Oakland Homes with Two Story Property Description

Oakland Homes with Two Story Property Description

Welcome to Oakland, Florida, a charming town nestled in the heart of Orange County, where Southern hospitality meets modern living. Known for its picturesque landscapes and friendly community, Oakland boasts a rich history and a vibrant culture that draws residents and visitors alike. With its close proximity to the bustling city of Orlando, Oakland offers the perfect blend of serene suburban life and easy access to urban amenities.

One of the standout features of Oakland is its array of beautiful homes, particularly the stunning two-story properties that grace the area. These homes are designed for both comfort and style, often featuring spacious layouts that are perfect for families and entertaining. Imagine stepping into a grand foyer that leads to open-concept living spaces filled with natural light, gourmet kitchens equipped with modern appliances, and cozy family rooms that invite relaxation.

The second story typically offers additional bedrooms and bathrooms, providing ample space for everyone. Many of these homes also come equipped with charming balconies or patios, perfect for enjoying your morning coffee or watching the sunset over the lush greenery that Oakland is known for.

In addition to the beautiful homes, residents of Oakland enjoy a plethora of parks, recreational activities, and community events that foster a close-knit atmosphere. Whether you're strolling through the quaint downtown area or exploring the scenic trails, Oakland is a place where you can truly feel at home. Discover your dream two-story home in this delightful town and experience the best of Florida living!

Newest Oakland Homes with Two Story Property Description

$2,595,000
5 Beds ⋅ 8 Baths ⋅ Grove/Oakland SubDv. ⋅ 34760 Zip Code
Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.

1134 Prado Lane, Oakland
$799,999
5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

16 Oakland Pointe Circle, Oakland
$1,125,000
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland
$629,999
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland
$1,975,000
5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1106 Sarah Mathews Drive, Oakland
$1,250,000
6 Beds ⋅ 8 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code
PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland
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