Courtesy: MS LAND & BUILDING LLC
407-512-1213
Welcome to this beautifully crafted custom-built two-story home in the highly desirable Town of Oakland—offering the perfect blend of quality construction, modern design, and small-town charm with NO HOA. The thoughtfully designed floor plan features all main living areas on the first floor, including a spacious living room, dining area, and a well-appointed kitchen with high-quality appliances. French doors open to the back porch, and both front and back porches are finished with pavers. Additional highlights include a 2-car garage and generous storage under the stairs. Upstairs offers a versatile family room/bonus space, three secondary bedrooms with walk-in closets, and a full bath with built-in shelving and a tub. A convenient laundry closet adds functionality. The primary suite, located at the rear of the home, features a custom walk-in closet, dual sink vanity, and a large walk-in shower. The home showcases high-end finishes throughout, including luxury vinyl plank flooring and porcelain tile in the bathrooms. Ideally located in the heart of Oakland, just minutes from the West Orange Trail, Downtown Winter Garden, Plant Street Market, and the Lake Apopka boat ramp—offering easy access to shopping, dining, and outdoor recreation. A rare opportunity to own a meticulously built home in one of Central Florida’s most desirable areas!
Courtesy: WRA BUSINESS & REAL ESTATE
407-512-1008
Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout. Designed for effortless entertaining, the open-concept layout showcases a chef’s kitchen with a waterfall quartz island, custom cabinetry, premium stainless steel appliances, and a full-slab backsplash, all flowing into an expansive living area with designer lighting and seamless indoor-outdoor access. The primary suite offers a private retreat with abundant natural light, custom closets, and a spa-inspired bath featuring a freestanding soaking tub and luxury walk-in shower. Step outside to a screened pool, upgraded travertine deck, and private pier, creating an unparalleled waterfront lifestyle ideal for relaxation and entertaining. Additional highlights include a concrete tile roof (maintained), smart home features, updated HVAC, epoxy garage, modern laundry room, and high-end upgrades throughout. Ideally located minutes from Downtown Winter Garden, premier dining, shopping, and top-rated schools, this is a rare opportunity to own an unparalleled lakefront property.
Courtesy: SOUTHERN REALTY GROUP LLC
407-217-6480
Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living area. The upgraded gourmet kitchen is a standout, featuring stainless steel GE Profile appliances, a gas range, quartz countertops, ceiling-height cabinetry, and a stunning oversized waterfall island with seating that overlooks the breakfast nook and family room. Perfect for entertaining, the main living space is filled with natural light from three large sliding doors that open to a covered lanai and private backyard, complete with a full outdoor bathroom. The first-floor primary suite serves as a relaxing retreat, offering a spa-like bathroom with dual vanities, a spacious shower, garden tub, and a generous walk-in closet. Upstairs, you will find three additional bedrooms and two bathrooms, including a secondary bedroom with a private en-suite, ideal for guests or multi-generational living. The expansive bonus/game room provides a versatile space for a home theater, gym, playroom, or lounge. This home is thoughtfully enhanced with wood-look tile flooring throughout the first floor, upgraded designer lighting, modern ceiling fans, decorator finishes, and abundant storage. Enjoy an elevated audio experience with integrated surround sound in the living room, lanai, primary suite, and upstairs bonus room, featuring built-in in-ceiling speakers for immersive TV and music throughout. Smart home features include Ecobee thermostats, a Ring doorbell, and a garage EV charger. Additional upgrades include 8-foot raised panel doors, a tankless gas water heater, an interior laundry room with utility sink and gas washer and dryer hookup, outdoor kitchen and pool prewiring, and a whole-house water softener. Residents of Hull Island enjoy resort-style amenities, including a pool and clubhouse, playground, dog park, dock, and fishing pier. Ideally located near the West Orange Trail, historic downtown Winter Garden, and Clermont’s lakefront dining, this home offers convenient access to shopping, dining, weekly farmers markets, major roadways, and Central Florida attractions. This is more than a home, it is a private retreat offering comfort, style, and an exceptional location.
Courtesy: SERHANT
786-296-8626
Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining. The kitchen, where matching marble countertops and cabinetry create a clean and cohesive look. A charming office nook on the first floor provides the perfect spot for working from home or managing daily tasks while staying connected to the living areas. Upstairs, each bedroom is thoughtfully designed as its own private suite, complete with a full bathroom and walk in closet, offering comfort and privacy for all occupants. The layout provides flexibility for a variety of living arrangements while maintaining a sense of personal space throughout. Enjoy quiet evenings on the private patio featuring outdoor lighting and a smart home dimmer system that sets the perfect ambiance. A covered walkway leads to the detached garage, offering convenience and protection from the elements. The garage also includes space for a personal workout setup, creating an easy option for staying active at home. Located in a convenient Central Florida area with easy access to major roadways, shopping, dining, and everyday essentials. Enjoy peace of mind with a newer construction and an added UV light system in the HVC to inmporve indoor air quality. It is truly ready for its new owner to come in and live.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), located in the heart of Oakland is just minutes from downtown Winter Garden. From the moment you step inside, you’ll appreciate the thoughtful design and elevated finishes throughout. This spacious home features a dedicated office, formal dining room, and formal living room—perfect for entertaining or creating flexible living spaces to fit your lifestyle. The open-concept layout seamlessly connects the kitchen and family room, complete with a cozy breakfast nook ideal for casual dining. The fully renovated interior showcases wood-look tile throughout the main living areas and plush carpet in all bedrooms. Shiplap accent walls and plantation shutters add warmth, character, and timeless charm. Each of the three bathrooms has been uniquely designed, offering its own distinct style and personality. Step outside to your private, fully fenced backyard that backs to a conservation area—ensuring no rear neighbors, ever. Enjoy peaceful views and added privacy in a serene natural setting. This home is less than a 2-minute walk to Oakland Avenue Charter School and sits within the highly desirable golf cart district of downtown Winter Garden—making it easy to enjoy local shops, dining, and community events. **Some of these photos have been virtually staged**
Courtesy: NEXT RESIDENCE REALTY LLC
407-463-9209
Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely reinvented since the current owners purchased it. Renovations include, a kitchen with all new appliances (2023), new granite countertops, additional lighting and a custom nook seating; enlargement of the 3-car garage door which now includes a custom workbench, storage closet, multi-level storage shelves, refrigerator and a Tesla Charger; new front door that opens into a newly tiled foyer with a view of the pool area; redesigned dining area to accommodate a larger table; FROG (Family Room Over Garage) now includes a Full Bathroom Addition with a storage closet, new vinyl flooring and big Samsung TV, great flex space…. or Man Cave; bedrooms have new windows and their adjacent bathrooms have new tile and countertops; and finally, the primary bathroom remodeled in 2023 includes new cabinets, countertops, lighting, faucets, tile floors, sinks, pull out laundry bin cabinets, ceiling fan, 2nd primary closet addition (now two closets) with custom storage system, heated bathroom floors, heated shower floor, heated shower bench, electric fireplace and an oversized steam shower (Kohler) with two separate shower head systems, truly a spa-like atmosphere. Outside renovations include: low maintenance Azek planks from home to private fire pit area, continuing on to the boathouse; 2023 new driveway pavers with a lit walkway to the front door; new paved front porch; new gutter system; plastic soffit replaced with wood; outdoor lighting; new outdoor storage area; 2023 home was painted; additional 200 amps (total 400 amps) and new garage door. The boathouse has water and power, can house two jet skis, a bass boat or ski boat or optional pontoon boat. The boat area has a Touchless Boat Cover with a remote control lift. Boathouse is approximately 23 1/2 ft by 33 ft. With a Southeast exposure, the pool area is the perfect Stay-cation place to relax and enjoy family time. The perfectly elevated pool area boasts a large patio that wraps around the entire back of the home allowing for a large dining or seating area for you and your guests. You’ll love choosing between watching the 9PM Disney fireworks from either your hot tub or the private fire pit. Location, location, location… All this is conveniently located near major highways and local restaurants and shops. Seize this opportunity to experience the finest in luxury lake living in Central Florida!
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, offers a private retreat with a spa-inspired bathroom and generous walk-in closet. Upstairs, you’ll find additional bedrooms along with a versatile loft space ideal for a media room, office, or play area. Designed for the Florida lifestyle, the outdoor living space is truly exceptional. Enjoy a resort-style pool and spa, expansive lanai, and dedicated firepit area—perfect for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage with a separate golf cart bay, high ceilings, and thoughtful architectural details throughout. This is a rare opportunity to own a beautifully crafted home in one of the area’s most desirable communities.
Courtesy: KELLER WILLIAMS ADVANTAGE III
407-207-0825
Welcome to 2120 Gopher Tortoise Terrace in charming Oakland, Florida, a beautifully maintained 3 bedroom, 2.5 bathroom townhome that offers comfort, style, and an incredible opportunity for qualified buyers to assume the seller’s low 2.75 percent mortgage rate, subject to lender approval, potentially providing significant monthly savings compared to today’s interest rates. From the moment you step inside, you’ll notice the bright and inviting feel created by the open floor plan, warm laminate flooring, and abundant natural light. The spacious living and dining areas flow seamlessly into the kitchen, making this home perfect for everyday living as well as hosting family and friends. The kitchen is the heart of the home, featuring granite countertops, stainless steel appliances, a large island with seating, and a stylish tile backsplash that adds both character and functionality. Thoughtful upgrades throughout the home include custom pantry storage, custom laundry room shelving with a drying pole, and custom closet systems designed to maximize organization and convenience. Upstairs, the primary suite offers a relaxing retreat with a custom walk in closet and an upgraded bathroom featuring elevated countertops and a frameless glass shower. Additional bedrooms provide comfortable space for family, guests, or a home office. Step outside to your private paved courtyard patio, the perfect place to enjoy your morning coffee, unwind after a long day, or gather with friends on beautiful Florida evenings. The location truly sets this home apart. Directly across the street from the West Orange Trail, you’ll have immediate access to one of Central Florida’s most popular biking, walking, and running trails. The home is also situated across from the Oakland Nature Preserve, offering scenic nature views, peaceful surroundings, and additional trails to explore. You’ll also enjoy being just a short drive from vibrant Downtown Winter Garden, known for its award winning farmers market, incredible restaurants, boutique shopping, and year round community events that bring the area to life. With its thoughtful upgrades, inviting layout, and unbeatable location surrounded by nature and community, this home offers a wonderful opportunity to enjoy everything the Oakland and Winter Garden area has to offer.
Courtesy: LPT REALTY, LLC
877-366-2213
YOU Can't miss this Gorgeous 3beds,3 full Bath townhouse in Oakland . near Winter Garden and Clermont..Perfect amenities for you enjoy the best of Florida lifestyle..This Property have absolutely the 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..
Courtesy: KELLER WILLIAMS ELITE PARTNERS III REALTY
321-527-5111
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!
Courtesy: RE/MAX TOWN & COUNTRY REALTY
407-695-2066
One or more photo(s) has been 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!
Courtesy: ASANO REAL ESTATE LLC
352-552-7232
This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling. Community amenities include a pool and playground, with nearby nature trails for walking and biking. Convenient access to major highways, shopping, dining, and downtown Winter Garden makes this location highly desirable.
Courtesy: DALTON WADE INC
888-668-8283
Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes from historic downtown Winter Garden's acclaimed restaurants, boutique shops, and cultural venues, this home offers the perfect balance of serene outdoor living and convenient community access. The neighborhood is known for its resort-style amenities, including community pools and walking trails, plus easy access to the 429 and Florida Turnpike for seamless access to downtown Orlando, area theme parks, and Orlando International Airport. Architectural Excellence and Light-Filled Interior will blow you away. Upon entering, you are immediately enchanted by the flowing design throughout, with USA-made Mannington laminate flooring flows throughout the first floor. Six handcrafted Bevolo lanterns add architectural detail and warmth to the exterior. Additional highlights include a combined mudroom and natural light pouring from expansive two-story windows and stunning designer lighting that complements the floor-to-ceiling stone fireplace, this focal point enhances the open-concept layout, creating a bright, inviting atmosphere throughout the home. A grand dual staircase with iron railings anchors the two-story living room, emphasizing the home's soaring volume ceilings and open, airy design. The oversized, black-framed sliding doors create effortless indoor-outdoor living for those social events. The Chef's Kitchen is quite the entertaining Hub with its elevated oversized quartz waterfall-edged island offering generous seating and a stunning focal point for entertaining. GE Café appliances with brushed bronze hardware, upgraded quartz countertops, and a spacious walk-in pantry support serious culinary pursuits. The seamless flow from kitchen to dining area, transforming entertaining into an effortless, connected experience. The second-floor primary suite features a tray ceiling and an expansive walk-in closet suitable for dressing room use. The spa-inspired bath is a private retreat, with a freestanding soaking tub set within a custom wood-accent alcove and quartzite vanity—the perfect escape after a busy day. Additional highlights include a generous sized laundry space for convenient household management, and a 3-car garage with custom overhead storage providing ample space for vehicles and seasonal storage. The outdoor Living Potential offers a partially fenced backyard with ample space for a future pool, ideal for creating your own resort-style retreat. The premium corner lot positioning provides privacy, abundant natural light, and those coveted Lake Apopka views. This is more than a home—it's a lifestyle positioned in one of Central Florida's most sought-after communities with uncompromising finishes. Don't miss out on this opportunity, Schedule you're showing today!
Courtesy: HOME INVEST REALTY INC
407-895-8891
Courtesy: YOUNG REAL ESTATE
407-904-0069
INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by newer(2024) luxury plank flooring, a large living/dining area, built-in OFFICE SPACE, and a half sized bathroom. The kitchen is a CHEF'S DREAM featuring granite counters, a large eat-in island, stainless steel appliances, built-in oven and microwave, designer pendant lighting, closet style pantry, and a dedicated coffee/work station. WOW! Head upstairs and pass through the BONUS LOFT area into an OVERSIZED MASTER SUITE with tray ceilings, a large split vanity master bath, and a MASSIVE WALK-IN CLOSET equipped with built-in shelving and organizers. The second floor also contains three secondary bedrooms, a full size hallway bathroom, and a large laundry room. Additional features of the home include: a FULL SOLAR PANEL SYSTEM(providing significant energy savings), an oversized two car garage, built-in security system, and paver driveway. The Oakland Trails community includes a community pool and clubhouse, dog park, playground, and walking trails. Located minutes away from the WEST ORANGE TRAIL this area is a hotbed for outdoor recreation and is ZONED FOR EXCELLENT SCHOOLS! In close proximity to major commuting highways, downtown Winter Garden, and ample shopping amenities, this is a PRIME LOCATION home and MOVE-IN ready for it's next owners. DON'T DELAY!! Book your private showing today.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
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.
Courtesy: LIBERTY HOME SALES INC
321-256-0500
Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to popular Johns Lake. Home is updated with the entire roof replaced in November 2019 and new A/C in 12/21/2020. Perfectly positioned minutes from Florida Turnpike and within 25 minutes from Disney, Universal Studios, Downtown Orlando, Downtown Clermont, Downtown Winter Garden, and the Bike Trail which connects Clermont, Oakland, Winter Garden, and Orlando. All measurements are approximate and should be verified.
Courtesy: PINK MIAMI
305-504-0807
Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential atmosphere. Oakland Trails is known for its top-rated schools, scenic walking and biking trails, and thoughtfully planned amenities, including a community pool, clubhouse, and dog park. The neighborhood features wide streets, attractive entryways, and a welcoming environment, with close proximity to Historic Downtown Winter Garden, offering popular restaurants, breweries, shops, and community events. Built with energy efficiency in mind, this Meritage Home includes spray foam insulation, helping maintain consistent indoor comfort while reducing utility costs. The home is equipped with an advanced HVAC system featuring enhanced air purification and fresh-air intake, ideal for comfortable and healthy living. The interior showcases a gourmet kitchen with KitchenAid appliances, quartz countertops, and a custom-tiled island, complemented by high ceilings and tall doorways that create an open, airy feel throughout. Additional features include a partially metal and shingle roof, a full gutter system, a custom wood staircase, and a spacious primary suite with a built-in closet system. Generous storage throughout the home makes it well suited for families of any size. The property is ideal for long-term rental use. While short-term rentals are restricted by the HOA, the home’s modern construction, low-maintenance design, and strong location support long-term value and rental stability. Notably, the home has been strictly pet-free under current ownership, making it an excellent option for buyers with sensitivities. A detailed list of builder upgrades and owner improvements will be provided with the listing, offering full transparency into the home’s added value. Additional features include installed security cameras and a custom Tesla charging outlet, included at no additional cost with a full-price offer. Furniture is not included; however, the seller is open to selling select items separately if desired. A well-maintained, energy-efficient home in one of the area’s most sought-after communities — offering quality construction, lifestyle amenities, and long-term appeal.
Courtesy: ORLANDO PROP MGMNT RLTY LLC
407-283-5065
Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere. The large open kitchen offers a large island with seating for four, granite countertops, 42-inch cabinetry, and stainless-steel appliances. Oversized windows fill the space with natural light, while the adjacent laundry room includes storage shelving and a walk-in pantry for added convenience. Step out of the kitchen to a private brick-paver courtyard perfect for relaxing or entertaining. Upstairs, the primary suite boasts a walk-in closet and an en-suite bath with dual granite vanities and a spacious walk-in shower. Two additional bedrooms and a full bathroom provide ample space for family or guests. The home is also pre-wired for a security system with the option to add cameras. Residents of Longleaf at Oakland enjoy community amenities including a pool, playground, and sidewalks throughout the neighborhood. Conveniently located near shopping, dining, and major roadways. Enjoy a hike at the Oakland Nature preserve with a boardwalk to Lake Apopka, and conveniently located next to the West Orange Trail.
Courtesy: MARKET CONNECT REALTY LLC
407-250-4708
Imagine coming home to a space that feels open, comfortable, and perfectly placed for everyday life. This corner-unit townhome in the desirable Longleaf at Oakland community offers added privacy, abundant natural light, and a thoughtfully designed layout that truly works for today’s lifestyle. Inside, the home features a clean, modern feel with plank vinyl flooring, granite countertops, and recessed lighting, creating a space that’s both stylish and easy to maintain. The open-concept main living area flows seamlessly, making it ideal for daily living and entertaining. Upstairs, a versatile loft provides the perfect bonus space for a home office, playroom, or second living area. Step outside to a private courtyard-style patio, ideal for grilling, relaxing, or enjoying your morning coffee—an inviting outdoor space that adds to the home’s functionality and charm. Life in Longleaf at Oakland extends beyond the home itself. Residents enjoy a community pool and playground, perfect for relaxing weekends and family fun. Outdoor enthusiasts will appreciate being close to nearby nature trails, offering scenic walks and bike rides just minutes from home. With quick access to major highways, commuting is simple while still enjoying a peaceful residential setting. You’re conveniently located near shopping, dining, downtown Winter Garden, and everyday essentials—making this an excellent place to call home. This move-in-ready corner unit offers comfort, convenience, and a lifestyle that’s hard to beat. Schedule your private showing and experience it for yourself.
Courtesy: NEW HOMES REAL ESTATE, INC.
407-947-2475
Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!
Courtesy: NUMBER 1 BROKER, LLC
407-566-3400
This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters, and center island with breakfast bar. The family room and the rear lanai feat peaceful views of the rear lawn and conservation area. The first floor master suite feat a large walk in closet and the master bath complete with dual sinks, walk in shower, and garden tub. Upstairs you will find 4 additional bedrooms all with large closets, and served by 2 additional full baths. The flexibility of this home is endless as the upstairs features an additional LOFT SPACE as well as a 2nd Floor DEN. You get a large house without large energy bills as Meritage Homes is relentless with energy efficiency in their products. The Oakland Trails community centers around a generous park area and includes community pool, playground, and dog park! The community is located near the West Orange Trail, historic downtown Plant Street, and a short drive from Winter Garden Village. The location of this home can't be beat for ease of access to the Turnpike, shopping, and dining. Call today to see this home!
Courtesy: KELLER WILLIAMS ADVANTAGE III
407-207-0825
THIS ONE IS A MUST SEE! Upgrades on upgrades on upgrades! Welcome to Oakland Trails in the charming City of Oakland. This spacious 5-bedroom, 3.5-bath home offers a flexible layout perfect for today’s lifestyle. Enjoy a cozy Great Room, formal Dining Room, and a stunning modern staircase that leads into an open-concept Living Room and beautifully upgraded Kitchen featuring ample cabinetry, generous counter space, and a designer backsplash. The first-floor primary suite is a private retreat with a luxurious bath, dual vanities, soaking tub, walk-in shower, and an oversized walk-in closet. Upstairs offers a large loft, spacious secondary bedrooms, and a versatile bonus room ideal for an office or optional 6th bedroom. Situated on a quiet cul-de-sac with no front neighbors and peaceful conservation views, the resort-style backyard showcases extended pavers and low-maintenance artificial grass—saving time while offering year-round beauty and convenience. The home is equipped with top-quality solar panels featuring over 400 watts per panel—the latest generation for maximum efficiency and performance. Paired with a premium Enphase inverter system, known as one of the best in the industry, this setup is designed to optimize energy production and deliver significant long-term savings.Solar Panel open to negotiation. Prime location near top-rated schools, the Florida Turnpike, Winter Garden, Clermont, and Orlando, with shopping, dining, and entertainment just minutes away. Space, privacy, upgrades, and location—this home truly has it all!
Courtesy: OAKSTRAND REALTY
888-912-5258
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!
Courtesy: WEMERT GROUP REALTY LLC
407-743-8356
Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, ideal for high-speed connectivity. The DREAM KITCHEN is a showstopper with stylish cabinetry, stone countertops, a breakfast bar, built-in oven, cooktop stove with POT FILLER, tile backsplash, walk-in pantry, and a GALLEY-STYLE COFFEE BAR AREA—perfect for morning routines or entertaining. A spacious Kitchen dinette area overlooks the backyard, adding a warm and functional touch to the heart of the home. In the Living room, enjoy a CUSTOM ACCENT WALL (2023) and views of the large backyard through dual sliding glass doors. A separate Dining room offers flexibility for family gatherings or can easily serve as a formal living room. The first floor also includes a VERSATILE OFFICE/PLAYROOM, convenient under-stair storage, and ONE OF THE FIVE BEDROOMS—complete with laminate wood flooring—located next to a full bathroom, providing a perfect space for guests or multigenerational living. Upstairs, a GENEROUS LOFT creates a perfect secondary living area. The UPDATED PRIMARY SUITE (2025) features a beautiful tray ceiling, a LUXURIOUS EN SUITE BATH with dual vanities, a step-in shower, and a huge walk-in closet. Three additional bedrooms and another full bath offer plenty of comfortable space for family and guests. A paver driveway leads to the generous 3-CAR GARAGE featuring epoxy flooring, additional kitchen-style cabinetry, and PREWIRING for an electric vehicle. Outside, enjoy a large covered patio and an EXPANSIVE BACKYARD, ideal for future customization, gatherings, or play. Oakland Trails is loved for its peaceful setting and small-town charm, offering access to the West Orange Trail, playgrounds, green spaces, and TOP-RATED SCHOOLS. Ideally positioned near DOWNTOWN WINTER GARDEN, residents enjoy quaint dining and gatherings spots, PLANT STREET MARKET, charming shops, and easy access to SR 429 for seamless commuting. Every detail has been thoughtfully crafted for ELEVATED LIVING—come experience the exceptional quality and SOPHISTICATION this home offers. Schedule your showing today!
Oakland is located in Florida. Oakland, Florida has a population of 3,444. Oakland is more family-centric than the surrounding county with 42.26% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Oakland, Florida is $124,856. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Oakland is 37.1 years.
The average high temperature in July is 92.2 degrees, with an average low temperature in January of 46.8 degrees. The average rainfall is approximately 52.1 inches per year, with 0 inches of snow per year.
