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$357,000
2 Beds ⋅ 2 Baths ⋅ Chelmsford Close SubDv. ⋅ 34235 Zip Code
Located in the desirable Chelmsford Close enclave of The Meadows, this well-maintained and freshly painted 2 bedroom, 2 bathroom villa with a 2-car garage offers over 1,500 square feet of comfortable living space and golf course frontage with peaceful fairway views. Built in 1990 and carefully cared for by the original owners, the home enjoys a prime setting close to the community pool and is surrounded by mature landscaping and manicured grounds. Chelmsford Close is known as one of the newer villa communities in The Meadows, featuring solid construction, attractive architecture and a quiet, private feel. Residents enjoy a park-like setting within a 1,600-acre master-planned community offering 14+ miles of walking and biking trails, lakes, green spaces, fitness facilities, pickleball and optional golf and tennis memberships. Ideally situated near Nathan Benderson Park, University Town Center shopping and dining, and just minutes to downtown Sarasota, cultural attractions and world-class Gulf beaches. Competitively priced, this villa presents an excellent opportunity to enjoy the Sarasota lifestyle—schedule your private showing today before it’s gone!

3350 W Chelmsford Court Unit 13, Sarasota
$510,000
3 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
Absolute stunner and an exceptional value. This fully remodeled (2025) 3-bedroom, 2-bath, 2-car garage home in The Meadows offers 2,205 sq. ft. of beautifully updated living space on just under a 1/3 of an acre (0.30-acre) lot. The property features an open, split-bedroom floor plan with 10-foot ceilings and a soaring cathedral ceiling in the great room. The brand-new kitchen includes stainless steel appliances, quartz countertops, new cabinetry, and updated lighting. Both bathrooms have been fully renovated with new tile, faucets, finishes, and fixtures. Additional upgrades include new laminate wood flooring throughout and fresh interior paint. The home offers a large living room with a fireplace, a formal dining room, and a spacious primary suite with an oversized walk-in closet, dual sinks, a large walk-in shower, and a stand-alone soaking tub. A 252 sq. ft. air-conditioned Florida room, a generous utility room with a sink, and an oversized garage provide added versatility and convenience. Enjoy a maintenance-free lifestyle with an HOA that covers landscaping, lawn care, irrigation, power washing, tree trimming, and exterior paint. The property is located in Flood Zone X, meaning flood insurance is not required—an excellent advantage for buyers. The Meadows is a highly sought-after, park-like community featuring extensive amenities, including social activities, miles of nature trails, three golf courses, 15 lighted tennis courts, pickleball and basketball courts, a new Lifestyle and Wellness Center, a Jr. Olympic pool and spa, and protected nature preserves. A professional, 24-hour vehicle-based security patrol provides added peace of mind. Ideally situated just minutes from the University Town Center Mall, boutique shopping and dining, Nathan Benderson Park, downtown Sarasota, and world-class Gulf beaches.

2960 Sandringham Place, Sarasota
$351,990
3 Beds ⋅ 3 Baths ⋅ Grand Park Phase 3a & 3b SubDv. ⋅ 34241 Zip Code
The Morgan floorplan townhome offers a spacious layout designed for comfortable gathering. The large living room is located at the entry and connects to the first-floor living areas, which feature designer-selected ceramic tile flooring. The kitchen includes all-wood, European-style slow-close cabinetry with bump and staggered upper cabinets, GE appliances, and a white quartz countertop that coordinates with the contemporary gray cabinetry. Upstairs, the loft and bedrooms include plush carpet flooring. All units feature impact-resistant windows on the second level, and the exterior construction is concrete block. The primary bedroom provides a private rear view, ideal for enjoying sunset vistas.

6068 Dry Tortugas Drive, Sarasota
$1,295,000
3 Beds ⋅ 3 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code
Welcome to this unique custom offering of blended versatility, which includes 3 bedrooms with 3 baths. A concrete block custom build in 2005. Directly across the road from Gillespie Park, a dazzling 10-acre monitored park. Ideal for extended family, visitors, artist studio, and/or additional rental income, so just let your imagination run wild. High-impact hurricane windows and a newly installed roof in 2024 with hurricane tie-downs. The freshly painted main house features a double sided gas fireplace, stained acid-washed floors, a common feature throughout the compound, newly installed granite-honed countertops, new subway tiles in the kitchen and freshly painted solid wood cabinets. If it is purity you want, try the Apec Reverse Osmosis dispenser at the newly installed kitchen sink. Bosch gas cooktop, dishwasher and convection wall oven, Whirlpool refrigerator with Electrolux washer and dryer. Tankless on-demand hot water, gas for the main house, and an additional electric unit for the guest suites. A well for irrigation, EV 220-volt 50-amp charging station, storage bins and racks for kayaks, two driveways, private hedging with magnolia, holly, black bamboo and hibiscus, or if it's the fruit you want, mango, avocado, lemon, papaya and banana trees. An outdoor shower, brick pavers throughout the inspiring courtyard with hanging lights, and a fire pit to capture those spectacular starry evenings. One guest suite was built with the original house with a kitchenette, while the second was built in 2022, complete with a full kitchen and washer/dryer combo. Both suites come complete with mini-split heat pumps, one installed in 2023, and are turnkey furnished. Gillespie Park, which is directly across the street, features grand oaks, recreational trails, a lake, tennis courts, a pickleball court, a gazebo, a dog park and a basketball court. Centrally located and within short distance of Sprouts, Whole Foods, restaurants and local shopping, this neighborhood offers a vibrant and ever-evolving downtown neighborhood.

640 N Osprey Avenue, Sarasota
$349,900
1 Beds ⋅ 1 Baths ⋅ Gulfstream Towers SubDv. ⋅ 34236 Zip Code
33 Gulfstream Towers #307—Updated 1BR/1BA, third floor. Across from Marina Jack, the bayfront park, and downtown dining, this turnkey condo blends city convenience with coastal living. The renovated kitchen features new stainless-steel appliances and contemporary finishes, while custom blinds and an open layout keep the living area bright and airy. The bath offers a relaxing tub/shower combo. Building amenities include a recently refurbished heated 30’×50’ pool with a large sun deck, a club room with a full kitchen, a fitness center, and on-site laundry. Location: steps to restaurants, shops, cultural venues, and events, minutes to Sarasota’s renowned beaches.“One or more photo(s) were virtually staged.”April 31, 2026. Disclosure: photos and rooms are virtually staged to illustrate furniture placement; furnishings do not convey.

33 S Gulfstream Avenue Unit 307, Sarasota
$4,925,000
3 Beds ⋅ 4 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code
Experience the epitome of island living in this luxurious three-bedroom, four-bath residence. With high-end finishes and spacious rooms featuring soaring ceilings, every detail exudes comfort and elegance. Enjoy leisure time with a ping-pong table, a theater room, and a pristine pool that basks in southern exposure, overlooking the tranquil open bayou. The kitchen, complete with a breakfast area, offers stunning views of the pool and bayou, while a cozy office space provides an ideal work-from-home environment. The home also features a beautiful dining room with a wet bar and a welcoming living room adorned with elegant wood floors throughout. Each bedroom offers luxurious en-suite baths, and the master bath is a true retreat. The expansive pool deck area and the convenience of a two-car garage and boat dock add to the home’s charm. Plus, with an elevator and a full-house generator, you’ll enjoy ultimate comfort and peace of mind.

340 Morningside Drive, Sarasota
$610,990
3 Beds ⋅ 3 Baths ⋅ Grand Park Phase 2 SubDv. ⋅ 34241 Zip Code
Under Construction. Welcome to the White Star by Neal Communities, a beautifully designed 3-bedroom home that blends privacy, luxury, and functionality. This spacious floor plan spans 40 feet wide and features an oversized den, a long, trayed-ceiling foyer, and a true butler’s kitchen—perfect for both everyday living and entertaining. The extra-long living room separates the primary suite from the guest bedrooms, offering a thoughtful sense of privacy. The on-trend kitchen showcases a dark-stained wood island paired with bright white linen cabinetry and white quartz countertops, creating a perfect balance of warmth and sophistication. Enjoy south-facing backyard views that capture full Florida sun throughout the day while overlooking a unique littoral shelf and nature preserve—a truly serene and environmentally distinctive setting. Just a short stroll to the community amenity center, you’ll have access to two resort-style pools, a stunning clubhouse, and more. Experience refined Florida living in the White Star—where modern design meets natural beauty.

6563 Big Bayou Drive, Sarasota
$268,000
3 Beds ⋅ 3 Baths ⋅ Willow Green SubDv. ⋅ 34235 Zip Code
Welcome to the Willow Green in THE MEADOWS, Rarely available and beautifully located, this spacious 3 Bedroom 2 Bath residence offers a peaceful Sarasota lifestyle in one of the areas most sought after communities. Featuring cathedral ceilings, formal dining room area, and a large primary suite walk in closest, the home provides comfort and style. The upper loft area opens to a private rooftop patio, perfect for enjoying morning coffee of Florida Sunsets. Optional furnishing available for move in ready home or vacation getaway. Covered parking is included for connivences. The Meadows Country Club Feature new management Benderson Dev along side golf, tennis, pickleball, fitness facilities, swimming pools, and vibrant social activities. Just minutes to University Town Center Mall (UTC) Downtown Sarasota, award winning beaches, and an incredible variety of restaurants and entertainment. Enjoy the private pool exclusively for Willow Green Residences - your own slice of paradise awaits.

3097 Willow Green Unit 32, Sarasota
$199,000
3 Beds ⋅ 2 Baths ⋅ Meadowlake SubDv. ⋅ 34235 Zip Code
Welcome to The Meadows in Sarasota! This 3-bedroom and 2-bath bright and spacious two-story condominium features an open layout with cathedral ceilings and abundant natural light. The primary bedroom is conveniently located on the ground floor, while the two upstairs bedrooms provide great extra space for guests, a home office, fitness, or hobbies. Enjoy two spacious patios — a screened front patio for morning coffee and a relaxing garden-style patio in the back to unwind at sunset. This unit offers plenty of storage, including a walk-in attic, under-stair storage, and a covered carport with its own storage area. Living in The Meadows feels like being at a resort all year long — with miles of walking and bike trails, lakes, lush mature landscaping, tennis courts, a pickleball complex featuring 8 new courts, a clubhouse, a fitness center, a playground, and a golf course throughout the community. The heated community pool is a few steps from the back porch. Take a short drive to UTC Mall, Benderson Park, Whole Foods, I-75, restaurants, shopping, Downtown Sarasota, St. Armand’s Circle, Siesta Key, or the stunning Gulf beaches. Country Club membership is optional. This is Sarasota living at its best — comfortable, stylish, and ready for you to enjoy.

2767 Horseshoe Court Unit Q-3, Sarasota
$1,140,990
3 Beds ⋅ 3 Baths ⋅ Grand Park Phase 2 SubDv. ⋅ 34241 Zip Code
Under Construction. This stunning Island-elevation home offers a perfect blend of luxury, comfort, and Florida living. Step onto the welcoming front porch and into a spacious foyer that opens to an extra-long living room seamlessly connected to the dining area. Pocketed sliding doors lead to the lanai, where serene pond and preserve views create the ultimate backdrop for relaxing or entertaining. Enjoy the sparkling pool and spa surrounded by pavered decking for effortless indoor-outdoor living. Inside, a club room with its own lanai access provides a versatile retreat, while the front den with French doors is ideal for a home office. The mudroom and utility space off the garage add everyday convenience. Guests will appreciate a private suite, and the primary bedroom features an impressive spa-style bath with a soaking tub. Designed for gathering, the gourmet kitchen and outdoor living spaces are truly the heart of this home. This home truly must be seen to be believed.

6336 Lake Woodruff Court, Sarasota
$2,250,000
4 Beds ⋅ 4 Baths ⋅ Burns Owen SubDv. ⋅ 34236 Zip Code
Welcome to your own private Spanish-Mediterranean-inspired sanctuary, perfectly nestled in the heart of Sarasota’s historical Laurel Park. This rare exquisitely updated 4-bedroom, 3.5-bath residence blends timeless charm with modern sophistication offering a dynamic combination of style, comfort, and versatility. This private gated home offers a separate guest or in-law suite with a full kitchen and en-suite bath ideal for extended family, visitors, or potential rental income. Step outside into a lush, resort-style backyard, where tropical landscaping frames a shimmering turquoise saltwater pool/spa and a retractable awning to enjoy your personal oasis for relaxing afternoons or elegant entertaining. Inside, the main home's fully renovated first level boasts European white oak flooring, a thoughtfully designed chef’s kitchen, and bespoke finishes throughout. Unique touches include a custom ventilated cat retreat tucked playfully beneath the staircase, blending charm and creativity. The newly crafted white oak staircase leads to the upper level, where the white oak floors continue and lime-washed plaster walls create a soft, elevated ambiance that’s both serene and stylish. All of this, just steps away from the vibrant lifestyle of downtown Sarasota; including Burns Court, Selby Gardens, and an abundance of dining, arts, and cultural attractions. There is also a kayak launch around the corner, so you're able to venture out via Hudson Bayou to the bay or to the neighborhood's "pocket park" on Laurel Street. With unmatched walkability and a one-of-a-kind design, this home offers a rare opportunity to live beautifully in one of Sarasota’s most beloved neighborhoods.

1724 Cherry Lane, Sarasota
$269,000
2 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
This delightful, turnkey-furnished 2-bedroom, 2-bathroom condo on the GROUND floor in The Meadows is ready for you to move in immediately. Recently updated, the condo boasts laminate wood flooring, tile in the kitchen and bathrooms (no carpet), elegant maple cabinetry, and charming Key West-style countertops in the kitchen. Ceiling fans are featured in both bedrooms and the GLASS SLIDER Florida room with Southern exposure, which also includes electric window shades. The split bedroom layout ensures privacy for you and your guests, with each bedroom having its own updated, ensuite bathroom. Enjoy tranquil views of the lake and pool from this serene retreat, which also offers a new natural gas BBQ grill area by the pool just steps away from the lanai. This property is not in a flood zone and is small dog-friendly (pending association approval), plus there’s a community dog park. Notable features include a walk-in laundry room with a stacked washer and dryer, as well as well-appointed furnishings. The primary bedroom features a king-size bed, beautiful walk-in shower and 2 closets, while the guest bedroom has a queen-size bed. Additional items such as games, dishes, pots and pans, two TVs, and all essential appliances for daily living are included. The condo comes with assigned parking, along with guest parking spaces. Conveniently located within walking distance of Meadows Village Shops, residents can enjoy dining, a spa, massage services, and medical offices, as well as the winter months’ Meadows Farmers Market. Please note that overnight parking of trucks or commercial vehicles is not permitted per association rules. The Meadows community offers a variety of amenities, including walking/biking trails, lakes, a fitness center, ten pickleball courts, a playground, a basketball court, a community pool and hot tub, 24-hour security, fishing, dining options, and a calendar of monthly community events, all included in the association dues. Tennis and golf are available for an additional fee. This condo allows you to move in worry-free, with everything provided at a very reasonable value.

5216 Lake Village Drive Unit 71, Sarasota
$309,000
2 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
Price Reduced! Lovely location on a cul-de-sac of swaying palms, Papillon consists of private enclaves of maintenance-free villas in The Meadows. You will be greeted by a paver sidewalk leading to the front entry with sidelight. Upon entry, wood flooring from the living room and dining room flow to form a cohesive foundation. The kitchen has a breakfast nook or space for cozy family dining. The living room with high ceilings leads to a wall of sliders opening onto a spacious glassed-in lanai offering you gorgeous water views framed by mossy Live Oak trees. The lanai floor was raised to allow flow from the living room and expands the living space and peaceful views. A fireplace with convenient electric insert provides ambiance on those cooler evenings. The spacious primary bedroom features an ensuite bathroom featuring split dual sinks, shower/tub combo, and ample walk-in closet. The guest bedroom is large and just steps away from the guest bathroom with shower/tub combo. A laundry closet houses the full-size washer and dryer and extra storage. Two car garage with extra depth for storage or workbench space and water heater 2017. Peace of mind with block construction and new tile roof 2012, exterior painted, new downspouts and window shutters, HVAC 2017. Above flood plain in zone x. Enjoy the most delightful resort-style heated community pool just steps away on its own private island for a quick dip or meet neighbors for an outdoor happy hour. Walk to The Meadows Shopping Village for restaurants, new neighborhood bar and restaurants , hair salon, massage therapist, and other convenient services. Papillon HOA has fully-funded reserves and takes pride in a well-managed neighborhood. Live in a friendly and very active community with 24 hour safety patrol and enjoy the carefree Florida lifestyle! The Meadows offers pay-to-play golf, a highly regarded tennis complex with 15 lighted Har-Tru courts, Jr. Olympic swimming pool with spa, private dog park, basketball, new fitness center, and 10 new pickleball courts. All located within 1,650 acres of tropical mature landscaping with miles of trails, wildlife preserves and over 80 lakes and ponds, while convenient to all that Sarasota offers! Minutes to luxury shopping and dining at UTC Mall, Mote SEA, Nathan Benderson Park for water sports and miles of recreational opportunities, downtown Sarasota for art and cultural activities and world class Gulf beaches.

3244 Ringwood Meadow Unit 77, Sarasota
$589,990
3 Beds ⋅ 3 Baths ⋅ Grand Park Phase 2 SubDv. ⋅ 34241 Zip Code
Competitively priced, this stunning White Star farmhouse-style home in Grand Park offers the perfect blend of comfort and design. The north-facing backyard keeps the home cool while providing sunshine on the lanai, which includes a gas hook-up for grilling. Tall privacy hedges line the paved walking trail just beyond the backyard, creating a peaceful, custom-landscaped feel. Enjoy quick, walking-distance access to the Grand Park clubhouse and community amenities directly from the trail. Interior highlights include impact glass windows, 8-foot interior doors, a double-door den, walk-in pantry, recessed ceilings, wood cabinetry, quartz countertops, and wood-look tile flooring throughout. This home combines high-quality finishes, energy efficiency, and a desirable location—all at a great value in Grand Park.

6568 Big Bayou Drive, Sarasota
$324,900
2 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
Virtual tour link in MLS is actual 3D tour, not a slideshow - please visit it! Furniture is optional with listing. Welcome to this beautifully maintained 2-bedroom, 2-bath villa located in the highly desirable Long Common enclave within The Meadows. This single-story home offers 1,264 square feet of bright, open living space, ideal for those seeking a low-maintenance Florida lifestyle. Step inside through a charming courtyard entry with a brick-paver driveway and a 2-car garage. Inside, the great room impresses with high ceilings, crown molding, and direct access to a Florida room that features a panoramic view of the pond and fairway in the distance—perfect for relaxing or entertaining year-round. The kitchen features stainless appliances, stone countertops, a cozy bay-window breakfast nook, and a convenient pass-through to the living and dining areas. A split-bedroom floor plan ensures privacy, with the primary suite offering a walk-in closet, dual sinks, and a walk-in shower. Residents of The Meadows enjoy access to three golf courses, tennis and pickleball courts, a Jr. Olympic-sized heated pool, clubhouse, fitness center, and miles of scenic walking and biking trails. The community is also ideally located near Nathan Benderson Park, the upcoming Mote Marine Aquarium, University Town Center Mall, and a wide variety of shopping, dining, and cultural attractions in downtown Sarasota.

5633 E Long Common Court Unit 20, Sarasota
$264,000
3 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
Centrally located townhouse, with main bedroom on first floor, in The Meadows, one of Sarasota’s sought-after neighborhoods just 15 minutes from downtown. A canopied street and a two-car garage welcome you home. Inside you’ll be greeted by a charming atrium that fills the space with gorgeous indirect light and cathedral ceilings in the living room providing an open and airy feeling. You will love relaxing in the 20-foot screened-in lanai overlooking a tranquil and lush garden. Upstairs, you will find soaring ceilings, abundant natural light, and the other two bedrooms and a bath. All across the street from the heated community pool and a mile to all the fun The Meadows has to offer. Set on 1,600 park-like acres, The Meadows is a resort-style community just 15 minutes from downtown. Enjoy 14 miles of scenic trails and, for a low fee, access to a fitness center, Junior Olympic pool, pickleball, golf, and Har-Tru tennis. You’ll be minutes to award-winning beaches, vibrant arts and culture, Whole Foods, Trader Joe’s, Nathan Benderson Park, Mote SEA Aquarium, the future Sarasota Orchestra, and University Town Center: a favorite shopping and dining destination. A fabulous Florida lifestyle awaits. With 2022 air conditoner, 2011 shingle roof (condominium's responsibility) and above flood plain in zone X

4983 Greencroft Road Unit 181, Sarasota
$319,000
2 Beds ⋅ 2 Baths ⋅ The Meadows SubDv. ⋅ 34235 Zip Code
Price reduction! Privacy is delivered in this 2 bedroom, 2 bathroom villa, located near the end of a cul-de-sac in Long Common in The Meadows. Beginning with the newer paver driveway and sidewalk leading to the private gated courtyard, this villa lives like a single-family home, without all that exterior maintenance to worry about! Enter through the screened vestibule to find high 10-foot ceilings topped off with crown molding leading to a knock-out view through the lanai sliders to stunning long water and golf course vistas. The kitchen has an open pass-through to enjoy those beautiful views while prepping meals or enjoying breakfast at the eat in area. The original dome kitchen light has been removed and updated ceiling and new lighting just installed. The living room and dining room are light-filled and spacious for entertaining. The split plan bedrooms allow for privacy when hosting guests. The primary bedroom has sliders to the lanai, lush greenery and water views, a very large walk in closet with organizers, linen closet and ensuite bathroom with step in shower. The guest bedroom enjoys close proximity to the guest bath with shower/tub combo. A roomy inside laundry room with full size washer and dryer also provides extra storage space. The two car garage provides room for the vehicles, bikes and pool toys and has a new overhead garage door opener. This villa has had all of the plumbing repiped for peace of mind. The community pool at the front entrance to Long Common provides a lovely heated pool and pool baths. This is a great place for a cooling dip in the pool or meet up with friends and neighbors for a libation during happy hour. Tile roof is maintained by the homeowner's association and is 12 years old. Water heater 2013. HVAC 2004 with regular bi-annual maintenance and a UV light. The sliding glass doors on the lanai were just serviced with new rollers installed. The Meadows offers 24 hour security patrol for peace of mind, an oasis of walking and biking trails, private dog park, pay-to-play golf, 15 lighted Har Tru tennis courts, Jr. Olympic pool and spa, pickleball and basketball courts and a new Lifestyle and Fitness center for all residents. Minutes to neighboring University Town Center Mall for luxury shopping and dining, Nathan Benderson Park for endless recreational and water activities, a short drive to downtown Sarasota for culture and the arts, and the powder sand beaches of the Gulf of Mexico. Live the laid back Florida lifestyle in The Meadows!

5662 Long Common Circle Unit 8, Sarasota
$42,000
1 Beds ⋅ 1 Baths ⋅ Tri-Par Estates SubDv. ⋅ 34234 Zip Code
This Tri-Par Estates lot is almost ready for your new home. Buyer is responsible for removing trailer. This home has been flooded and mold is present. Selling for land value only. This site offers a great private location with no neighbors behind you and within walking distance to the many amenities available at this great community; a large pool, spa, tiki hut, pickleball courts, fitness center, shuffleboard, miniature golf, horseshoes, and clubhouse. RV and boat storage are available. Convenient to Sarasota’s downtown, world class beaches, UTC mall, and truly minutes from the airport. Low annual fees and land ownership are two big advantages to this community.

4845 Boca Raton Avenue, Sarasota
$500,000
3 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code
West of The Trail with endless potential in Prime Location – Nightly Rentals Allowed! Welcome to this charming 3-bedroom, 2.5-bath Pool home in the highly desirable Whitfield Estates neighborhood where opportunity meets location! Whether you’re looking for your first home, a winter escape, or an income-producing Airbnb, this property is a rare find with no CDD, no monthly HOA, and the flexibility for nightly rentals. Set on a spacious quarter-acre, fully fenced lot, the home features a large pool, perfect for soaking up the Florida sunshine. The half bath is conveniently located poolside, ideal for entertaining guests outdoors. Inside, you’ll find a thoughtful layout with a primary suite addition that includes two separate walk-in closets and a cozy sitting area. The first guest room offers impact sliding doors leading directly to the pool, while an additional family/bonus room provides extra flexibility for a game room, office, or guest space. While the home retains some original finishes, including carpet, it’s bursting with potential just waiting for your personal touch and updates. The whole house was repiped in 2020 and roof replaced 2015. AC is 2014. Located between Downtown Bradenton and Downtown Sarasota, Whitfield Estates places you minutes from Sarasota Airport, IMG Academy, St. Armand’s Circle, Anna Maria Island, Lido Key, and all the fine dining, shopping, and entertainment the Gulf Coast has to offer. Enjoy the perks of a voluntary neighborhood association with no mandatory fees. For just $30/year for access to a culinary membership at SaraBay Country Club. Boaters will love being close proximity from SaraBay Marina, offering boat slips and dry dock storage. Whether you’re dreaming of a Florida beach house, a rental investment, or a full-time residence, this home is your blank canvas in one of the area’s most sought-after communities.

139 Adair Avenue, Sarasota
$229,000
2 Beds ⋅ 2 Baths ⋅ Las Palmas SubDv. ⋅ 34235 Zip Code
Lease to Own available! Two-bedroom two bath townhome in the popular gated community of Las Palmas. The luxury condominium community of Las Palmas has a superior Sarasota location in close proximity to UTC Mall, Benderson Park, popular local golf courses, downtown activities and local beaches! This gated, resort community offers not one but two heated pools, two gyms, a clubhouse, pickleball, tennis, walking trails, dog park, and playgrounds. The two-bedroom townhouse has a beautiful preserve view from the large, screened lanai. There is a one car garage on first level, large enough to store all your toys and car. The second level has the open kitchen, living room and dining room and a guest bedroom and bath. The 3rd floor has the primary suite with the large bath and walk in closet. The kitchen boasts wood cabinets, quartz countertops and new stainless appliances. This community offers an affordable Florida lifestyle for both the first-time buyer or retiree. Large pets are welcome! Why rent when you can own this home for less, call and ask about the affordable terms.

5711 Bentgrass Drive Unit 19-203, Sarasota
$354,999
2 Beds ⋅ 3 Baths ⋅ Woodbrook SubDv. ⋅ 34243 Zip Code
One or more photo(s) has been virtually staged. Home has an active annual lease with tenants moving in on June 15, 2026. This beautiful Key West–style courtyard home in the highly desirable gated community of Woodbrook offers exceptional value with over $35,000 in recent improvements and updated mechanicals throughout. Ideally located on a premium lot directly across from open green space, this two-story residence features a rare and versatile layout with two private en-suite bedrooms, making it ideal for guests, multi-generational living, or a dedicated work-from-home setup. The bright, open-concept main level showcases 18"x18" tile flooring throughout the living, dining, and kitchen areas, along with a well-appointed kitchen featuring Cumberland cherry wood cabinetry, solid-surface countertops, new stainless-steel appliances, a large center island, breakfast bar, and a spacious walk-in pantry. A convenient half bath and laundry closet with newer washer and dryer complete the first floor. Upstairs, both bedrooms are generously sized with full baths, including a spacious primary suite with vaulted ceilings, an oversized walk-in closet, and a private balcony overlooking peaceful green-space views; carpeting was updated in 2022. The private brick-paved courtyard offers an ideal outdoor retreat for dining, relaxing, or gardening and provides direct access to the detached two-car garage with its own A/C and additional storage. Recent upgrades include a Trane HVAC system (2024), ductwork cleaning and sealing (2025), new ceiling fans (2024), a new hot water heater (11/2025), an updated electrical panel (2026), and window seal replaced 4/26, allowing for true move-in-ready convenience. Residents of Woodbrook enjoy low HOA fees, no CDD, and access to resort-style amenities including a pool, spa, cabana, grills, playground, and park, all just minutes from UTC, Lakewood Ranch, downtown Sarasota, Nathan Benderson Park, I-75, golf, shopping, dining, St. Barbara’s, and the Gulf beaches.

4811 Woodbrook Drive, Sarasota
$199,900
2 Beds ⋅ 1 Baths ⋅ Park View SubDv. ⋅ 34237 Zip Code
Now is the time for you to purchase this property that is so close to downtown, you could walk. Fine restaurants, the arts, theater, shopping, and the beautiful, award-winning beaches are all minutes away from this community. Legacy Trail is a minute away for biking, running or just meandering on a beautiful day. Or stay in your own gated community and enjoy the acres of park-like setting, swim in one of the two pools (one is heated), exercise in the private gym or just sit in the shade at the clubhouse and read a book. This is one of the best values so convenient to all that the downtown lifestyle. Ed Smith Stadium, home for the Orioles during Spring Training, is just around the corner. Residents have been known to walk to baseball games, it is so close! This two-bedroom, one bath unit is located on the first floor and is an end unit with beautiful views of the park. Stainless Steel appliances and granite countertops accent the solid wood cabinets. Hurricane windows and slider are added protection and security. New railings along the fronts of the buildings have been replaced, the lanais are being replaced and most are completed, and the buildings are scheduled to be painted a new, updated color in 2024 with current style light fixtures to add to the update look. A new gate entry system has been implemented. Improvements continue to be made to increase the value of the property. This area is definitely in the gentrification process with lots of added future value just around the corner. This is the perfect property for personal use or invest in it as a rental. Schedule your appointment today!

966 La Costa Circle Unit 1, Sarasota
$475,000
2 Beds ⋅ 2 Baths ⋅ Schindler Sub SubDv. ⋅ 34236 Zip Code
Short Sale. SHORT SALE!!! Modern Luxury Meets Urban Oasis Living. Enjoy refined living in this custom-built townhome overlooking Gillespie Park. Featuring 2 bedrooms, 2 baths, and a spacious open-concept layout. This townhome offers exceptional craftsmanship and thoughtful design throughout. Dramatic 20-foot ceilings and floor-to-ceiling windows fill the space with natural light. Interior highlights include 8-foot solid wood doors, oversized ceramic tile flooring, LED lighting, and automated window treatments. Stylish kitchen complemented by soft-close cabinetry, stainless steel appliances, vent hood and gorgeous granite counter tops. Upstairs, the loft-style primary suite provides a peaceful retreat with a spa-like bathroom featuring custom tiled walls, LED mirrors, and high-end fixtures. A large walk-in closet with built-in organizers adds to the home’s functional luxury. Additional features include WiFi-enabled thermostats, Ring video doorbell. Home equipped with hurricane-impact windows and doors, two assigned parking spaces, and a dedicated EV charger. Located directly across from Gillespie Park with its fenced dog area, playground, and sports courts, and just minutes to downtown Sarasota’s dining, shopping, and cultural attractions. Come and See!!! Sale contingent on Lender's approval.

941 N Osprey Avenue, Sarasota
$5,495,000
4 Beds ⋅ 3 Baths ⋅ Bay Point Park SubDv. ⋅ 34236 Zip Code
Being in the same family for 75 years, this is a rare opportunity to own a stunning, nearly half-acre waterfront lot in the highly desirable Bay Point Park neighborhood of Sarasota. Situated on protected sailboat water with no bridges to the Gulf of Mexico, this unique property offers unparalleled access to the serene waters of Sarasota Bay, with breathtaking views of the iconic Ringling Bridge and the vibrant downtown Sarasota skyline. Enjoy a truly walkable lifestyle with the best of Sarasota at your doorstep. Stroll to Marie Selby Botanical Gardens, the charming shops and gourmet restaurants of downtown, the quaint Southside Village, and the renowned Morton's Gourmet Market—all just moments away. Tucked away in a tropical oasis, this secluded lot offers privacy, tranquility and convenience, providing the perfect setting for a custom-built home with sweeping waterfront views. Located in one of the most sought-after West of the Trail neighborhoods, this large waterfront parcel presents a unique opportunity to create a luxurious sanctuary in one of Sarasota's most coveted locations. Whether you’re an avid sailor or simply appreciate the beauty of coastal living, this property is your perfect canvas. Don’t miss the chance build your dream home on this exceptional slice of Sarasota paradise—where the natural beauty, luxury, and lifestyle you’ve always dreamed of can finally become a reality.

1479 Bay Point Drive, Sarasota
$420,000
2 Beds ⋅ 2 Baths ⋅ Chelmsford Close SubDv. ⋅ 34235 Zip Code
This beautiful villa sits at the end of a dead-end street, a few steps from the community pool and has stunning lake and golf course views. As you enter the walkway you are greeted by a gated entry gaining access to the front loggia that is accented with pavers and leads to your private entrance. The grand foyer is large and is the perfect space to display your art or family heirlooms. The kitchen has been professionally updated with stunning finishes and features high-end appliances. There is an office or den off the kitchen through dual pocket tiffany doors. The guest bedroom is spacious and provides a view to the front lanai. The living room and dining room provide for gracious living and entertaining allowing expansive views of the golf course and lake. Golf views are also from the primary suite with its large bathroom and walk-in closet. This home features high ceilings throughout, extensive levels of crown moldings, elegant features and finishes and is perfect for year-round living or as a wonderful getaway home for seasonal or frequent visitors.

3416 W Chelmsford Court Unit 2, Sarasota
$295,000
3300 Professional Center SubDv. ⋅ 34241 Zip Code
Here is an incredible opportunity to build your dream home in a picturesque setting at Cassia Skye Ranch! Preserving the natural beauty of Florida with grand old oaks, lush palms, and pristine lakes creates an ideal backdrop for anyone looking to connect with nature and enjoy the outdoors. The planned amenities, including miles of trails and parks, add even more appeal, promising a lifestyle that blends tranquility with recreation. Whether it's enjoying the serenity of the forested wetlands or exploring the diverse wildlife, this lot offers a chance to create a home that perfectly complements the surrounding environment while catering to your individual tastes and preferences.

9260 Starry Night Avenue, Sarasota
$295,000
Ranch Acres SubDv. ⋅ 34241 Zip Code
Here is an incredible opportunity to build your dream home in a picturesque setting at Cassia Skye Ranch! Preserving the natural beauty of Florida with grand old oaks, lush palms, and pristine lakes creates an ideal backdrop for anyone looking to connect with nature and enjoy the outdoors. The planned amenities, including miles of trails and parks, add even more appeal, promising a lifestyle that blends tranquility with recreation. Whether it's enjoying the serenity of the forested wetlands or exploring the diverse wildlife, this lot offers a chance to create a home that perfectly complements the surrounding environment while catering to your individual tastes and preferences.

9268 Starry Night Avenue, Sarasota
$599,000
Forest At The Hi Hat Ranch SubDv. ⋅ 34241 Zip Code
Embrace the beauty and diversity of nature at The Forest at Hi Hat Ranch, a secluded enclave set amid Florida’s unspoiled countryside. This exceptional homesite spans nearly four acres of pristine, wooded land, offering a peaceful retreat surrounded by natural beauty. The Forest at Hi Hat Ranch is comprised of just 54 estate-sized homesites, ranging from 3 to 6 acres, providing a rare sense of space, privacy, and tranquility. The community features an Approved Builder Program with a distinguished selection of custom builders, including Anchor Builders, Arthur Rutenberg Homes, Lee Wetherington Homes, John Cannon Homes, Nautilus Homes, Yoder Homes, and Nutter Construction. Ideally located near shopping, dining, and Gulf Coast beaches, and situated within an A-rated school district, The Forest at Hi Hat Ranch offers the perfect blend of serene natural surroundings and modern convenience.

9255 Swaying Branch Road, Sarasota