Orange, FL Homes

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  /42

  $779,000

  • 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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  /34

  $3,300 per month

  • 3 Beds
  • 2.5 Baths
  • 2,148 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

  $840,000 Sold Aug 29, 2025

  • 3,290 Sq Ft
  • $255/SF
  • 80 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2006

  413 MacChi Ave, Oakland, FL 34787

  RARE OPPORTUNITY in the highly desirable Winters Landing community – golf cart accessible to downtown Winter Garden and steps to the tree-shaded, 22 mile long West Orange Trail! Upon entering this David Weekly-designed home, you’ll be captivated by the inviting nature of this single-story property loaded with upgrades. No stone has been left unturned, including crown molding, five-inch

  Sophia Ferrara COLDWELL BANKER REALTY

  413 MacChi Ave, Oakland, FL 34787
• 

  

  /2

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft

  6253 Blissful St, Oakland, FL 34787

  6253 Blissful St, Oakland, FL 34787
• 

  

  

  /54

  $510,000 Open Sun 1PM - 5PM

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

  1143 Bobcat Chase Blvd, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Take advantage of a 1% of the loan amount lender credit towards buy downs or closing costs when utilizing our preferred lender. Looking for a stunning 3-bedroom, 2.5-bathroom home with a spacious 2-car garage, built in 2020 and thoughtfully designed for today’s lifestyle?From the moment you arrive, you’ll be greeted by a serene water view in

  

  Vincent Cordaro

  SERHANT

  (321) 567-1890

  1143 Bobcat Chase Blvd, Oakland, FL 34787
• 

  

  /16

  $1,465 - $3,190 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

  $375,000 Sold Aug 27, 2025

  • 1,620 Sq Ft
  • $231/SF
  • 22 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  5840 Meditation Dr, Oakland, FL 34787

  Under Construction. Refresh your lifestyle with the Wilshire! This magnificent townhome covers two stories and includes three bedrooms, two and one-half bathrooms and a two-car rear load garage. Front door opens onto the spacious open concept combination living room and dining room. There is also a laundry room with washer and dryer and a fully equipped kitchen that leads to an enticing patio.

  Ben Goldstein LENNAR REALTY

  5840 Meditation Dr, Oakland, FL 34787
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  /31

  Est $465,098 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
• 

  

  /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
• 

  

  /8

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,451 Sq Ft
  • Condo for Rent

  12028 Holystone St, Oakland, FL 34787

  ATTENTION GOOD RENTERS!! COME TO SHOW THIS WONDERFUL OPORTUNITY FOR RENT YOUR DREAM TOWNHOUSE IN WINTER GARDEN. THE COMMUNITY IS BEAUTIFUL, GREAT SCHOOLS, GREAT AREAS FOR LIVING. ONCE YOU ENTER TO THE PROPERTY, YOU WILL FEEL LIKE YOU ARE AT HOME. THE DISTIBUTION ON FIRST FLOOR IS NICE BECAUSE YOU WILL SEE THE FAMILY ROM, DINING ROOM AND KITCHEN ALL INTEGRATED IN ONE OPEN SPACE. THE SECOND FLOOR

  Maria G Camacho ORLANDO KEY REALTY LLC

  12028 Holystone St, Oakland, FL 34787
• 

  /2

  $439,990 Sold Aug 25, 2025

  • 1,753 Sq Ft
  • $251/SF
  • 52 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2018

  2405 Standing Rock Cir, Oakland, FL 34787

  Beautifully maintained 3-bedroom, 2.5-bath home featuring inviting outdoor and indoor living spaces. Enjoy the convenience of a garage, providing ample parking and storage options. The second floor offers a large, versatile area ideal for a family room, home office, playroom, or media space. Inside, you'll find a comfortable and functional layout with a bright and airy atmosphere, perfect for

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  2405 Standing Rock Cir, Oakland, FL 34787
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  /49

  Est $597,173 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
• 

  

  /38

  $645,000 Pending

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

  829 Cura Ct, Oakland, FL 34787

  Under contract-accepting backup offers. Discover this fantastic 4-bedroom, 3-bathroom home located at 829 Cura Ct in beautiful Oakland, Florida. This property offers an incredible ********SOLOR energy system installed in 2021 that's completely PAID IN FULL********, meaning you can enjoy virtually no electric bills.The home features attractive laminate flooring throughout and has been

  

  Deanna Meredith

  LUXE PROPERTIES LLC

  (321) 326-9187

  829 Cura Ct, Oakland, FL 34787
• 

  

  /10

  $745 per month

  • 1 Bed
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  501 W Herriot Ave, Oakland, FL 34760

  Move into a comfortable House today! Newly-renovated and comfortable, this is the perfect place to call home. The kitchen comes equipped with a fridge, sink, oven, stovetop, as well as upgraded appliances, making it the perfect spot to whip up a meal or two.The neighbourhood is near the Florida turnpike and it is on a small dead-end street so the area is quiet.

  501 W Herriot Ave, Oakland, FL 34760
• 

  /2

  $853,595 Sold Aug 22, 2025

  • 3,300 Sq Ft
  • $259/SF
  • 26 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  5320 Citrus Leaf Blvd, Oakland, FL 34787

  Brand new, energy-efficient home ready NOW! No side neighbors. This functional floorplan has a spacious family room that’s open to an expansive kitchen. A combination dining and living room provides ideal space for indoor entertaining or moving the party outdoors to the private lanai. Now selling from the mid $500's, Silverleaf Reserve offers spacious open floorplan concepts fit for every

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  5320 Citrus Leaf Blvd, Oakland, FL 34787
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  /32

  Est $450,074 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
• 

  

  /47

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft

  2375 Standing Rock Cir, Oakland, FL 34787

  Welcome to your perfect blend of serenity and convenience! This stunning 3-bedroom, 2.5-bath home offers over 2,000 square feet of living space and more than 3,200 square feet total. Situated on a corner lot, built in 2018, with a recently re-painted exterior and paid off solar panels, this home has curb appeal. The beautifully maintained property sits just steps from the West Orange Trail and

  

  Jarred Denison

  POP REALTY POWERED BY SELLSTATE

  (321) 415-7083

  2375 Standing Rock Cir, Oakland, FL 34787
• 

  

  /22

  $4,400 per month

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft
  • House for Rent

  16207 Point Rock Dr, Oakland, FL 34787

  BRAND NEW HOME!! Welcome to The Torrey in Waterleigh, Winter Garden – a spacious two-story home featuring 5 bedrooms, 4.5 bathrooms, and a versatile open-concept design. The gourmet kitchen offers a large island, walk-in pantry, and stainless steel appliances, flowing seamlessly into the dining area, family room, and covered lanai. A private den with French doors and powder room provide flexible

  Cristiano Gomes De Almeida AUTHENTIC REAL ESTATE TEAM

  16207 Point Rock Dr, Oakland, FL 34787
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  /2

  $625,000 Sold Aug 20, 2025

  • 2,060 Sq Ft
  • $303/SF
  • 39 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2018

  2390 Standing Rock Cir, Oakland, FL 34787

  Stunning 3-Bedroom Home with Upgraded Outdoor Oasis in Oakland TrailsWelcome to this immaculate 3-bedroom, 2.5-bathroom home nestled in the highly sought-after Oakland Trails community in Oakland, Florida steps away from the West Orange Trail. Boasting a beautifully maintained living space, this move-in-ready home combines comfort, elegance, and modern upgrades throughout.Step

  Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC

  2390 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,794 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /33

  $514,913

  • 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

  $2,800 per month

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

  10678 Words Dr, Oakland, FL 34787

  The most desirable townhome floorplan in the community! This gorgeous Townhome features 4 bedrooms, a Master Suite on the first floor,beautifully upgraded tile floor. Great private area on the back all covered with bricks and two cars garage. The owner will pay HOA, which covers the lawn maintenance! The clubhouse has an incredible swimming pool, splash zone, fitness center, basketball court,

  Renato Oliveira LA ROSA REALTY LLC

  10678 Words Dr, Oakland, FL 34787
• 

  /2

  $400,000 Sold Aug 18, 2025

  • 1,795 Sq Ft
  • $223/SF
  • 31 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  5693 Meditation Dr, Oakland, FL 34787

  Under Construction. Welcome to the refreshing 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.

  Ben Goldstein LENNAR REALTY

  5693 Meditation Dr, Oakland, FL 34787
• 

  /2

  Est $631,648 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,908 Sq Ft

  12891 Westhaven Oak Dr, Oakland, FL 34787

  12891 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  /64

  $749,999

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

  1301 Johns Cove Ln, Oakland, FL 34787

  Back on the market! 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 own private boat ramp, providing access to

  

  Heidi Pfeffer-Morgan

  DALTON WADE INC

  (321) 327-9550

  1301 Johns Cove Ln, Oakland, FL 34787
• 

  

  /54

  $4,500 per month

  • 5 Beds
  • 3 Baths
  • 3,359 Sq Ft
  • House for Rent

  11168 Robert Frost Dr, Oakland, FL 34787

  Lake home - Fully Furnished home for rent just minutes from Disney.Enjoy comfort and convenience in this beautifully furnished home with gorgeous water view , perfectly located close to the magic of Disney yet set in a quiet area away from the hustle and bustle. With no rear neighbors, you’ll have complete privacy and a peaceful atmosphere.The spacious loft is perfect for relaxing

  Iluska Kruse ORLANDO BROTHERS REAL ESTATE LLC

  11168 Robert Frost Dr, Oakland, FL 34787
• 

  /2

  $915,000 Sold Aug 15, 2025

  • 2,683 Sq Ft
  • $341/SF
  • 94 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2022

  908 Tilden Oaks Trail, Winter Garden, FL 34787

  In the enchanting enclave of Oakland Park lies a home that seamlessly marries design with tranquility—welcome to 908 Tilden Oaks Trail. This Rockwell Homes masterpiece is more than just a residence; it is an experience of sophisticated living, smart-home innovation, and breathtaking natural beauty.As you approach, a serene landscape unfolds before you, with no neighbors to the front or

  Matt McKee COMPASS FLORIDA LLC

  908 Tilden Oaks Trail, Winter Garden, FL 34787
• 

  

  /9

  Est $439,852 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
• 

  

  /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
• 

  

  /21

  $2,700 per month

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

  13982 Title Way, Winter Garden, FL 34787

  Welcome to this spacious 4-bedroom, 3-bathroom townhome nestled in Winter Garden's desirable Storey Grove community. This almost 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. There is also a private courtyard between the home and the etached garage. Storey Grove offers an

  Sharon Paramo MACK 1 REALTY GROUP

  13982 Title Way, Winter Garden, FL 34787
• 

  /2

  $585,000 Sold Aug 13, 2025

  • 1,995 Sq Ft
  • $293/SF
  • 50 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  1740 Standing Rock Cir, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Exceptional POOL HOME with SOLAR PANELS and Many Other ENERGY-EFFICIENT FEATURES!Welcome to a home that truly impresses from the moment you arrive. As you step inside, you’re greeted by seamless WOOD PLANK TILE FLOORING that flows throughout the home, creating a warm and cohesive aesthetic. The heart of the home is a show-stopping kitchen

  Melissa Vance MAINFRAME REAL ESTATE

  1740 Standing Rock Cir, Oakland, FL 34787
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  /2

  Est $454,630 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
• 

  

  /27

  $829,207 Open Sun 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
• 

  

  /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

  $2,454,640 Sold Aug 08, 2025

  • 4,778 Sq Ft
  • $514/SF
  • 0 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2026

  1186 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious,open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family livingand entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas,

  Alexis Anderson REGENCY REAL ESTATE LLC

  1186 Water Maple Dr, Oakland, FL 34787
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  /4

  Est $859,019 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
• 

  

  /44

  $489,000 Open Sun 1PM - 2PM

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

  2163 White Feather Loop, Winter Garden, FL 34787

  ***Seller is offering $10,000 closing cost contribution to any buyer!***This recently built energy-efficient home, constructed by Meritage Homes in September 2019, boasts approximately $15,000 in furnishings, artwork, and pendant lighting—all negotiable with the purchase! Enjoy a large, covered front porch and a spacious open first floor. Upon entering, you'll find wood-look grey tile flooring

  Joshua Earley OPTIMA ONE REALTY, INC.

  2163 White Feather Loop, Winter Garden, FL 34787
• 

  

  /69

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft
  • Townhouse 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

  $810,000 Sold Aug 01, 2025

  • 2,720 Sq Ft
  • $298/SF
  • 76 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  3182 Sailing Pier Ave, Oakland, FL 34787

  ***Motivated Sellers just reduced more than $50K BELOW RECENT APPRAISAL!!!*** Welcome home to this 2024 built custom Pulte luxury pool home nestled within the highly desirable gated community of Estates at Lakeview Preserve in Winter Garden. This practically brand new 3 bedroom, 2.5 bathroom, with office/flex room, home offers an impressive array of features that combine elegance and comfort.

  Ron Howell, II EXP REALTY LLC

  3182 Sailing Pier Ave, Oakland, FL 34787
• 

  /2

  Est $443,610 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  6519 Glory Bower Dr, Oakland, FL 34787

  6519 Glory Bower Dr, Oakland, FL 34787

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