0.35 mi
Distance
Lilly, Osprey, FL, USA
Osprey, Florida, United States
Homes for sale near Lilly, Osprey, FL, USA
| Address | Bed / Bath | Listing Price |
|---|---|---|
75 OSPREY POINT DRIVE
**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters… situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, lau
Living Area:
4001 Sqft.
|
4
Beds,
4
Baths
|
$1,975,000 |
102 WINDWARD DRIVE
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large
Living Area:
2134 Sqft.
|
3
Beds,
3
Baths
|
$800,000 |
730 SARABAY ROAD
Premier Intracoastal Estate in Osprey
4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres
A rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is a
convergence of residential luxury and unparalleled waterfront living. The two-story home sits at
th
Living Area:
6308 Sqft.
|
4
Beds,
6
Baths
|
$5,495,000 |
403 LONGBOW TRAIL
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 Florid
Living Area:
2770 Sqft.
|
4
Beds,
3
Baths
|
$1,197,000 |
232 WOODLAND DRIVE
This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey
Living Area:
1325 Sqft.
|
2
Beds,
2
Baths
|
$269,900 |
3936 WAYPOINT AVENUE
Discover the charm of coastal living with the convenience of a mainland location in this beautifully furnished Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residenc
Living Area:
2323 Sqft.
|
3
Beds,
3
Baths
|
$1,089,000 |
49 OSPREY POINT DRIVE
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedro
Living Area:
3953 Sqft.
|
4
Beds,
4
Baths
|
$2,595,000 |
804 SHADOW BAY WAY
Located in one of Osprey’s most desirable neighborhoods, this well-maintained 3 bedroom, 2 bath home with a den offers an unbeatable location just a short walk to Pine View School and minutes to Casey Key and Siesta Key. Enjoy peaceful pond and greenbelt views from the screened lanai, which featur
Living Area:
2279 Sqft.
|
3
Beds,
2
Baths
|
$660,000 |
315 BAYSHORE DRIVE
Welcome to Bay Acres - a hidden coastal enclave West of the Trail where timeless Florida living meets everyday comfort. Situated on a generous corner lot with a circular driveway, this 3-bedroom, 3-bath single-family pool home offers a spacious and functional split floor plan designed for both priva
Living Area:
2384 Sqft.
|
3
Beds,
3
Baths
|
$659,000 |
9528 HAWKSMOOR LANE
Welcome to 9528 Hawksmoor Lane, located in the highly sought-after gated community of Stoneybrook Estates on Palmer Ranch. This spacious home features over 2,000 sq. ft. of living space, a two-car garage, and a crystal-clear pool recently resurfaced. It is loaded with curb appeal, from the pavered d
Living Area:
2007 Sqft.
|
3
Beds,
2
Baths
|
$615,000 |
700 FAITH AVENUE
One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools i
Living Area:
2474 Sqft.
|
4
Beds,
3
Baths
|
$1,300,000 |
538 DOVE POINTE DRIVE
**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the p
Living Area:
4346 Sqft.
|
4
Beds,
6
Baths
|
$2,300,000 |
691 EAGLE WATCH LANE
Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.² of conditioned living space, the residence has undergone an extraordinary transformat
Living Area:
6705 Sqft.
|
4
Beds,
7
Baths
|
$3,995,000 |
889 MACEWEN DRIVE
**INCREDIBLE TRANSFORMATION OF THIS MOVE-IN READY, GOLF COURSE ESTATE** From the Reimagined Entryway and through the Stunning Iron double front door, you will be captivated by the attention to detail throughout this elegantly appointed residence located on an Over Half Acre, Private lot on the Inte
Living Area:
3235 Sqft.
|
4
Beds,
4
Baths
|
$2,300,000 |
903 TRANQUILITY CIRCLE
**IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom-built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3-BED + Office/Den, 3 FULL BATH, 2-Car Garage residence affords wonderful privacy and features 2622sf of heated livin
Living Area:
2622 Sqft.
|
3
Beds,
3
Baths
|
$879,000 |
600 EAGLE WATCH LANE
One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre
Living Area:
3681 Sqft.
|
3
Beds,
3
Baths
|
$2,195,000 |
854 MACEWEN DRIVE
One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living
Living Area:
9081 Sqft.
|
4
Beds,
6
Baths
|
$3,950,000 |
4223 BALMORAL WAY
Seller is offering a $20,000 dollar closing credit, can be used to reduce the price or buy down a rate with your lender. Charming and spacious updated two-story Stoneybrook home perfectly designed for both comfort and entertaining! This bright and inviting residence features large impact hurricane r
Living Area:
2803 Sqft.
|
4
Beds,
5
Baths
|
$749,000 |
1036 OAK MEADOW LN
Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built i
Living Area:
2186 Sqft.
|
4
Beds,
2
Baths
|
$599,000 |
32 BAY AVENUE
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 and waterfront lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb includ
Living Area:
2148 Sqft.
|
2
Beds,
2
Baths
|
$463,000 |
85 SUGAR MILL DRIVE
**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainsco
Living Area:
4191 Sqft.
|
3
Beds,
3
Baths
|
$2,150,000 |
38 W BAY STREET
Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings wi
Living Area:
2124 Sqft.
|
3
Beds,
2
Baths
|
$925,000 |
742 HARMS DRIVE
Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been succe
Living Area:
1293 Sqft.
|
3
Beds,
2
Baths
|
$545,000 |
123 WINDWARD DRIVE
This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bat
Living Area:
1894 Sqft.
|
3
Beds,
2
Baths
|
$850,000 |
370 SUGAR MILL DRIVE
**Meticulously maintained, architectural perfection, this bright, spectacular estate featuring incredibly spacious first floor living space, with 5-Beds, 6.5 Baths, private second floor family, au pair and/or guest quarters, new pool, ideal Flood Zone X location, important updates, property wide lan
Living Area:
4783 Sqft.
|
5
Beds,
6
Baths
|
$2,650,000 |
21 BAYHEAD LANE
Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to main
Living Area:
2216 Sqft.
|
3
Beds,
2
Baths
|
$925,000 |
508 MEADOW SWEET CIRCLE
PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well
Living Area:
1604 Sqft.
|
2
Beds,
2
Baths
|
$465,000 |
701 EAGLENOOK WAY
A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses.
Conveniently positioned one mile East of US 41, within a mile of
Living Area:
3533 Sqft.
|
4
Beds,
5
Baths
|
$1,075,000 |
17 BAYHEAD LANE
Welcome to an exquisitely revitalized estate set amidst a stunning landscape that is sure to impress. Located “West of Trail” in The Oaks Preserve, you will experience an unparalleled country club lifestyle on Florida’s Gulf Coast. As you step through the grand front entry, you are welcomed
Living Area:
2850 Sqft.
|
3
Beds,
2
Baths
|
$1,300,000 |
614 BAYSHORE DRIVE
New Seawall / Waterside deck, New Automated Gate, Lanai Automated Screens
Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water vie
Living Area:
4048 Sqft.
|
3
Beds,
5
Baths
|
$5,500,000 |
827 PLACID LAKE DRIVE
This lot and location really stands out! Set back on a quiet street, on a beautifully landscaped oversized lot, and a huge lawn in the backyard with a preserve as the backdrop, this well maintained, light-filled residence offers a rare combination of elegance, security, privacy, efficiency, value, a
Living Area:
1875 Sqft.
|
2
Beds,
2
Baths
|
$544,700 |
4098 WESTBOURNE CIRCLE
Welcome to this beautifully updated 3BR,2BA home with a 2-car garage, nestled beneath a canopy of shady trees and lush greenery, within the gated, non-golf section of the highly desirable Stoneybrook at Palmer Ranch. From the moment you arrive, the curb appeal and tranquil setting set the tone for t
Living Area:
1442 Sqft.
|
3
Beds,
2
Baths
|
$445,000 |
852 MACEWEN DRIVE
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails
Living Area:
4519 Sqft.
|
3
Beds,
4
Baths
|
$2,550,000 |
471 PARK TRACE BOULEVARD
SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4 bedroom, 3 bathroom residence perfectly blends luxury, comfort, and location for the ideal Florida lifestyle. This home is nestled in a highly sought-after neighborhood offering peace, privacy, and a vibrant c
Living Area:
2267 Sqft.
|
4
Beds,
3
Baths
|
$699,000 |
851 PLACID LAKE DRIVE
One or more photo(s) has been virtually staged. Your dream home is waiting for you! Enjoy a bright interior decorated with a neutral color palette. You'll love cooking in this kitchen, which includes a spacious center island and a sleek backsplash. Retreat to the spacious primary suite, designed wit
Living Area:
3395 Sqft.
|
5
Beds,
4
Baths
|
$750,000 |
819 SHADOW BAY WAY
A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully! This maintenance-free, tropically landscaped corner lot home has been eloquently updated and maintained. Featuring four bedrooms, formal dining room, two baths, two-car garage, f
Living Area:
2145 Sqft.
|
4
Beds,
2
Baths
|
$689,000 |
4207 BALMORAL WAY
Welcome to your new home in Stoneybrook Estates! This 3-bedroom, 2-bath offers the perfect blend of comfort, style, and functionality. Step inside to find an open and inviting layout ideal for both everyday living and entertaining.
Enjoy peaceful mornings or relaxing evenings in the new screened-
Living Area:
1961 Sqft.
|
3
Beds,
2
Baths
|
$579,000 |
4428 CONCHFISH LANE
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 th
Living Area:
1861 Sqft.
|
4
Beds,
2
Baths
|
$599,000 |
140 SUGAR MILL DRIVE
**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown
Living Area:
3286 Sqft.
|
4
Beds,
4
Baths
|
$1,970,000 |
866 OAK BRIAR LANE
**NEW ROOF** Welcome to the highly desirable Park Trace Estates where residents enjoy low HOA fees! This beautiful pool home is move-in ready and features a split floor plan with three bedrooms and a 4th-bedroom/office giving you lots of space and flexibility. Many upgrades include pool resurfaci
Living Area:
2434 Sqft.
|
4
Beds,
2
Baths
|
$699,900 |
296 PINE RANCH TRAIL
**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 e
Living Area:
3481 Sqft.
|
5
Beds,
4
Baths
|
$1,350,000 |
352 GLENWOOD AVE
Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions
Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with
Living Area:
1300 Sqft.
|
3
Beds,
2
Baths
|
$444,000 |
5301 BARTOLOMEO STREET
Discover the exceptional lifestyle offered in Esplanade on Palmer Ranch with this beautiful Arrezo model home, perfectly situated on a private cul-de-sac. This vibrant and active community boasts a wealth of amenities, including the Bahama Bar for dining and social activities, pickleball and tennis
Living Area:
1918 Sqft.
|
3
Beds,
2
Baths
|
$679,000 |
1363 NEW FOREST LANE
Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with ple
Living Area:
1738 Sqft.
|
2
Beds,
2
Baths
|
$499,000 |
901 REFLECTION WAY
LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of t
Living Area:
2443 Sqft.
|
3
Beds,
2
Baths
|
$795,000 |
110 PINE AVENUE
Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the
Living Area:
2058 Sqft.
|
3
Beds,
2
Baths
|
$705,000 |
340 OSPREY POINT DR
Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and priva
Living Area:
6001 Sqft.
|
5
Beds,
7
Baths
|
$2,395,000 |
13 BAYHEAD LANE
**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent upd
Living Area:
2310 Sqft.
|
2
Beds,
2
Baths
|
$965,000 |
236 SAINT JAMES PARK
Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers. A Loui
Living Area:
6246 Sqft.
|
6
Beds,
7
Baths
|
$2,900,000 |
820 PLACID LAKE DRIVE
Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool
Living Area:
3938 Sqft.
|
5
Beds,
4
Baths
|
$1,095,000 |
227 SAINT JAMES PARK
**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking t
Living Area:
2071 Sqft.
|
2
Beds,
2
Baths
|
$995,000 |
909 MACEWEN DRIVE
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Exe
Living Area:
4241 Sqft.
|
3
Beds,
4
Baths
|
$1,695,000 |
