Oakhurst Homes under $500,000

Oakhurst Homes under $500,000

Welcome to Oakhurst, a hidden gem nestled in the heart of Florida, where charm meets modern living. This delightful subdivision offers an inviting atmosphere, characterized by its lush landscapes and friendly community spirit. Oakhurst is perfect for families, retirees, and anyone seeking a tranquil lifestyle without sacrificing convenience. With its proximity to stunning beaches, vibrant shopping districts, and top-rated schools, residents enjoy the best of both worlds.

One of the standout features of Oakhurst is its diverse range of homes available for under $500,000. Whether you’re a first-time homebuyer or looking to downsize, you’ll find a variety of options that cater to your needs and budget. From cozy single-family homes to well-appointed townhouses, each property boasts unique architectural styles and modern amenities. Many homes are surrounded by beautifully landscaped yards, perfect for outdoor gatherings or simply soaking in the Florida sunshine.

Living in Oakhurst means embracing a lifestyle filled with outdoor activities, thanks to nearby parks and recreational facilities. Imagine weekend strolls along tree-lined streets or enjoying a family picnic at one of the local parks. The community also hosts various events throughout the year, fostering a sense of belonging among neighbors.

If you're looking for a place where you can create lasting memories and enjoy a vibrant community, Oakhurst is the perfect choice. With homes under $500,000, now is the ideal time to explore what this charming subdivision has to offer. Your dream home awaits!

Newest Oakhurst Homes under $500,000

10038 Oakhurst Way, Fort Myers
$475,000
3 Beds ⋅ 2 Baths ⋅ Oakhurst SubDv.
Golf membership is included, offering the opportunity to enjoy the full Colonial Country Club lifestyle from day one. This beautifully maintained 3-bedroom, 2-bath furnished pool home enjoys an exceptional setting overlooking the 7th hole, with expansive golf course, lake, and tropical views from the screened lanai. Inside an updated kitchen with granite countertops, beautiful white cabinetry, and stainless steel appliances. Tile flooring complements the kitchen and bathrooms. Step outside to your private screened lanai, where the resurfaced patio pool and spa create the perfect setting for relaxing or entertaining while taking in the peaceful golf course and lake views. Colonial Country Club offers an impressive collection of amenities, including an 18-hole championship golf course, clubhouse, resort-style pool, fitness facilities, tennis, pickleball, bocce, and two on-site restaurants. Conveniently located near I-75, RSW International Airport, Gulf Coast Town Center, shopping, dining, and JetBlue Park, with easy access to everything Fort Myers and Southwest Florida have to offer.

10038 Oakhurst Way, Fort Myers
4206 Oakhurst Circle E Unit 3075, Central Sarasota
$269,900
2 Beds ⋅ 2 Baths ⋅ Oakhurst SubDv.
Virtually Staged. Welcome to easy Florida living in the beautiful, established 55+ community of Oakhurst! This freshly painted 2-bedroom, 2-bath villa offers a low-maintenance lifestyle in a convenient Sarasota location. New roof in 2025, new AC in 2026, newer appliances. Enjoy the benefits of community-covered exterior maintenance, including the roof, landscaping and building exterior, along with cable TV, giving you more time to enjoy everything Sarasota has to see. One of the highlights of this villa is the peaceful setting behind the home. Step onto the lanai with your morning coffee and enjoy views of a spacious green area framed by beautiful mature oak trees—a welcome sense of openness and privacy without looking directly into a neighbor’s backyard. Inside, the home is freshly painted, move-in ready and offers a comfortable layout perfect for full-time living or a seasonal Florida retreat. Oakhurst residents enjoy access to a community clubhouse, gathering spaces, shuffleboard courts and a refreshing community pool. Located just off Bee Ridge Road, the community offers convenient access to shopping, dining, downtown Sarasota and the area’s renowned arts and cultural attractions. And when it’s time for the beach, the world-famous white quartz sands of Siesta Key are just a drive away. If you’re looking for a low-maintenance Sarasota home surrounded by mature landscaping in an established 55+ community, 4206 Oakhurst Circle deserves a closer look. Schedule your private showing today!

4206 Oakhurst Circle E Unit 3075, Central Sarasota
4021 Oakhurst Drive Unit 3121, Central Sarasota
$291,000
2 Beds ⋅ 2 Baths ⋅ Oakhurst SubDv.
Tucked into a quiet, maintained 55+ community, this 2-bedroom, 2-bath villa offers the kind of low-maintenance lifestyle that lets you spend less time on upkeep and more time enjoying everything Sarasota has to offer. The home sits on a peaceful interior lot backed by mature trees and wide green space, with reduced through-traffic giving it an especially calm, private feel. A brand-new roof (December 2025) and updated interior finishes mean the big-ticket items are already handled, while the enclosed, all-season lanai with sliding glass windows gives you flexible indoor-outdoor living year-round. Inside, updated flooring and modernized baths carry a fresh, comfortable feel throughout the single-story floor plan, and the two-car garage adds convenient parking and storage. Life here comes with built-in ease: the HOA covers exterior maintenance and landscaping, and the community's pool and clubhouse are just steps from your door. Location adds even more to love — Publix and Detwiler's Farm Market are both about a mile away for everyday errands, Urfer Family Park (1.6 miles) offers trails and green space for outdoor time, and downtown Sarasota's restaurants, arts venues, and waterfront parks are a quick 5.6-mile drive. When it's time for the Gulf, Siesta Key Beach is just 6.3 miles from your front door. This is Sarasota living made simple — a comfortable, move-in-ready home in a setting that lets you relax and enjoy the location around you.

4021 Oakhurst Drive Unit 3121, Central Sarasota
3925 Oakhurst Boulevard, Central Sarasota
$299,999
2 Beds ⋅ 2 Baths ⋅ Oakhurst SubDv.
This stunning 2-bedroom,2-bath Villa. Has the feel of a single family home 1374 sq ft, Open concept floor plan with Cathedral ceiling’s . Included is a 2 car garage and a generous size lanai overlooking the private natural space for you to enjoy. Luxury vinyl plank flooring, lighting, baseboards, paint, ceiling re textured and window coverings throughout the entire home. Bathrooms have been beautifully updated. Kitchen offers soft closing cabinetry. Upgraded appliance package and gorgeous quartz countertops. The HVAC system is 2022 and the hot water heater is 2024. New Hurricane rated garage door. To top it off. A brand new roof in 2026. Oakhurst is a pet friendly 55+ community . Maintenance fees include :Cable TV, INTERNET, the roof, pest control, exterior maintenance and landscaping are ALL INCLUDED in the monthly condo fee ($662).The community offers a seperate gated entrance to less traveled roads. For shopping and travel convienence. This home is a must see to appreciate all it has to offer.

3925 Oakhurst Boulevard, Central Sarasota
10055 Oakhurst Way, Fort Myers
$428,900
3 Beds ⋅ 2 Baths ⋅ Oakhurst SubDv.
Enjoy sweeping golf course views and bundled golf living at its finest from this beautifully maintained Brentwood model in Colonial Country Club! Located at 10055 Oakhurst Way, this 3BR/2BA single-family home offers 1,509 sq. ft. of living space with a desirable split floor plan and a FULL GOLF MEMBERSHIP included. Best of all — NO FLOOD INSURANCE REQUIRED. The backyard overlooks Hole #9 of the Gordon Lewis championship course, a dogleg-left par 4 known for its challenging layout with hazards lining both sides of the fairway and a preserve area to the left. The pro tee box is prominently visible from the property, creating a scenic and dynamic view across the fairway and toward the sand traps. Enjoy golf course views from both the front and rear of the home. Inside, the home features new Noble 9x60 LVP plank flooring throughout the main living areas, a formal dining area, breakfast bar, pantry, walk-in closets, and updated lighting fixtures throughout. The kitchen is equipped with stainless steel appliances, and the home is truly move-in ready. Recent upgrades include a brand new 2024 tile roof, newer exterior paint, and electric/accordion hurricane shutters for added protection and peace of mind. Step outside to an oversized 20’ x 33’ screened paver lanai featuring picture window screens, a private jacuzzi, and an outdoor shower, all perfectly positioned to capture tranquil golf course views—ideal for entertaining or relaxing. Additional highlights include a spacious 2-car garage and meticulously maintained landscaping. Colonial Country Club is a premier gated, guard-secured community offering exceptional amenities including a Gordon Lewis championship golf course, clubhouse with dining, fitness center, tennis, pickleball, bocce, resort-style pool, spa, walking trails, and more. Conveniently located near I-75, RSW International Airport, shopping, dining, and spring training stadiums. Resort-style golf living in the heart of Fort Myers—don’t miss this opportunity!

10055 Oakhurst Way, Fort Myers
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