOCIATION IS A PET FRIENDLY COMMUNITY, ADMIRAL WALK IS FULLY GATED COMMUNITY, WITH SECURITY ENTRANCE. HOA HAS RESONABLE FEES THAT ALSO INCLUDES WATER & SEWER UTILITY. THERE IS A LOVELY CLUB HOUSE WITH LAKE VIEW, POOL AND SPA, FITNESS ROOM, BATHROOMS, GAME ROOMS AND TENNIS COURT. CALL TODAY FOR A SHOW, YOUR IDEAL HOME AWAITS!!
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Karelys Diaz (813-997-6775)
4323 PINE MEADOW TER, SARASOTA, FL 34233
$515,00037 Days on yellowkey MLS ID: A4692509
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1494 Built: 1978Monthly Fee: $25 Tax: $5,227 (2025)Community: Pine MeadowSpa: NoSingle Family
Taxes:$5,227
Remarks: Under contract-accepting backup offers. You found it! A newly renovated pool home directly bordering the Legacy Trail and just a short drive to Siesta Key Beach! This home is in the highly sought-after community of Pine Meadow. Positioned on an oversized, private corner lot with an extended driveway, this property also offers direct and private access to the Legacy Trail through a custom door built into the fully fenced backyard. Extensive and thoughtful interior updates include a renovated kitchen with granite countertops, matching stainless steel appliances, and luxury tile flooring that flows seamlessly throughout the home. The split-bedroom floor plan complements the master bedroom, which offers an abundance of natural light and quaint charm. Accented by a modern farmhouse sliding door, this room features a large walk-in closet and an updated en-suite bathroom with a walk-in shower and floor-to-ceiling tile. Both additional bedrooms also feature large walk-in closets. The home was FULLY RENOVATED in 2019, receiving a new roof, fully updated electrical system, new hot water heater, custom 10x16 storage shed, new garage epoxy flooring, and a new garage door. The pool was also resurfaced and upgraded with a new pool cage and pump equipment. Embrace the private, tranquil backyard setting complemented by a variety of mature trees and lush landscaping. Enjoy the pool and lanai from the shaded, covered section, or soak up the warm Florida sun while relaxing poolside. This home is in a highly desirable Sarasota location, just 5.5 miles from Siesta Key Beach. It is assigned to all A-rated schools, offers direct access to the Legacy Trail, and provides quick access to I-75 and Sarasota Memorial Hospital.
Listing Agent: Allen Smith, Iv (407-460-1564)
4867 HUNTLEIGH DR, SARASOTA, FL 34233
$499,000103 Days on yellowkey MLS ID: A4685110
REDUCED by $26,000 (5.0%) on 06/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1937 Built: 1980Monthly Fee: $29 Tax: $3,040 (2025)Community: Beneva PinesSpa: NoSingle Family
Taxes:$3,040
Remarks: Under contract-accepting backup offers. In the desired community of Beneva Pines in the heart of Sarasota, just five miles to the south bridge to the quartz sugar sand beaches of Siesta Key and Capt Curt's Restaurant and Tiki Bar! This smartly designed split plan home features an open plan, vaulted ceilings, and beautiful screened pool and lanai. The kitchen is the heart of this home and is surrounded by multiple gathering and dining areas. Impact sliders open off the Florida room to the pool. Most windows have been updated to impact rated as well. All four bedrooms are generous size and feature walk-in closets. The primary bedroom features an en-suite bath and two walk-in closets. Freshly painted inside, this home is ready for you to make it your own. Roof in 2022.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
4243 MIRIANA WAY, SARASOTA, FL 34233
$529,900102 Days on yellowkey MLS ID: A4685208
1 Days Off yellowkey (back on 6/8/2026)
REDUCED by $10,000 (1.9%) on 05/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2149 Built: 2003Monthly Fee: $312 Tax: $4,049 (2025)Community: Villa RosaSingle Family
Taxes:$4,049
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom plus den home, located in the gated community of Villa Rosa — a hidden gem of maintenance-free single-family homes in the heart of Sarasota. Sitting high and dry in the desirable Flood Zone X (no flood insurance required), this residence is perfectly positioned on a serene lake with views of a lovely magnolia tree and fountain. The oversized screened patio—featuring all new screens and stainless steel screws (2025)—is ideal for relaxing, dining al fresco, or soaking up the sun with a great book. Enjoy complete peace of mind with a NEW tile roof (2022), NEW air conditioning system (December 2024), hurricane shutters throughout, and a hurricane-impact garage door. Additional upgrades include whole-house gutters with new gutter guards (2025), a brick paver driveway and walkway in classic herringbone design, landscape curbing, plantation shutters, custom Hunter Douglas blinds, and professionally installed surround sound for your AV equipment and entertainment needs. Step inside this one-owner, meticulously cared-for home with an open and thoughtfully designed floor plan—offering the open living concept you desire while maintaining the privacy everyone appreciates. A versatile den at the front of the home features French doors with custom blinds, wood flooring, and a charming bay window, making it an ideal home office, reading room, or bonus space. The two guest bedrooms and guest bath featuring a TOTO comfort height toilet are tucked away in their own private hallway and provide comfort for family or visitors. The primary suite is situated in its own wing, showcasing peaceful pond views, one walk-in closet plus a second spacious closet, and an ensuite bath with dual sink vanities, a large soaking tub, shower with grab bars, a private water closet, and an upgraded TOTO comfort-height toilet. At the heart of the home, the great room, with trey ceiling, kitchen with island and bar seating, and the eat-in dining area all open to the screened lanai overlooking the water—offering tranquil views from every angle. The kitchen boasts Silestone countertops, an abundance of cabinetry, a generous pantry, and a pocket door separating the kitchen and formal dining room. High ceilings, crown molding, extra closets, and abundant natural light flow throughout. The laundry room with pocket door and extra large closet includes a newer LG washer and dryer (2022) and the two-car garage is upgraded with high ceilings, built-in cabinetry, and an epoxy-surfaced floor. Living is easy within the gates of Villa Rosa, where lawn maintenance and cable TV are included and residents enjoy access to a heated community pool, spa, fitness and club room. You’ll love connecting with neighbors through the many community events. From your front door, take a leisurely stroll to Urfer Family Park’s scenic walking trails. This peaceful yet central location puts you close to shopping, hospitals, doctors’ offices, and only 8 miles from world-renowned Siesta Key Beach. Indulge in Sarasota’s vibrant arts and dining scene with the nearby ballet, opera, restaurants, and Saint Armands just minutes away. Perfect as a year-round residence or a seasonal retreat, this Villa Rosa home offers the best of Sarasota living—comfort, convenience, and community. Furnishings available on a separate contract
Listing Agent: Laura Way (941-321-6449)
3757 COUNTRYSIDE RD, SARASOTA, FL 34233
$685,00044 Days on yellowkey MLS ID: A4692427
REDUCED by $30,000 (4.2%) on 06/05/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2694 Built: 1981Monthly Fee: $50 Tax: $5,257 (2025)Community: Country PlaceSpa: NoSingle Family
Taxes:$5,257
Remarks: Beautiful home in a prime location, this three-bedroom, three-bath residence offers the perfect blend of comfort, space, and effortless Florida living. Designed with an open layout, the home features a bright and inviting kitchen that flows seamlessly into the main living areas, creating an ideal setting for everyday living and entertaining. Step outside to a spacious lanai overlooking a private pool and an expansive backyard, offering plenty of room to relax, host, play, garden, or simply enjoy the outdoors in complete privacy. With generous yard space, ample interior living areas, and a highly desirable location, this home delivers the lifestyle buyers are looking for: open, easy, and beautifully connected to the outdoors. Extensively updated and meticulously maintained home featuring a new roof (2018), impact glass windows, slider and front door, updated AC systems with new ductwork, and numerous interior and exterior improvements throughout. Recent upgrades include new vinyl flooring, plumbing updates, bathroom vanities, fresh interior paint, updated landscaping, irrigation pump repair, pool heater repair, and professionally cleaned ductwork. Additional enhancements include a screened and enlarged paver entry, resurfaced outdoor living areas, updated lighting and electrical, KitchenAid gas cooktop and refrigerator, newer Maytag washer/dryer, tile backsplash, rescreened pool enclosure, and exterior siding repairs with fresh paint. Property also offers central vacuum, NEST thermostat, irrigation system, wood-burning fireplace, pull-down attic ladder in garage, wood/tile/vinyl flooring, covered patio with ceiling fan, Ring doorbell, and beautifully maintained tropical landscaping. Receipts, maintenance records, and termite inspection reports available.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Inbal August (917-957-8111)
4470 NARRAGANSET TRL #90A, SARASOTA, FL 34233
$199,00011 Days on yellowkey MLS ID: A4696073
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1182 Built: 1976 Tax: $867 (2025)Community: Lake TippecanoeCondo
Taxes:$867
Remarks: Enjoy the best view in Tippecanoe from this beautifully maintained 2-bedroom, 2-bath condo overlooking the lake. Features include granite countertops, an open-concept layout, and a screened-in patio ideal for enjoying the scenery year-round. A perfect blend of comfort, style, and waterfront living.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Curtis Andrews (941-914-3253)
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