Oakland, FL Homes

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  $500,000

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

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (321) 495-8074

  2755 Bobcat Chase Blvd, Oakland, FL 34787
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  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 2,148 Sq Ft
  • House for Rent

  12832 Lavender Bloom Aly, 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 Aly, Oakland, FL 34787
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  $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

  Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

  829 Cura Ct, Oakland, FL 34787
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  Est $371,893 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  2226 Gopher Tortoise Terrace, Oakland, FL 34760

  2226 Gopher Tortoise Terrace, Oakland, FL 34760
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  /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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  /30

  $2,850 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
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  $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

  Last Listing Agent Vincent Cordaro SERHANT

  1143 Bobcat Chase Blvd, Oakland, FL 34787
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  Not Listed For Sale

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

  13437 Princess St, Oakland, FL 34787

  13437 Princess St, Oakland, FL 34787
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  $499,999

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

  651 Regina Cir, Oakland, FL 34787

  ***SELLER SAYS SELL! BEST priced home in the community!*** 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,

  

  Savina Delgado Rodriguez

  THE PROPERTY FIRM

  (321) 495-8335

  651 Regina Cir, Oakland, FL 34787
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  /23

  $4,200 per month

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • House for Rent

  13673 Fresh Ivy St, Oakland, FL 34787

  Welcome to this fully furnished 3-bedroom, 2-bath single-story home in the highly sought-after 55+ Del Webb Oasis community of Winter Garden. Designed with both comfort and style in mind, this home offers flexible living spaces and access to resort-style amenities just minutes from Orlando’s world-class attractions.Inside, you’ll find a spacious kitchen with a gas stove, ample cabinetry,

  

  Fernanda Negromonte

  NOVA REAL ESTATE SERVICES INC

  (321) 529-0749

  13673 Fresh Ivy St, Oakland, FL 34787
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  $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 $446,477

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13461 Princess St, Oakland, FL 34787
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  /2

  Est $634,857 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,789 Sq Ft

  15022 Summer Harvest St, Oakland, FL 34787

  15022 Summer Harvest St, Oakland, FL 34787
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  $2,200,000

  • 5 Beds
  • 5 Baths
  • 5,143 Sq Ft

  9008 Morgana Ct, Oakland, FL 34787

  Set along the shoreline of Lake Hickorynut in the boutique community of Avalon Cove, this 2022-built lakefront residence combines modern design, thoughtful detail, and a lifestyle centered around light, space, and water. Positioned on a cul-de-sac corner lot of approximately 0.35 acres, the home captures long, open-water views and effortless indoor-outdoor living. Sunsets unfold across the lake

  

  Bent Danholm

  MAXIM Realty Orlando

  (321) 290-8436

  9008 Morgana Ct, Oakland, FL 34787
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  $1,530 - $2,865 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
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  $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 $619,161

  Last Listing Agent Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC

  2390 Standing Rock Cir, Oakland, FL 34787
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  Est $679,821 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,350 Sq Ft

  13534 Parkfield Way, Oakland, FL 34787

  13534 Parkfield Way, Oakland, FL 34787
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  $535,000

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

  9029 Sonoma Coast Dr, Oakland, FL 34787

  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 discover a beautifully updated interior with

  

  Abraham Mendez

  NONA LEGACY POWERED BY LA ROSA

  (321) 766-5509

  9029 Sonoma Coast Dr, Oakland, FL 34787
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  $3,300 per month

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

  16862 Hypatia Aly, Oakland, FL 34787

  Spacious size Lot without neighbor on the left side! Located in PERFECT Community - Waterleigh in Winter Garden Horizon West. Rent includes lawn maintenance and all clubhouses amenities access. 2500 sft, 4 bedrooms & 3.5 baths & Loft/retreat upstairs and Balcony upstairs. Main master bedroom upstairs and 2nd master bedroom downstairs. Upgraded cabinet and flooring. Great school zone. Waterleigh

  Jacky Liu YORK MILLS REALTY LLC

  16862 Hypatia Aly, Oakland, FL 34787
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  $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
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  /31

  Est $471,115 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
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  $535,000 Pending

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

  610 Strihal Loop, Oakland, FL 34787

  Under contract-accepting backup offers. Welcome to 610 Strihal Loop, a beautifully updated home in a desirable Oakland location. Step inside to discover a bright and airy open-concept living space, featuring new, rich wood-look flooring that flows throughout the entire home, creating a cohesive and elegant feel. The main living areas are bathed in natural light, showcasing the neutral paint

  

  Matthew Wheatley

  WHEATLEY REALTY GROUP

  (321) 462-5593

  610 Strihal Loop, Oakland, FL 34787
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  /23

  $2,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,577 Sq Ft
  • Townhouse for Rent

  17568 Northlake Grv Dr, Oakland, FL 34787

  This property is available. Please inquire on this site to schedule a showing. ? Lakefront Luxury Living in Winter Garden – Brand New 3BR Townhome at Northlake at Ovation ?Discover the perfect blend of comfort, style, and convenience in this brand-new, lakefront townhome located in the highly desirable Northlake at Ovation community. Nestled in the heart of Winter Garden and just

  17568 Northlake Grv Dr, Oakland, FL 34787
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  $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 $859,026

  Last Listing Agent Jayme Taylor SAGE REALTY FLORIDA, INC.

  1102 Eagles Pass Way, Oakland, FL 34787
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  /49

  Est $586,513 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
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  /16

  $999,563 New Construction

  • 4 Beds
  • 3 Baths
  • 2,686 Sq Ft

  Mabel Plan at Oakland Park - Park Series, Winter Garden, FL 34787

  David Weekley Homes Builder

  884 Tilden Oaks Trail Unit 36446359, Winter Garden, FL 34787
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  /14

  $2,500 per month

  • 3 Beds
  • 3 Baths
  • 1,577 Sq Ft
  • Townhouse for Rent

  17592 Northlake Grove Dr, Oakland, FL 34787

  New Ashtonwoods Townhouse outside the booming area of Winter Garden/Hamlin. Lots of NEW!!! New restaurants, new schools, new shopping and most of all A NEW TOWNHOME.Quiet neighborhood close to everything and ready to move-in.

  Dane Bradley CELEBRATION RENTAL GROUP

  17592 Northlake Grove Dr, Oakland, FL 34787
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  /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 $980,201

  Last Listing Agent Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  1206 Civitas, Oakland, FL 34787
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  /2

  Est $603,504 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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  $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
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  $2,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,027 Sq Ft
  • House for Rent

  16190 Harbor Mist Aly, Winter Garden, FL 34787

  Beautiful 3-bedroom, 2.5-bath home in Waterleigh Winter Garden, with a main floor master bedroom! This charming Cordale model by D.R. Horton has a welcoming covered front porch, and an open kitchen complete with a butler's pantry. The modern kitchen has stainless appliances with washer/dryer included . Upstairs, two bedrooms plus a loft make the perfect movie room, play room or office/gym area.

  16190 Harbor Mist Aly, Winter Garden, FL 34787
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  $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 $1,005,258

  Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

  1175 Celadon St, Oakland, FL 34787
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  Est $456,462 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
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  $830,266 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
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  $4,500 per month

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft
  • House for Rent

  16771 Oakboro St, Oakland, FL 34787

  One or more photo(s) has been virtually staged. This stunning 5 bedroom, 4 bathroom home offers the perfect blend of luxury and comfortable everyday living. From the moment you enter, you will notice thoughtful details throughout including elegant crown molding. The home features a guest bedroom and full bathroom on the first floor, ideal for visitors or multigenerational living, along with USB

  Fanny Stollmeyer LPT REALTY, LLC

  16771 Oakboro St, Oakland, FL 34787
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  /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
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  Est $477,999 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
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  /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
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  $3,650 per month

  • 4 Beds
  • 3.5 Baths
  • 2,929 Sq Ft
  • House for Rent

  9753 Lost Creek Dr, Oakland, FL 34787

  Incredible Lake views from this four year old home, 4 bedroom 3.5 bath water front home in highly desirable Waterleigh west of Disney. With great curb appeal, this home has a brick paved driveway and covered front porch. As you walk into this home, you are greeted by tall coffered ceiling, an elegant arch hallway, a side wide-opened Office/den with lots of natural light and wrought iron designer

  Bryce Rysewyk SPRING REALTY ONE LLC

  9753 Lost Creek Dr, Oakland, FL 34787
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  /2

  $404,990 Sold Jul 29, 2025

  2907 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,647 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $246/SF
  • 18 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2907 Transformation Way, Oakland, FL 34787
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  /2

  Est $653,583 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

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