The Oaks Homes under $500,000

The Oaks Homes under $500,000

Welcome to The Oaks, a picturesque subdivision nestled in the heart of sunny Florida, where the charm of suburban living meets the vibrancy of nature. This delightful community is perfect for families, retirees, and anyone looking to embrace a relaxed lifestyle without sacrificing modern conveniences. With its tree-lined streets, beautifully landscaped parks, and friendly neighbors, The Oaks offers a welcoming atmosphere that feels like home from the moment you arrive.

One of the standout features of The Oaks is its diverse selection of homes, with many options available for under $500,000. Whether you’re a first-time homebuyer or seeking a cozy retreat, you’ll find a variety of well-designed residences that cater to your needs. From charming single-family homes to spacious townhouses, each property is thoughtfully crafted to provide comfort and style. Many homes boast modern amenities, open floor plans, and beautiful outdoor spaces, perfect for family gatherings or quiet evenings under the stars.

Living in The Oaks means enjoying easy access to local attractions, shopping centers, and top-rated schools. Spend your weekends exploring nearby parks, indulging in delicious dining options, or taking in the vibrant arts scene that Florida is known for. With its ideal location and affordable housing options, The Oaks is not just a place to live; it’s a community where you can thrive.

Discover the charm of The Oaks today, and take the first step toward making this wonderful community your new home!

Newest The Oaks Homes under $500,000

2912 Boating Boulevard, Kissimmee
$470,000
4 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34746 Zip Code
Virtually Staged. Welcome to this beautifully renovated home offering the perfect blend of luxury, comfort, and resort-style living! This move-in ready home features a brand-new roof installed in 2025, stylish tile flooring throughout, a fully updated interior, new appliances, and a built-in wine cooler that’s perfect for entertaining. Step outside to your private backyard oasis featuring a stunning screened-in pool completed in 2021, a fully equipped outdoor kitchen, and built-in speakers, creating the ideal space for relaxing or hosting family and friends. As a resident, you’ll also enjoy access to the community’s boating dock, tennis courts, and playground, providing endless opportunities for recreation and outdoor enjoyment. With modern upgrades, exceptional amenities, and a fantastic lifestyle, this home is one you won’t want to miss!

2912 Boating Boulevard, Kissimmee
6519 W Newberry Road Unit 108, Gainesville
$114,900
2 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 32607 Zip Code
Fully updated 2 bed 2 bath in The Oaks. Great location near the University of Florida, Santa Fe College, and walking distance to North Florida Hospital. This second floor condo has every update imaginable. As you enter you are greeted with a large living room flowing to a screened patio with new tile flooring throughout. Both bedrooms are spacious, with plenty of closet space and room for a desk or additional seating. Bathrooms feature tile flooring and new vanities. Upgrades include new kitchen cabinets, wood countertops, flooring, freshly painted walls, trim, vanities, HVAC, and appliances. Community amenities include a pool, fitness center, and clubhouse. Perfect for primary residence or renting out while your son or daughter goes to school at UF or Santa Fe. Airbnb and short term rentals are allowed. Direct bus routes on Newberry Rd.

6519 W Newberry Road Unit 108, Gainesville
6519 W Newberry Road Unit 204, Gainesville
$89,000
2 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 32605 Zip Code
Attention Investors! Prime Location on Newberry Road Excellent opportunity in a highly desirable area—directly across from HCA Florida North Florida Hospital with easy access to I-75. Just a short walk to the Oaks Mall and minutes from restaurants, shopping, Santa Fe College, the University of Florida, and public transportation—making this an ideal rental property. Located in Building 200 on the first floor, this 2-bedroom, 1-bath unit features an open-concept floor plan, new refrigerator and stove, and in-unit laundry for added convenience and tenant appeal. The community offers great amenities, including a clubhouse, pool, fitness center, sidewalks, and ample open parking. Move-in ready with strong rental potential—an excellent addition to any portfolio!

6519 W Newberry Road Unit 204, Gainesville
51 Mac Ewen Drive Unit 14, Osprey
$285,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey
51 Macewen Drive Unit 5, Osprey
$235,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
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
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