Homes for Sale in Oakland
Homes in Oakland offer buyers an amazing lifestyle, active trailside and easy access to the shopping and dining of Downtown Winter Garden. The Oakland Realtors of the Erica Diaz Team offer home buyers a quick and easy transaction in most cases closing faster and less money than your average agent. We’ll help you find your next historic Oakland home with shade trees and mature neighborhoods. Take some time to browse the homes below or reach out to the Erica Diaz Team and let us find the dream home for you.
$1,990,000
1202 JOHNS COVE LANE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
71Picture(s)
5,117Sqft
SPECTACULAR LAKE FRONT OPPORTUNITY, in desirable John's Cove, a small, sought after gated community ideally located for Downtown Clermont, Old Winter Garden, the Airport and the Attractions. Schedule your personal tour of this captivating and desirable luxury lakefront home.
$589,999
1590 STONE ARROW COURT
OAKLAND, Florida
4Bedroom(s)
2Bathroom(s)
53Picture(s)
3,451Sqft
his beautiful 4 bedroom/2.5 bathroom,not back neighbor you can build the pool you want , formal dining/living room, family room, and entertainment area, also has extra room that would make a great bonus room, den/office, or 5th bedroom. This home is in the sought-after community of Oakland Trails.
$2,595,000
402 POLLARD STREET
OAKLAND, Florida
5Bedroom(s)
5Bathroom(s)
8Picture(s)
4,813Sqft
Pre-Construction. To be built. Introducing Briley Farm, an exquisite 111-acre sanctuary nestled in the historic charm of Oakland, Florida. Designed by renowned Element Home Builders, this brand-new architectural masterpiece seamlessly blends French Farmhouse and Transitional styles, epitomizing modern luxury with a touch of heritage. A welcoming front porch creates small town charm.
$1,695,000
511 BRILEY AVENUE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
10Picture(s)
3,665Sqft
Pre-Construction. To be built. Pre-construction Welcome to your dream retreat in Central Florida's most coveted new community, Briley Farm consists of 111 acres of lush landscape in Oakland, Florida. Element Home Builders' newest home design exudes luxury and comfort. The gourmet kitchen connects to the family gathering space.
$2,499,000
515 NIXON STREET
OAKLAND, Florida
5Bedroom(s)
5Bathroom(s)
16Picture(s)
4,584Sqft
Pre-Construction. To be built. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida.
$1,749,000
110 RAILWAY AVENUE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
14Picture(s)
3,876Sqft
Pre-Construction. To be built. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. This custom-built masterpiece by Pioneer Builders blends timeless elegance with modern convenience, offering a quintessential French farmhouse style that exudes warmth and charm.
$1,430,000
1216 HULL ISLAND DRIVE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
52Picture(s)
4,224Sqft
Welcome to your unparalleled lakefront sanctuary! This stunning home exudes luxury at every turn, with over $200k in upgrades meticulously added atop the already exquisite builder standards.
$415,000
2115 GOPHER TORTOISE TERRACE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
46Picture(s)
1,620Sqft
Beautifully upgraded spacious 3 bedroom 2 1/2 bath townhome with private courtyard and 2 car garage. This home offers open floor plan downstairs and had LVP flooring, Ceiling fans, Upgraded lighting, Whirlpool Gold Stainless Steel Refrigerator, Stove, Microwave, Dishwasher, Granite Counters, Gray Cabinets and drawers, double sink, Island and outlet with night lighting.
$459,900
636 STRIHAL LOOP
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
35Picture(s)
2,054Sqft
Welcome to the epitome of refined living where luxury meets practicality. This immaculate residence, nestled within a gated community, not only boasts a brand-new roof for worry-free living but also showcases exquisite upgrades throughout. Marvel at the sleek granite countertops and stylish backsplash in the chef's kitchen.
$1,995,000
100 MILLHOLLAND STREET
OAKLAND, Florida
5Bedroom(s)
5Bathroom(s)
59Picture(s)
3,747Sqft
Introducing 100 Millholland St, an immaculate modern contemporary Custom-Built Home in the heart of Oakland! Situated in the coveted community of Southern Oaks, this home sits on just under a Half-Acre Elevated Lot boasting unparalleled Sunset Lakefront Views.
$480,000
339 LARGOVISTA DRIVE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
22Picture(s)
1,956Sqft
Discover serenity in this charming 3-bedroom, 2-bathroom home nestled within a gated community boasting picturesque pond views. Enjoy the tranquility of nature from your own backyard oasis, where the shimmering pond sets a peaceful backdrop for relaxation and outdoor gatherings.
$465,000
2289 WHITE FEATHER LOOP
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
32Picture(s)
1,744Sqft
Location is everything! Look no further than this highly sought after community of Oakland Trails. This family friendly community is nestled just west of the town of Oakland, and close to the West Orange Trail. Close to Downtown Winter Garden, great shops and restaurants.
This exquisite home is located on the inner loop, step outside and enjoy walking trails without the worry of traffic.
$495,000
2151 WHITE FEATHER LOOP
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
24Picture(s)
2,069Sqft
Welcome to this beautiful, move-in ready 3-bedroom, 2.5-bath home located in the highly sought after community of Oakland Trails! This community features an oasis pool, playground, pavilion and a dog park all being only minutes from the West Orange Trail.
$2,250,000
15255 OAKLAND AVENUE
WINTER GARDEN, Florida
5Bedroom(s)
3Bathroom(s)
88Picture(s)
5,754Sqft
Discover the epitome of luxury living in this stunning custom-built RCB Homes masterpiece, nestled on an exquisite tree-lined street in the sought-after Oakland Park subdivision. This exquisite residence is the true definition of a “forever” home and boasts an array of premium features and sits on one of the largest lots in the community, offering unparalleled space and privacy.
$215,000
112 OAKLAND STREET
LEESBURG, Florida
3Bedroom(s)
2Bathroom(s)
37Picture(s)
1,286Sqft
Explore this charming residence nestled in the heart of Leesburg, FL, situated on a spacious corner lot. This inviting home features three bedrooms and two bathrooms, providing ample space for a growing family or those seeking comfortable living quarters. The galley kitchen showcases stylish two-toned cabinets and luxurious vinyl flooring, adding a touch of modern elegance.
$115,000
1114 OAKLAND CIRCLE
TAVARES, Florida
2Bedroom(s)
2Bathroom(s)
13Picture(s)
624Sqft
Come See this updated 2 bedroom 2 bath home in a highly desirable 55 plus area. When you walk into this home you can really feel the space. The kitchen has plenty of cabinet space and room for an island. The Family room can fit a large entertainment center and couch. The laundry room has washer and dryer hook-up and another full bathroom .
$649,900
302 LARGOVISTA DRIVE
OAKLAND, Florida
5Bedroom(s)
4Bathroom(s)
86Picture(s)
3,863Sqft
Unbeatable Deal Alert! Don't miss out on this incredible opportunity to own your dream home at an unbelievable price! Our listing just got a massive price drop, making it the perfect time to make your move. Nestled within the tranquil, gated community at Johns Landing, awaits a captivating opportunity for discerning homeowners seeking to personalize their dream retreat.
$253,000
1948 OAKLAND PARK DRIVE
LAKE WALES, Florida
3Bedroom(s)
2Bathroom(s)
20Picture(s)
1,352Sqft
Sitting at the end of a dead end street, on OVER 1/4 ACRE lot in Lake Wales, this 3 Bedroom, 2 Bath house is a solid starter home or investment opportunity! Inside, you'll find there's plenty of space in the living room for all your entertaining needs that leads out to your very own, fully enclosed Sun Room. Perfect for enjoying the outdoors of Florida year round.
$799,990
2340 STANDING ROCK CIRCLE
OAKLAND, Florida
5Bedroom(s)
3Bathroom(s)
45Picture(s)
3,416Sqft
NEW PRICE-This is it! The home is in the highly sought after Oakland Trails. Oakland Trails is a neighborhood of single-family residential homes located in Oakland, a small community on the edge of Winter Garden. This neighborhood is perfectly situated south of Florida’s third largest lake, the 30,000-acre Lake Apopka, and just north of Johns Lake.
$460,000
202 OAKLAND AVENUE
OAKLAND, Florida
3Bedroom(s)
2Bathroom(s)
7Picture(s)
1,600Sqft
Beautiful oversized corner lot in charming Oakland. Nice open floor plan. Workshop is in the Garage and offers tons of storage. There is no HOA, so bring your boats and RV's to this property that has plenty of room to park/store them. This house has been under renovation, so requires work including a new roof. However, the property offers many possibilities to suit your vision of a dream home.
Who’s Your Oakland Buyer’s Agent?
Every home buyer should have a buyer’s agent negotiating on their behalf. It’s completely free to the buyer and the Erica Diaz Team can help you close quicker and for less money than the average Oakland realtor. Tell our team of buyers about the perfect Oakland home for you and we’ll find it!