Oakwood Homes under $500,000

Oakwood Homes under $500,000

Welcome to Oakwood, a charming subdivision nestled in the heart of Florida, where the sun shines bright and community spirit thrives. Oakwood is more than just a place to live; it’s a lifestyle that invites you to embrace the beauty of nature, convenience, and comfort. With its picturesque tree-lined streets and welcoming atmosphere, this neighborhood is perfect for families, young professionals, and retirees alike.

One of the standout features of Oakwood is the incredible range of homes available, especially for those seeking options under $500,000. Here, you can find beautiful single-family homes that boast modern designs, spacious layouts, and inviting outdoor spaces. Whether you’re looking for a cozy starter home or a larger residence to accommodate a growing family, Oakwood offers a variety of choices that cater to different tastes and budgets.

Living in Oakwood means having access to a wealth of amenities. Residents enjoy nearby parks, walking trails, and recreational facilities that encourage an active lifestyle. The community is also conveniently located near shopping centers, dining options, and top-rated schools, making it an ideal choice for families.

Moreover, Oakwood's friendly community fosters a sense of belonging, where neighbors become friends and gatherings are common. With its affordable housing options and vibrant community spirit, Oakwood is a hidden gem in Florida that awaits your discovery. Come explore the possibilities and find your dream home in this delightful subdivision today!

Newest Oakwood Homes under $500,000

2711 51st Avenue W Unit 2711, West Bradenton
$129,000
2 Beds ⋅ 2 Baths ⋅ Oakwood SubDv.
Your Florida lifestyle awaits! Discover this exceptional opportunity to enjoy comfort, convenience, and carefree living in West Bradenton's Oakwood Villas community! Whether you are searching for a year-round residence, or a seasonal Florida retreat, this charming 2-bedroom, 2-full-bath villa offers the perfect place to call home. Combining a convenient location with the ease of low-maintenance living, this villa presents an excellent opportunity to embrace the Florida lifestyle at a price that is equally appealing! The comfortable open-floor plan provides an inviting and spacious setting for both everyday living and entertaining family and friends. This desirable end-unit location adds to the property's appeal while the additional lanai and adjoining outdoor patio provide extra space to enjoy Florida's beautiful weather. A full home Moen leak detection system is among the home's notable features, providing an added level of protection and peace of mind whether you are home enjoying the Florida lifestyle or away for an extended period. This thoughtful feature is especially appealing to seasonal residents who appreciate the added reassurance of water leak monitoring while their Florida home is unoccupied. Additional conveniences include assigned covered parking and a private exterior storage room, perfect for keeping beach chairs, bicycles, tools, and seasonal belongings neatly tucked away. Oakwood Villas is a well-established community offering the benefits of low-maintenance Florida living, with beautifully maintained grounds, a community swimming pool, community clubhouse, recreational amenities, and the added convenience of an on-site coin-operated laundry facility. Conveniently situated in the heart of West Bradenton, you will appreciate easy access to shopping, restaurants, medical facilities, golf courses, and everyday conveniences. The beautiful Gulf beaches of Anna Maria Island are just a short drive away, offering spectacular sunsets, waterfront dining, boating, and coastal recreation. Simply minutes from vibrant Downtown Bradenton, home to the Riverwalk, farmers markets, live music, and excellent dining presenting an excellent opportunity to experience the very best of Florida's Gulf Coast lifestyle. Schedule your private showing today!

2711 51st Avenue W Unit 2711, West Bradenton
2905 51st Avenue W, West Bradenton
$127,000
2 Beds ⋅ 1 Baths ⋅ Oakwood SubDv.
Welcome to Oakwood Villas! This move-in-ready 2-bedroom, 1-bath villa offers comfort, convenience, and peaceful pond views. Featuring a NEW ROOF, NEW HVAC, updated IMPACT windows, carpet throughout, and an open living and dining area, this home offers valuable upgrades and functional living space. Enjoy the enclosed Florida room or step outside to a brick-paver patio overlooking the water, perfect for relaxing or entertaining. Covered parking and an exterior laundry closet add everyday convenience. Oakwood Villas offers a relaxed Florida lifestyle with community amenities including a swimming pool, clubhouse, BBQ area, and shuffleboard courts, all surrounded by mature landscaping. Conveniently located in West Bradenton, you're just minutes from shopping, dining, and GT Bray Park, with the beautiful beaches of Anna Maria Island only 8 miles away. Whether you're looking for a full-time residence or seasonal retreat, this villa has plenty to offer. Schedule your showing today!

2905 51st Avenue W, West Bradenton
20281 Calice Court NW Unit 2201, Estero
$415,000
3 Beds ⋅ 2 Baths ⋅ Oakwood SubDv.
Golf Course Views & Resort Style Living! Located in the highly desirable Grandezza Country Club community, this well-maintained 1st floor condo has easterly morning sun exposure and peaceful golf course views, this tastefully furnished home offers a bright, inviting setting from the moment you step inside. The 3 bedroom, 2 bathroom floor plan features an open concept design that is light, fresh and newly painted. The fully updated kitchen and eat-in area create an ideal space for entertaining, seamlessly connecting to the large main living area. The private primary suite provides a quiet retreat, while the separate guest quarters include an updated bathroom for added comfort and privacy. The 2 car garage features brand new epoxy flooring, and the paved driveway offers additional parking. Enjoy the screened lanai with its relaxing views of the golf course and expansive green space- perfect for morning coffee or evening unwinding. This home is just a short walk to the private community pool and clubhouse as well as Grandezza's main clubhouse, offering a cabana, Olympic-size pool, tennis courts, bocce, basketball, fitness/wellness center, plus a full calendar of social activities and amenities. Grandezza's is home to the Darwin Sharpe III 18-hole Championship golf course, where full golf memberships are currently available. Located minutes from I-75, SWFL International Airport, shopping, dining and the beautiful Southwest Florida beaches, this home is an exceptional opportunity in the booming Estero FL market.

20281 Calice Court NW Unit 2201, Estero
20211 Calice Court Unit 2802, Estero
$425,000
2 Beds ⋅ 2 Baths ⋅ Oakwood SubDv.
Mornings here start on the lanai, with coffee in hand and the sun rising over the lake and fairway. Eastern exposure brings morning light into the great room and afternoon shade to your outdoor retreat. Set in Oakwood at Grandezza, this first-floor coach home offers golf course and water views, an attached two-car garage, and just four residences in the building. No stairs, no elevator, no shared hallway. Two bedrooms plus a den provide room to work, unwind, and welcome guests. The split floor plan places the guest bedroom in its own wing, while the primary suite overlooks the rear of the home and features dual sinks and a walk-in shower. The den offers flexible space for a home office or occasional guests. Thoughtful updates include new quartz countertops in the kitchen and both bathrooms, new carpeting in both bedrooms, and new ceiling fans throughout. Tile flooring runs through the main living areas, complemented by kitchen appliances and air conditioning updated in 2022, a water heater replaced in 2025, and electric storm shutters on the lanai. Grandezza’s Darwin Sharp III-designed championship course provides a beautiful backdrop, with optional golf membership. Social membership is required, and the community’s amenities include a 53,000-square-foot clubhouse, indoor and outdoor dining, a resort-style pool, Har-Tru tennis courts, bocce, and fitness facilities, with access based on membership level. Shopping and dining at Miromar, Coconut Point, University Village, Gulf Coast Town Center, RSW Airport, Gulf beaches, and Naples offer plenty of reasons to explore. But your favorite place may be right at home on the lanai, overlooking the water.

20211 Calice Court Unit 2802, Estero
1104 Connie Avenue N, Lehigh Acres
$284,900
3 Beds ⋅ 2 Baths ⋅ Oakwood SubDv.
Welcome to Oakwood in Lehigh Acres. This 3-bedroom, 2-bathroom home offers comfortable living in a convenient location with no HOA. The property features a functional layout, a patio, and a spacious backyard with plenty of room for outdoor activities and the potential to add a pool. A nearby park provides additional recreational space. Enjoy easy access to I-75, shopping, dining, schools, and other local amenities. Whether you are looking for a primary residence or an investment opportunity, this property offers a great combination of location, space, and flexibility. Schedule your showing today and submit your offer.

1104 Connie Avenue N, Lehigh Acres
502 Elaine Avenue N, Lehigh Acres
$275,000
3 Beds ⋅ 2 Baths ⋅ Oakwood SubDv.
ATTENTION! Not just another home for sale in Lehigh Acres! This 3-bedroom, 2-bath home sits on a spacious 0.40-acre lot with plenty of room for a pool and outdoor recreation. Located in one of the few areas in Lehigh offering both central water and city sewer, a valuable feature in Lehigh Acres. The home has a new roof and water heater (2023) and A/C (2021). Wood flooring in the bedrooms and tile throughout the main living areas. The spacious garage includes multiple cabinets and a refrigerator. Low HOA fee with community amenities including BBQ/picnic area, bike & jogging path, community park, and volleyball. SHORT SALE – NOT YET APPROVED. All offers are subject to seller’s lender approval. Agents, please read the MLS remarks and make sure your clients understand the short-sale process.

502 Elaine Avenue N, Lehigh Acres
233 S Rhodes Street, Mount Dora
$249,000
2 Beds ⋅ 2 Baths ⋅ Oakwood SubDv.
Virtually Staged. PRICE IMPROVEMENT — NOW OFFERED BELOW $250,000! A ONE-YEAR PREPAID HOME WARRANTY IS INCLUDED WITH THE HOME. Discover a fully remodeled 2-bedroom, 2-bath Mount Dora bungalow approximately half a mile from the lighthouse, marina, waterfront parks, and historic downtown. With no HOA, a fenced backyard, and an inviting covered outdoor area, the property offers flexibility for a primary residence, seasonal retreat, or an investor evaluating short-term rental potential. Inside, the renovation brings together the home’s bungalow character and modern finishes: a refreshed kitchen with quartz countertops, updated bathrooms, luxury vinyl flooring, recessed lighting, and fresh interior and exterior paint. The bright layout makes the home easy to enjoy from day one. Its location near Mount Dora’s lakefront makes this a compelling property to tour and evaluate in person. Home warranty coverage is subject to the provider’s terms, limitations, and exclusions. Short-term rental use is subject to applicable licensing and regulations. Schedule your showing today.

233 S Rhodes Street, Mount Dora
5064 Live Oak Cir Unit 5064, West Bradenton
$85,000
1 Beds ⋅ 1 Baths ⋅ Oakwood SubDv.
Enjoy affordable Florida living in this turnkey furnished 1-bedroom, 1-bath villa-style condominium located in the desirable Oakwood Villas community! This light and bright one-story unit offers a very comfortable living space with a spacious living/dining room combination, walk-in closet, and the convenience of washer and dryer hookups located in the private carport storage closet. Important updates include a new shingle roof, new electric panel, A/C replaced in 2015, and a new garbage disposal (2026). Whether you're looking for a full-time residence or a seasonal getaway, this home is ready for your personal touches. Pets not allowed.... and no investors please, rentals not allowed at this time. The monthly condo fee includes cable TV, internet, exterior maintenance, community pool, clubhouse, recreational facilities, private roads, professional management, and escrow reserves, making for easy, low-maintenance living. Conveniently located close to shopping, restaurants, public transportation, medical facilities, golf courses, and just a short drive to the beautiful Gulf beaches. Not in a flood zone! Don't miss this opportunity to own an affordable Florida home at an exceptional value!

5064 Live Oak Cir Unit 5064, West Bradenton
5061 Live Oak Circle, West Bradenton
$167,000
2 Beds ⋅ 1 Baths ⋅ Oakwood SubDv.
Virtually Staged. Great opportunity to own a maintenance-free, end unit villa in West Bradenton with no age restrictions. This move in ready home features a bright and functional layout with a glassed in lanai that provides additional living space for year round enjoyment. The property includes an interior washer and dryer, an attached carport with parking at your door, and over $30,000 in recent upgrades. Major components are less than 3 years old including impact windows, new HVAC system, new roof, and all new appliances, offering comfort and peace of mind. Located just steps from the community clubhouse with a heated pool, shuffleboard, billiards, library, and planned social activities, plus a scenic pond for fishing. The well maintained community features beautifully landscaped grounds and a quiet residential feel. Situated in Flood Zone X and just minutes to Anna Maria Island and the Gulf beaches, with convenient access to shopping, dining, and medical facilities. A fantastic opportunity and excellent value in today’s market.

5061 Live Oak Circle, West Bradenton
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