Location: Osprey , 34229
Do Not Show Listings
1337 COPPERWOOD DR, OSPREY, FL 34229
$550,000198 Days on yellowkey MLS ID: A4666722
REDUCED by $19,000 (3.3%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2172 Built: 2004Monthly Fee: $397 Tax: $4,420 (2025)Community: Willowbend Phase 3Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,420
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
4226 FRONTIER LN #103, OSPREY, FL 34229
$319,0009 Days on yellowkey MLS ID: A4687965
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2018Monthly Fee: $475 Tax: $3,542 (2025)Community: Bay Street VillageCondo
Taxes:$3,542
Remarks: Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kate Kwiecinski (412-477-9720)
140 SUGAR MILL DR, OSPREY, FL 34229
$1,695,00037 Days on yellowkey MLS ID: A4684805
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3286 Built: 1989Monthly Fee: $483 Tax: $12,040 (2025)Community: OaksSpa: YesSingle Family
Taxes:$12,040
Remarks: BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you'll enjoy 4 bedrooms and 4 full baths - all on one level - within a bright, open floor plan with custom architectural details throughout. The impressive chef’s kitchen is both stylish and functional, featuring Silestone countertops, premium Sub-Zero and Wolf appliances, an expansive island with seating and a striking bar—perfect for hosting gatherings or enjoying relaxed mornings at home. Separate dining and living spaces allow room for dedicated entertaining - making any occasion a treat! The private primary suite is "magazine worthy" - a sublime but peaceful retreat complete with a tremendous walk-in closet, custom built-ins and a beautifully appointed bath showcasing dual vanities, quartz countertops and a seamless walk-in glass shower. The home is truly a split plan - offering privacy with three additional suites - perfect for guests, a study or exercise/hobby room. The home takes every advantage of space and storage - and you'll be the envy of the neighborhood with the "thought of everything" laundry room and spacious garage. Step outside to exceptional outdoor living - designed for year-round Florida enjoyment. The expansive screened lanai features a heated pool and spa, elegant travertine pool deck, turfed yard with putting-green surface (only home in the Oaks) and new remote-controlled hurricane screens. Surrounded by mature, lush landscaping and a privacy wall, you'll feel the design intent for ultimate seclusion and relaxation. The home not only looks beautiful - it's been maintained to provide peace of mind with a newer roof (2021); impact-rated windows & doors (2021); 2 new HVAC units with UV purification (2021); motorized exterior hurricane shutters (2025); air conditioned garage and hurricane doors; 500 gallon propane tank (2022); electrical service panel (2021); rear yard golf turf (2025) and fresh interior & exterior paint. The Oaks - Bayside is a gated neighborhood with a private day dock on Little Sarasota Bay - perfect for launching kayaks or simply enjoying the sunset. The Oaks is one of the region’s most prestigious 24-hour guard-gated country club communities, residents enjoy an extraordinary lifestyle that includes: two championship 18-hole golf courses; three dining options and ballroom; tennis with 12 Har-Tru Hydro-Grid tennis courts; four pickleball courts; croquet lawns; fitness center and Junior Olympic heated pool; bocce, basketball, playground and extensive social opportunities. Perfectly located west of the trail in Osprey, you're just minutes from Sarasota's outstanding dining and cultural offerings, gorgeous beaches, Legacy Trail and Pine View School for the Gifted. A wonderful opportunity to enjoy Florida's ideal county club lifestyle! (Club membership is required with no waitlist at the current time.)
Listing Agent: Monica Verinder (941-704-4040)
7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229
$474,900281 Days on yellowkey MLS ID: D6142543
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1883 Built: 1985 Tax: $4,800 (2024)Community: Heron HouseCondo
Taxes:$4,800
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: PENTHOUSE CONDO IN WATERFRONT COMMUNITY! Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views. The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, and a separate shower for ultimate relaxation. Additional highlights include a wet bar for entertaining and three separate balconies for outdoor living. Enjoy resort-style amenities such as tennis courts, pickleball, shuffleboard, a heated pool, clubhouse, walking paths, a workout facility, and a convenient kayak launch for endless waterfront adventures. Bring your own boat and take advantage of your separately available assigned boat dock area! When you’re ready to explore, you’ll find yourself just 10 minutes from several Gulf Coast beaches, thousands of acres of parks and preserves, and world-class shopping, dining, and fishing. Quick connections to Sarasota’s vibrant arts scene, the new Mote Marine Aquarium, Spanish Point, the Legacy Trail, and Oscar Scherer State Park are all just minutes away. All of this and you will just be 5 minutes from I-75 where the rest of the world awaits you. Take the elevator to your nearby 2 assigned parking spots under the building. Don’t miss your chance to own this exceptional penthouse—schedule your private showing today!
Listing is courtesy of: KW COASTAL LIVING (941-473-7399)
Listing Agent: Toy Coxey (941-662-0010)
120 VILLA DR #120, OSPREY, FL 34229
$510,000366 Days on yellowkey MLS ID: N6138441
REDUCED by $5,000 (1.0%) on 04/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1404 Built: 1978Monthly Fee: $529 Tax: $5,056 (2025)Community: Sorrento Villas 1Villa
Taxes:$5,056
Remarks: Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just lower it into the water and you are a short ride out to the intracoastal, the Venice Jetties and Midnight Pass. There are many great waterfront restaurants you can access by boat. If you happen to catch some fish while you are out enjoying the boat, there is a fish cleaning station on the dock. Located between Sarasota and Venice with easy access to I-75. Close to shopping, beaches, restaurants, Oscar Scherer Park and so much more.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Hansel Pitts, Jr. (941-800-6076)
472 PARK TRACE BLVD, OSPREY, FL 34229
$609,00076 Days on yellowkey MLS ID: A4680326
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2217 Built: 2002Monthly Fee: $58 Tax: $5,925 (2025)Community: Park Trace EstatesSingle Family
Taxes:$5,925
Remarks: Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. Park Trace Estates has low HOA fees, and is in a prime location close to top-rated schools, shopping, restaurants, Legacy Trail, Oscar Scherer State Park, and Gulf Coast beaches.
Listing is courtesy of: SUNDANCE REAL ESTATE SERVICES (941-780-6710)
Listing Agent: Damon Zuchelli (941-448-5686)
1116 BEACHCOMBER CT #3, OSPREY, FL 34229
$545,00013 Days on yellowkey MLS ID: A4688310
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 2005Monthly Fee: $1,133 Tax: $5,376 (2025)Community: Blackburn Point Marina VillageCondo
Taxes:$5,376
Remarks: LOCATION, LOCATION, LOCATION! Nestled within the highly desirable gated enclave of Blackburn Point Marina Village, this beautifully maintained 3-bed, 2.5 bath residence is ready to welcome its new owners. This bright and airy two-story unit features soaring ceilings and a spacious open floor plan, creating an inviting and comfortable living environment. The main living areas are enhanced with tile flooring and flow seamlessly into a well-appointed kitchen, complete with Corian countertops, a breakfast bar, center island, closet pantry, and stainless-steel appliances, perfect for both everyday living and entertaining. The dining area features pocketing sliders that extend the living space to the enclosed lanai, already plumbed for a full outdoor kitchen, offering the ideal indoor-outdoor Florida lifestyle. The primary suite is conveniently located on the ground floor and offers a private retreat with an ensuite bathroom featuring dual vanities, a garden tub, and a walk-in shower. Upstairs, two additional bedrooms and a full bath provide privacy and comfort for guests or family. Step outside to the patio, an ideal setting to relax and enjoy a quiet afternoon or evening cocktail in the Florida sunshine. Additional features include an oversized one-car garage with under-stair storage, a new A/C system (2025), and a new roof (2025), providing peace of mind for years to come. Residents of Blackburn Marina Village enjoy access to a heated community pool, a fully equipped outdoor kitchen, and a vibrant social calendar for those who wish to participate. Ideally located with easy access to Gulf beaches, Blackburn Point Marina, dining, and shopping, this exceptional property truly offers the best of Florida living!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christine Green (941-914-2463)
296 PINE RANCH TRL, OSPREY, FL 34229
$1,250,000327 Days on yellowkey MLS ID: A4653218
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3481 Built: 1995 Tax: $5,492 (2024)Community: Pine Ranch EastSpa: YesSingle Family
Taxes:$5,492
Middle School: Sarasota Middle
Remarks: **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a nearby golf course, offering tranquil views and peaceful surroundings. With no rear neighbors, you'll enjoy the privacy and serenity that your 1 acre+ lot affords. Have a boat or RV? This community is deed restricted but there is plenty of space to build an oversized garage to house vehicles or create a dream workshop. Inside, you'll find a timeless blend of comfort and sophistication. The spacious interior boasts high ceilings, large windows that fill the rooms with natural light, and an open floorplan that seamlessly connects the living spaces. Nestled amid lush greenery and serene surroundings, this property stands out as more than just a house—it's a haven awaiting its next resident. Designed with both comfort and elegance in mind, every detail speaks to a lifestyle where relaxation and convenience coalesce effortlessly. Step inside, and you'll discover a space that beckons you to make it your own sanctuary. Located in a quiet, upscale neighborhood with a charming, country-like feel, this home is just minutes from everything that makes Sarasota County one of Florida’s most sought-after destinations. The world-renowned Nokomis Beach and Siesta Key, are a short drive away, offering sun, surf, and sand any time you desire. Pine View School, consistently ranked among the top public schools in the nation, is only a few minutes away. Outdoor enthusiasts will love the easy access to the Legacy Trail, a scenic multi-use path perfect for biking, running, and leisurely strolls through nature preserves. Whether you're looking to settle into a peaceful primary residence or seeking a second home close to golf, beaches, and top-tier schools, this home offers the perfect balance of nature, convenience, and lifestyle. The home features 5 bedroom and 3.5 bathrooms, and an oversized 2 car garage. The open concept floorplan and expansive covered patio are perfect for entertaining. The main master suite has vaulted ceilings, sliding glass doors leading to the pool and spa, an oversized walk-in closet, and the bathroom is plumbed for a soaker tub. On the other side of the home there are 4 more bedrooms, one of which also has an en-suite bathroom. For added peace of mind, this home comes with many newer updates such as: Roof 2016, Pool heater 2024, Septic tank 2024. Both HVAC units and Pentair pool Wi-Fi controlled equipment have been updated and home has been replumbed with CPVC. Call today to schedule a showing before this home is gone! Property is in Probate.
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Deborah Frederick (941-544-6493)
107 SORRENTO DR, OSPREY, FL 34229
$425,00043 Days on yellowkey MLS ID: N6143210
REDUCED by $24,000 (5.3%) on 04/12/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1284 Built: 1963Monthly Fee: $10 Tax: $2,566 (2025)Community: Sorrento ShoresSingle Family
Taxes:$2,566
Remarks: This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, offering gently used stainless KitchenAid Gallery appliances, space-saving self-closing cabinetry, and a generous open breakfast bar ideal for casual dining and gathering. Baths have been tastefully modernized with updated cabinets, countertops, fixtures and lighting. Major improvements provide peace of mind, including 2025 sewer pipes relined, a 2022 air-conditioning system, 2015 re-roof, 2015 hurricane-impact windows, 2015 gutters plus interior and exterior paint, and refreshed landscaping. Additional highlights include a two-car attached garage, dedicated workshop space and access to boat docks (Contact HOA for details). Ideally West of the Trail between Sarasota and Venice, with convenient access to Highway 681 and Interstate 75, this home places you close to everything. Top-rated schools nearby include Pine View School for gifted and Venice High School, known for strong sports and arts programs. Outdoor enthusiasts will love being just 5 to 10 minutes from Nokomis Beach, Blackburn Point Park kayak and boat launch, Oscar Scherer State Park, offering hiking, camping, cycling, kayaking, boating and fishing, and the Legacy Trail, which is ideal for biking with family or friends. Dining options abound, including waterfront favorites nearby. This is Florida living at its finest, with modern design, natural beauty, boating access and an unbeatable location.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)
Listing Agent: Crystal Cosby, Llc (941-882-0070)
408 PARK TRACE BLVD, OSPREY, FL 34229
$625,00042 Days on yellowkey MLS ID: A4685004
REDUCED by $5,000 (0.8%) on 04/11/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2003Monthly Fee: $54 Tax: $4,652 (2025)Community: Park Trace EstatesSingle Family
Taxes:$4,652
Remarks: Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central courtyard with a saltwater pool, around which the main living spaces are thoughtfully arranged. An en-suite guest bedroom with private courtyard access provides a secluded retreat perfect for visitors. The open-concept interior flows seamlessly from the kitchen, complete with a signature royal blue Hestan refrigerator, into an inviting living room ideal for entertaining. From there, step out to a screened patio overlooking the water to relax in total comfort. The spacious master suite features dual California Closets, a luxurious remodeled bathroom, and an adjoining room that serves as a private office or reading nook. Throughout the home, plantation shutters provide elegant light control and privacy. The property is finished with a side-entry two-car garage featuring custom California Closets storage and a Tesla charger. Positioned just steps from the pristine Legacy Trail for biking and recreation, this home provides the perfect combination of style and lifestyle. Home is available fully furnished. The home is exceptionally well-maintained, featuring a high-efficiency HVAC system (New AC 2017/Air Handler 2020) with a programmable thermostat, a central vacuum system, and an artistic hidden TV in the living room. Recent kitchen and laundry upgrades include a 2018 washer and dryer alongside newer appliances (2020–2022). The private courtyard is equally impressive, boasting a new pool screen (2022), new pool equipment (2024), and an Endless Pool Fastlane feature for a premium fitness experience. Property is located in Flood Zone X (flood insurance generally not required).
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jennie Lascelle (941-504-0102)
362 MACEWEN DR, OSPREY, FL 34229
$2,249,00094 Days on yellowkey MLS ID: A4676567
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4117 Built: 1998Monthly Fee: $142 Tax: $10,742 (2025)Community: The OaksSingle Family
Taxes:$10,742
Remarks: Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.
Listing Agent: Steve Abbe (941-400-3969)
32 BAY AVE, OSPREY, FL 34229
$415,000187 Days on yellowkey MLS ID: N6140978
2 Days Off yellowkey (back on 4/9/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2148 Built: 1962Monthly Fee: $13 Tax: $3,612 (2024)Community: Bay Acres - ResubSingle Family
Taxes:$3,612
Remarks: Under contract-accepting backup offers. Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Michelle Richardson (954-683-1002)
4235 EXPEDITION WAY #102, OSPREY, FL 34229
$379,90012 Days on yellowkey MLS ID: N6143716
0 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1574 Built: 2016 Tax: $4,410 (2025)Community: Bay Street VillageCondo
Taxes:$4,410
Remarks: Under contract-accepting backup offers. This well-maintained first-floor condominium offers an ideal opportunity for full-time living or a seasonal Florida retreat. Featuring the desirable Osprey floor plan, this open-concept residence includes two bedrooms, two bathrooms both with granite vanity tops, and a bonus room/office. The unit is conveniently located on the first floor with no stairs and provides easy access to the community’s heated resort-style pool, fitness center, and clubhouse. The kitchen is appointed with 42-inch cabinetry and granite countertops. The primary bathroom features a tiled walk-in shower and dual vanity. Additional highlights include a screened lanai, Huge 2.5-car garage, and two-car driveway, offering ample parking and storage. The condominium has been meticulously maintained and is move-in ready. Located in the gated, maintenance-free community of Bay Street Village, the property is ideally situated between Sarasota and Venice, with convenient access to dining, shopping, the Legacy Trail, Pine View School, and nearby beaches including Siesta Key, Nokomis, Casey Key, and Venice Beach. Additional features include concrete block construction, impact-resistant windows and doors, tile roof, and paver driveway. Water and sewer are included in the HOA fee, and there is no CDD fee. Furniture is available under a separate contract between buyer and seller.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
409 N POINT RD #601, OSPREY, FL 34229
$1,250,00072 Days on yellowkey MLS ID: A4679994
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2594 Built: 2004Monthly Fee: $400 Tax: $10,238 (2025)Community: Meridian At The Oaks PreserveCondo
Taxes:$10,238
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: **FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spacious, light-filled corner unit offers nearly 2,600 sq. ft. of living space and features 3 bedrooms plus a study/den, 3 full baths, two elevator banks, two assigned second-level parking spaces, and climate-controlled storage. Located behind the secure gates of The Oaks Preserve Country Club, this residence combines privacy with resort-style living. The stunning interior showcases an open floor plan with hardwood and tile flooring throughout, crown molding, two wine reserve refrigerators, and a smart Nest thermostat. The updated kitchen is appointed with granite countertops and stainless-steel appliances, including Bosch and GE Monogram. The owner’s suite offers private balcony access, a walk-in closet, and an updated bath featuring dual vanities, a custom-tiled shower, and a soaking tub. Step onto the spacious balcony—complete with hurricane shutters—and unwind while taking in gorgeous sunset views over the Gulf and Bay. Meridian residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s exceptional amenities. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
348 TROPIC DR, OSPREY, FL 34229
$109,000186 Days on yellowkey MLS ID: A4668240
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 864 Built: 1977Monthly Fee: $215 Tax: $884 (2024)Community: ArborsManufactured Home
Taxes:$884
Remarks: Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in right away and make some upgrades as needed. YOU and your fellow homeowners will own the company that owns the park. it's a Co-Op park for over-55 owner residents. Therefore, everybody takes pride in keeping it wonderfully maintained and reasonably priced with low HOA dues. Better take a look before the bidding war starts.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: John Alexander (941-724-5907)
385 NORTH POINT RD #701, OSPREY, FL 34229
$1,399,00051 Days on yellowkey MLS ID: A4683454
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2594 Built: 2000Monthly Fee: $400 Tax: $6,082 (2025)Community: Meridan At The Oaks PreserveCondo
Taxes:$6,082
Remarks: Situated on the 7th floor of The Meridian, this sophisticated three-bedroom plus den, three-bath residence with private two-car garage offers elevated waterfront living behind the gates of the prestigious The Oaks Preserve and within the exclusive Oaks Club community. Every detail has been carefully curated for refined comfort, luxury, and effortless Florida indoor-outdoor living. A private elevator opens directly into your personal foyer, adorned with marble flooring, creating an immediate sense of privacy and elegance. Expansive water views greet you from the main living areas and primary suite, filling the home with natural light and serene vistas. The expansive lanai provides the perfect setting to begin and end each day, whether savoring morning coffee or an evening beverage as the sun rises and sets over the water. The open living and dining area is framed by waterfront vistas, offering a tranquil backdrop for entertaining or everyday enjoyment. The gourmet eat-in kitchen is appointed with marble countertops, stainless steel appliances, breakfast bar seating, and a reverse osmosis and water softener system, blending elegance with practicality. The primary suite is a private sanctuary, featuring a sitting area overlooking the water, a walk-in closet, and a spa-inspired bathroom with spa tub, separate shower, dual vanities, and water closet. The second guest bedroom is ensuite, while the third bedroom and den provide flexible spaces for family, guests, or a home office. A separate laundry room with laundry tub completes the residence. Additional highlights include secured building access, private under-building parking, and the elevated vantage point of the 7th floor, which enhances panoramic water views. The Meridian neighborhood offers a community pool, fitness center, and walking trails throughout The Oaks Preserve. Residents enjoy membership to The Oaks Club, Sarasota’s unmatched Country Club lifestyle, featuring: 36 championship fairways, 16 courts, croquet, fitness and recreational facilities, refined and casual dining, pool and a vibrant social calendar. Membership is required, with options for Equity or Social Memberships. The coastal, sophisticated lifestyle within The Oaks Club combines privacy, resort-style amenities, and close proximity to Sarasota’s world-famous beaches, cultural landmarks, shopping, and dining, creating a lifestyle designed for the refined and active Florida living. This is a rare opportunity to experience luxury waterfront living, elevated elegance, and exclusive club access in one of Sarasota’s most distinguished communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
819 SHADOW BAY WAY, OSPREY, FL 34229
$615,00045 Days on yellowkey MLS ID: N6143162
REDUCED by $24,000 (3.8%) on 04/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2145 Built: 2002Monthly Fee: $170 Tax: $6,288 (2024)Community: RivendellSingle Family
Taxes:$6,288
Middle School: Venice Area Middle
Remarks: Welcome to this stunning 2,145 square foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include 2026 irrigation valves, 2025 roof replacement, 2024 pool pump and a 2017 air conditioning system, providing peace of mind for years to come. Go onto the inviting front porch, the ideal setting for morning coffee. Enter through the elegant glass front door into a bright, open foyer filled with natural light. The spacious split floor plan seamlessly connects the great room, formal dining room, kitchen, and cafe, creating an ideal layout for everyday living and entertaining. The chef’s kitchen is beautifully updated with granite countertops, stainless steel appliances, custom wine racks, rich cabinetry, a built-in desk, pantry and breakfast bar. The adjacent cafe features a stunning aquarium window overlooking the sparkling heated pool, an ideal spot for casual meals before heading to the beach. The generous primary suite is a private retreat, offering dual walk-in closets, sliding glass doors to the lanai, and a luxurious en-suite bath complete with solid wood cabinetry, granite countertops, dual sinks, a soaking garden tub, walk-in shower, linen closet, and private water closet. On opposite side of the home, guests will enjoy their own private wing with two bedrooms and a full bath separated by a pocket door. The third bedroom features built-in cabinetry and offers wonderful flexibility, easily functioning as an additional office, study, or peaceful reading retreat. The fourth bedroom at front of the home is suited as a den, office or playroom. The spacious laundry room offers a utility sink, additional cabinetry and ample storage. Outdoor living shines in the screened lanai and beautifully updated paver pool area. The fenced area is ideal for pets, and the expansive patio provides a backdrop for relaxing or hosting gatherings. Rivendell residents enjoy low HOA fees that include lawn and shrub care, a heated community pool, playground and scenic recreational trails all with no CDD fees. The irrigation system is connected to a private well, providing an efficient and cost-effective way to maintain the lush tropical landscaping year-round. This neighborhood offers a private path to Pine View School for the Gifted and borders Oscar Scherer State Park and 200 acres of preserved land. Outdoor enthusiasts will appreciate easy access to the Legacy Trail. Ideally in south Sarasota, this serene enclave offers convenient access to pristine Gulf beaches and sits between Sarasota and Venice for exceptional dining, shopping and cultural attractions. Furnishings are available for purchase!
1471 SHOAL WAY, OSPREY, FL 34229
$1,499,00052 Days on yellowkey MLS ID: A4683702
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2798 Built: 1985Monthly Fee: $219 Tax: $6,036 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$6,036
Remarks: One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the end of a quiet cul-de-sac and overlooking an expansive green space, the property feels even more open and serene. No expense has been spared in the home’s extensive upgrades, evident the moment you step inside. Eight-inch wide white oak flooring, custom cabinetry, and high-level quartz countertops create a refined yet inviting aesthetic throughout. A striking, oversized fireplace crafted from natural coral stone anchors the living space and is beautifully framed by solid iron double doors—an architectural feature unique to this home. The layout is equally impressive, offering two distinct living areas, four bedrooms, and three baths, thoughtfully designed to maximize both functionality and flow. The oversized garage includes a workshop area and a climate controlled storage space! With every detail already complete, this home allows you to fully enjoy the idyllic waterfront lifestyle Southbay is known for—whether boating, playing pickleball or tennis, or simply relaxing poolside. Boating in Southbay is made easy with its marina located in the center of the development. Peace of mind comes standard with a metal roof designed to resemble barrel tile, hurricane-rated windows, and a location outside of the flood zone, offering both resilience and long-term value. Pack your bathing suit and bring your boat – live the Florida lifestyle to the fullest. Exclusions: mounted tv/screens, potted plants Pool heater conveys as is
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Lauren Doyle (941-993-9733)
409 N POINT RD #1001, OSPREY, FL 34229
$2,750,0009 Days on yellowkey MLS ID: A4689096
1 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3029 Built: 2004Monthly Fee: $400 Tax: $16,089 (2025)Community: Meridian At The Oaks PreserveSpa: YesCondo
Taxes:$16,089
Elementary School: Pine View School
Middle School: Pine View School
Remarks: Under contract-accepting backup offers. **STUNNINGLY RENOVATED, MOVE-IN READY 10th FLOOR PENTHOUSE CORNER RESIDENCE WITH GULF AND BAY VIEWS.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional, 3029sf condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
313 LOOKOUT POINT DR, OSPREY, FL 34229
$5,999,9999 Days on yellowkey MLS ID: A4688995
Bed: 4 Bath: 4.5 Gar: 5 Liv Area Sq Ft: 5337 Built: 2016 Tax: $20,559 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$20,559
Remarks: Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
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