The Oaks Real Estate

The Oaks Real Estate

Welcome to The Oaks, a stunning subdivision nestled in the heart of Florida, where luxury meets tranquility. Located in the picturesque landscape of the Sunshine State, The Oaks offers a unique blend of natural beauty and modern living, making it an ideal choice for those seeking a serene yet vibrant community.

As you enter The Oaks, you are greeted by lush greenery and beautifully manicured landscapes, creating an inviting atmosphere that feels like home. This exceptional neighborhood features a variety of elegant homes, each designed with meticulous attention to detail, catering to diverse lifestyles and preferences. From charming single-family residences to spacious estates, there’s a perfect fit for everyone.

The Oaks is not just about stunning homes; it’s also about a lifestyle. Residents enjoy access to top-notch amenities, including a sparkling community pool, well-equipped fitness center, and inviting parks that encourage outdoor activities. The community is designed with families in mind, offering playgrounds, walking trails, and gathering spaces for neighbors to connect and create lasting memories.

Conveniently located near major highways, The Oaks provides easy access to nearby shopping, dining, and entertainment options. Whether you’re exploring local boutiques, indulging in gourmet cuisine, or enjoying a day at one of Florida’s beautiful beaches, everything you need is just a short drive away.

Experience the charm and warmth of The Oaks, where community spirit thrives and every day feels like a vacation. Discover your dream home in this idyllic Florida subdivision today!

Newest Listings in The Oaks

$6,449,000
6 Beds 6 Baths A4702047 MLS
A rare combination of timeless grandeur and effortless waterfront living, this bayfront estate in The Oaks Bayside commands approximately 150 feet of Bay frontage across 0.60 acres, with water views framing nearly every principal room. The residence offers 6 bedrooms, 5.5 baths, multiple covered balconies overlooking the Bay, additional ground-level flex space and a side-entry 3-car garage. A circular brick-paver driveway, tropical landscaping and a stately columned entrance create an unforgettable arrival. The dramatic two-story foyer features architectural columns, custom millwork and a wood-clad ceiling accent. European French white oak engineered flooring flows through the main living spaces. The living and family rooms feature soaring ceilings, extensive millwork, statement lighting, carved-stone fireplaces and oversized windows framing expansive water views. An adjoining sitting area features arched windows, a wood-clad ceiling and multiple glass doors opening to the waterfront balcony. The new kitchen is appointed with ceiling-height Shaker cabinetry, champagne-bronze hardware, marble countertops and an oversized waterfall island with seating for five. A GE Monogram appliance suite includes a professional gas range with griddle, refrigerator and dishwasher. A custom range hood, dimensional tile backsplash, apron-front sink and walk-in pantry complete the space. The waterfront dining nook incorporates built-in cabinetry, a stone serving counter and beverage cooler, while the formal dining room features a tray ceiling, paneled walls and columns. A waterfront office with built-in bookshelves, fireplace and balcony access, an updated laundry room and multiple en-suite guest accommodations complete the main level. Upstairs, the landing overlooks the living spaces beneath a crystal chandelier. The primary suite offers separate sleeping and sitting areas, a carved-stone fireplace, wide water views, private balcony access and two walk-in closets with custom storage. Its spa-inspired bath includes dual furniture-style vanities, a freestanding soaking tub beneath a picture window and an oversized frameless shower with marble-look tile, rainfall and handheld fixtures. Additional bedrooms offer en-suite or nearby baths, walk-in closets, abundant natural light and water or tropical views. Multiple covered balconies overlook the newly resurfaced pool, paver terrace, manicured lawn and waterfront. The pool features a 7-foot depth, entry steps, seating or sun-shelf areas, lighting, a self-cleaning system and a new pump. A private walkway through the mangroves leads to a new 5-by-60-foot composite dock completed in 2026, equipped with electric, water and a 6,000-pound boat lift. The property also features a concrete seawall and direct boating access. The lower level provides substantial additional flexibility for recreation, fitness, media or entertaining. Further updates include a newer 2023 tile roof, new HVAC, all-new appliances and flooring, new interior doors and moldings, hurricane protection and exterior lighting. The renowned Oaks Club is one of the area’s premier member-owned clubs, featuring two championship 18-hole golf courses, a full slate of tennis and fitness facilities, and an elegant clubhouse offering fine dining and a vibrant social calendar. Ideally situated in Osprey, the property offers convenient access to Gulf beaches, the Legacy Trail, dining and shopping, with downtown Sarasota and Venice both within easy reach.

112 Osprey Point Drive, Osprey/Nokomis

Listing courtesy of DOUGLAS ELLIMAN. 941-867-6199

$1,900,000
5 Beds 8 Baths A4698153 MLS
Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey/Nokomis

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-364-4000

$159,000
2 Beds 3 Baths 2150493 MLS
MAINTENANCE FREE, END UNIT, GOLF Course Views. RELAX AND UNWIND! Newer HVAC, Newer Tankless Water Heater. Completely REMODELED! Close to the SPACE CENTER and the Port. Year-round residence, Investment Income, or a Seasonal Retreat, ENJOY MORE and worry less! Nestled along the Fairways of the PRIVATE Rockledge Country Club, this charming END UNIT offers the perfect blend of PEACEFUL GOLF COURSE LIVING and convenient access to everything the Space Coast has to offer! Start your mornings with coffee on the SCREENED PORCH as the sun rises over the lush greens and natural surroundings. Spend your afternoons enjoying the community POOL, playing a round of GOLF, exploring nearby BEACHES, or dining at one of the area's favorite local RESTURAUNTS. In the evenings, unwind in the comfort of your SPACIOUS home while taking in the tranquil views and gentle Florida BREEZES. Inside, you'll find a welcoming Open Layout designed for both RELAXATION and ENTERTAINING, with bright living spaces, a cozy fireplace, and 2 PRIVATE bedroom SUITES that provide comfort and flexibility for guests or family. Located in the heart of Rockledge, you're just minutes from waterfront parks, the Indian River, Cocoa Village, world-famous beaches, Kennedy Space Center, and easy access to Orlando. Embrace a LIFESTYLE FILLED WITH SUNSHINE, recreation, and the laid-back charm of FLORIDA LIVING. Come experience golf course living, natural beauty, and everyday convenience all in one exceptional Space Coast location!

1600 Woodland Drive Unit 8201, Rockledge

Courtesy of UNITED REAL ESTATE GALLERY

Listing courtesy of UNITED REAL ESTATE GALLERY.

Listing courtesy of TERESA MAZZARELLA from UNITED REAL ESTATE GALLERY.

$1,595,000
4 Beds 4 Baths A4695145 MLS
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.

75 Osprey Point Drive, Osprey/Nokomis

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411

$1,289,000
3 Beds 4 Baths A4691664 MLS
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless luxury residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac in Bishops Court, an intimate gated enclave within The Oaks Preserve in Osprey, Florida. Framed by lush conservation views and a canopy of mature oaks, the property blends classic architectural character with thoughtfully curated updates in one of the Sarasota area’s most prestigious private country club communities. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. 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 areas, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen. Custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting define the space. A Sonos sound system extends throughout the residence. The primary suite is a private retreat featuring vaulted ceilings, a bay-window sitting area, outdoor access, and a fully renovated, spa-inspired bathroom 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. The additional bathrooms have also been extensively renovated with elevated finishes and designer fixtures. In the laundry room, custom storage, shiplap detailing, and functional built-ins boast a refined aesthetic. Upstairs, a spacious bonus room, freshly painted in 2026, features a fireplace and opens directly to a newly renovated second-story deck overlooking the treetops. Complete with a full bathroom, this highly versatile level can serve as private guest accommodations, a recreation or media room, home office, art studio, creative retreat, or secluded lounge. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and peaceful 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; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club. The Oaks offers an exceptional club-centered lifestyle just south of Sarasota, with two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active year-round social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has earned recognition as a Platinum Club of America, a Distinguished Emerald Residential Country Club, and an Audubon International Certified property, reinforcing its standing as a premier private residential club. The Oaks delivers an exceptional lifestyle in Osprey between Sarasota and Venice. Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota, and historic Venice are all within easy reach.

156 Bishops Court Road, Osprey/Nokomis

Listing courtesy of DOUGLAS ELLIMAN. 941-867-6199

$1,950,000
5 Beds 6 Baths A4691789 MLS
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.

97 Sugar Mill Drive, Osprey/Nokomis

Listing courtesy of PALM PARADISE REALTY GROUP. 239-955-7256

$235,000
1 Beds 1 Baths A4689838 MLS Windsor Lodge BLDG.
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey/Nokomis

Listing courtesy of 342 REAL ESTATE. 941-685-0509

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