Osprey Florida Real Estate Listings

Osprey, Florida is a historic city on Florida’s southwest coast. Osprey is a diverse community featuring multi-million dollar homes among the intercostal highway. 

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View all real estate for sale in Osprey, Florida below with RoseBay International Realty. Contact us if you have questions or would like to schedule a showing. 

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4192 Expedition Way Osprey FL 34229

Osprey, FL4192 Expedition Way

Price$400,000

Est. Mortgage: $/month

MLS Number A4541014

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 1,135
  • Bathroom 2

Relax and enjoy the good life at Bay Street! Oversized windows permits Florida sunshine to illuminate this home with 9 ft + ceilings. Spacious Heron floor plan with 12''x24'' floor tile laid on the brick pattern makes great use of space with two bedrooms, two baths and an attached one-car garage. The kitchen features a large center island that any chef would love. Stylish design elements including 42'' cabinetry and Granite with an under-mount large single bowl stainless steel sink and back splash. Stainless steel Frigidaire appliances and a closet pantry. Bathrooms have matching cabinets and granite countertops. Double slider opens to an arched and screened corner balcony. Master suite features large walk-in closet, walk-in shower, and double vanity. In home utility with washer and dryer. Maintenance free community includes gated entry, resort style community pool, fully equipped fitness room, cabana and community clubroom. Quality features include concrete block construction, impact glass windows, tile roofs, paver driveways, exterior stucco finish with corbels and cove molding. Conveniently located between downtown Sarasota and Venice, Bay Street has it all nearby The Legacy Trail, Oscar Scherer Park, the areas top-rated sandy beaches, and countless dining and shopping venues. Start living the Florida lifestyle today at Bay Street. Come see what we have for you!

Listed by ALL COUNTY PROP MGMT PROS

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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429 Patterson Avenue Osprey FL 34229

Osprey, FL429 Patterson Avenue

Price$329,000

Est. Mortgage: $/month

MLS Number A4540663

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 1,173
  • Bathroom 1

Live within minutes of the beach~! Move-in ready, charming 3 bedroom, 1 bathroom home with NO HOA or CDD fees now available! This recently upgraded Osprey Park residence features an extended driveway, complete with a concrete pad to park your boat, RV, or water toys in the side yard! Two sets of gates in the fence offer access to both roads, one at the front and one in the rear of the property. A truly open concept main living area offers the perfect arena for entertaining with plank tile flooring throughout. Enough space for all of your furniture, the large living room offers room for everyone to stretch their legs. The well-appointed kitchen provides all the essentials to cook and bake to your heart's content, with stainless steel appliances and plenty of counter space. Serve meals in the eat-in space in the kitchen, where you can use the side counter and cabinets as a buffet for the dining area. Three comfortable bedrooms provide plenty of room for everyone. The master bedroom features a private entry to the lanai. Outdoors, enjoy a fully screened and covered lanai, perfect for barbecuing and outdoor gatherings. The fully fenced yard offers privacy and there is space for a garden or outdoor activities. Store all of your lawn equipment in the utility shed. Located just minutes from world famous beaches, shopping, dining, Marie Selby Botanical Gardens, and more.

Listed by THE ORANGE REAL ESTATE GROUP

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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340 Pennsylvania Avenue Osprey FL 34229

Osprey, FL340 Pennsylvania Avenue

Price$369,000

Est. Mortgage: $/month

Pending

MLS Number A4540560

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 967
  • Bathroom 2

IF YOU LOVE A "COUNTRY FEELING' WITHOUT BEING FAR FROM SHOPPING AND BEACHES, WITH NO HOA FEES, check out this one! It is on THREE LOTS. This beautiful home is on the middle lot so there is a lot on each side! 153 feet wide! Exterior just painted, flooring replaced, and is move-in ready! Lovingly maintained by the original owner with no pets. You will fall in love with this little gem!

Listed by A & D EDWARDS AMERICAN DREAM

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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579 Oak Bay Drive Osprey FL 34229

Osprey, FL579 Oak Bay Drive

Price$824,900

Est. Mortgage: $/month

Pending

MLS Number A4540445

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 2,721
  • Bathroom 3

This enchanting Bay Oaks Estates home, with a new roof in 2021, has amazing curb appeal with circular drive and double front door entry. Serenity and tranquility are assured; bordering a large community preserve with privacy fences, sparkling pool and lush landscaping. The deep 17-by-31-foot pool has a powerful 135 BTU new heater and it has been recently re-marcited. Ideally located just south of Sarasota, near Pine View School, Legacy Bike Trail, Costco, Total Wine and between Siesta and Nokomis beaches. Wrap yourself in luxury in a sophisticated and spacious home boasting soaring 13-foot ceilings, four bedrooms, three baths and den/office space. (The fourth bedroom to the rear is an en-suite configuration, which also serves as the pool bath.) The brilliantly designed updated kitchen has plenty of cabinetry in trending white with granite and stainless steel appliances, new in 2019. Wide plank tile flooring throughout the residence with remodeled baths in granite, floor-to-ceiling tile in showers and everything in neutral palettes. The bedroom sizes are very generous. Views of the pool and preserve from a large, covered lanai, make for blissful outdoor living. On a practical note: the air conditioning was replaced in 2019, hurricane shutter protection, 6,500-watt generator and numerous smart home features. Excellent location, lifestyle and value complete this incredible residence.

Listed by PREMIER SOTHEBYS INTL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4401 Conchfish Lane Osprey FL 34229

Osprey, FL4401 Conchfish Lane

Price$756,000

Est. Mortgage: $/month

MLS Number A4540170

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,370
  • Bathroom 3

Beautiful 4 bed, 3 bath, 2 car garage home in Osprey, just a short walk to Pine View School! 2018 built home shows brand new with a number of quality upgrades. Among the many additions, there are newly added gorgeous light fixtures throughout the home, custom window treatments with tie backs to enjoy the natural light, and beautiful updated flooring in every room. The open floor plan is perfect for entertaining family and friends. Upon entering the foyer a sense of home welcomes you leading into the open den/kitchen and great room. A Gourmet kitchen with granite center island, stainless steel appliances, and pantry equates to a chef's dream. The lovely master suite boasts large windows with views of the peaceful treed backyard and elegant bathroom featuring dual vanities, large walk in closet and convenient access to the spacious laundry area. Three additional bedrooms and two baths complete the space for comfortable family living. An attractive paved walkway has been added around the perimeter of the home opening to a paved backyard patio for relaxing in the Florida sunshine. Enjoy morning coffee on the screened lanai facing a private nature setting, complete with mango, dragon fruit, and other lovely trees in the backyard. Additional features include water filtration and softener systems, and electric car charging in the oversized garage. The popular legacy trail, Spanish Point and Oscar Scherer State Park are nearby, as is the nationally ranked Pine View school. Enjoy the convenience of walking to and from Pine View, as well as shopping, dining, and world class beaches nearby. DON'T DELAY! SCHEDULE A SHOWING TODAY!

Listed by COMPASS FLORIDA LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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409 N Point Road Osprey FL 34229

MLS Number A4540108

  • Condo
  • Mls Status Active
  • Square Feet 2,203
  • Bathroom 3
  • Area Osprey

Escape to the casual elegance of your peaceful and private sanctuary at the Meridian, offering the best of luxury coastal living in Sarasota's premiere country club community. Upon entering through the guarded gate, you are enveloped in lush tropical landscapes as you drive to the Meridian towers perched on Little Sarasota Bay, well secluded from the hustle bustle. Through the secure lobby entrance, the elevator carries you to your private foyer which opens to the spacious residence inside, its tasteful updates awash in natural light. Style unfolds at every turn with timeless wood inspired porcelain tile floors, plantation shutters adorning the High-Energy Impact windows and doors, elegant light fixtures, and 9' ceilings with crown molding throughout. Relax on your large, screened terrace while gazing through the treetops at the surrounding natural beauty. Enjoy preparing meals in the signature kitchen, complete with bar seating, granite counters, induction cook top, convection oven/microwave, build-in wall oven and ample cabinet space. This Chambord floor plan offers 3 bedrooms and 3 bathrooms plus a large flexible space currently used as a formal dining room, but alternatively may be the perfect office or den space. The laundry room and guest rooms are situated away from the main living areas for added privacy. As a resident, you will appreciate the convenient garage parking, with a dedicated oversized parking space, and climate-controlled storage, as well as the onsite fitness center and large community pool with compelling outdoor gathering spaces. Pet owners rest assured, two pets of any size are welcome here! A stone's throw away, The Oaks Club welcomes you to fully enjoy the country club lifestyle afforded by its world class array of amenities including two 18-hole championship golf courses, 12 Har-Tru lit tennis courts, 4 pickle-ball courts, croquet and bocce, acclaimed wellness facilities, a variety of year-round dining options at 3 restaurants, plus frequent organized social events. Either social or equity membership is available and required. Information on membership is attached for your convenience. Adding to the endless enjoyment options of this uniquely special area are the stunning nearby beaches, as well as the vibrant and diverse Sarasota cultural scene. Start living the dream when you make this beautiful condominium your home!

Listed by MICHAEL SAUNDERS & COMPANY

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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642 Crane Prairie Way Osprey FL 34229

Osprey, FL642 Crane Prairie Way

Price$830,000

Est. Mortgage: $/month

Pending

MLS Number A4538082

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 3,319
  • Bathroom 4

Experience tranquil, private living in this well-appointed Lee Wetherington-designed pool home bordering the lush natural surroundings of Oscar Scherer State Park. Located in the coveted maintenance-free community of Willowbend, the residence's versatile floorplan offers family and guests privacy and space as well as an upstairs bonus room with a powder bath and closet space that can serve as a theater, game room or extra bedroom. Abundant natural light and refined finishes are found throughout this lovely home, including crown molding, coffered ceilings and elegant archways. Chefs will relish creating culinary masterpieces in the expansive gourmet kitchen, which has a natural gas stove, stone countertops, glass cabinets, large island with breakfast bar and adjacent nook with glass sliders to the covered lanai dining area. The kitchen opens to the family room, making it an ideal gathering area for family and friends. A sophisticated formal dining room, featuring a built-in dual-sided buffet and custom overhead glass cabinetry, is perfect for entertaining, with an adjoining formal sitting room for savoring picturesque views of the saltwater pool and lush landscape just beyond the backyard. Sliding glass doors offer access to a private covered lanai with abundant space for relaxing, dining and entertaining amid a preserve teeming with birds, deer and other fauna. A serene retreat awaits you in the owner's suite, which has a sitting area, dual walk-in custom closets, pool access, gorgeous views and a bathroom with separate vanities, soaker tub and open spa shower. Two first-floor guest bedrooms share a full bath and small office nook, and a custom dual office has a built-in desk, shelving and cabinetry. Other notable features include plantation shutters throughout, a water filtration system and three-car garage with built-in shelves and storage. Willowbend offers grounds maintenance, a community pool, pickleball, exercise facility and social events, and is conveniently located near shopping, beaches, the Legacy Trail, dining and more.

Listed by MICHAEL SAUNDERS & COMPANY

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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327 Sea Anchor Drive Osprey FL 34229

Osprey, FL327 Sea Anchor Drive

Price$1,349,000

Est. Mortgage: $/month

MLS Number A4540135

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,521
  • Bathroom 3

Open the double glass entry doors to this stunning turnkey, furnished home in Southbay Yacht and Racquet Club and you'll immediately fall in love. This beautifully renovated pool home features two bedrooms, three full baths, a dedicated office with custom built-ins and it's located close to the community-owned marina. The expansive covered lanai and pool area, which can be accessed from the living room, primary suite and family room, is the perfect place for entertaining and grilling. The residence boasts volume ceilings, two fireplaces, built-in cabinetry, spacious open rooms, impact-resistant windows, travertine tile and a lovely entertainment kitchen that services a breakfast area and family room. The expansive primary suite, which has a sitting area and overlooks the pool, offers a walk-in closet and reach-in closet with private washer and dryer. The master bath has a walk-in shower, and dual vanity sinks. The guest bedroom is also spacious with a pullout sofa and large reach-in closet. This home is ready to move in and has a two-car garage, brick paver circular driveway, expansive covered pool area for entertaining and mature landscaping. Add a second floor for amazing water views or add on and make the home fit for a growing family. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht and Racquet Club features a 7-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a 6-foot depth at mean low tide, the marina can accommodate 175 boats owned by its residents. In Southbay, the HOA fees are only $408 per quarter and it is so affordable to keep your boat in a slip that affords water and electric. The newly renovated clubhouse overlooks the marina and inside there's a 99-person ballroom with catering kitchen and dance floor, community room with kitchen, piano and entertainment area, a fitness room with aerobic and strength training equipment, a card room, library and meeting room. The community also has a geothermal-heated pool, a children's pool, covered outdoor patios with furniture, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboards courts, kids' basketball court, kayak storage area, a waterfront park, 20 acres of common ground and five miles of winding sidewalks. The development is golf cart-friendly and the community hosts weekly, monthly and multiple annual events, plus there's even a Power and Sail Club. Great location and close to shopping, restaurants, Publix, the beaches and Pine View School.

Listed by PREMIER SOTHEBYS INTL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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828 Placid Lake Drive Osprey FL 34229

Osprey, FL828 Placid Lake Drive

Price$699,000

Est. Mortgage: $/month

Pending

MLS Number G5057239

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 2,258
  • Bathroom 2

Lush landscaping surrounds this spacious, immaculate home located on a premium waterfront lot in a very desirable community. Peaceful and private views of Placid Lake from the Master and second bedrooms, great room, and kitchen. Fully repainted inside and out including pool deck. New carpet and new lighting. New professionally installed epoxy garage floor. New A/C system with heat pump. Irrigation well. Prime location in Rivendell convenient to Pine View and the Legacy Trail.

Listed by LIST NOW REALTY,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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232 Hidden Bay Drive Osprey FL 34229

MLS Number C7462647

  • Condo
  • Mls Status Active
  • Square Feet 1,943
  • Bathroom 2
  • High School Venice Senior High

WATERFRONT 3 Bedroom, 2 Bathroom, + FLORIDA ROOM, PENTHOUSE located in Baypoint Vista in Osprey. CLICK ON THE VIRTUAL TOUR LINK 1 FOR A 3D INTERACTIVE WALK THROUGH AND VIRTUAL LINK 2 FOR THE VIDEO. This lovely condo features an OPEN FLOOR PLAN, beautiful bamboo wood flooring throughout, Crown Molding, Laundry Room with Sink, PLANTATION SHUTTERS, recessed and pendant lighting, and SPECTACULAR WATER VIEWS. As you step into the welcoming foyer with HIGH CEILINGS, you will be led into the FULLY REMODELED GOURMET KITCHEN with GRANITE countertops, plenty of cabinetry for storage, stainless appliances, designer backsplash, and breakfast bar with pendant lighting. The kitchen flows seamlessly into the adjacent dining room/living room combo, perfect for entertaining! A large living room offers plenty of room for relaxing and opens up to a beautiful FLORIDA ROOM with a wall of sliding glass doors providing great natural light and amazing views of the Intracoastal Waterway and Gulf of Mexico. The Master Suite features a large walk-in closet with an attached Master Bathroom with dual sinks, granite countertops, tiled WALK-IN shower and separate corner soaking tub. The additional bedrooms are on a split floor plan for extra privacy and have easy access to the guest bathroom. The 3 car Garage is an added BONUS. Baypoint Vista is a Gated Community and offers a TON of amenities including a Full Clubhouse, Fitness Center, Computer Room, Library, Conference and Banquet Rooms, Tiki Bar & BBQ Area, 2 Tennis Courts, 2 Pickleball Courts, and Community Pool and Spa that were refurbished in 2022. Prime location and conventionally located near local shopping, dining, and other amenities. Close to award winning beaches: Venice Beach, Manasota Key, Nokomis & Siesta Key Beach where you will find white sand and beautiful water views. Schedule your showing TODAY!

Listed by KW PEACE RIVER PARTNERS

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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250 Hidden Bay Drive Osprey FL 34229

MLS Number A4534945

  • Condo
  • Mls Status Active
  • Square Feet 2,168
  • Bathroom 3
  • Area Osprey

This beautiful second floor end-unit condo is located on Little Sarasota Bay and the Intracoastal Waterway in Edgewater at Hidden Bay, a gated 14 acre resort-style community of bay front condominiums. The open floor plan is bright and spacious, with three bedrooms + den, two bathrooms and a powder room, a full size laundry room and expansive screened-in lanai. The kitchen features a breakfast bar, granite countertops, and stainless steel appliances. The master suite showcases two walk-in custom closets, granite countertops with dual sinks, and a large walk-in shower. The separate dining room and den makes this condominium feel like a Single Family Home. The oversized terrace is the perfect place to relax and enjoy the sunsets. Other upgrades include plantation shutters throught, hurricane impact resistant windows, built in Murphy bed and desk, crown molding and tray ceilings. Hidden Bay offers a lakefront clubhouse, with a heated community pool and spa, fitness facility, tennis, two pickleball courts, tiki bar, kayak storage and a fishing pier. Close to restaurants, shopping, great school district including the number one rated school in Florida Pine View, close priximity to Nokomis beach, Venice beach and Siesta Key. Come and enjoy this piece of paradise, either you can make this your full-time residence or a peaceful and quiet getaway.

Listed by CORCORAN DWELLINGS REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4429 Conchfish Lane Osprey FL 34229

Osprey, FL4429 Conchfish Lane

Price$649,000

Est. Mortgage: $/month

MLS Number A4539920

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,008
  • Bathroom 2

Beautiful newly constructed home located in The Palms of Casey Key! New carpet in all bedrooms. This 2,008-square-foot home is designed to entertain, with an expansive great room at its center, perfect for gathering the whole family in one place. A sumptuous master suite creates a personal retreat set apart at the back of the home, with walk-in closet, dual-sinks, soaking tub and standing shower. This home is complete with a spacious lanai and two-car garage. Close to the beaches of Sarasota, Casey Key and Venice which are world-renowned. Within a 1/2 mile of Pine View School. Easy access to US 41 and I-75.

Listed by HOME REALTY & MANAGEMENT LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to StellarMLS as of July 3, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or StellarMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.