Oakland, FL Homes

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  /37

  $540,000

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  651 Regina Cir, Oakland, FL 34787

  Welcome to John’s Landing, a gated lakefront community in the charming town of Oakland, offering private lake access and a community dock on Johns Lake.Step inside this spacious 4-bedroom, 3-bathroom home with a 3-car garage and make it your own. The thoughtfully designed split floor plan includes a family room, formal living room, kitchen nook, and a formal dining area—perfect for both

  

  Savina Delgado Rodriguez

  THE PROPERTY FIRM

  (407) 455-4444

  651 Regina Cir, Oakland, FL 34787
• 

  

  

  /35

  $3,300 per month

  • 3 Beds
  • 2.5 Baths
  • 2,925 Sq Ft
  • House for Rent

  12832 Lavender Bloom Alley, Oakland, FL 34787

  Welcome to your dream home in the heart of Winter Garden! This beautifully maintained 3-bedroom, 1 office, 2.5-bath residence is nestled in the highly sought-after Waterleigh community, offering a perfect blend of comfort, style, and convenience.Designed for modern living, the open-concept floor plan seamlessly connects the spacious living and dining areas to a gourmet kitchen with

  

  Ursula Garcia Moraes

  PRISTINE INTERNATIONAL REALTY LLC

  (321) 529-1696

  12832 Lavender Bloom Alley, Oakland, FL 34787
• 

  

  /2

  $449,490 Sold Jul 22, 2025

  • 1,795 Sq Ft
  • $250/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  2915 Transformation Way, Oakland, FL 34787

  Welcome to the stunning & welcoming Autumn, that includes three bedrooms, two and a half baths, with a two-car garage. This is a modern classic two-story home with a detached rear load garage. The kitchen has a large island, fabulous panty and opens to the elegant dining room and spacious family room. There is a laundry room with washer and dryer and a half bathroom on the first floor. The three

  Ben Goldstein LENNAR REALTY

  2915 Transformation Way, Oakland, FL 34787
• 

  

  /2

  Est $648,488 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  13121 Tollcross Way, Oakland, FL 34787

  13121 Tollcross Way, Oakland, FL 34787
• 

  

  

  /42

  $779,000 Open House 8/02

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  14399 Wabasso Loop, Oakland, FL 34787

  Your New Home in Tilden Place!..From the moment you walk through the front door, you'll feel like you've arrived. This beautiful 4Bedroom, 3.5Bathroom home in the cozy, gated community of Tilden Place is more than just a place to live it’s a place to make memories. A Warm Welcome. As you step inside, you'll be greeted by soaring vaulted ceilings that fill the space with light and warmth. The

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 541-4279

  14399 Wabasso Loop, Oakland, FL 34787
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  /16

  $1,553 - $3,175 per month

  AVENUE ON OAKLAND

  Studio-3 Beds

  751 W Oakland Ave, Oakland, FL 34787

  Perfectly located in Oakland, Florida with easy access to the West Orange bike trail and minutes from the historic downtown Winter Garden and the Florida Turnpike. The Avenue offers unparalleled amenities and an exquisite collection of studios, one, two- and three-bedroom apartment homes.

  751 W Oakland Ave, Oakland, FL 34787
• 

  /2

  $384,900 Sold Jul 21, 2025

  • 1,620 Sq Ft
  • $238/SF
  • 50 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2019

  1324 Painted Bunting Ave, Oakland, FL 34760

  Back-up OFFERS are always encouraged. Call today to view! *** ASSUMABLE LOAN at 3.125% is available with a negotiated offer (~248K) *** Discover refined living in the heart of Oakland and just a short drive or bike ride to historic downtown WINTER GARDEN. Welcome to this enchanting END UNIT townhome nestled in the charming community of LONGLEAF. Thoughtfully designed with modern elegance, this

  Ashley Boyd BHHS FLORIDA REALTY

  1324 Painted Bunting Ave, Oakland, FL 34760
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  /31

  Est $463,193 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,759 Sq Ft

  2441 Standing Rock Cir, Oakland, FL 34787

  2441 Standing Rock Cir, Oakland, FL 34787
• 

  

  /33

  $529,500

  • 3 Beds
  • 2.5 Baths
  • 1,822 Sq Ft

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland community, where you'll find a modern 3-bedroom home with a bonus room—built in 2020, filled with upgrades and situated on a quiet cul-du-sac street. Located in Oakland, one of Central Florida’s most quaint and desirable small towns, 2755 Bobcat Chase offers a rare blend of peaceful living with unbeatable

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (321) 495-8074

  2755 Bobcat Chase Blvd, Oakland, FL 34787
• 

  

  /20

  $2,750 per month

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • House for Rent

  14078 Frasier St, Oakland, FL 34787

  Charming 4-Bedroom Home in Desirable Orchard Hills Winter Garden, FLWelcome to 14078 Frasier St a beautifully maintained single-family home nestled in the highly sought-after Orchard Hills community of Winter Garden. This spacious 4-bedroom, 2.5-bathroom home offers over 2,300 square feet of comfortable living space, perfect for families or working professionals.Step inside to

  Asher Chen AAA GLOBAL VENTURES PA

  14078 Frasier St, Oakland, FL 34787
• 

  /2

  $846,381 Sold Jul 21, 2025

  • 3,225 Sq Ft
  • $262/SF
  • 11 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2025

  16207 Point Rock Dr, Oakland, FL 34787

  Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual

  Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16207 Point Rock Dr, Oakland, FL 34787
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  /49

  Est $579,852 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,638 Sq Ft

  2550 Standing Rock Cir, Oakland, FL 34787

  2550 Standing Rock Cir, Oakland, FL 34787
• 

  

  /30

  $899,000

  • 4 Beds
  • 4.5 Baths
  • 2,741 Sq Ft

  3375 Hanging Tide St, Oakland, FL 34787

  A fully upgraded sanctuary of elegance, where every detail has been meticulously curated for ultimate comfort and sophistication. Welcome home to this stunning 4-bedroom, 4.5-bathroom home nestled within the exclusive gated community of Lakeview Preserve. Situated on a private cul-de-sac, this residence offers breathtaking sunset views over the pool and an inviting indoor-outdoor living

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 456-9179

  3375 Hanging Tide St, Oakland, FL 34787
• 

  

  /16

  $2,775 per month

  • 3 Beds
  • 2.5 Baths
  • 1,756 Sq Ft
  • Townhouse for Rent

  8937 Matriarca Alley, Oakland, FL 34787

  Check this home out! Freshly painted last year in “North Star” inside, and luxury vinyl plank flooring in this end townhouse just minutes away from theme parks and great shopping at Legado community in Windermere. 3 spacious bedrooms, and 2.5 bathrooms combine with generous living space in this 2-story townhome. Designed for entertaining, the "Minneola" features a large gathering room bathed in

  Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

  8937 Matriarca Alley, Oakland, FL 34787
• 

  /2

  $1,025,000 Sold Jul 21, 2025

  • 2,711 Sq Ft
  • $378/SF
  • 77 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2023

  936 Allendale Ln, Winter Garden, FL 34787

  Exquisite Craftsman-Coastal Home Featured in Stroll Oakland Park Magazine!Welcome to the Mabel, a show-stopping 4-bedroom, 3-bathroom masterpiece by David Weekley Homes, built in 2023. Boasting 2,640 sqft of meticulously designed living space, this Craftsman-Coastal beauty seamlessly blends modern elegance with timeless charm.Step inside to soaring 10’ ceilings and an inviting open

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  936 Allendale Ln, Winter Garden, FL 34787
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  /32

  Est $438,798 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,744 Sq Ft

  2289 White Feather Loop, Oakland, FL 34787

  2289 White Feather Loop, Oakland, FL 34787
• 

  

  /64

  $796,900 Pending

  • 4 Beds
  • 2 Baths
  • 2,495 Sq Ft

  1301 Johns Cove Ln, Oakland, FL 34787

  Under contract-accepting backup offers. Viewings are welcome. Huge price improvement!! Motivated sellers! Don’t miss out on this incredible opportunity within the sought-after Johns Cove gated community! This small, sought-after gated community on Johns Lake is ideally located just off the Florida Turnpike, close to Old Winter Garden, the airport, and all the Attractions. The community has its

  

  Heidi Pfeffer-Morgan

  DALTON WADE INC

  (321) 327-9550

  1301 Johns Cove Ln, Oakland, FL 34787
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  /35

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft
  • House for Rent

  15817 Tollington Alley, Oakland, FL 34787

  Townhouse located in Winter Garden, just minutes from Horizons West and Disney. This 3-bedroom/2 bath home offers an open space concept which features a bright, open floorplan and kitchen with plenty of upgrades such as beautiful 42-inch shaker cabinets; quartz counter tops witha large island for entertaining; stainless steel appliances including range, dishwasher, and microwave, refrigerator,

  Eusebio Salas LA ROSA REALTY LLC

  15817 Tollington Alley, Oakland, FL 34787
• 

  /2

  $795,000 Sold Jul 18, 2025

  • 2,505 Sq Ft
  • $317/SF
  • 25 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2014

  101 W Oakland Ave, Oakland, FL 34760

  Experience the charm of Oakland living in this beautifully updated custom built home located in the heart of town—just minutes to Downtown Winter Garden, Plant Street Market, the West Orange Trail, the Lake Apopka boat ramp/dock and so much more! This move-in ready home is situated on a .27-acre corner lot with no HOA. When entering this 4-bedroom, 3-bathroom home, you’re welcomed by a spacious

  Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

  101 W Oakland Ave, Oakland, FL 34760
• 

  

  /54

  Est $1,162,439 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,914 Sq Ft

  845 Heiston Ln, Oakland, FL 34787

  845 Heiston Ln, Oakland, FL 34787
• 

  

  /31

  $2,195,000

  • 4 Beds
  • 4 Baths
  • 3,616 Sq Ft

  15198 E Oakland Ave, Winter Garden, FL 34787

  Price reduction! Welcome to this stunning farmhouse-style home nestled on a premium corner lot in one of the most sought-after communities near Historic Winter Garden. Thoughtfully designed and beautifully maintained, this home offers modern comfort with timeless charm. This is part of one of only 17 exclusive oversized luxury custom residences. Set in a thriving, close-knit neighborhood the area

  Melody Niederst IAD FLORIDA LLC

  15198 E Oakland Ave, Winter Garden, FL 34787
• 

  

  /24

  $3,295 per month

  • 4 Beds
  • 2 Baths
  • 2,278 Sq Ft
  • House for Rent

  13227 Spring Grove Way, Oakland, FL 34787

  This 4 bedroom, 2 bathroom home in the Encore at Ovation community is located near local shops and restaurants, Hamlin Town Center, theme parks, Orange County National Golf course, SR429, and the Florida Turnpike. The open floor plan features luxury vinyl plank throughout with a large family room and kitchen with stainless steel appliances, quartz counter-tops, breakfast bar, and pantry. The

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  13227 Spring Grove Way, Oakland, FL 34787
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  /2

  $387,900 Sold Jul 17, 2025

  • 1,809 Sq Ft
  • $214/SF
  • 144 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2019

  1509 Sweet Apple St, Oakland, FL 34787

  Welcome to lovely 3 bed 3 bath townhome in the heart of Oakland. This end unit town home is modern with luxury vinyl plank floors and new carpet in the bedrooms. On the first level you will find your open concept living space with access to your private courtyard which is an extension of the entertainment space of this home. The kitchen is modern with 42" upper cabinets, granite countertops,

  Robert Jones OFFERPAD BROKERAGE FL, LLC

  1509 Sweet Apple St, Oakland, FL 34787
• 

  

  /9

  Est $442,874 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft

  10665 Words Dr, Oakland, FL 34787

  10665 Words Dr, Oakland, FL 34787
• 

  

  /85

  $1,100,000

  • 4 Beds
  • 3 Baths
  • 3,025 Sq Ft

  100 Demens St, Oakland, FL 34760

  Custom Entertainer’s Dream Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living.From the

  David Dorman CENTURY 21 CARIOTI

  100 Demens St, Oakland, FL 34760
• 

  

  /15

  $3,999 per month

  • 4 Beds
  • 3 Baths
  • 2,931 Sq Ft
  • House for Rent

  17882 Adrift Rd, Oakland, FL 34787

  Welcome to this beautiful and spacious lakefront home in the desirable Waterleigh community of Winter Garden! This 4-bedroom, 3-bath residence features an open-concept layout with a modern kitchen, stainless steel appliances, and a large island perfect for entertaining. Enjoy a bright living space, generously sized bedrooms, and a private, spacious backyard. Community amenities include

  Winnie Tam FLORIDA REALTY INVESTMENTS

  17882 Adrift Rd, Oakland, FL 34787
• 

  /2

  $430,000 Sold Jul 16, 2025

  • Land
  • 0.37 Acre
  • $1,162,162 per Acre

  • 0 Days On Market

  1113 Prado Ln, Oakland, FL 34787

  Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is 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

  Alexis Anderson REGENCY REAL ESTATE LLC

  1113 Prado Ln, Oakland, FL 34787
• 

  /2

  Est $455,840 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft

  13133 Bounty Ave, Oakland, FL 34787

  13133 Bounty Ave, Oakland, FL 34787
• 

  

  /66

  $829,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,260 Sq Ft

  1212 Civitas Way, Winter Garden, FL 34787

  Welcome to this beautifully crafted one-story home in the heart of the desirable Oakland Park community, built by award-winning David Weekley Homes in 2022.. Offering the perfect balance of comfort, functionality, and style, this thoughtfully designed residence is ideal for relaxed Florida living. Step inside to a spacious open-concept main living area that seamlessly integrates the kitchen,

  Kathie Glass BHHS FLORIDA REALTY

  1212 Civitas Way, Winter Garden, FL 34787
• 

  

  /28

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,861 Sq Ft
  • House for Rent

  15030 Summer Harvest St, Oakland, FL 34787

  Welcome to this stunning two-story home, offering spacious bedrooms and bathrooms in a bright, open layout. The modern kitchen features granite countertops, stainless steel appliances, and ample storage, making it perfect for both everyday living and entertaining. Upstairs, the generously sized bedrooms provide comfort and privacy, with plenty of natural light. The primary suite offers a relaxing

  Elio Serpa AUTHENTIC REAL ESTATE TEAM

  15030 Summer Harvest St, Oakland, FL 34787
• 

  /2

  $900,000 Sold Jul 11, 2025

  • 4,041 Sq Ft
  • $223/SF
  • 232 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  13193 Tollcross Way, Oakland, FL 34787

  Priced to Sell...Welcome to 13193 Tollcross Way, a stunning residence nestled in the heart of Winter Garden's most desirable Horizon West community. This expansive home boasts over 4,000 square feet of luxurious living space, featuring five spacious bedrooms and four and a half elegantly appointed bathrooms. As you enter, you'll notice the beautiful tiled floors and designer Zebra builds

  Chandra Maraj WATSON REALTY CORP.

  13193 Tollcross Way, Oakland, FL 34787
• 

  

  /4

  Est $849,361 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,409 Sq Ft

  1112 Eagles Pass Way, Oakland, FL 34787

  1112 Eagles Pass Way, Oakland, FL 34787
• 

  

  /53

  $899,000

  • 4 Beds
  • 4 Baths
  • 2,831 Sq Ft

  931 Kylee Alley, Winter Garden, FL 34787

  PRICE REDUCED! Welcome exceptional, elegant and innovative comforts to your life in this beautiful home in sought-after Oakland Park known for its community amenities including three swimming pools, a clubhouse, playgrounds, a dog park plus access to the famous 23-mile West Orange Trail for cycling, rollerblading running and walking. Just two years young, this meticulous home features an open

  Sean Spencer PREMIER SOTHEBYS INT'L REALTY

  931 Kylee Alley, Winter Garden, FL 34787
• 

  

  /28

  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,868 Sq Ft
  • Townhouse for Rent

  15220 Blue Peacock Ln, Oakland, FL 34787

  ** TENANT OCCUPIED until July, 30th** Beautiful Home with Open Floor Plan! Welcome to this stunning property that perfectly combines comfort, style, and functionality. Featuring a spacious open floor plan filled with natural light, this home is designed for both relaxing living and effortless entertaining. The inviting living room provides a warm and cozy setting for family gatherings, while the

  Ricardo Molina TALENT REALTY SOLUTIONS

  15220 Blue Peacock Ln, Oakland, FL 34787
• 

  /2

  $800,000 Sold Jul 10, 2025

  • Land
  • 0.95 Acre
  • $842,105 per Acre

  • 0 Days On Market

  517 N Pollard St, Winter Garden, FL 34787

  As Central Florida newest custom home 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 friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

  Blaine Dooley REGENCY REAL ESTATE LLC

  517 N Pollard St, Winter Garden, FL 34787
• 

  /2

  Est $549,182 Not Listed For Sale

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

  14086 Frasier St, Oakland, FL 34787

  14086 Frasier St, Oakland, FL 34787
• 

  

  /27

  $829,207 Open Fri 1PM - 5PM

  • 5 Beds
  • 3.5 Baths
  • 3,076 Sq Ft

  14014 Lanyard Way, Oakland, FL 34787

  Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. Anna Maria Bonus C with Stone on Lot 114 offers 5 Bedrooms: 3 baths and a 2 Car Garage. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando, where Dream Finders Homes proudly present Serenade at Ovation. Nestled amidst picturesque lakes and pristine

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14014 Lanyard Way, Oakland, FL 34787
• 

  

  /30

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Townhouse for Rent

  10660 Words Dr, Oakland, FL 34787

  Welcome to 10660 Words Drive, a spacious 4-bedroom, 3-bathroom townhome nestled in Winter Garden's desirable Storey Grove community. This 2,000 sq ft residence features an open-concept layout with a first-floor owner's suite, a modern kitchen, and a private patio—perfect for both relaxation and entertaining. Storey Grove offers an array of amenities, including a resort-style pool, fitness center,

  Ashley Porto FLORIDA CONNEXION PROPERTIES

  10660 Words Dr, Oakland, FL 34787
• 

  /2

  $800,000 Sold Jul 10, 2025

  • Land
  • 1.03 Acres
  • $776,699 per Acre

  • 0 Days On Market

  525 N Pollard St, Winter Garden, FL 34787

  As Central Florida newest custom home 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 friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

  Blaine Dooley REGENCY REAL ESTATE LLC

  525 N Pollard St, Winter Garden, FL 34787
• 

  /2

  Est $439,592 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,688 Sq Ft

  15805 Tollington Alley, Oakland, FL 34787

  15805 Tollington Alley, Oakland, FL 34787

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