Three Oaks Real Estate

Three Oaks Real Estate

Welcome to Three Oaks, a serene and inviting subdivision nestled in the heart of Central Sarasota, Florida. Known for its lush landscapes and family-friendly atmosphere, Three Oaks offers a perfect blend of suburban charm and modern conveniences.

As you explore this delightful community, you’ll discover a variety of beautifully designed homes that cater to diverse lifestyles, from cozy single-family residences to spacious properties ideal for growing families. The architecture reflects a harmonious blend of contemporary aesthetics and classic Florida style, ensuring that every home feels like a personal sanctuary.

Three Oaks is not just about stunning homes; it’s also about a vibrant community. Residents enjoy access to a range of amenities, including well-maintained parks, walking trails, and recreational facilities. The nearby playgrounds and picnic areas provide the perfect backdrop for family gatherings and outdoor activities, fostering a sense of camaraderie among neighbors.

Location is key, and Three Oaks excels in this regard. Situated in Central Sarasota, residents are just a short drive away from the beautiful Gulf Coast beaches, renowned shopping districts, and top-rated schools. The area boasts a variety of dining options, from casual eateries to fine dining, ensuring there’s something for every palate.

Whether you’re seeking a peaceful retreat or an active lifestyle, Three Oaks is the ideal place to call home. Experience the charm of this exceptional subdivision, where community spirit and Florida living come together in perfect harmony. Come and discover why Three Oaks is the perfect place for your next chapter!

Newest Listings in Three Oaks

4 Beds ⋅ 4 Baths ⋅ Three Oaks SubDv. ⋅ 34233 Zip Code

One or more photo(s) has been virtually staged. Welcome to Three Oaks—where refined living meets natural serenity. This exceptional 4-bedroom + den, 3.5-bath home with a 3-car garage is perfectly positioned along a 125-acre private preserve and lake, offering rare privacy and breathtaking, unobstructed views—truly a bird-watcher’s paradise. Step through elegant double glass entry doors into a home defined by timeless architectural details, including graceful arches, tray ceilings, crown molding, and custom niches—features rarely found at this price point. Soaring ceilings, rich bamboo and plank wood flooring, and expansive windows fill the home with warmth and natural light. The thoughtfully designed layout offers a first-floor primary suite and den for convenient single-level living. At the heart of the home, the gourmet kitchen features granite countertops, custom wood cabinetry, and ample space for both casual dining and entertaining. Step outside to your private retreat. The screened lanai boasts a sparkling pool and spa, and peaceful preserve and lake views—perfect for relaxing evenings or hosting guests in complete privacy. Recent updates provide peace of mind, including a new roof (April 2026), fresh interior and exterior paint, new second-floor flooring, a new pool pump (2026), lanai hurricane shutters, and a brand-new portable grill. Ideally located near top-rated schools, premier shopping and dining, and the world-renowned beaches of Sarasota, this home offers the perfect balance of luxury, comfort, and location. Schedule your private showing today and experience the best of Three Oaks living.

5684 Eastwind Drive, Sarasota

4 Beds ⋅ 3 Baths ⋅ Three Oaks SubDv. ⋅ 34233 Zip Code

This is it. All the top boxes are checked: 4 Bedrooms, Plus a Den, 3 Full Bathrooms, Beautiful Pool, 3 Car Garage. Not only that, the home is in beautiful condition, and it backs up to ….Wait? ….Nothing?....No house behind me?.... That’s right, I can look at greenery instead of another house! I think I want to see this one pretty soon. Three Oaks is an upscale community west of I-75 between exits 205 (Clark Rd.) and 207 (Bee Ridge Rd.). The home is about 5 minutes to shopping including Publix and many other businesses, Doctor’s Hospital, restaurants, strip malls, and parks. This is a great home for families that need space. The primary bedroom is split from the other 3 bedrooms, and there are 2 bathrooms near those 3 BRs. The kitchen/great room opens to the pool area. The kitchen has a walk in pantry for that active family. The great room has built in shelving and an electric fireplace. The home has both a formal dining room and an eating area with an aquarium window to the pool. There are many closets for storage, plus a unique electric storage lift for the garage and attic. The home is about 15 minutes to downtown Sarasota, the Intracoastal Waterway, the barrier islands, and to the UTC Mall with the brand new Mote Science Education Aquarium. This is a great home and a great opportunity for an active, growing family. Come and see it soon.

5608 Eastwind Drive, Sarasota

3 Beds ⋅ 2 Baths ⋅ Three Oaks SubDv. ⋅ 34233 Zip Code

Short Sale. SHORT SALE: Listing price may not be sufficient to pay the total of all liens and costs of sale, and sale of property at full listing price may require approval of seller's lender(s) All room dimension are estimates. Property sold as is with right to inspect. The AC system does not work. Proof of Funds must accompany all offers. Seller has no information regarding HOMEOWNER association and documents if applicable. All information pertaining to these docs, financials, & costs associated with obtaining them shall be the responsibility of Buyer. Inspections must be done within 10 days of effective date not short sale approval date.

Sarasota

3 Beds ⋅ 2 Baths ⋅ Three Oaks SubDv. ⋅ 34233 Zip Code

Welcome to this well-loved 3-bedroom, 2-bath home located in a quiet, beautifully maintained community that offers a blend of comfort, care, and easy Florida living. Every space has been thoughtfully maintained, creating a truly move-in-ready home. Inside, you'll find a bright and inviting layout with comfortable living areas, a functional kitchen ideal for everyday use, and bedrooms that each provide a cozy retreat, and a generous office space. Step outside to a peaceful backyard—perfect for morning coffee, evening sunsets, or simply enjoying the Florida outdoors. Big-ticket updates are already done, including a NEW roof 25', NEW pool heater, and a NEW HVAC 25', offering added peace of mind. Conveniently located near shopping and dining, just 8 miles from the world-famous Siesta Key Beach, and with easy access to I-75. This charming property is ready for its next chapter—schedule your showing today.

5723 Eastwind Drive, Sarasota

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Mikel Chaffee

Mike understands that buying and selling your home is one of, if not the biggest, financial decisions you will make. He knows first-hand the unparalleled value of hard work, dedication and exemplary service. With 13 homes sold in 2025 alone, putting him in the top percentile across the nation. Mike often works with his mom, Debi Chaffee Rose, as a mother-son team. Clients love their collaborative work and combined focus. Mike has a degree in management and operations, and for a number of years held his PGA Golf Certification. This experience gives him an intimate knowledge of many diverse golf and country club communities that make up the Florida lifestyle. 13 Years licensed as a Realtor, he is ready to put his experience to work, for you in any facet. Mike spends his free time with his beautiful wife Meghan, and their 4 Kids here in the town he was raised in, Bradenton Florida. They enjoy going and exploring the sunshine state together as a family.

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