Oakland, FL Homes

• 

  

  

  /4

  Est $278,520 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,029 Sq Ft

  411 W Hull Ave, Oakland, FL 34760

  411 W Hull Ave, Oakland, FL 34760
• 

  

  

  /24

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  14099 Lochend Way, Oakland, FL 34787

  Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining

  Anahi C Rosario INTERNATIONAL REAL ESTATE LLC

  14099 Lochend Way, Oakland, FL 34787
• 

  

  /2

  $522,000 Sold May 23, 2025

  • 1,685 Sq Ft
  • $310/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2021

  15657 Pelican Cay Dr, Oakland, FL 34787

  This immaculate, 3 bedroom, 2 bath block constructed home has been perfectly kept and appars like a model home located in the desirable Horizon West community of WATERLIEGH. The home has 1,685 square feet under air and is situated on a beautiful OVERSIZED CORNER LOT. The home is very inviting and is bright inside with an open floor plan making it perfect for any lifestyle. The home has curb

  Kevin Pribell ACRES INC

  15657 Pelican Cay Dr, Oakland, FL 34787
• 

  

  

  /5

  Est $557,765 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  15105 Summer Harvest St, Oakland, FL 34787

  15105 Summer Harvest St, Oakland, FL 34787
• 

  

  

  /45

  $534,900

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft

  233 Largovista Dr, Oakland, FL 34787

  Luxury, Convenience, and Comfort in John’s Landing! This thoughtfully updated and move-in ready 4-bedroom, 2-bath home offers flexible living in one of Oakland/Winter Garden’s most desirable gated communities, the gorgeous John’s Landing. You will feel welcomed home with mature landscaping, an extended driveway, a covered entry, Ring doorbell, and exterior lighting—perfect for a warm arrival day

  Rachael Segarra EXP REALTY LLC

  233 Largovista Dr, Oakland, FL 34787
• 

  /2

  $555,000 Sold May 21, 2025

  • 2,152 Sq Ft
  • $258/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2017

  1763 White Feather Loop, Oakland, FL 34787

  OAKLAND TRAILS community just off the WEST ORANGE TRAIL and just steps away from amenities !!! Don't miss the opportunity to own this TURN-KEY beautifully constructed 3 Bedroom / 2.5 Bathroom ENERGY EFFICIENT home built by Meritage Homes. You are sure to love the spacious living areas, with seamless transitions between rooms, making it ideal for both entertaining and comfortable day-to-day

  Kim Byerly THE REAL ESTATE COLLECTION LLC

  1763 White Feather Loop, Oakland, FL 34787
• 

  

  /17

  Est $602,381 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,338 Sq Ft

  15113 Summer Harvest St, Oakland, FL 34787

  15113 Summer Harvest St, Oakland, FL 34787
• 

  

  /52

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  13293 Pontoon Rd, Oakland, FL 34787

  Sometimes the right home just feels easy. This 3-bedroom, 3-bath corner unit townhome was built in 2023 and sits in one of Winter Garden’s most sought-after neighborhoods, Waterleigh. From the moment you pull into the driveway, you’ll notice how clean, simple, and ready it feels. No projects. No waiting. Just move in and enjoy.Inside, natural light pours through every room, highlighting

  Mark Raumaker SERHANT

  13293 Pontoon Rd, Oakland, FL 34787
• 

  /2

  $3,175,000 Sold May 20, 2025

  • 6,428 Sq Ft
  • $494/SF
  • 0 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2026

  410 Briley Ave, Oakland, FL 34787

  Pre-Construction. To be built. Custom Home to be built by Element Home Builders. 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. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and

  Alexis Anderson REGENCY REAL ESTATE LLC

  410 Briley Ave, Oakland, FL 34787
• 

  

  /17

  Est $661,141 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,963 Sq Ft

  15149 Summer Harvest St, Oakland, FL 34787

  15149 Summer Harvest St, Oakland, FL 34787
• 

  

  /77

  $997,000 Open Sat 11AM - 2PM

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft

  3179 Sailing Pier Ave, Oakland, FL 34787

  Welcome to 3179 Sailing Pier, a stunning residence offering refined living with thoughtful upgrades. This home features custom lighting and elegant laminate flooring throughout, creating a warm and inviting atmosphere. The newly upgraded garden enhances the private backyard, perfect for relaxation and entertaining, with a picturesque view showcasing horses grazing most mornings and vibrant

  Vivian Saavedra LPT REALTY, LLC

  3179 Sailing Pier Ave, Oakland, FL 34787
• 

  /2

  $420,000 Sold May 20, 2025

  • 1,568 Sq Ft
  • $268/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  16926 Reseda Alley, Oakland, FL 34787

  Welcome home to this MOVE IN READY townhome in Winter Garden’s desirable Waterleigh Community! This DR Horton “Ibis” floorplan features 3 beds, 2.5 baths, an open floor plan with a family room, drop zone by the garage, private brick paver patio, a 1 car garage and has lot of upgrades! You will love the green space in front of the townhome – a great space to meet up with friends and neighbors or

  Eve Metlis WATSON REALTY CORP

  16926 Reseda Alley, Oakland, FL 34787
• 

  

  /59

  Est $447,589 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft

  10786 Rhett Butler Alley, Winter Garden, FL 34787

  10786 Rhett Butler Alley, Winter Garden, FL 34787
• 

  

  /5

  $435,000

  • Land
  • 0.25 Acre
  • $1,740,000 per Acre

  1225 Water Maple Dr, Oakland, FL 34760

  Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home. Set in the illustrious community of The Grove, Lot 41 is a generously sized corner lot ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal location. Access to modern amenities,

  Darby Shields HAVEN PROPERTY GROUP LLC

  1225 Water Maple Dr, Oakland, FL 34760
• 

  /2

  $575,000 Sold May 16, 2025

  • 2,200 Sq Ft
  • $261/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2023

  11015 Bostwick Alley, Oakland, FL 34787

  Beautiful, Energy-Efficient, and Smart Home! This spacious 3-bedroom, 2.5-bath single-family home is filled with natural light and modern features. The kitchen boasts sleek solid countertops, stainless steel appliances, and an oversized island, seamlessly flowing into the open-concept family room perfect for entertaining. Step outside and unwind on the covered porch, complete with a retractable

  Marcos Del Nero LA ROSA REALTY KISSIMMEE

  11015 Bostwick Alley, Oakland, FL 34787
• 

  

  /21

  Est $982,890 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,693 Sq Ft

  1100 Ridge Lake Way, Oakland, FL 34787

  1100 Ridge Lake Way, Oakland, FL 34787
• 

  

  /38

  $777,000

  • 4 Beds
  • 3 Baths
  • 2,181 Sq Ft

  8935 Sonoma Coast Dr, Oakland, FL 34787

  BEAUTIFUL HOME!!! WATER WATER WATER view !! All furniture are negotiable … Immerse yourself in luxury living with this meticulously designed 4-bedroom/3-bathroom home, gorgeous private pool oasis and a stylish with a summer kitchen. Enjoy the perfect blend of elegance and comfort as you entertain guests in the spacious living areas. Or unwind in the tranquility of your own backyard retreat with

  Bruno Dasilva, LLC MS LAND & BUILDING LLC

  8935 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  $770,000 Sold May 16, 2025

  • 1,982 Sq Ft
  • $388/SF
  • 32 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  1118 Eagles Pass Way, Winter Garden, FL 34787

  Nestled on a premium corner lot in the sought-after Oakland Park community, this stunning 3-bedroom, 2.5-bathroom home plus an office offers the perfect blend of charm and modern luxury. A welcoming covered front porch invites you to relax and connect with neighbors while enjoying the beautiful Florida weather. Step inside to a bright foyer with luxury vinyl plank flooring that flows throughout

  Alex Vastardis COLDWELL BANKER REALTY

  1118 Eagles Pass Way, Winter Garden, FL 34787
• 

  /2

  Est $852,959 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,247 Sq Ft

  1173 Wilder Oaks Way, Oakland, FL 34787

  1173 Wilder Oaks Way, Oakland, FL 34787
• 

  

  /16

  $555,000

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft

  2035 White Feather Loop, Oakland, FL 34787

  Welcome to 2035 White Feather Loop, a stunning haven nestled in the serene community of Oakland Trails. This meticulously crafted residence offers an unparalleled blend of modern elegance and timeless charm, providing a sanctuary for luxurious living. Upon arrival, you'll be captivated by the impeccable curb appeal of this home, showcasing lush landscaping and a grand entrance. Step inside to

  James Goodyear REAL BROKER, LLC

  2035 White Feather Loop, Oakland, FL 34787
• 

  /2

  $650,000 Sold May 16, 2025

  • 1,934 Sq Ft
  • $336/SF
  • 140 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  15086 Summer Harvest St, Oakland, FL 34787

  *SPECIAL RATE PROMOTION* This single-story Hemingway Cottage design by RockWell Homes features 3 bedrooms, 2 bathrooms, flex room, dining area, 2 car garage, covered front porch, and covered back yard lanai. Kitchen features eat-in island, solid surface countertops, stainless steel appliances, gas cooktop, microwave, oven, dishwasher, vent hood, upgraded 42-inch cabinets, upgraded flooring,

  Jasmine Martz OLYMPUS EXECUTIVE REALTY INC

  15086 Summer Harvest St, Oakland, FL 34787
• 

  

  /53

  Est $663,571 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,274 Sq Ft

  2252 Bay Line Rd, Oakland, FL 34760

  2252 Bay Line Rd, Oakland, FL 34760
• 

  

  /36

  $535,000

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  1787 White Feather Loop, Oakland, FL 34787

  **This property qualifies for a closing cost credit up to $8,400 through the Seller’s preferred lender.** Welcome to a beautifully designed two-story single-family home featuring 3 bedrooms, 2.5 bathrooms, and a detached garage, nestled in a serene and manicured community. As you arrive, you're greeted by a welcoming front porch and an upstairs balcony offering peaceful views of a sleekly

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1787 White Feather Loop, Oakland, FL 34787
• 

  /2

  $1,080,000 Sold May 14, 2025

  • 3,800 Sq Ft
  • $284/SF
  • 168 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  627 Largovista Dr, Oakland, FL 34787

  Back on market! Huge price improvement... Schedule your personal tour of this captivating and stunning custom home. This is truly a luxury move-in ready, turn-key home, situated in the highly desirable Johns Landing gated community on Johns Lake. Recently remodeled throughout and fully furnished with all high-end desirable furniture that can be purchased with the home. Whether entertaining

  Heidi Pfeffer-Morgan DALTON WADE INC

  627 Largovista Dr, Oakland, FL 34787
• 

  

  /36

  Est $537,248 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  2520 Standing Rock Cir, Oakland, FL 34787

  2520 Standing Rock Cir, Oakland, FL 34787
• 

  

  /30

  $585,000

  • 4 Beds
  • 2 Baths
  • 2,490 Sq Ft

  610 Strihal Loop, Oakland, FL 34787

  Welcome to your beautifully updated home in the coveted gated community of John’s Landing in Oakland, Florida! Nestled near the shores of Johns Lake, this stylish residence combines modern upgrades with timeless appeal, all in one of Central Florida’s most desirable locations.Step inside to discover an open and airy floor plan, highlighted by a completely renovated kitchen featuring sleek

  Julie Arnold REAL BROKER, LLC

  610 Strihal Loop, Oakland, FL 34787
• 

  /2

  $582,000 Sold May 13, 2025

  • 1,853 Sq Ft
  • $314/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  2683 Bobcat Chase Blvd, Oakland, FL 34787

  Imagine coming home to your very own slice of paradise nestled in the heart of Winter Garden. 3-bedrooms, 2.5-bathrooms offering 1,853 sq ft of thoughtfully designed living space, perfectly blending comfort and style.This backyard will make all of your friends jealous. The custom-designed pool features a pebble tec finish, in-water bar stools, dual waterfalls, a sun shelf for lounging, and an

  Matthew Sutton BERGER REALTY & INVESTMENTS

  2683 Bobcat Chase Blvd, Oakland, FL 34787
• 

  

  /19

  Est $705,898 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,296 Sq Ft

  9518 Beautiful Way, Oakland, FL 34787

  9518 Beautiful Way, Oakland, FL 34787
• 

  

  /63

  $495,000

  • 4 Beds
  • 2 Baths
  • 1,681 Sq Ft

  312 W Hull Ave, Oakland, FL 34760

  Welcome to this beautifully updated 4-bedroom, 2-bath home located in the heart of Oakland.Nestled in the golf cart district of the charming local town, this home has the blend of small-town charm and modern convenience.Within a short 10-minute walk, youll enjoy local shopping, the West Orange Biking Trail, and a quaint downtown area. Conveniently located 2 miles from the main highway

  Steven Koleno BEYCOME OF FLORIDA LLC

  312 W Hull Ave, Oakland, FL 34760
• 

  /2

  $879,000 Sold May 13, 2025

  • 2,246 Sq Ft
  • $391/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2023

  1073 Sadler Oaks Way, Winter Garden, FL 34787

  Welcome to 1073 Sadler Oaks, a stunning home in the sought-after Oakland Park community. This exceptional 3-bedroom, 3-bathroom home was completed in 2023. This award-winning floorplan offers upgraded features like: crown molding on the first level, a downstairs dedicated flex room, a 3-car garage, upgraded luxury vinyl plank flooring throughout and an impeccable design. Step inside from the

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  1073 Sadler Oaks Way, Winter Garden, FL 34787
• 

  

  /21

  Est $754,534 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,114 Sq Ft

  15121 Canopy Cover Dr, Oakland, FL 34787

  15121 Canopy Cover Dr, Oakland, FL 34787
• 

  

  /9

  $780,000

  • Land
  • 0.39 Acre
  • $2,000,000 per Acre

  1281 Ridge Lake Way, Winter Garden, FL 34787

  LOT 258 final opportunity to build your dream custom home in Oakland Park!!!! Such a charming golf cart community along Lake Apopka and the West Orange Trail. This is the last lake lot on well known Lake Apopka of the final phase. Don't miss your chance to build your dream lake front home that is only 2 miles from adorable Downtown Winter Garden, and 20 minutes to world famous theme parks or 30

  Samantha Andrade KELLER WILLIAMS ELITE PARTNERS III REALTY

  1281 Ridge Lake Way, Winter Garden, FL 34787
• 

  /2

  $690,000 Sold May 13, 2025

  • 2,274 Sq Ft
  • $303/SF
  • 69 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2020

  2157 Bay Line Rd, Oakland, FL 34787

  Welcome to your dream home in the heart of Hull Island at Oakland. This stunning home features a serene saltwater pool and is on a peaceful lot with conservation views. The open floor plan, high ceilings, and windows create an energizing flow of natural light throughout. Rich colors and lighting enhance its beauty. At the center of the home is the gourmet kitchen with an oversized island and

  Jamie Stolinas Crame CENTURY 21 CARIOTI

  2157 Bay Line Rd, Oakland, FL 34787
• 

  

  /12

  Est $477,258 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft

  15157 Aqua Sol Ln, Oakland, FL 34787

  15157 Aqua Sol Ln, Oakland, FL 34787
• 

  

  /26

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft

  310 E Gulley Ave, Oakland, FL 34760

  Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space.Inside, enjoy a warm and functional layout with 1,419 sq ft of

  Liam Lugo LPT REALTY, LLC

  310 E Gulley Ave, Oakland, FL 34760
• 

  /2

  $890,000 Sold May 12, 2025

  • 2,268 Sq Ft
  • $392/SF
  • 57 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  896 Tilden Oaks Trail, Winter Garden, FL 34787

  Welcome to 896 Tilden Oaks Trail in Winter Garden, FL 34787—A great opportunity to own a home in the highly sought-after Oakland Park community. This former builder’s model has been thoughtfully upgraded throughout, offering a blend of modern luxury and timeless elegance. Only steps away from the West Orange Trail and only two miles from the historic Downtown Winter Garden, the home’s elegant

  Rema Perras CORCORAN PREMIER REALTY

  896 Tilden Oaks Trail, Winter Garden, FL 34787
• 

  

  /11

  Est $453,988 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft

  15186 Aqua Sol Ln, Oakland, FL 34787

  15186 Aqua Sol Ln, Oakland, FL 34787
• 

  

  /35

  $648,900

  • 4 Beds
  • 3 Baths
  • 2,268 Sq Ft

  1382 Foltz Loop, Oakland, FL 34787

  ***ASSUMABLE VA MORTGAGE AT A 5.375 INTEREST RATE*** Absolute model condition—and that’s not said lightly. From the moment you arrive, the charm and care put into this home are undeniable. A cozy front porch with ample seating and attractive brick pavers sets the tone, leading to an upgraded 9-foot leaded glass front door that opens into a meticulously maintained interior.The upgraded

  Brooke Cangro RE/MAX 200 REALTY

  1382 Foltz Loop, Oakland, FL 34787
• 

  /2

  $620,000 Sold May 12, 2025

  • 2,811 Sq Ft
  • $221/SF
  • 124 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2003

  1215 Johns Cove Ln, Oakland, FL 34787

  Motivated SELLER! Price adjustment. Don't miss out on this AMAZING opportunity to own this adorable 4-bedroom, 2-bathroom custom pool home in the highly desirable Johns Cove community. If you love to fish, boating, skiing or jet-skiing this is the home for you. This small, sought-after gated community on Johns Lake with its own community boat ramp is ideally located just off the Florida Turnpike,

  Heidi Pfeffer-Morgan DALTON WADE INC

  1215 Johns Cove Ln, Oakland, FL 34787
• 

  /2

  Est $426,965 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  8103 Sayings Dr, Oakland, FL 34787

  8103 Sayings Dr, Oakland, FL 34787

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