Oakland, FL Homes

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  /33

  $495,000 Pending

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

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  Under contract-accepting backup offers. 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

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (321) 495-8074

  2755 Bobcat Chase Blvd, Oakland, FL 34787
• 

  

  

  /19

  $2,500 per month

  • 3 Beds
  • 3 Baths
  • 1,647 Sq Ft
  • House for Rent

  6080 Zen Way, Oakland, FL 34787

  Beatiful home located in a desirable Clermont community. This property offers a functional floor plan with comfortable living spaces, a bright kitchen, and spacious bedrooms, conveniently located near US-27, shopping, dining, and major attractions, with easy access to Orlando and surrounding areas. A mandatory Resident Benefit Package of $50/month is required and includes renters insurance (up to

  

  Juliana Garcia Moraes

  PRISTINE INTERNATIONAL REALTY LLC

  (321) 321-7380

  6080 Zen Way, Oakland, FL 34787
• 

  

  /2

  $645,000 Sold Sep 24, 2025

  829 Cura Ct, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,329 Sq Ft
  • Built 2002

  Last Sold Summary

  • $277/SF
  • 3 Days On Market

  Current Estimated Value $635,588

  Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

  829 Cura Ct, Oakland, FL 34787
• 

  

  /2

  Est $696,312 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,179 Sq Ft

  14219 Spring Garden Dr, Oakland, FL 34787

  14219 Spring Garden Dr, Oakland, FL 34787
• 

  

  

  /25

  $1,000,000

  • 4 Beds
  • 2 Baths
  • 2,708 Sq Ft

  624 Hull Island Dr, Oakland, FL 34787

  Find out about the unique chance to be the owner of a 2,700 sqft home which sits on 2.55 private acres which we think is the ideal setting for space, privacy, and great growth. This 1983 built home has been very well preserved in it’s original condition which makes it the perfect choice for buyers who are after land, character and the freedom to update the home to suit their own style. In the

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 449-7661

  624 Hull Island Dr, Oakland, FL 34787
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  /53

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Townhouse for Rent

  10672 Words Dr, Winter Garden, FL 34787

  Welcome home in the master planned community of Storey Grove! Minutes from Downtown WINTER GARDEN, this stunning 3-Bedroom, 2 1/2 Bath, 2 car garage Townhome property is situated just minutes from world class theme parks and attractions. Enjoying local restaurants and shopping just a short drive away. Love the outdoors? Slow down the pace and explore nearby parks and farmer's markets. Your home

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (321) 483-8669

  10672 Words Dr, Winter Garden, FL 34787
• 

  /2

  $500,000 Sold Oct 09, 2025

  1143 Bobcat Chase Blvd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $276/SF
  • 15 Days On Market

  Current Estimated Value $499,039

  Last Listing Agent Vincent Cordaro SERHANT

  1143 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $419,697 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,759 Sq Ft

  1171 Railside Way, Oakland, FL 34787

  1171 Railside Way, Oakland, FL 34787
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  /92

  $2,100,000

  • 5 Beds
  • 5 Baths
  • 4,934 Sq Ft

  9008 Morgana Ct, Oakland, FL 34787

  Set along the shoreline of Lake Hickorynut in Avalon Cove, this 2022-built lakefront residence blends refined design with the ease of modern Florida living. Positioned on a cul-de-sac corner lot of approximately 0.35 acres, the home offers long, open-water views and a lifestyle centered around indoor–outdoor connection, afternoon breezes off the lake, and sunsets enjoyed from the covered balcony

  

  Bent Danholm

  MAXIM REALTY ORLANDO

  (321) 290-8436

  9008 Morgana Ct, Oakland, FL 34787
• 

  

  /16

  $1,584 - $2,825 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

  $440,000 Sold Apr 01, 2025

  13461 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  Last Sold Summary

  • 12% Below List Price
  • $279/SF
  • 61 Days On Market

  Current Estimated Value $445,875

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13461 Princess St, Oakland, FL 34787
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  /49

  Est $597,144 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
• 

  

  /20

  $395,000 Pending

  • Land
  • 0.28 Acre
  • $1,410,714 per Acre

  321 E Gulley Ave, Oakland, FL 34760

  Looking for the best little town near Orlando? Oakland has so much character and charm. New construction in all around up to 4M. You now have the chance to build your custom dream home. The parcel next to this is also for sale separately but combined can be over 1/2 acre of total land.

  

  Deanna Meredith

  LUXE PROPERTIES LLC

  (321) 220-3404

  321 E Gulley Ave, Oakland, FL 34760
• 

  

  /19

  $3,500 per month

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • House for Rent

  17727 Sharp Pummelo Aly, Oakland, FL 34787

  This stunning new home features premium upgrades throughout. The first floor boasts 8-foot exterior and interior doors, a gourmet kitchen, and a private bedroom with a full bathroom featuring an upgraded walk-in shower. The kitchen, family room, and dining area flow seamlessly together and open onto an extended lanai. Upstairs, you'll find the remaining bedrooms, including a primary suite with a

  Angela Magac THE PROPERTY STOP LLC

  17727 Sharp Pummelo Aly, Oakland, FL 34787
• 

  /2

  $360,000 Sold Feb 06, 2026

  507 W Oakland Ave, Oakland, FL 34760

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $269/SF
  • 50 Days On Market

  Last Listing Agent Jennifer Ibarra REAL BROKER, LLC.

  507 W Oakland Ave, Oakland, FL 34760
• 

  /2

  Est $601,457 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,245 Sq Ft

  306 W Hull Ave, Oakland, FL 34760

  306 W Hull Ave, Oakland, FL 34760
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  /52

  $535,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft

  9029 Sonoma Coast Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Experience modern Florida living in this stunning, move-in-ready home at 9029 Sonoma Coast Dr, Winter Garden. Built in 2020, this light-filled residence features 3 spacious bedrooms, 2.5 bathrooms, and an open-plan layout that blends comfort with contemporary style, offering over 2,000 square feet of thoughtfully designed living space.? Step inside to

  

  Abraham Mendez

  NONA LEGACY POWERED BY LA ROSA

  (321) 766-5509

  9029 Sonoma Coast Dr, Oakland, FL 34787
• 

  

  /15

  $3,185 per month

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • House for Rent

  2648 Bobcat Chase Blvd, Oakland, FL 34760

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2648 Bobcat Chase Blvd, Oakland, FL 34760
• 

  /2

  $625,000 Sold Aug 20, 2025

  2390 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft
  • Built 2018

  Last Sold Summary

  • 11% Below List Price
  • $303/SF
  • 39 Days On Market

  Current Estimated Value $621,403

  Last Listing Agent Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC

  2390 Standing Rock Cir, Oakland, FL 34787
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  /32

  Est $454,675 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
• 

  

  /32

  $1,450,000

  • 3 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  101 N Starr St, Oakland, FL 34760

  Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney. Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set

  

  Andrew Kincaid

  BHHS FLORIDA REALTY

  (321) 321-2133

  101 N Starr St, Oakland, FL 34760
• 

  

  /16

  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 2,103 Sq Ft
  • House for Rent

  17609 Japonica Bloom Dr, Oakland, FL 34787

  Welcome to 17609 Japonica Bloom Drive—a brand new home designed for modern living and effortless entertaining. Soaring 8-foot doors throughout the first floor create an impressive, open atmosphere. The gourmet kitchen flows seamlessly into the dining area, making it easy to host while you cook. Step outside to the extended lanai, perfect for outdoor gatherings and relaxation. Upstairs, you'll

  Angela Magac THE PROPERTY STOP LLC

  17609 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  $862,000 Sold Jun 25, 2025

  13133 Sunny Retreat Ln, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,808 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $307/SF
  • 47 Days On Market

  Last Listing Agent Roo Klaers COLDWELL BANKER REALTY

  13133 Sunny Retreat Ln, Oakland, FL 34787
• 

  /2

  Est $480,428 Not Listed For Sale

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

  1793 White Feather Loop, Oakland, FL 34787

  1793 White Feather Loop, Oakland, FL 34787
• 

  

  /4

  $505,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,078 Sq Ft

  Cooper Plan at Serenade at Ovation, Oakland, FL 34787

  Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36487507, Oakland, FL 34787
• 

  /2

  $3,400 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  15129 Summer Harvest St, Winter Garden, FL 34787

  Property Id: 2341266Welcome to your DREAM RENTAL HOME in the heart of the magical Flamingo Crossings area! This stunning home boasts 4 spacious bedrooms (including TWO ENSUITES!), providing ample space for your family to relax and unwind. With 3 and a half bathrooms, morning routines will be a breeze, and everyone can enjoy their privacy. Spanning over 2300 square feet, this beautiful

  15129 Summer Harvest St, Winter Garden, FL 34787
• 

  /2

  $869,900 Sold Feb 28, 2025

  1102 Eagles Pass Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 2023

  Last Sold Summary

  • $385/SF
  • 4 Days On Market

  Current Estimated Value $856,599

  Last Listing Agent Jayme Taylor SAGE REALTY FLORIDA, INC.

  1102 Eagles Pass Way, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,867 Sq Ft

  3119 Armstrong Ave, Oakland, FL 34787

  3119 Armstrong Ave, Oakland, FL 34787
• 

  

  /58

  $395,000

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  2100 Gopher Tortoise Terrace, Oakland, FL 34787

  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

  Stiliany Collado LLC MARKET CONNECT REALTY LLC

  2100 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  

  /50

  $6,000 per month

  • 4 Beds
  • 4 Baths
  • 3,760 Sq Ft
  • House for Rent

  705 Largovista Dr, Oakland, FL 34787

  Come view this newly built 4 bed/4 bath two-story home in the gated community of John’s Landing! Inside, you’ll find a bright and airy open layout featuring an impressive vaulted ceiling, large windows, and elegant flooring throughout. The stunning kitchen includes custom built-in Thermador appliances and solid wood cabinetry. The primary suite features vaulted ceilings, a spa-style bath with a

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  705 Largovista Dr, Oakland, FL 34787
• 

  /2

  $980,000 Sold Jul 08, 2025

  1206 Civitas, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,765 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $354/SF
  • 6 Days On Market

  Current Estimated Value $983,135

  Last Listing Agent Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  1206 Civitas, Oakland, FL 34787
• 

  /2

  Est $647,714 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  15191 Blue Peacock Ln, Oakland, FL 34787

  15191 Blue Peacock Ln, Oakland, FL 34787
• 

  $829,346 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,718 Sq Ft

  15075 Tea Tree Dr, Oakland, FL 34787

  The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

  Dream Finders Homes Builder

  15075 Tea Tree Dr, Oakland, FL 34787
• 

  

  /18

  $2,550 per month

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Townhouse for Rent

  17604 Northlake Grove Dr, Oakland, FL 34787

  PRIME LOCATION IN HORIZON WEST – WINTER GARDEN | ONLY 10 MINUTES FROM DISNEYEnjoy living in this beautiful corner townhome located in the highly desirable Northlake at Ovation community, right in the heart of Horizon West. Built by Ashton Woods, this stunning townhouse is surrounded by serene lakes and natural conservation areas, offering both comfort and tranquility. This charming home

  Isabel Sirizzotti SUNNY 365 REALTY GROUP

  17604 Northlake Grove Dr, Oakland, FL 34787
• 

  /2

  $1,010,000 Sold Mar 31, 2025

  1175 Celadon St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,751 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $367/SF
  • 8 Days On Market

  Current Estimated Value $1,001,766

  Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

  1175 Celadon St, Oakland, FL 34787
• 

  /2

  Est $660,385 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 2,861 Sq Ft

  15014 Summer Harvest St, Oakland, FL 34787

  15014 Summer Harvest St, Oakland, FL 34787
• 

  

  /25

  $645,990 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  Anna Maria w/ Bonus Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36501514, Oakland, FL 34787
• 

  

  /26

  $3,750 per month

  • 4 Beds
  • 3.5 Baths
  • 2,489 Sq Ft
  • House for Rent

  15663 Pelican Cay Dr, Oakland, FL 34787

  Welcome to this beautifully maintained two-story home located in the heart of Winter Garden, FL, within one of the area’s most sought-after communities. This spacious residence features 4 bedrooms, including a convenient in-law suite, and 3.5 bathrooms, providing a flexible and functional layout.The open-concept kitchen includes stainless steel appliances and granite countertops, flowing

  Steven Koleno BEYCOME OF FLORIDA LLC

  15663 Pelican Cay Dr, Oakland, FL 34787
• 

  /2

  $1,600,000 Sold Feb 21, 2025

  10081 Atwater Bay Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,920 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $408/SF
  • 5 Days On Market

  Current Estimated Value $1,583,962

  Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

  10081 Atwater Bay Dr, Oakland, FL 34787
• 

  /2

  Est $1,766,152 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,020 Sq Ft

  1243 Civitas Way, Winter Garden, FL 34787

  1243 Civitas Way, Winter Garden, FL 34787

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