Oakland, FL Homes

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  $360,000

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

  1318 Painted Bunting Ave, Oakland, FL 34760

  One or more photo(s) has been virtually staged. You’re going to love this beautifully maintained 2-bedroom, 2.5-bath Townhome in the highly desirable Longleaf At Oakland which is perfectly located just a 1/2 mile from the Florida Turnpike, offering easy access to everything Central Florida has to offer. The entire interior was freshly painted in March 2026, giving the home a bright, fresh feel

  

  Randy Adams

  RE/MAX TOWN & COUNTRY REALTY

  (689) 399-4178

  1318 Painted Bunting Ave, Oakland, FL 34760
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  /20

  $2,400 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
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  $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

  Current Estimated Value $358,206

  Last Listing Agent Jennifer Ibarra REAL BROKER, LLC

  507 W Oakland Ave, Oakland, FL 34760
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  Est $785,631 Not Listed For Sale

  16685 Oakboro St, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,227 Sq Ft
  • Built 2021

  16685 Oakboro St, Oakland, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $242/SF
  • 72 Days On Market

  • Last Sold Price $780,000
  • May 06, 2025

  Last Listing Agent Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY
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  $849,000

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

  624 Hull Island Dr, Oakland, FL 34787

  Discover a rare opportunity to own a private estate property in one of West Orange County’s most desirable corridors. Situated in Oakland, this 2.55-acre parcel offers space, privacy, and future potential just minutes from the conveniences of West Colonial Drive, Florida Turnpike (Exit 275), Clermont, and the vibrant districts of Oakland and Downtown Winter Garden. Properties like this are

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 449-7661

  624 Hull Island Dr, Oakland, FL 34787
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  /16

  Starting at $1,466

  Total Monthly Price

  • 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.

  AVENUE ON OAKLAND

  (352) 717-7596

  

  751 W Oakland Ave, Oakland, FL 34787
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  $672,590 Sold Mar 05, 2026

  4743 Forest Haven Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,946 Sq Ft
  • Built 2026

  Last Sold Summary

  • $228/SF
  • 0 Days On Market

  Current Estimated Value $471,000

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  4743 Forest Haven Way, Oakland, FL 34787
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  Est $734,339 Not Listed For Sale

  3394 Buoy Cir, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,747 Sq Ft
  • Built 2021

  3394 Buoy Cir, Oakland, FL 34787

  Last Sold Summary

  • 5% Above List Price
  • $187/SF
  • 453 Days On Market

  • Last Sold Price $701,000
  • May 02, 2025

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP
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  $975,000 Pre-Foreclosure

  • 7 Beds
  • 4.5 Baths
  • 4,720 Sq Ft

  5074 Breezy Acres St, Oakland, FL 34787

  MOVE-IN READY | EASY OWNER FINANCING AVAILABLE | FURNITURE NEGOTIABLE WITH PURCHASE Welcome to an exceptional opportunity in the heart of Winter Garden’s highly sought-after Wincey Groves community. This beautifully upgraded Sweetwater model by Dream Finders Homes, built in 2021, offers over 4,700 square feet of refined living space with 7 bedrooms and 4.5 bathrooms, plus two additional flex

  

  Daniel Rodriguez

  NEW HEIGHTS REALTY GROUP

  (321) 471-0799

  5074 Breezy Acres St, Oakland, FL 34787
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  $3,500 Per Month

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

  15141 Summer Harvest St, Oakland, FL 34787

  is a newly built single-family home completed in 2024 featuring approximately 2,450 square feet of living space. The property offers 4 bedrooms and around 3.5 to 4 bathrooms, designed with a modern open-concept layout. It includes a spacious gourmet kitchen with a large island, stainless steel appliances, and granite countertops, along with a comfortable living area ideal for entertaining. The

  

  Elaine Garcia

  GARCIA REALTY GROUP

  (321) 252-2876

  15141 Summer Harvest St, 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 $603,397

  Last Listing Agent Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC

  2390 Standing Rock Cir, Oakland, FL 34787
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  Est $537,002 Not Listed For Sale

  1763 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2020

  1763 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $262/SF
  • 33 Days On Market

  • Last Sold Price $545,000
  • May 08, 2025

  Last Listing Agent Paulette Korr DALTON WADE INC
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  $635,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,445 Sq Ft

  16186 Honey Harvest St, Oakland, FL 34787

  Move-In Ready Luxury in Harvest at Ovation — Taylor Morrison Popular Baldwin Floor Plan. Sellers had change of plans. Brand new home available for immediate move-in! Why wait months to build when this stunning, just-completed Taylor Morrison Baldwin floor plan is ready for you right now? Located in the highly sought-after Harvest at Ovation community in Orlando, this exceptional 4-bedroom,

  

  Nicole Rader

  MAINFRAME REAL ESTATE

  (689) 303-5944

  16186 Honey Harvest St, Oakland, FL 34787
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  $2,715 Per Month

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • House for Rent

  27 Oakland Pointe Cir, Oakland, FL 34760

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2859.90. That covers your base rent, $2715.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  (321) 475-2523

  27 Oakland Pointe Cir, Oakland, FL 34760
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  $578,310 Sold Feb 12, 2026

  4759 Forest Haven Way, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 1,882 Sq Ft
  • Built 2025

  Last Sold Summary

  • $307/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  4759 Forest Haven Way, Oakland, FL 34787
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  Est $572,462 Not Listed For Sale

  2550 Standing Rock Cir, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,638 Sq Ft
  • Built 2018

  2550 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $220/SF
  • 137 Days On Market

  • Last Sold Price $580,000
  • Mar 08, 2024

  Last Listing Agent Monica Restrepo UNITED REALTY GROUP INC
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  $455,900 New Construction

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  15157 Aqua Sol Ln, Oakland, FL 34787

  Welcome to Del Webb Oasis, a gated community in Winter Garden's Horizon West, Get ready to live your best life in this vibrant, 55+ boutique community. It’s not just a home—it’s a feeling of pure community where every day is a chance to connect with your peers and jump into fun. Say goodbye to chores with our luxury, low-maintenance lifestyle and hello to endless activities! And the location?

  

  Jason Price

  RE/MAX SELECT GROUP

  (321) 486-6916

  15157 Aqua Sol Ln, Oakland, FL 34787
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  /22

  $3,149 Per Month

  • 3 Beds
  • 3.5 Baths
  • 1,894 Sq Ft
  • Townhouse for Rent

  6678 Juneberry Way, Oakland, FL 34787

  LIVE WHERE LIFESTYLE MEETS LOCATION • MOVE-IN READY • HEART OF HAMLIN Experience elevated living in this stunning three-story townhome in Parkview at Hamlin featuring 3 BEDROOMS, 2.5 BATHROOMS, and over 1,850 SQ FT of bright, modern space designed to impress. From the moment you walk through the 8’ entry door, you’re welcomed by a versatile FLEX SPACE perfect for a home office or gym, leading

  Marisol Goncalvez De Ayala AGENT TRUST REALTY CORPORATION

  6678 Juneberry Way, 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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  Est $623,051 Not Listed For Sale

  306 W Hull Ave, Oakland, FL 34760

  • 3 Beds
  • 2.5 Baths
  • 2,245 Sq Ft
  • Built 2020

  306 W Hull Ave, Oakland, FL 34760

  Last Sold Summary

  • 8% Above List Price
  • $256/SF
  • 74 Days On Market

  • Last Sold Price $575,000
  • Sep 30, 2024

  Last Listing Agent Justin Adams EXP REALTY LLC
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  $649,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  Biscayne Plan at Serenade at Ovation - Single Family Homes, 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

  14229 Lanyard Way Unit 36496529, Oakland, FL 34787
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  $2,850 Per Month

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • House 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

  10672 Words Dr, Winter Garden, FL 34787
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  $3,470,000 Sold Mar 12, 2026

  521 N Pollard St, Winter Garden, FL 34787

  • 5 Beds
  • 5.5 Baths
  • 4,808 Sq Ft
  • Built 2026

  Last Sold Summary

  • 35% Above List Price
  • $722/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  521 N Pollard St, Winter Garden, FL 34787
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  Est $427,780 Not Listed For Sale

  2289 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,744 Sq Ft
  • Built 2017

  2289 White Feather Loop, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 29 Days On Market

  • Last Sold Price $440,000
  • Jun 07, 2024

  Last Listing Agent Mandy Morgan TEAM DONOVAN
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  $603,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

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

  The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36464429, Oakland, FL 34787
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  $2,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft
  • Townhouse for Rent

  6224 Aralia Ivy Ln, Oakland, FL 34787

  Located in the heart of Horizon West and the Highly Desired Hamilton Gardens Community, this spacious open-concept 3-bedroom, 2.5-bath townhome blends modern convenience, smart-home technology, and resort-style community living. Easy access to 429, providing a smooth commute to Disney Parks, Universal, and all major Central Florida destinations also walkable to Hamlin Town Center, this home

  Yesenia Reyes ALL REAL ESTATE & INVESTMENTS

  6224 Aralia Ivy Ln, Oakland, FL 34787
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  $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 $971,556

  Last Listing Agent Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  1206 Civitas, Oakland, FL 34787
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  Est $476,395 Not Listed For Sale

  1793 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2017

  1793 White Feather Loop, Oakland, FL 34787

  Last Sold Summary

  • $228/SF
  • 105 Days On Market

  • Last Sold Price $475,000
  • Nov 25, 2024

  Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
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  $505,990 New Construction

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

  Cooper Plan at Serenade at Ovation - Bungalow, 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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  $2,950 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,094 Sq Ft
  • Coming Soon! Gorgeous Townhome For Rent in Horizon West Winter Garden just west of Disney off th...

  14387 Braemar St, Oakland, FL 34787

  Visit the full 360 Video here: Gorgeous Brand-New construction Townhome just west of Disney off the 429 located in the Highland Ridge subdivision, offers modern living at its finest!This spacious two-story, 4-bedrooms, 2.5 bathrooms, residence provides ample space for comfortable, energy efficient living under 2,114 sq ft. Enjoy the convenience of a fully equipped kitchen

  14387 Braemar St, Oakland, FL 34787
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  $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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  Not Listed For Sale

  16465 Hamlin View St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • Built 2025

  16465 Hamlin View St, Oakland, FL 34787

  Last Sold Summary

  • $293/SF
  • 0 Days On Market

  • Last Sold Price $538,491
  • Feb 27, 2025

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $375,000

  • 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
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  $3,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • House for Rent

  9588 Jacques Aly, Oakland, FL 34787

  Welcome to Waterleigh in the desirable area of Horizon West located in Winter Garden, FL. “Come Here and Stay” in this stunning community situated on over 1,400 acres of land with over a dozen lakes and ponds. Check out one of Waterleigh’s most popular bungalow floor-plans the Cordale offering 4 bedrooms, 2.5 bathrooms, and an attached 2 car garage. Enjoy the water view, while sitting on the

  Teresa Valdes VALSTAR REALTY LLC

  9588 Jacques Aly, Oakland, FL 34787
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  $455,000 Sold Dec 23, 2025

  2023 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $218/SF
  • 123 Days On Market

  Current Estimated Value $461,979

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  2023 White Feather Loop, Oakland, FL 34787
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  Not Listed For Sale

  16459 Hamlin View St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,078 Sq Ft
  • Built 2024

  16459 Hamlin View St, Oakland, FL 34787

  Last Sold Summary

  • $260/SF
  • 26 Days On Market

  • Last Sold Price $540,000
  • Apr 25, 2025

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $549,900

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

  2065 White Feather Loop, Oakland, FL 34787

  Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential

  Denis Bochkov PINK MIAMI REAL ESTATE

  2065 White Feather Loop, Oakland, FL 34787
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  /26

  $3,595 Per Month

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

  15663 Pelican Cay Dr, Oakland, FL 34787

  PRICE REDUCED – Now $3595 for immediate move-in! This well-maintained 2021-built home is located in the Waterleigh community in Winter Garden. The two-story layout includes 4 bedrooms and 3.5 bathrooms, including a private first-floor bedroom with an attached full bath, providing a flexible living arrangement. The open-concept main living area features a kitchen with stainless steel appliances

  Steven Koleno BEYCOME OF FLORIDA LLC

  15663 Pelican Cay Dr, Oakland, FL 34787
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  $465,597 Sold Dec 22, 2025

  17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,696 Sq Ft
  • Built 2025

  Last Sold Summary

  • $275/SF
  • 20 Days On Market

  Last Listing Agent Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787
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  Est $852,869 Not Listed For Sale

  932 Tilden Oaks Trail, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,362 Sq Ft
  • Built 2021

  932 Tilden Oaks Trail, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $355/SF
  • 6 Days On Market

  • Last Sold Price $837,500
  • Mar 20, 2025

  Last Listing Agent Tony Marino REAL LIVING R E SOLUTIONS

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