Refine Search
Map
Sort by
$500,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Welcome to your peaceful retreat in the heart of Oakland! Nestled within the highly sought-after Longleaf at Oakland community, this impeccably maintained 3-bedroom, 2 1/2-bathroom residence offers the perfect blend of 2020 construction and timeless Florida charm. Step inside to discover 1,811 square feet of bright, open-concept living space designed for both effortless entertaining and cozy family nights. The chef-inspired kitchen serves as the centerpiece, boasting sleek quartz countertops and modern stainless appliances, flowing seamlessly into the dining and living areas. Touches of refinement extend throughout the home, including elegant marble sinks in every bathroom. What truly sets this property apart is its rare positioning, with no neighbors directly in front or behind, providing an incredible sense of privacy especially as you enjoy morning coffee or an evening glass of wine on the screened lanai that provides a forest like feel of trees that are continuing to grow and provide a peaceful and private retreat. The details matter here, from the stylish paver driveway to the two-car attached garage featuring a professionally finished floor coating and recently replaced garage door springs. Living in Longleaf at Oakland means more than just a beautiful home; it’s a lifestyle. Residents enjoy access to a community pool, playground and beautifully maintained landscaping. The location offers the ultimate Central Florida convenience, situated just minutes from the historic charm of Downtown Winter Garden, the West Orange Trail, and the Oakland Nature Preserve, with easy access to Highway 50, SR-429, and the Florida Turnpike. Don't miss your chance to own a piece of Oakland’s finest—schedule your private showing today!

2660 Bobcat Chase Boulevard, Oakland
$500,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Take advantage of a 1% of the loan amount lender credit towards buy downs or closing costs when utilizing our preferred lender. Looking for a stunning 3-bedroom, 2.5-bathroom home with a spacious 2-car garage, built in 2020 and thoughtfully designed for today’s lifestyle? From the moment you arrive, you’ll be greeted by a serene water view in the front and a private conservation view in the back, creating a peaceful and private setting with no rear neighbors. The fenced yard adds extra comfort for pets, play, or gardening. Step inside to a modern and functional layout, or step out back to the incredible screened lanai with retractable screens and a built-in outdoor kitchen—a true entertainer’s dream and the perfect place to relax year-round. This home is located in one of Central Florida’s most convenient and desirable spots—just minutes from Downtown Winter Garden’s shops, restaurants, and farmer’s market, with easy access to the Florida Turnpike, and only 20 minutes from Orlando’s world-class theme parks. Whether you’re looking for tranquility, entertainment, or quick access to all Orlando has to offer, this home delivers it all.

1143 Bobcat Chase Boulevard, Oakland
$495,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a large pantry, and a functional layout ideal for everyday living or entertaining. Upstairs, the bonus room provides flexible space for an office, media room, or play area. The primary suite includes a walk-in closet and private bath with dual sinks, while two additional bedrooms and a full bath complete the second level. Additional highlights include energy-efficient construction, a two-car garage, an inside laundry room, a screened lanai, and a fully fenced backyard. Located minutes from Downtown Winter Garden and directly across from the Oakland Nature Preserve and the West Orange Trail, this home offers the rare blend of peaceful living and exceptional convenience. Enjoy access to miles of walking and biking trails, scenic boardwalks, parks, and year-round community activities. With nearby access to the Florida Turnpike, commuting to Orlando, the airport, or the theme parks is quick and easy. This move-in-ready Oakland home is the perfect combination of comfort, style, and location.

2755 Bobcat Chase Boulevard, Oakland
$450,000
3 Beds ⋅ 2 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Love Where You Live — in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land—so you’ll enjoy privacy, stunning views, and no rear neighbors. Built in 2020 and cared for like new, this home blends comfort, efficiency, and style. The exterior features upgraded pavers, clean neutral tones, and meticulous landscaping. Inside, you’ll find a bright, open floor plan designed for today’s lifestyle—perfect for entertaining or relaxing at home. The spacious kitchen offers a breakfast bar, rich cabinetry and counters, and stainless-steel appliances that flow seamlessly into the great room and dining area, creating an inviting gathering space for family and friends. Enjoy energy-efficient living with a fully paid-for solar panel system—providing ultra-low or near-zero electric bills year-round. You’ll also appreciate the covered patio that opens to a lush, tree-lined backdrop, ideal for morning coffee or peaceful evenings outdoors. Additional highlights include: Interior laundry room and generous storage Smart, low-maintenance design—the HOA maintains all lawn and exterior care Community amenities: sparkling pool, playground, common areas. Quiet, walkable streets with scenic views throughout Outdoor enthusiasts will love being just minutes from the West Orange Trail and Oakland Nature Preserve, perfect for biking, walking, and weekend adventures. And when you want city-style convenience, it’s only a short drive to Historic Downtown Winter Garden—known for its restaurants, boutique shops, and famous Saturday Farmers Market. Easy access to Hwy 50, Florida’s Turnpike, and 429 makes commuting to Orlando, theme parks, and nearby attractions simple and stress-free. If you’ve been searching for a move-in ready home that combines energy savings, low maintenance, and a prime location, this is it. Experience Florida living at its finest—peaceful, practical, and picture-perfect. Come see why homeowners fall in love with Longleaf at Oakland and make this solar-powered retreat your next address!

2690 Bobcat Chase Boulevard, Oakland
$415,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
YOU Must see this absolutely Gorgeous 3BEDS,3 FULL BATH Townhouse in Oakland. located Between Winter Garden and Clermont..Great amenities for you enjoy the best of Florida lifestyle..This Property is the LARGEST SQ FT in the community and Best Floor Plan : Open floor concept ,that integrate Living space, Kitchen and Dinner space. Surrounded with sunlight windows. Engineering floor, granite counters, stainless appliances. Perfect for family and Plus Downstairs FLEX room,Office or used as a Bedroom equipped with Murphy Bed and along with Full Bathroom Downstairs as well. Enjoy the enclosed Patio Privacy and perfect for grilling,Bath tube, much more... LOCATION-LOCATION .. minutes from Historic Winter Garden Downtown ,Stores, Hospitals, costco, restaurants and Main Roads... Upstairs Enjoy the spacious primary bedroom amazing space, along with large Bathroom and walking closet. The secondary bedroom is also located upstairs with their own en-suite bathroom, For privacy for family or guests. The community Offers an amazing pool, relaxing in the launch chairs..Community mailbox, playground and much more...Dont forget about the Famous West Orange Trail—designed for biking, walking or running few mins aways. come see today... This Jewel won't last..

2222 Gopher Tortoise Terrace, Oakland
$389,000
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Enjoy low-maintenance living in this beautifully kept 2-bedroom, 2.5-bathroom townhome. The open main level offers seamless flow with plank flooring and thoughtfully designed spaces for everyday living. The kitchen showcases quartz countertops, an upgraded backsplash, stainless steel appliances, and bar seating that opens to the living area. A dedicated nook provides the perfect spot for a home office or additional storage. Both bedrooms upstairs have walk-in closets and private en-suite baths, while the spacious primary suite adds a walk-in shower and separate water closet for added comfort and privacy. Thoughtfully updated with modern fixtures, this home is truly move-in ready. The Longleaf community offers the perfect blend of nature and modern-day convenience, featuring direct access to the West Orange Trail and located across from the Oakland Nature Preserve. Enjoy community amenities such as a pool with cabana, playground, walking trails, centralized mailboxes, and included lawn care—all just minutes from downtown Oakland, Winter Garden, and Florida’s Turnpike.

2218 Gopher Tortoise Terrace, Oakland
$350,000
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. You’re going to love this beautifully maintained 2-bedroom, 2.5-bath Townhome in the highly desirable Longleaf At Oakland which is perfectly located just a 1/2 mile from the Florida Turnpike, offering easy access to everything Central Florida has to offer. The entire interior was freshly painted in March 2026, giving the home a bright, fresh feel from the moment you walk in. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, making it ideal for both everyday living and entertaining. The inside utility room is conveniently located on the first floor with additional storage under the stairway. Upstairs you’ll find two private master suites, each with its own full bathroom. The primary suite boasts a massive walk-in closet with a window and the en-suite offers dual vanities and an easily accessible walk-in shower. The second bedroom includes a tub/shower combo and its own walk-in closet. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. This home is equipped with Google smart lighting switches, and a Google thermostat can easily be installed and controlled through your app. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community offers everything the Florida Lifestyle has to offer!

1318 Painted Bunting Avenue, Oakland