1216 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 6 Bath · 2 Half Baths · 8,050 SqFt · $1,335/SqFt
Days on Market: 311
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1999
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.10
This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water ... Read more....»
121 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,096 SqFt · $1,581/SqFt
Days on Market: 191
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1969
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to ... Read more....»
313 LOOKOUT POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 5,337 SqFt · $1,124/SqFt
Days on Market: 10
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 2016
Garage: Yes 5 vehicles
Private Pool: Yes
Waterfront: Yes
Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property ... Read more....»
730 SARABAY ROAD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 6,308 SqFt · $792/SqFt
Days on Market: 145
County: Sarasota
Subdiv/Community Name: Sarabay Acres
Legal Subdivision Name: SARABAY ACRES
Year built: 2011
Garage: Yes 7 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 2.00
One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of ... Read more....»
324 BAYSHORE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,389 SqFt · $968/SqFt
Days on Market: 22
County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 2000
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to the Intracoastal Waterway. Even more spectacular is the beautiful water and natural beauty of Midnight Pass which is just to the north of this property and sandbar relaxation just a short boat ride away. This home features all the right spaces and updates- it features a smartly renovated main house comprised of three bedrooms, three and a half bathrooms and spacious office, as well ... Read more....»
854 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 2 Half Baths · 9,081 SqFt · $417/SqFt
Days on Market: 175
Cumulative Days on Market: 465
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 2003
Garage: Yes 4 vehicles
Private Pool: Yes
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 spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen. The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private ... Read more....»
1042 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,781 SqFt · $784/SqFt
Days on Market: 109
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: PALMER
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
One or more photo(s) has been virtually staged. Exceptional Waterfront Estate on North Casey Key. Set along the coveted shores of North Casey Key, this exceptional waterfront residence presents a rare opportunity to experience the very best of coastal Florida living. Nestled within the sought-after Palmer neighborhood and lovingly maintained by the same discerning owners since 1999, the home reflects a true sense of pride, care, and thoughtful stewardship throughout. Positioned on an expansive 0.68-acre parcel with 131 feet of Sarasota Bay frontage and two deeded private beach access points, the property is surrounded by lush tropical landscaping and majestic ... Read more....»
14401 MASTHEAD DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 2,665 SqFt · $1,220/SqFt
Days on Market: 19
County: Sarasota
Subdiv/Community Name: Bayside
Legal Subdivision Name: BAYSIDE
Year built: 2017
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
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 ... Read more....»
662 FERNWALK LANE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 4,359 SqFt · $654/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 3 vehicles
Private Pool: Yes
**EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN VIEWS** ideally positioned on a serene interior cul-de-sac lot in Flood Zone X (no flood insurance required). Located behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. This expansive residence features 4 Bedrooms and 4 Full Bathrooms within a thoughtfully designed floor plan. A comprehensive list of upgrades and amenities is available upon request and includes soaring 16-foot and vaulted ceilings, white oak and marble flooring, custom crown molding, plantation shutters, and extensive built-ins. The stunning ... Read more....»
236 SAINT JAMES PARK
OSPREY FL 34229
Residential / Single Family Residence
6 Bed · 6 Bath · 1 Half Bath · 6,246 SqFt · $432/SqFt
Days on Market: 343
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1986
Garage: Yes 2 vehicles
Private Pool: Yes
Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace anchors the dramatic sunken living room, while French doors and expansive windows flood the sunroom with natural light and frame sweeping golf course views. Step outside to three inviting patios—ideal for sunset cocktails, lively gatherings, or peaceful mornings overlooking the greens. A ... Read more....»
49 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,953 SqFt · $632/SqFt
Days on Market: 105
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
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 bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, ... Read more....»
852 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 4,519 SqFt · $552/SqFt
Days on Market: 174
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes
**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 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, ... Read more....»
230 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 3,586 SqFt · $696/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 2014
Garage: Yes 3 vehicles
Private Pool: Yes
Designed by Las Casitas Architects, this Spanish-style residence, featuring 3 bedrooms, 3.5 baths, a den/study with built-in Murphy bed and a 3-car garage, sits on an oversized .59-acre preserve lot with circular drive and courtyard entry. The light-filled, open floorplan features wood and marble flooring, crown molding, tray ceilings, and custom built-ins throughout. The chef’s kitchen is a standout with solid wood cabinetry, granite countertops, a large island with prep sink, counter seating, and premium appliances including Thermador and Bosch. The expansive master suite includes multiple walk-in closets and a luxurious bath with dual vanities and a large custom-tiled shower. ... Read more....»
433 E MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 4,012 SqFt · $561/SqFt
Days on Market: 72
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1998
Garage: Yes 3 vehicles
Private Pool: Yes
An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior craftsmanship designed to accommodate the seamless indoor-outdoor transfer so critical to Florida living. Most prominently the home features 12 foot high ceilings in most rooms, designed to maximize the home's grander, air ... Read more....»
180 LOOKOUT POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,236 SqFt · $695/SqFt
Days on Market: 132
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1986
Garage: Yes 2 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this never-lived-in five-bedroom, 3.5 ... Read more....»
362 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 4,117 SqFt · $546/SqFt
Days on Market: 80
County: Sarasota
Complex/CommunityName: THE OAKS
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1998
Garage: Yes 3 vehicles
Private Pool: Yes
Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with ... Read more....»
600 EAGLE WATCH LANE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 3,681 SqFt · $596/SqFt
Days on Market: 140
Cumulative Days on Market: 327
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes
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 Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3 BEDROOMS + STUDY/DEN, 3 FULL BATHS, High Ceilings, Crown Moldings, Gas Fireplace, Engineered Hardwood Flooring, Spacious Kitchen with New QUARTZ Counters and Stainless Steel appliances including premium brands such as SUBZERO and KITCHENAID, 3-Car Garage, Etc. An Expansive Primary Bedroom Suite ... Read more....»
642 TRENTON WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 3,939 SqFt · $546/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 2002
Garage: Yes 4 vehicles
Private Pool: Yes
Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wall ovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, ... Read more....»
448 E MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,768 SqFt · $557/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1998
Garage: Yes 3 vehicles
Private Pool: Yes
**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid ... Read more....»
18 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,977 SqFt · $1,012/SqFt
Days on Market: 153
County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: CASEY KEY
Year built: 1973
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal for quiet retreats, reading or working from home. Enjoy serene views of the bay and Intracoastal Waterway from the primary suite, a coastal sanctuary. Set on over half an acre, the expansive backyard features a large screened-in pool and lush landscaping, ... Read more....»
312 YACHT HARBOR DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 4 Bath · 2,572 SqFt · $776/SqFt
Days on Market: 193
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1978
Garage: Yes 3 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s seven-acre deep water boat basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet, with six feet of water at mean low tide and slips for 175 resident owned boats. Even more remarkable, Southbay’s HOA fees are only $218.87 per month ... Read more....»
538 DOVE POINTE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 4,346 SqFt · $449/SqFt
Days on Market: 145
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 4-C PT 3
Year built: 2002
Garage: Yes 3 vehicles
Private Pool: Yes
**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 perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE ... Read more....»
401 WALLS WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 4,387 SqFt · $410/SqFt
Days on Market: 52
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1990
Garage: Yes 3 vehicles
Private Pool: Yes
Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar ... Read more....»
402 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 3,565 SqFt · $491/SqFt
Days on Market: 2
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1999
Garage: Yes 3 vehicles
Private Pool: Yes
Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that stretch endlessly from the expansive screened lanai. Spanning over 3,500 square feet, this beautifully appointed single level home features three generously sized bedrooms, a dedicated office, and three-and-a-half baths, all thoughtfully designed to balance sophistication with everyday ... Read more....»
25 SUGAR MILL DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 3,066 SqFt · $553/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1998
Garage: Yes 2 vehicles
Private Pool: Yes
METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite Bedrooms, 3 Full and 1 Half Baths. The Updated Kitchen features Quartz countertops, custom hardwood cabinetry, and premium appliances, including Sub-Zero and Wolf. A cozy family room with a wood-burning fireplace provides an inviting gathering space, while impressive Brazilian ... Read more....»
228 SAINT JAMES PARK
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,425 SqFt · $699/SqFt
Days on Market: 24
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1997
Garage: Yes 2 vehicles
Private Pool: Yes
Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new ... Read more....»
140 SUGAR MILL DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 3,286 SqFt · $516/SqFt
Days on Market: 33
Cumulative Days on Market: 293
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 2 vehicles
Private Pool: Yes
BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you'll enjoy 4 bedrooms and 4 full baths - all on one level - within a ... Read more....»
909 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 4,241 SqFt · $400/SqFt
Days on Market: 467
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PHASE 2
Year built: 1991
Garage: Yes 2 vehicles
Private Pool: Yes
**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 Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private ... Read more....»
75 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 4,001 SqFt · $424/SqFt
Days on Market: 146
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1983
Garage: Yes 2 vehicles
Private Pool: Yes
**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, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks’ Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as ... Read more....»
422 BLUE GARDEN LANE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 3,872 SqFt · $413/SqFt
Days on Market: 99
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: THE OAKS BAYSIDE
Year built: 1984
Garage: Yes 2 vehicles
Private Pool: Yes
A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
