Location: Sarasota
Do Not Show Listings
5475 CHANTECLAIRE #58, SARASOTA, FL 34235
$525,00011 Days on yellowkey MLS ID: A4695707
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985 Tax: $5,106 (2025)Community: ChanteclaireVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,106
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: One of a kind! Welcome to this beautifully updated villa on the 14th fairway of the Meadows Golf Course. Enjoy stunning golf course views from the builder’s choice lot in Chanteclaire. Fully updated in 2023, the interior features luxury vinyl flooring, crown molding and abundant natural light. The open kitchen boasts stainless-steel appliances, Malibu quartz countertops, a new tile backsplash and Oxford Maple soft-close cabinetry with direct access to the grilling patio. Perfect for entertaining, the living room includes new custom cabinetry, a matching quartz countertop and a built-in wine fridge. The spacious primary suite serves as a true retreat, complete with a custom walk-in closet and a sliding door that opens to peaceful nature views. The present owners have added extensive premium updates for ultimate comfort and peace of mind. The home features full-height, custom PGT hurricane-rated windows and doors throughout, powered aluminum hurricane shutters and plantation shutters in the dining room and bedrooms. Mechanical and structural upgrades include a high-efficiency Trane variable-speed HVAC unit and a new shingle roof installed in 2025 with 71 additional joist clips for enhanced wind protection. This property sits at a 33-foot elevation in Flood Zone X, making it the perfect choice for a secure, lock-and-leave Florida lifestyle. Outside, a quiet cul-de-sac location, paver driveway and charming courtyard welcome you home. Mature shade trees, colorful sunsets and a daily parade of local birds frame the golf course views. The villa is also just a short distance from two heated community pools. The comprehensive HOA fee covers exterior insurance, maintenance-free yard care, irrigation, pest control, exterior cleaning and painting, roof maintenance, dryer vent cleaning, neighborhood pools and basic cable. Set within the 1,600 park-like acres of The Meadows, this resort-style community offers an active social calendar, 14 miles of scenic trails, championship golf courses, a junior Olympic pool, pickleball, Har-Tru tennis and a fitness center. You are just 15 minutes from downtown Sarasota, Bradenton, Lakewood Ranch and Sarasota International Airport and mere minutes from Whole Foods, Trader Joe’s, Nathan Benderson Park, the Legacy Trail and premier dining at University Town Center. Experience worry-free Florida living at its finest!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Fernando Viteri, Pa (941-400-7676)
4391 WOODMANS CHART #155, SARASOTA, FL 34235
$349,00032 Days on yellowkey MLS ID: A4694064
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1535 Built: 1977 Tax: $3,452 (2025)Community: Woodmans ChartVilla
Taxes:$3,452
Elementary School: Gocio Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Nestled in the highly sought after community of Woodmans Chart, this 2 bedroom/2 bath villa combines architectural character, abundant natural light, and a resort style lifestyle just 15 minutes from downtown Sarasota and about 30 minutes from world-renown Siesta Key Beach. Soaring vaulted ceilings with striking wood beams create warmth and charm throughout most of the home, while recent interior paint and new plank-style tile flooring add a fresh, modern touch. The spacious living area also has a sun room adjoining it with a large skylight that basks the area in light, and creates a bright and welcoming gathering space. A spacious primary suite features a row of French doors that open to the main living area, enhancing the home's airy, open feeling. What was most likely once an open atrium has been thoughtfully enclosed to create a stunning sunroom featuring three skylights set into the vaulted ceiling. Bathed in natural light and surrounded by two walls of French doors, this inviting space would make an exceptional art studio, reading room, or extra sleeping area for guests. The entire rear of the home is designed to bring the outdoors in, with walls of glass featuring dual four-paneled sliding glass doors and a large picture window overlooking the expansive 35-foot screened lanai-perfect for entertaining, relaxing, or enjoying peaceful garden views. Just off the dining room, a door leads to a private outdoor patio finished with charming brick pavers-an ideal setting for relaxing outdoors in complete privacy, enjoying morning coffee, or soaking up the Florida sunshine. From the patio, you have direct access to the spacious two-car garage, offering both convenience and ample storage. Residents of Woodmans Chart enjoy access to two community pools as well as a private tennis court tucked away among mature trees and lush landscaping, adding to the peaceful, resort-style that makes The Meadows such a sought-after community. The 1600 acres of The Meadows offers 14 miles of scenic trails and optional memberships to a fitness center, tennis and pickleball courts, a Junior Olympic pool, and golf. Everyday conveniences are close at hand, with easy access to premium shopping, dining, and entertainment including The Fresh Market, Whole Foods, UTC Mall, the new Mote Marine Laboratory & Aquarium, and the popular Waterside district in Lakewood Ranch. This central location places the very best of the Sarasota lifestyle right at your doorstep. There is a One Time $1000.00 Capital Improvement fee at Closing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Stacy Liljeberg (941-544-6103)
4937 CHASE OAKS DR, SARASOTA, FL 34241
$365,00043 Days on yellowkey MLS ID: A4692927
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1572 Built: 1997Monthly Fee: $370 Tax: $2,373 (2025)Community: Heritage Oaks Golf & Country ClubVilla
Taxes:$2,373
Elementary School: Lakeview Elementary
High School: Riverview High
Middle School: Sarasota Middle
Remarks: Not just another lovely home on a street, this "Buttonwood" Club Home, former builder's model, is ready for the opportunity to make it your own. With classic design and fully furnished, the home is waiting for the right touch. The kitchen is spacious and conveniently designed, with granite countertops. The Breakfast Nook has a buffet server with overhead lighting and extra cabinet space. Washer/dryer laundry room is in a separate utility room, conveniently adjacent to the kitchen. The den has a built-in entertainment center and an integrated desk/computer work space. The Primary bedroom is more spacious due to the optional bay window which overlooks the water and the golf course. The en-suite bath has double sinks, a step-in shower and an enormous walk-in closet. Situated on a semi private street, in proximity to the tennis courts, Pro Shop, Jr. Olympic pool and spa, and the main clubhouse with the 19th Hole, dining rooms and meeting rooms. Through the breezeway takes you to the newly renovated fitness center, complete with first class fitness equipment and a full-time director and specialty adjunct instructors. All conveniently located and accessible to your new home. In fact, one of the neighborhood pools is located in the other direction and about the same distance. Heritage Oaks Golf and Country Club is a bundled community (all owners are members of the club and enjoy access to the amenities) situated on 550 acres, five miles of walking trails, four neighborhood pools, gated with a 24-hour guard on duty. Sarasota is "The Arts Capital of Florida, and as such, has many cultural and artistic venues: restaurants, world class beaches, Selby Gardens, Mote Marine St. Armand's Circle and the three convenient airports. Come and enjoy the Heritage Oaks Lifestyle in Sunny Sarasota.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: R Glen Ridgeway (941-302-2376)
4601 LAS BRISAS LN, SARASOTA, FL 34238
$625,00052 Days on yellowkey MLS ID: A4690192
REDUCED by $20,000 (3.1%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2428 Built: 1988Monthly Fee: $800 Tax: $5,706 (2025)Community: Prestancia/Villa D'esteVilla
Taxes:$5,706
Remarks: Tucked within the charming Villa d’Este enclave of TPC Prestancia, this beautifully updated villa welcomes you with a relaxed coastal feel and an easy sense of home from the moment you step inside. Natural light fills the space, enhanced by soaring ceilings and an open layout that allows each room to flow comfortably into the next. The kitchen sits at the heart of it all, where quartz countertops are paired with a soft aqua subway tile backsplash—adding just the right touch of color and personality while keeping a clean, coastal look. The primary suite is set apart for privacy, creating a quiet retreat, while the guest bedrooms are located on the opposite side of the home—ideal for hosting family or friends. Each bedroom is generously sized and bright, offering comfortable, airy spaces throughout. Step outside to a cozy lanai, perfect for a quiet morning coffee, then continue to the additional outdoor seating area just beyond—an inviting spot to relax, gather, or enjoy Sarasota’s year-round sunshine. Practical updates add to the home’s appeal, including a new roof, fascia, skylights and gutters completed within the past year. The property is sold furnished for your convenience. Whether you’re here full-time or seasonally, the ease of living stands out. The community takes care of the exterior of the villa and of the landscaping, so you can simply enjoy your time without the upkeep. TPC Prestancia community provides 24/7 gated security and is recognized as an Audubon Certified Sanctuary, with 565 acres of mature trees, wildlife, and walking paths. Fine dining, shopping is only minutes away! Located only 4 miles from world-renowned Siesta Key Beach, this home offers you piece of mind in the most upscaled golf community in Palmer Ranch, Sarasota. TPC Prestancia social, sports (tennis, brand new pickleball courts, gym in construction) and golf memberships are available and optional. This is a rare opportunity to own a turnkey villa, move in condition that combines space, thoughtful updates in one of the best locations in Sarasota. Schedule your private showing today (Floorplan and 3D tour available)!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Pascale Durand (973-727-9784)
1732 KESTRAL PARK WAY S #43, SARASOTA, FL 34231
$534,00072 Days on yellowkey MLS ID: A4686630
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1368 Built: 1982Monthly Fee: $167 Tax: $5,360 (2025)Community: The LandingsVilla
Taxes:$5,360
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: THIS RARELY AVAILABLE and highly sought-after Landings Carriage Home, nestled within mature landscaping and offering verdant vistas from every room, is ready for its next owner. This residence lives like a single-family home, featuring a charming living area with a wood-burning fireplace, custom mantle, glass-topped shelf divider, and LVT plank flooring. Abundant windows fill the home with natural light, while plantation shutters provide privacy and character. The surrounding landscaping includes hibiscus, palms, ferns, and flowering trees, supported by an irrigation system, creating a peaceful garden setting. A paver driveway and walkway enhance the welcoming curb appeal. The split floor plan offers privacy, with a spacious primary suite featuring a dressing-room-style closet. The updated primary bathroom includes a walk-in shower with travertine, stone vanity top, high ceilings, and mirrored and tiled accents. The suite also features a ceiling fan and access to a private patio. The guest bedroom offers two closets and a full patio door for natural light. The second bathroom includes a granite-top vanity and tub/shower combination. The dining area is highlighted by a coastal-style glass bead chandelier. A glass-enclosed lanai provides flexible space for an office, den, or guest area. The kitchen features newer stainless steel appliances, granite countertops, a breakfast area, and a patio door leading to a private walled courtyard with a ceramic tiled fountain—ideal for relaxing or outdoor dining. Residents of The Landings enjoy scenic nature trails leading to Roberts Bay, along with a private fishing gazebo and kayak launch. Conveniently located between the Siesta Key bridges and approximately seven miles to downtown Sarasota. THIS IS THE LOCATION!! New additional gutters (2025), new TPO lanai roof (2026), new barrel tile roof (2022 association maintained), tankless hot water heater, new GE stacked full size washer and dryer with wifi capability (2021), new stainless steel Kitchen Aid appliances (2023), new garbage disposal (2024), new wifi controlled thermostat (2022), newer A/C system, create a home for you to easily move right into. Landscaping and building exterior maintenance are included in the monthly fees, so you are free to take advantage of the ideal Landings location—strategically developed as one of Sarasota’s premier gated communities with optional Racquet Club membership with 8 Har-Tru tennis courts, pro shop, fitness center, meeting rooms, pool and spa. The Landings has a lush well maintained nature trail that leads to Roberts Bay with a private fishing gazebo and rental space to park your kayak. Midway between the two Siesta Key bridges and approximately 7 miles from downtown—this is THE LOCATION.”
Listing Agent: Heather Chase (941-320-3121)
1141 MERLE WAY #14, SARASOTA, FL 34232
$210,000142 Days on yellowkey MLS ID: TB8470330
REDUCED by $10,000 (4.5%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1500 Built: 1974 Tax: $2,581 (2025)Community: Glen Oaks Ridge Villas 1Villa
Taxes:$2,581
Elementary School: Tuttle Elementary
Remarks: SELLER CONCESSION** SELLER IS OFFERING 1K TOWARDS CLOSING COSTS IF BUYER USES PREFERRED LENDER. As you step into 1141 Merle Way, you’re welcomed into a bright and comfortable living space designed for easy everyday living. The home has been thoughtfully maintained and updated, with fresh interior paint completed in 2021, giving it a clean and inviting feel throughout. The layout flows effortlessly from the living room into the kitchen and dining area, creating a functional and open atmosphere. The kitchen has been upgraded with new cabinetry and Formica countertops that were redesigned and shortened to improve both movement and usability. Brand-new LG fluorescent lighting enhances the space, making it bright and practical for daily cooking and entertaining. Automatic shades in the living room, kitchen, dining area, and bedroom provide added convenience and light control at the touch of a button. Moving through the home, you’ll find a comfortable bedroom with new blinds installed in 2025, providing privacy and a fresh, updated look. The bathroom has been thoughtfully renovated to include a walk-in sit-in tub, offering both comfort and accessibility. Hurricane-rated doors add peace of mind, while a sensor light outside enhances safety and security. Recent upgrades continue outside the home, including new gutters installed in 2025. The property is located in a welcoming 55+ community known for its friendly atmosphere and well-maintained amenities. Residents enjoy access to a clubhouse, workout center, pool, and outdoor shower, as well as nearby nature trails and close proximity to three golf courses. With easy access to Honore Avenue via 17th Street, the location provides a perfect balance of tranquility and convenience. HOA INCLUDES exterior maintenance, water, sewer, cable, and amenities This home offers a comfortable, low-maintenance lifestyle, ideal for those looking to enjoy Sarasota living with ease.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Rotosha Cormier (941-210-2062)
4439 DEER TRAIL BLVD, SARASOTA, FL 34238
$479,999158 Days on yellowkey MLS ID: A4677582
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1939 Built: 1992Monthly Fee: $282 Tax: $4,835 (2025)Community: Villas At Deer CreekVilla
Taxes:$4,835
Elementary School: Gulf Gate Elementary
Remarks: Just reduced $30,000 and Seller offering a $30,000 credit at closing. Seller is highly motivated. Mesmerizing scenic lake views from this sought after Deer Creek Villa home located in the heart of Palmer Ranch. This Villa home offers close to 2,000 sq ft with enclosed Lanai with sliding doors to enjoy the warm breezes. Spacious rooms sizes, vaulted ceilings and lots of light in this 2-bedroom, 2-bath floor plan with large den/office. Lovely living room, dining room & white cabinetry kitchen with granite counters & decorative tile backsplash. Separate laundry room with cabinetry. Large Primary Suite with high ceilings & walk-in closet. The Primary Bath with granite double vanity, soaking tub & tiled shower. Split double bedroom & bath. The den/office could be a 3rd bedroom or exercise room. Deer Creek is one of the more established gated communities that offers residents gorgeous tree lined street, lush tropical flora & tranquil lakes. Deer Creek is a gated community with 24 hr. security that is low maintenance with a wonderful Community Pool & great social activities for all residents to enjoy. Close to everything in Sarasota, including top-rated schools, world-class golf courses, 8 miles to Downtown Sarasota, including Marie Selby Gardens. Shopping, all within 1 mile. Costco, Target, Sprouts, Starbucks, Kohls, the soon to be re-developed Sarasota Square Mall and a new Trader Joe's opening in Spring. The famous Legacy Trail is just a short distance away. Easy to schedule a showing.
Listing Agent: Betsy Campbell (203-554-8349)
5793 ITHACA WAY, SARASOTA, FL 34238
$439,0007 Days on yellowkey MLS ID: A4696958
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 2002Monthly Fee: $473 Tax: $4,942 (2025)Community: VillagewalkSpa: NoVilla
Taxes:$4,942
Elementary School: Ashton Elementary
Remarks: New on the market is this rarely available extended Capri III Villa w/heated swimming pool! This villa has been well maintained and recently upgraded with double pane storm windows. The home was “Built Solid” by DiVosta Homes utilizing poured concrete and steel walls with a cement tile roof. Designed for full time or “lock n’ leave” seasonal owners you will enjoy virtual maintenance free living in VillageWalk. The split 2 bedroom, 2 bath floor plan offers privacy for you and your guests. Both bedroom suites offer walk-in closets w/modular organizers. The kitchen countertops and appliances have been upgraded as well. A recently installed efficient A.C. system will keep you cool for less. VillageWalk is one of Sarasota county's jewels. A true lifestyle community VillageWalk has a full time activities director, 2 heated pools, 6 HAR-TRU tennis courts, Pickleball and basketball courts plus a State-of-the-Art fitness Center and miles off walking trail's. The community TownCenter hosts a variety of activities daily activities incl. card games, club meetings, guest speakers, stretching and Pilates classes and much more. While there residents can get bite at the onsite Cafe' or visit to the gift shop or hair salon. There's even a gas station for convenience!! Schedule a showing today!
Listing is courtesy of: TOWN CENTER REALTY (941-929-9333)
Listing Agent: Scott Albert (941-929-9333)
3825 WILSHIRE CIR #1, SARASOTA, FL 34238
$335,00030 Days on yellowkey MLS ID: A4693723
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2223 Built: 1985 Tax: $2,233 (2025)Community: Lakeshore Village SouthVilla
Taxes:$2,233
Remarks: Exceptional value in Sarasota with a NEW TILE ROOF recently installed. Located in Lakeshore Village South, with over 2,223 square feet of air-conditioned living space, this 3-bedroom, 2-bath, 2-car garage, attached villa, offers an incredible opportunity for buyers seeking space, location, and potential at an affordable price point. Lakeshore Village South is a 55+, PET FRIENDLY section of the community with its own heated pool for community enjoyment. Featuring concrete block construction, a spacious great room floor plan, with vaulted ceilings, galley kitchen, enclosed screened lanai, mature landscaping, and peaceful greenbelt view. The home provides strong fundamentals for future customization and personal design updates. The property has been meticulously maintained and is ready to move in while personal choice upgrades and improvements could be added over time. Quarterly fees include lawn service, cable and internet and exterior maintenance, adding additional value and convenience. Ideal for year-round residents, seasonal owners, or buyers looking to personalize a spacious Sarasota home without paying premium prices for someone else’s renovations. Additional OPTIONAL community opportunity to enjoy amenities: tennis courts, pickleball courts, an additional heated saltwater pool, horseshoe pits, clubhouse with a kitchen, library, table tennis, bocce ball, billiard room and countless community events for only $200/yr, see listing agent for details. When location, price and community come together, bring your vision and enjoy the lifestyle of ease, the home offers comfort, space, and privacy in a highly convenient location, close to area restaurants, the beautiful SIESTA KEY BEACH, shopping, airports and so much more. This home is also conveniently positioned near the communities private ( homeowners only) rear entrance, for easy access in and out to Beneva RD.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Maggie Nasser (941-780-1006)
4531 LAS BRISAS LN, SARASOTA, FL 34238
$625,00094 Days on yellowkey MLS ID: A4686168
REDUCED by $24,000 (3.7%) on 06/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2227 Built: 1987Monthly Fee: $802 Tax: $4,963 (2025)Community: Villa D EsteVilla
Taxes:$4,963
Remarks: Virtually Staged. Enjoy maintenance-free living at its finest in this stunning 2-bedroom, 2-bath villa + den, located within the 24/7 guard-gated (with two entrances) Prestancia golf community, in the highly sought-after enclave of Villa D’Este. A picturesque drive along Prestancia Boulevard, lined with majestic oak trees forming a beautiful canopy, leads you into this serene neighborhood. Surrounded by two championship golf courses, wetlands, cypress heads, ponds, and lagoons teeming with wildlife, Prestancia is proudly recognized as a sanctuary by the Audubon Society. This residence features soaring ceilings and multiple skylights throughout, creating a bright, open, and inviting Florida-style atmosphere. Plantation shutters adorn all exterior windows, adding both elegance and functionality. A brand-new concrete tile roof, along with new skylights, gutters, downspouts, and fascia, ensures peace of mind for years to come. The spacious living room showcases a wood-burning fireplace and built-in wet bar, seamlessly connecting to the tiled lanai via pocket sliders. This villa offers a rare extended lanai—stretching nearly the full length of the rear of the home —a feature found in very few villas in the community. The adjacent dining room, complete with a built-in buffet, continues the home’s modern elegance. The large eat-in kitchen is light and bright, featuring newer cabinetry, granite countertops, stainless steel appliances, a breakfast nook, a separate desk area, soffit lighting that highlights the volume ceilings, and ample storage. Recent upgrades include a home security system with an electronic lock, a new secure locking screen door at the lanai, privacy screens, and interior locking hurricane shutters. The primary suite serves as a private retreat with direct lanai access and a spa-like bathroom featuring a Jacuzzi tub, walk-in shower, dual marble vanities, and a generous walk-in closet. The guest bathroom includes a soaking tub and a stylish glass vessel sink. A spacious den with a skylight and contemporary ceiling fan offers flexible space for a media room, office, or additional living area. The rear bedroom is equipped with a queen Murphy bed, built-in cabinetry, and a desk, making it ideal as either a guest room or home office. Residents of Villa D’Este enjoy access to a beautifully maintained community pool and spa. Optional membership to TPC Prestancia Golf Club provides access to two 18-hole championship courses, along with dining and social activities. Conveniently located near shopping, dining, the Legacy Trail, and world-renowned Siesta Key Beach, this exceptional villa offers the perfect blend of elegance, modern upgrades, and the Sarasota lifestyle.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
3952 ASHWOOD LN #37, SARASOTA, FL 34232
$179,900262 Days on yellowkey MLS ID: A4663160
REDUCED by $20,000 (10.0%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1040 Built: 1973 Tax: $2,584 (2024)Community: Glen Oaks Ridge Villas 1Villa
Taxes:$2,584
Tax Year: 2024
Remarks: Welcome to easy Florida living in the heart of Sarasota. Tucked inside an active 55+ community, this beautifully updated 2-bedroom, 2-bath villa offers the perfect combination of comfort, style, and convenience for both seasonal escapes and full-time living. Partially furnished and truly move-in ready, this inviting home is designed for enjoying the relaxed Sarasota lifestyle from day one. Inside, you’ll immediately notice the light-filled open feel and thoughtful upgrades throughout. Luxury vinyl flooring with Air Guard underlayment flows seamlessly throughout the home, while Soft-Lite impact windows provide added peace of mind and energy efficiency. Recent improvements include a new A/C compressor (2025), upgraded laundry room with fresh drywall, painted flooring, utility sink, and tile backsplash, along with refreshed bathrooms featuring updated vanities and toilets. The screened front entry creates a welcoming and private outdoor space, complemented by added gutters and attractive paver details. The spacious primary suite features a walk-in closet and private en-suite bath with a wheelchair-accessible shower for added comfort and accessibility. A generous guest bedroom offers flexibility for visitors, hobbies, or a home office setup. Enjoy peaceful mornings and relaxing evenings in the enclosed lanai, or take advantage of the community’s outstanding amenities, including a heated pool, shuffleboard courts, fitness room, clubhouse, game room, and a full calendar of social events. From bingo nights to potluck dinners, this is a neighborhood where neighbors quickly become friends. Ideally located just minutes from downtown Sarasota, Siesta Key Beach, shopping, dining, medical facilities, and the area’s renowned arts and cultural attractions, this charming villa delivers the best of low-maintenance Florida living in one exceptional location.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Brooks Cundiff (941-374-6848)
3721 COLLINS ST #812, SARASOTA, FL 34232
$300,000214 Days on yellowkey MLS ID: A4672044
REDUCED by $19,900 (6.2%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1584 Built: 1972Monthly Fee: $460 Tax: $1,271 (2024)Community: Forest Pines 08Villa
Taxes:$1,271
Elementary School: Alta Vista Elementary
High School: Sarasota High
Remarks: This Forest Pines condo can be your slice of Sarasota paradise in a highly sought-after 55+ community.! This beautifully updated Villa combines comfort, convenience, and that easy coastal lifestyle you’ve been dreaming about. The seller has just recently reduced the asking price again. It's located just minutes from Siesta Key Beach, downtown Sarasota, and the popular Der Dutchmen Restaurant, this location puts you right in the heart of it all. Love to golf or bike? You’ll be half a mile from the nearest golf course, and the Legacy Trail—perfect for long, scenic rides—starts only 1.5 miles away. Inside 3721 Collins St, you’ll find bright, welcoming spaces designed for relaxation. The home features newer upgrades including solid surface and granite countertops, modern kitchen cabinets, a walk-in shower in the primary suite, and luxury vinyl plank flooring in all main areas. This home has a living room and a family room where the original porch was properly permitted and enclosed for additional living space under air. Earth-toned colors and plantation shutters throughout add warmth and timeless charm. A new roof was installed in 2022. Forest Pines takes care of exterior maintenance so you can spend your days lounging by the community pool, meeting neighbors at the clubhouse, or enjoying a friendly game on the shuffleboard courts. Move-in ready, this condominium - villa style home invites you to settle in and start your next chapter in sunny Sarasota.
Listing is courtesy of: FLORIDA INTERNET REALTY LLC (941-961-4983)
Listing Agent: Steve Rider (941-504-5163)
4154 CENTER POINTE CIR #57A, SARASOTA, FL 34233
$249,000355 Days on yellowkey MLS ID: A4657470
REDUCED by $16,000 (6.0%) on 06/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1029 Built: 1983 Tax: $2,861 (2024)Community: Courtyard VillasVilla
Taxes:$2,861
Remarks: This bright and beautiful villa is just waiting for a snowbird or a year-round owner to enjoy this well-maintained, perfectly-located home. It's low-maintenance and high-enjoyment living. The A/C is only 2 years old and everything works just perfectly. The home has a large attached courtyard-patio area PLUS a neighborhood pool just a few doors down the street, PLUS 2 pets under 30 pounds are okay, PLUS new kitchen cabinets. GREAT ROOF NEWS: The Homeowners' Association will pay to fix any repairs to the roof. It has cash reserved for this purpose. It is financed by your low monthly HOA fees. THERE'S MORE !! PLUS new carpeting. PLUS recently painted. PLUS you are close to: 4 banks PLUS 12 restaurants P LUS 2 fitness centers PLUS Publix, Home Depot, Walmart ,Doctor’s hospital, PLUS 2 fitness centers and you are near I-75. You can park two cars in the driveway. GREAT LOCATION. GREAT PLACE. GREAT VALUE. GREAT PRICE. Better hurry before the bidding war starts ! ! !
Listing Agent: John Alexander (941-724-5907)
5071 BARRINGTON CIR #1602, SARASOTA, FL 34234
$149,90056 Days on yellowkey MLS ID: A4691290
0 Days Off yellowkey (back on 5/19/2026)
REDUCED by $15,000 (9.1%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1982 Tax: $497 (2025)Community: Barrington WoodsVilla
Taxes:$497
Elementary School: Emma E. Booker Elementary
Remarks: Spectacular Sarasota end-unit villa offering 2 bedrooms and 2 bathrooms, perfectly positioned with a 1-car carport conveniently located near the unit entry. Enjoy serene pond views from the primary bedroom, living room, and glass-enclosed lanai, creating a peaceful and private retreat. Features include a screened front entry leading into a welcoming foyer, a spacious kitchen with eat-in area and breakfast bar, and an in-unit laundry closet with full-size washer & dryer. Additional highlights include a large exterior storage closet, security system, central vacuum, impact glass windows, and major updates with a new AC (October 2023) and hot water heater (February 2022). Offered as an estate sale and sold with all contents in the unit and storage closet. Residents also enjoy access to a community pool and a prime location just minutes from Gulf beaches, the Ringling Museum, Sarasota-Bradenton International Airport, and vibrant downtown Sarasota.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Mike Bridges (941-316-6530)
266 OAK HILL DR #34, SARASOTA, FL 34232
$285,0008 Days on yellowkey MLS ID: A4696620
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1024 Built: 1985Monthly Fee: $559 Tax: $2,638 (2025)Community: Village Oaks Sec AVilla
Taxes:$2,638
Remarks: Welcome to this beautifully maintained 2BR/2BA villa with a private single-car garage, offering comfort, updates, and peace of mind in a prime Sarasota location. Major improvements have already been done, including impact windows and sliding glass doors (2025), a new A/C system (2025), new roof and gutters (2024), and water heater (2020), updated master bathroom making this home truly move-in ready with lower maintenance costs for years to come Located in a quiet, established community surrounded by mature oak trees and lush green space, this villa offers a relaxed Florida lifestyle just minutes from everything: Downtown Sarasota, I-75, UTC Mall, St. Armands Circle, and the world-famous Lido Key beaches. Residents enjoy resort-style amenities including a lakeside heated pool, tennis courts, and pickleball—perfect for staying active or socializing with neighbors in a friendly, well-kept neighborhood.
Listing Agent: Julianna Kovacs (941-518-6485)
6283 GREEN VIEW CIR S #102, SARASOTA, FL 34231
$179,90011 Days on yellowkey MLS ID: D6147713
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1545 Built: 1973Monthly Fee: $656 Tax: $260,930 (2024)Community: Village In The PinesVilla
Taxes:$260,930
Remarks: One or more photo(s) has been virtually staged. Bright and Open floor plan, immaculate villa has many updates including new in 2025 roof, refrigerator, washer and dryer. Other important upgrades included are whole house re-pipe, new plumbing from the villa to outside. (no cast iron) Primary bath has been remodeled with walk in shower, updated kitchen with recent granite. Great versatile floor plan, Tile floors throughout all main areas, this well maintained villa is ready for a new owner who would like a wonderful carefree lifestyle in this active over 55 community with large heated pool, clubhouse with lovely new updates. Just minutes to Siesta key and its world famous white sand beaches. Plus walk to Publix and restaurants. Great south Sarasota location. Sellers will also entertain an annual rental.
Listing Agent: Gail Cristello (941-400-8878)
7755 WANING MOON WAY, SARASOTA, FL 34241
$399,678121 Days on yellowkey MLS ID: A4683307
1 Days Off yellowkey (back on 6/13/2026)
REDUCED by $50,000 (11.1%) on 05/28/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1533 Built: 2026Monthly Fee: $448Community: Esplanade At Skye RanchVilla
Taxes:$0
Remarks: Under Construction. What's Special: Pond View | Close to Amenities | Close to Trails | Dedicated Study. New Construction – June Completion! Built by America's Most Trusted Home Builder. Welcome to the Ibis at 7755 Waning Moon Way in Esplanade at Skye Ranch! The Ibis offers a bright and thoughtfully designed layout that feels warm and welcoming from the moment you enter. The gathering room opens gracefully to the large designer kitchen, creating a comfortable space for cooking, conversation, and everyday living. A flexible space near the entry provides the perfect spot for work, hobbies, or quiet moments at home. The primary suite serves as a peaceful retreat with a spacious walk-in closet, dual vanity sinks, an expansive shower, and a private commode. A secondary bedroom and full bathroom complete the home and offer comfort for family or guests. Additional Highlights Include: tray ceiling package, study with pocket doors, extended patio cage with screened roof, 8' interior doors throughout, whole house impact windows, pre-plumbed for laundry sink in laundry room, apron front kitchen sink, additional flush mount LED lights, tile--plank, upgraded 42" kitchen cabinets and upgraded quartz countertops. Photos are for representative purposes only. MLS#A4683307 - Live your dream vacation every day in Esplanade at Skye Ranch! Esplanade offers a vibrant, resort-style lifestyle with endless opportunities to energize your body, mind, and spirit. From the moment you arrive, you’ll experience a world of fun and relaxation, with access to the Hub, Rendezvous Park, and Turner Park and soon, The Venue! Get ready for exciting amenities like a Bahama Bar and Grill, resort-style pool, state-of-the-art fitness center, bocce ball courts, bark park, and more. With community parks, sports fields, and a pet park, Esplanade is your personal playground. Stay active, stay relaxed, and embrace a lifestyle filled with adventure, every single day!
Listing is courtesy of: TAYLOR MORRISON RLTY OF FLA (866-495-6006)
Listing Agent: Michelle Campbell (866-495-6006)
7456 MOONBEAM AVE, SARASOTA, FL 34241
$429,14837 Days on yellowkey MLS ID: A4693652
REDUCED by $46,000 (9.7%) on 05/28/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1533 Built: 2026Monthly Fee: $448Community: Esplanade At Skyle RanchVilla
Remarks: Under Construction. What's Special: Corner Lot | Dedicated Study | Close to Amenities | Close to Trails. New Construction - June Completion! Built by America's Most Trusted Home Builder. Welcome to the Ibis at 7448 Moonbeam Avenue in Esplanade at Skye Ranch! Step into a warm and inviting home filled with natural light and an easy, open feel. The great room flows effortlessly into a beautifully designed kitchen, creating the perfect space for gathering and everyday living. Tucked at the back of the home, the primary suite offers a peaceful retreat with a spacious walk-in closet, dual sink vanity, and a relaxing shower. At the front, you will find a secondary bedroom, a full bath, and a private study that is perfect for working from home or quiet moments. Enjoy a thoughtfully designed community with nearby parks, convenient shopping, and dining options that make it easy to feel right at home. Additional Highlights Include: an extended lanai with a screened in patio, and a study in place of a flex room. Photos are for representative purposes only. MLS#A4693652 - Live your dream vacation every day in Esplanade at Skye Ranch! Esplanade offers a vibrant, resort-style lifestyle with endless opportunities to energize your body, mind, and spirit. From the moment you arrive, you’ll experience a world of fun and relaxation, with access to the Hub, Rendezvous Park, and Turner Park and soon, The Venue! Get ready for exciting amenities like a Bahama Bar and Grill, resort-style pool, state-of-the-art fitness center, bocce ball courts, bark park, and more. With community parks, sports fields, and a pet park, Esplanade is your personal playground. Stay active, stay relaxed, and embrace a lifestyle filled with adventure, every single day!
4481 ASCOT CIR N, SARASOTA, FL 34235
$285,000304 Days on yellowkey MLS ID: A4662740
REDUCED by $13,000 (4.4%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1376 Built: 1994Monthly Fee: $894 Tax: $3,753 (2025)Community: Longwood VillasVilla
Taxes:$3,753
Remarks: Welcome to Tivoli Village—an exclusive, private community of just 100 residences nestled among mature trees and lush landscaping. This beautifully maintained 2-bedroom, 2-bath villa with a den/office and 2-car garage offers the perfect blend of tranquility and convenience. Step inside this home peacefully knowing the major concerns have been upgraded a NEWER ROOF, A/C 2023, WATER HEATER 2023, EXTERIOR PAINT IN 2023 AND NEW BACKFLOW METER IN 2026. Seller is offering a $3000 CREDIT for HOA fees! Ideally located near UTC shopping and dining, I-75, Nathan Benderson Park, Sarasota-Bradenton International Airport (SRQ), and just a short drive to downtown Sarasota and Gulf Coast beaches. Step inside to an open-concept floor plan featuring soaring cathedral ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The updated kitchen showcases newer stainless steel appliances, ample cabinetry with slide-out shelving, a breakfast nook, and an extended breakfast bar overlooking the main living space. Sliding glass doors lead to an enclosed lanai, with additional paver patio space extending into a private, tropical outdoor retreat complete with native Florida landscaping and a custom tiled table and seating area. The spacious primary suite is privately situated at the rear of the home and features an updated en-suite bath with dual vanities, granite countertops, and a walk-in shower with built-in bench. A split-bedroom layout ensures privacy for guests, with a secondary bedroom and full bath located at the front of the villa. The versatile den/office includes a skylight and closet, making it ideal for a home office or potential third bedroom. Tivoli Village residents enjoy a scenic setting with four spring-fed lakes, fishing opportunities, majestic oak trees, and a tranquil nature trail. The HOA provides exceptional value, covering major expenses such as property insurance, exterior maintenance (including power washing and painting), roof replacement and repairs, as well as lawn care and irrigation—delivering low-maintenance, worry-free living. Don’t miss this opportunity to own a move-in-ready villa in one of Sarasota’s most charming and conveniently located communities!
Listing Agent: Diane Goodwin (941-706-6620)
2731 RIVERBLUFF WAY #V76, SARASOTA, FL 34231
$229,0008 Days on yellowkey MLS ID: A4696921
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1480 Built: 1971Monthly Fee: $725 Tax: $3,438 (2025)Community: Strathmore Riverside ISpa: NoVilla
Taxes:$3,438
Remarks: TURN-KEY OR UNFURNISHED | FULLY RENOVATED | 55+ WATERFRONT COMMUNITY Less than 18 minutes to Siesta Key Beach, this renovated 2 bedroom, 2 bath villa with two bonus rooms offers the Florida lifestyle many buyers are searching for. Residents enjoy a heated and chilled waterfront pool overlooking the marina, clubhouse, fitness center, residents' library, shuffleboard courts, and marina access. Boat slips are available for rent, providing direct boating access through Phillippi Creek to the Gulf of America. This home offers more usable living space than many comparable units in the community, with two bonus rooms ideal for a home office, hobby room, reading area, or guest space. Major updates include impact windows (2020), newer roof, 2022 A/C, updated plumbing and electrical systems, a whole house surge protector, fresh insulation, laminate flooring, sliding barn doors, granite countertops, under-cabinet lighting, and modern finishes throughout. Offered turn-key, furnished or unfurnished, this move-in-ready home is conveniently located near shopping, dining, medical facilities, downtown Sarasota, St. Armands Circle, and Siesta Key Beach. A rare opportunity to enjoy boating, resort-style amenities, and a renovated home in one of Sarasota's desirable 55+ waterfront communities.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: David Valencia (647-686-7973)
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