Location: Osprey
Do Not Show Listings
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000364 Days on yellowkey MLS ID: A4656074
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1861 Built: 2018Monthly Fee: $147 Tax: $5,936 (2024)Community: Palms/Casey KeySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,936
Elementary School: Laurel Nokomis Elementary
High School: Pine View School
Tax Year: 2024
Middle School: Laurel Nokomis Middle
Remarks: Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mariana Georgieva (941-809-0416)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000104 Days on yellowkey MLS ID: A4685004
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $20,000 (3.3%) on 06/01/2026
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
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. 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 heated saltwater pool with a FastLane system, 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)
619 OAK RIVER CT, OSPREY, FL 34229
$609,90034 Days on yellowkey MLS ID: A4692331
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2047 Built: 1997Monthly Fee: $25 Tax: $5,484 (2025)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$5,484
High School: Venice Senior High
Remarks: Virtually Staged. BACK ON THE MARKET. Buyer's financing fell through. Great opportunity for you! Welcome to this thoughtfully renovated pool home in sought-after Bay Oaks Estates, perfectly positioned on an oversized 0.38-acre corner lot in the heart of Osprey. Featuring 3 bedrooms plus a dedicated office, 10-foot ceilings, a huge fenced backyard, and extensive modern updates throughout, this move-in-ready residence offers a rare blend of style, comfort, and effortless indoor-outdoor living. One of the home’s standout features is the oversized fenced backyard, offering a rare combination of space, privacy, and flexibility. The screened lanai, private pool, and expansive outdoor area create the perfect setting for entertaining and year-round enjoyment. Framed by mature landscaping and a newer concrete tile roof (2021), the home creates a welcoming first impression from the moment you arrive. A large driveway and covered parking area provide abundant convenience. New flooring throughout (2025), updated lighting, fresh interior paint, and carefully selected finishes create a clean, cohesive modern aesthetic rarely found in the neighborhood. Inside — 10-foot ceilings, abundant natural light, and a thoughtfully designed layout create an elevated sense of space and openness. Smart-home features include an ecobee thermostat, keypad entry, and a Samsung all-in-one smart washer and dryer. At the center of the home, the fully remodeled kitchen combines style and function with granite countertops, white shaker cabinetry, stainless steel appliances, modern finishes, and an expansive breakfast bar that opens seamlessly to the main living areas. The spacious primary suite serves as a true retreat with two walk-in closets and a beautifully remodeled bath featuring quartz countertops, dual vanities, a freestanding soaking tub, and a frameless glass walk-in shower. Perfectly positioned between The Oaks Club and Stoneybrook Golf & Country Club, Bay Oaks offers the feel of luxury golf-course living without the fees. Families will especially appreciate being just 3 miles from Pine View School, consistently ranked among the top public schools in the nation. Just 6 miles from Siesta Key and 4 miles from Casey Key, this prime Osprey location places you near marinas, golf courses, the Legacy Trail, shopping, dining, and Sarasota’s coastal lifestyle.
Listing is courtesy of: FISHMAN GROUP REALTY LLC (763-443-1761)
Listing Agent: Ross Fishman (763-443-1761)
1361 NEW FOREST LN, OSPREY, FL 34229
$545,00054 Days on yellowkey MLS ID: A4691036
REDUCED by $5,000 (0.9%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2074 Built: 2002Monthly Fee: $292 Tax: $5,783 (2025)Community: Rivendell WoodlandsSingle Family
Taxes:$5,783
Remarks: One or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
1474 LANDVIEW LN, OSPREY, FL 34229
$1,475,0004 Days on yellowkey MLS ID: A4696853
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3246 Built: 1977Monthly Fee: $219 Tax: $9,834 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$9,834
Remarks: Elevated luxury throughout this Southbay beauty! Step inside this one of a kind two story home and you will feel like you are a top notch resort! You will enter the foyer overlooking the living room and dining room area, just perfect for entertaining highlighting a built-in buffet with wine cooler. Open the sliding glass doors ahead and enter the exquisite out door living area, heated salt water pool, hot tub, outdoor kitchen and dining area, all adding up to the feeling of relaxed elegance. The kitchen is a dream! Top of the line Thermador appliances including a smooth induction top stove, built in oven and microwave and for the ultimate in extravagance - a built in Thermador coffee maker. Quartzite counter tops, over sized island, custom pantry, sliding glass doors to exterior help complete this gathering spot. Located on the first floor is the spacious master suite with triple sliding doors looking onto the lanai area. Master bath with tub and an oversized window looking onto a private zen garden. The spacious second bedroom currently used as an office features corner windows and has a full luxury guest bath right out side its door. The oversized family room with vaulted ceiling and wood beam accents will be a great family retreat with a built in new state of the art fireplace and TV. Unique pebbled wallpaper adorns one wall to help maintain the resort feel. First floor laundry with built in cabinets is also on the first level. Upstairs you will find two nice sized bedrooms plus a full bath with double bowl sinks. The upstairs bonus room is a fun hideaway for a play room, office, or workout room, featuring glass French doors. Plenty of storage in this home with several attic accesses. Other important features include plantation shutters through-out, one new A/C unit in 2025, attic TAP insulation installed 2025, stackable washer and dryer 2024, new GAF coating on TPO flat roof (lanai), interior painted 2024, extensive landscaping 2025 including addition of a side private patio, and lanai wood ceiling 2025 and new hurricane rated glass in double front door. All the beautiful furnishings and decor items in the home are negotiable as well. So many more details you will just have to come and see for yourself. The Southbay Yacht and Racquet Club is a vibrant community with many amenities, activities and offers it’s own marina to residents. The marina dock fees are low and has space for most boat sizes. Also in the marina is a kayak launch and storage on site. The renovated clubhouse offers a fitness center, 99 person ballroom, livingroom, two kitchens, pool, bocce balls, tennis and pickleball. Centrally located between Sarasota and Venice, area beaches, restaurants and shopping. The local favorite restaurant, Casey Key Fish House & Tiki Bar is right down the road! Southbay is a fabulous place to live and play - and as they say, come and buy your boat a home!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
156 BISHOPS COURT RD, OSPREY, FL 34229
$1,289,00040 Days on yellowkey MLS ID: A4691664
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3112 Built: 1990Monthly Fee: $858 Tax: $8,394 (2025)Community: OaksSpa: YesSingle Family
Taxes:$8,394
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, new air conditioning for the main floor, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
360 N POINT RD, OSPREY, FL 34229
$1,495,0009 Days on yellowkey MLS ID: A4695959
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2913 Built: 2022Monthly Fee: $400 Tax: $9,588 (2025)Community: OaksSpa: NoSingle Family
Taxes:$9,588
Remarks: Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
314 S SHORE DR, OSPREY, FL 34229
$1,495,00023 Days on yellowkey MLS ID: TB8510971
REDUCED by $154,000 (9.3%) on 06/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3853 Built: 1981Monthly Fee: $15 Tax: $8,819 (2025)Community: Sorrento Shores Unit 1Spa: NoSingle Family
Taxes:$8,819
Remarks: Rare Gulf-access waterfront opportunity in desirable Sorrento Shores in Osprey. This spacious residence is set on a generous 0.54-acre waterfront lot with a private dock, screened pool, outdoor kitchen/grill area, paver patio, mature landscaping, and peaceful canal views. The home offers 3 bedrooms, 3 full baths, 3,853 sq ft, and a large flex room currently used as a studio with possible 4th bedroom potential. The open ranch-style layout includes comfortable living, dining, and entertaining spaces filled with natural light. The updated kitchen and bar area feature Viking Professional double ovens, a Viking Professional gas stove, Sub-Zero refrigerator, newer dishwasher, and microwave. Additional spaces include a private office with built-in cabinetry, large flex room, and an air-conditioned tackle/hobby/storage room with an additional Sub-Zero refrigerator. Major system updates noted by seller include a newer roof, full-house generator, impact windows and doors, two AC systems, new central vacuum system, tankless water heater, fireplace, and propane service for the grill, stove, dryer, fireplace, tankless water heater, and full house generator. Located near Casey Key, Nokomis Beach, Venice, Sarasota, marinas, dining, shopping, golf, parks, and coastal amenities.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
353 S SHORE DR, OSPREY, FL 34229
$999,00077 Days on yellowkey MLS ID: A4688006
REDUCED by $26,000 (2.5%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $11 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Spa: NoSingle Family
Taxes:$3,904
Remarks: Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this beautifully updated waterfront pool home delivers the lifestyle buyers come to Florida searching for. Welcome to Sorrento Shores — a hidden gem perfectly positioned between Venice Island and Siesta Key, where every day feels like a vacation. Situated on an oversized canal-front lot, this move-in ready 3-bedroom, 2-bath home offers quick deep-water access to the Intracoastal and Gulf beyond. Bring your boat, your paddleboards, your fishing gear, and start living the coastal lifestyle immediately. This home is Offered TURNKEY (minus select personal items), has a Private dock with quick open-water access, a 27x40 screened lanai with resurfaced pool for plenty of lazy pool days, and sits on an Oversized .36-acre lot. No need to store your boat trailer off site, there is ample parking for your boat trailer right on your own property. No CDD fees + voluntary HOA only $130/year And the Big-Ticket items have been taken care of: NEW ROOF 2025, NEW SEPTIC SYSTEM 2024, NEW POOL CAGE 2025 SEWER PIPES RELINED 2023-2024, IMPACT WINDOWS 2018, NEW POOL HEATER 2025, NEW WATER HEATER 2024 Newer A/C 2018 Updated baths + fresh interior finishes 2025 Cruise by boat to Casey Key Fish House, Pops Sunset Grill, Snake Island, Midnight Pass, Venice waterfront restaurants, and the Gulf of Mexico — all from your own backyard. This is not just a home… It’s the waterfront lifestyle buyers dream about!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
75 OSPREY POINT DR, OSPREY, FL 34229
$1,649,0006 Days on yellowkey MLS ID: A4695145
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4001 Built: 1983Monthly Fee: $950 Tax: $14,636 (2025)Community: OaksSpa: NoSingle Family
Taxes:$14,636
Middle School: Sarasota Middle
Remarks: Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.
4424 CONCHFISH LN, OSPREY, FL 34229
$585,00028 Days on yellowkey MLS ID: A4691622
REDUCED by $30,000 (4.9%) on 06/07/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2370 Built: 2017Monthly Fee: $125 Tax: $4,467 (2026)Community: Palms/Casey KeySpa: YesSingle Family
Taxes:$4,467
Tax Year: 2026
Remarks: Situated in the highly sought-after community of Palms at Casey Key, this beautifully maintained 2017-built home offers the perfect blend of comfort, style, and location. With low HOA fees and no CDD fees, this property delivers exceptional value in one of Osprey’s most desirable areas. From the moment you arrive, the paver driveway and lush tropical landscaping create a warm and welcoming first impression. Inside, the home opens to a bright and airy great room where tray ceilings and expansive triple-panel sliding glass doors allow natural light to pour in, creating an effortless connection between indoor and outdoor living. Designed with both everyday living and entertaining in mind, the kitchen serves as the heart of the home with a large center island offering ample seating, white cabinetry, stainless steel appliances, and a spacious corner pantry for additional storage. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the owner’s suite feels like a relaxing retreat with tray ceilings, a large walk-in closet, dual vanities, and a walk-in glass shower. Step outside to your private patio overlooking the in-ground spa — the perfect place to unwind after a beach day, enjoy a quiet evening under the stars, or cool off during warm Florida afternoons. Location is everything, and this home truly delivers. Ideally situated just minutes from nationally ranked Pine View School, less than a mile from the Casey Key boat launch and waterfront tiki bar, and only about 15 minutes to both Nokomis Beach and Siesta Key Beach, you’ll enjoy easy access to some of the area’s best boating, dining, shopping, golf, parks, and coastal lifestyle amenities. Whether you're looking for a full-time residence or the perfect Florida retreat, this home offers the lifestyle so many buyers are searching for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ashley Wallace (941-302-2586)
403 LONGBOW TRL, OSPREY, FL 34229
$1,095,000212 Days on yellowkey MLS ID: A4672081
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2770 Built: 1978Monthly Fee: $42 Tax: $9,020 (2024)Community: Pine RanchSingle Family
Taxes:$9,020
Remarks: Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. A newly remodeled kitchen with ample cabinetry and a seamless flow for entertaining. The primary suite provides a peaceful retreat with generous closet space and an en-suite bath and balcony with stunning views. Additional bedrooms are well-sized, making this home ideal for guests or a growing household. Enjoy Florida living at its best with an inviting private backyard inground pool framed by mature landscaping perfect for relaxing, gardening, or creating your own outdoor oasis. The backyard showcases a picturesque large pond, with a deck, making it an ideal spot for relaxing evenings. Additionally, this property features an in-law suite with one bedroom and one bathroom, ideal for guests or extended family. Whether you're seeking a full-time residence or a seasonal getaway, this Osprey gem delivers comfort, location, and value. With its prime Osprey location, easy access to Sarasota and Venice, and the natural beauty of the Gulf Coast just minutes away, this home offers exceptional value and an unbeatable lifestyle. A wonderful opportunity to own in one of Sarasota County's most desirable communities don't miss your chance to make 403 Longbow Trail your next home.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Edward Bieker, Pa (941-525-6473)
523 OAK BAY DR, OSPREY, FL 34229
$540,0005 Days on yellowkey MLS ID: A4696725
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2399 Built: 1998Monthly Fee: $25 Tax: $3,448 (2025)Community: Bay Oaks EstatesSingle Family
Taxes:$3,448
Remarks: Welcome home to this beautifully maintained 3-bedroom + den, 2-bath pool home nestled on a desirable corner lot, in a cul-de-sac, in Osprey. This home has been impeccably maintained and is an unbeatable location, this is the effortless Florida lifestyle you've been searching for. Peace of mind comes standard here. The roof is less than 7 years old, the AC was replaced just 2½ years ago, and the hot water heater is under 3 years old... meaning the big-ticket items are already handled, so you can simply move in and enjoy. You will find vinyl plank flooring, tile and carpet throughout. The care and attention put into this home shows in every corner. This home offers space to rest, work, entertain and relax...The flexible den offers the perfect home office, creative studio, 4th bedroom or guest retreat, whatever your lifestyle calls for? along with two spacious bathrooms. Then, step outside to your private screened pool, where the corner lot provides extra breathing room, privacy, and that open, airy feel that's so rare to find. Positioned in the heart of Osprey, this home is only minutes from the beloved Legacy Trail? which is ideal for cycling, jogging, and morning walks through some of Florida's most scenic natural surroundings. Nature lovers will also enjoy the proximity to Oscar Scherer State Park, offering kayaking, wildlife watching, and over 15 miles of trails. And when the beach calls, it's answered quickly. Nokomis Beach is just a short drive away for a casual sunset stroll, while the world-famous Siesta Key Beach, home to some of the whitest, finest sand on the planet, is within easy reach for those perfect beach excursions. 523 Oak Bay Drive checks every box: updated systems, private pool, flexible living space, and access to the very best of Florida's Gulf Coast. People also love the access to top-rated schools, including the nationally acclaimed Pine View School and Laurel Nokomis Elementary, making this the complete package for anyone looking to plant roots in one of Sarasota County's most sought-after communities. Homes like this don't last long. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
21 BAYHEAD LN, OSPREY, FL 34229
$789,000275 Days on yellowkey MLS ID: A4664085
REDUCED by $61,000 (7.2%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2246 Built: 2002Monthly Fee: $458 Tax: $4,221 (2024)Community: Bishopscourt At The Oaks PreserveSpa: YesSingle Family
Taxes:$4,221
Remarks: Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing…what you see, and what you don’t see, is what you get! From the moment you arrive at the pavered driveway, the pride of ownership is unmistakable. Double leaded-glass front doors open to a light-filled interior designed for effortless Florida living. Just off the entry, a dedicated home office features plantation shutters and a ceiling fan. The formal dining room showcases a decorative ceiling and a beautiful built-in buffet with glass-front cabinetry. The open kitchen features new granite countertops, stainless appliances, a breakfast bar, chef’s desk, and built-in wine and beverage cooler. The adjoining breakfast nook with an aquarium window, overlooks the sparkling pool and spa. The master suite is exceptionally spacious, offering a sitting area with built-in window seat and large walk-in closets with glass-front storage. The updated en suite bathroom has granite countertops, dual sinks, a soaking tub, separate shower, and marble accents. Two well-sized guest bedrooms provide generous closet space, and the updated guest bath includes granite and marble finishes. The air conditioned 2-car garage with epoxy flooring offers abundant storage. This home backs to a lush, tropical preserve, ensuring privacy for the pool and spa. The lanai features two distinct areas: a large, covered space with outdoor kitchen and ceiling fan for shaded dining, and a sun-splashed pool and spa area under a screened enclosure. You can also enjoy the nearby Bishopscourt community pool. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership
157 LOOKOUT POINT DR, OSPREY, FL 34229
$875,00020 Days on yellowkey MLS ID: A4694878
0 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1859 Built: 1981Monthly Fee: $219 Tax: $4,950 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$4,950
Remarks: Under contract-accepting backup offers. This one is an impressive little gem located in sought after Southbay Yacht & Racquet Club. So many improvements, upgrades and updates all you need to do is bring your furniture and move right in. As we approach the hurricane season, you will enjoy the sense of security provided by the replacement of all windows, sliders and doors with hurricane impact glass. A secluded back yard retreat awaits you with a spacious covered lanai looking onto the updated heated self draining pool and the wooded back yard. Some of the home highlights are: UPDATED KITCHEN AND BATHS, PORCELAIN TILE IN THE MAIN LIVING AREAS, IMPACT WINDOWS ABOUT 11-12 YEARS AGO. The owners have continued with the updates including: NEW METAL ROOF 2023, REPLACED MAIN ELECTRICAL PANEL AND ADDED 220 OUTLET FOR FUTURE GENERATOR. ADDED WHOLE HOUSE AIR PURIFICATION 2022, NEW EPOXY GARAGE FLOOR 2020, A/C AND HEAT PUMP SYSTEM 2018, REPLACED 3 DOORS WITH IMPACT GLASS, REPLACED 3 SLIDING GLASS DOORS WITH IMPACT GLASS 2015, COMPLETE POOL AND LANAI RENOVATION INCLUDING HEAT PUMP AND DECK PAVERS 2017, REPLACED GARAGE DOOR WITH IMPACT RESISTANT DOOR AND VENTS. REPLACED APPLIANCES: MICROWAVE 2025, REFRIGERATOR AND WINE COOLER 2024, RANGE, WASHER, DISHWASHER, 2023, HOT WATER HEATER 2023, REPLACED CARPET WITH CERAMIC TILE 2021 AND CUSTOM PLANTATION SHUTTERS THROUGHOUT THE HOUSE. There are more items I haven’t mentioned but you need to come take a look for yourself. There is a detailed list of improvements available. The Southbay community has much to offer! One of the few neighborhoods with its own exclusive marina. Dock space is only available to residents and is offered at very reasonable rates and can accommodate almost any size boat. Southbay is an active community with many clubs and gatherings at the remodeled clubhouse overlooking the marina. The clubhouse features two kitchens, ballroom, fitness center, card room, even a “livingroom” with grand piano. There’s something for everyone! Pickleball courts, tennis courts, bocce ball, community pool, playground, kayak launch and storage. Southbay is also a golf cart community! The Southbay location is in easy reach of shopping, grocery stores, restaurants, main roads, downtown Sarasota and downtown Venice. Local beaches including Nokomis (5 miles away), Siesta Key (10 miles away), Venice (7 miles) are all within an easy drive. Local restaurants including the famous Casey Key Fish House and Tiki bar are close at hand. Come and see what makes this home and Southbay so special!
557 CRANE PRAIRIE WAY, OSPREY, FL 34229
$599,0005 Days on yellowkey MLS ID: A4696823
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2172 Built: 2005Monthly Fee: $397 Tax: $3,953 (2025)Community: Willowbend Ph 4Single Family
Taxes:$3,953
Remarks: Welcome to this impeccably maintained, MAINTENANCE FREE home in the highly desirable Willowbend community, with tranquil LAKEVIEWS, exceptional amenities and an unbeatable LOCATION. Built by renowned Lee Wetherington and lovingly maintained by its original owner, this quality-constructed residence features a spacious open split-bedroom floor plan with 3 bedrooms plus den, 2 baths, and abundant storage throughout. The kitchen boasts natural wood cabinets with granite counters, a breakfast bar and newer stainless appliances with natural gas for cooking and a pantry for additional storage. The heart of the home opens to a stunning extended screened lanai surrounded by lush vegetation overlooking a private water view, where you can enjoy breathtaking sunrises and watch Florida's natural wildlife in a peaceful setting. Additional upgrades to this immaculate home include an EV charging station, whole-house carbon water filtration system, and natural gas service for the stove, dryer, and water heater. HOA fees provide outstanding value and include lawn maintenance, irrigation, high-speed internet, cable, and access to resort-style amenities including a community heated pool, fitness center, playground and pickleball courts. Ideally situated within a mile of Pine View School and just moments from Oscar Scherer State Park and the Legacy Trail, this home also offers quick access to Nokomis Beach, only two miles away. Trader Joe's, Whole Foods, shopping, dining, and everyday conveniences are all nearby, making this location truly second to none. Enjoy the perfect combination of comfort, convenience, low-maintenance living, and the Florida lifestyle in one of the area's most sought-after neighborhoods. Whether you're enjoying your morning coffee while watching the sunrise over the water, biking the nearby Legacy Trail, or spending the afternoon at Nokomis Beach, this exceptional home offers the very best of Florida living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Lori Lockhart, Pa (941-724-0595)
61 BAYHEAD LN, OSPREY, FL 34229
$1,185,00063 Days on yellowkey MLS ID: A4685559
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 1993Monthly Fee: $458 Tax: $4,573 (2025)Community: OaksSpa: YesSingle Family
Taxes:$4,573
Remarks: Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters thoughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB EQUITY MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. Buyer Bonus: Seller is offering $40,000 towards Buyer's Equity Club Membership!!! ***Most Furnishings are Available Under a Separate Contract.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Anne Thomas, Pa (941-993-7700)
14401 MASTHEAD DR, OSPREY, FL 34229
$2,995,000104 Days on yellowkey MLS ID: A4684834
REDUCED by $155,000 (4.9%) on 06/12/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2665 Built: 2017Monthly Fee: $643 Tax: $874 (2025)Community: BaysideSpa: YesSingle Family
Taxes:$874
Remarks: Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Mackenzie Longueuil (941-961-4023)
347 BAYSHORE DR, OSPREY, FL 34229
$739,00036 Days on yellowkey MLS ID: A4693374
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 2216 Built: 2013 Tax: $879 (2025)Community: Bay Acres - ResubSingle Family
Taxes:$879
Remarks: Who needs a space for a possible Mother-In-Law Quarters or a space that could possibly hold 4 plus cars ? This is your chance to live West of the Trail in the coveted Bay Acres community. This waterfront community has no deed restrictions so you can keep your boat or golf cart right on your property. With over 1400 Sq. Ft. of garage space the possibilities are endless here- use for your 4 plus cars, storage , recreational vehicles or jet skis, or maybe make it into a Mother-In-Law space . Part of the garage is air conditioned. The garage plus living space is over 4,000 Sq. Ft. The home itself has many nice features including a very nice large kitchen, dining room with tray ceiling, floors are gorgeous real Hardwood and wide planked. This custom built home has impact windows, a metal roof, a large covered porch, and a fenced back yard. Bay Acres has a waterfront park with boat slips that can be rented for a small yearly fee, Kayak storage and a kayak launch to be out in the Gulf waters in minutes. This home is ideally located right around the corner from the public Blackburn Point Boat Ramp, within minutes of many waterfront restaurants, and just 11 miles up the road is Downtown Sarasota. Come see why this friendly neighborhood and home can make your dreams a reality.
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: Sharon Sprow (813-817-9931)
97 SUGAR MILL DR, OSPREY, FL 34229
$1,950,00047 Days on yellowkey MLS ID: A4691789
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4885 Built: 1990Monthly Fee: $483 Tax: $16,651 (2025)Community: OaksSingle Family
Taxes:$16,651
Remarks: Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)
Listing Agent: Maria Domenech (978-204-3219)
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