Winter Garden, FL Homes for Sale under $500,000

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  /3

  $449,900

  • Land
  • 0.23 Acre
  • $1,956,087 per Acre

  1203 Ridge Lake Way, Winter Garden, FL 34787

  LOT 244: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1203 Ridge Lake Way, Winter Garden, FL 34787
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  /95

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,689 Sq Ft

  16626 Point Rock Dr, Winter Garden, FL 34787

  Beautiful nearly-new home in the sought-after Waterleigh community of Winter Garden! This stunning property seamlessly blends modern design and comfort, offering an exceptional living experience. Situated on a desirable corner lot, this home features 3 spacious bedrooms and 2 beautifully appointed bathrooms, providing ample space for relaxation and entertaining. All bedrooms have been upgraded

  Martonio Pinto AMERICAN HORIZONS REALTY

  16626 Point Rock Dr, Winter Garden, FL 34787
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  /21

  $409,000

  • 3 Beds
  • 2.5 Baths
  • 1,996 Sq Ft

  16180 Arbor Crest Aly, Winter Garden, FL 34787

  Enjoy this beautiful and spacious townhouse with a garage and a huge driveway, located in a charming full of nature neighborhood with a pool, gym, putt-putt golf,BBQ/Picnic area, dog park, tennis courts, beach volleyball court and many amazing lakes just 5 minutes walking from home! Feel the magic of Disney by being only minutes away and experiencing some of its fireworks at home! More than a

  Moe Mossa SAVVY AVENUE, LLC

  16180 Arbor Crest Aly, Winter Garden, FL 34787
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  /40

  $429,375

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

  13545 Pearl Beach St, Winter Garden, FL 34787

  PRICE REDUCTION!!! Just 2 miles from DISNEY! FURNISHED! 2025 like-new and under BUILDER'S WARRANTY! With HOA dues paid through September 2027 this amazing Del Webb Oasis villa combines convenience and peace of mind in an exceptional living experience, all with a superb location. Simple, convenient, and a GREAT VALUE!Put on your sunglasses as you step into this BRIGHT and airy home. So light

  Dustin Eshenroder IMAGINATION REALTY, INC

  13545 Pearl Beach St, Winter Garden, FL 34787
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  /21

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 1,696 Sq Ft

  9338 Tyrella Pine Trail, Winter Garden, FL 34787

  Beautiful 4 bedrooms, 2.5 bathrooms, 2 car garage home located in the desirable Watermark community in Winter Garden. Home is perfectly located near the clubhouse (5min walk distance), all tile on the first floor and tray ceiling in the master suite. Watermark has resort-like amenities that includes a pool with splash pad, playground, club house, fitness center, tennis court and nearby

  Mengshi Lu JOY ESTATE ENTERPRISE INC

  9338 Tyrella Pine Trail, Winter Garden, FL 34787
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  /40

  $435,000

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

  13562 Pearl Beach St, Winter Garden, FL 34787

  Welcome to this stunning, bright, airy nearly new villa (occupied for only a few months), offering 2 bedrooms, 2 full bathrooms, and a den/office, in the highly sought-after 55+ community of DEL WEBB OASIS, nestled in the heart of Horizon West - just five minutes from the magical Mickey arches of Walt Disney World. This move-in ready home boasts an open floor plan with high-end finishes

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  13562 Pearl Beach St, Winter Garden, FL 34787
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  /49

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  16125 Azure Key St, Winter Garden, FL 34787

  Welcome to your new home in the highly sought-after Waterleigh community of Horizon West! This charming single-story 3-bedroom, 2-bath home feels bright and inviting from the moment you walk in. The primary bedroom is a true retreat, with lots of natural light, direct access to the primary bath featuring dual sinks, a spacious shower, and a custom-designed walk-in closet. The heart of the home is

  Jessica Estrada KELLER WILLIAMS ADVANTAGE III

  16125 Azure Key St, Winter Garden, FL 34787
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  /19

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft

  12253 Bracco St, Winter Garden, FL 34787

  NEW! NEW! CONSTRUCTION! Move-in ready! You can be the very first to peel the plastic off the brand-new appliances! This beautiful energy-efficient home in the sought-after Highland Ridge community offers a spacious open floor plan perfect for modern living. The stylish kitchen features a large island overlooking a generous dining area and family room. Ideal for entertaining or everyday family

  Gil Semedo LIFESTYLE INTERNATIONAL REALTY

  12253 Bracco St, Winter Garden, FL 34787
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  /62

  $490,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  8024 Bluejack Oak Dr, Winter Garden, FL 34787

  Welcome to this cozy and modern 3-bedroom, 2.5-bath townhouse located in the highly sought-after Summerlake community of Winter Garden. Featuring a well-designed split floor plan. Upstairs, the owner suite is a private retreat with a walk-in closet, dual sinks, a stand-up shower, and a separate garden tub, while the additional bedrooms are positioned on the opposite side for added privacy. The

  Rachael Connors WEICHERT REALTORS HALLMARK PRO

  8024 Bluejack Oak Dr, Winter Garden, FL 34787
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  /3

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  15684 Orange Harvest Loop, Winter Garden, FL 34787

  Welcome to 15684 Orange Harvest Loop, a 3-bedroom, 2.5-bath townhouse with a loft, located in the highly desirable Hickory Hammock neighborhood of Winter Garden, Florida. Known for its charming architecture and resort-style amenities, Hickory Hammock offers an exceptional lifestyle in one of Winter Garden's most sought-after communities.This inviting townhouse features a bright, open floor

  Sue Piesik Charles Rutenberg Realty Inc

  15684 Orange Harvest Loop, Winter Garden, FL 34787
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  /25

  $450,000

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

  12004 Holystone St, Winter Garden, FL 34787

  This townhome is sure to impress with an open floor plan, loads of natural light and a delightful kitchen. Upon entering the home, you immediately see the spacious downstairs open floor plan with a living room, dining and kitchen all seamlessly flowing into the other. The kitchen boasts granite counter, breakfast bar and a closet pantry. The openness allows for ease of entertaining. A half

  Beth Logullo KELLER WILLIAMS WINTER PARK

  12004 Holystone St, Winter Garden, FL 34787
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  /35

  $482,000

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  10231 Meadow Brook Dr, Winter Garden, FL 34787

  This is a perfect family home with 3 bedrooms and 2 bathrooms. It features a spacious living and dining room with a nightly view of Disney fireworks. Conveniently located directly across from great amenities, including a Resort-Style Pool, Clubhouse, Community classes, Gym, community garden, Sports Fields, walking distance to Nature Trails, an Outdoor Exercise/Fitness Station, a Tot lot, a Dog

  Tabatha Pera-Alves A BETTER CHOICE REALTY, INC.

  10231 Meadow Brook Dr, Winter Garden, FL 34787
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  /25

  $451,090 New Construction

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

  15843 Gem View St, Winter Garden, FL 34787

  Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  15843 Gem View St, Winter Garden, FL 34787
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  /27

  $456,496 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

  13282 Serene Glade Rd, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Under Construction. Sample Images Harbor Town Home – Stylish End Unit Living Beautiful end-unit townhome offering 1,644 sq. ft. of thoughtfully designed living space, featuring three bedrooms, two and a half baths, and a spacious two-car garage with a charming paver driveway. Step inside to impressive tall ceilings, enhancing the natural light and

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  13282 Serene Glade Rd, Winter Garden, FL 34787
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  $469,000

  • 4 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  12049 Bracco St, Winter Garden, FL 34787

  Beautiful home on one of the largest lots in the community! This unique property offers over 21 feet of space from each side neighbor, providing extra privacy and comfort. Ideally located close to the clubhouse, with top-rated schools, easy access to shopping, dining, major highways, and just minutes from Disney parks.Whether you are an investor or a homebuyer, this home is a perfect choice.

  Bruna Canesin Motta PRISTINE INTERNATIONAL REALTY LLC

  12049 Bracco St, Winter Garden, FL 34787
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  /9

  $456,635 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  13278 Serene Glade Rd, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Under Construction. Sample ImagesPorter Town Home – Stylish Living Beautiful townhome offering 1,715 sq. ft. of thoughtfully designed living space, featuring three bedrooms, two and a half baths, and a spacious two-car garage with a charming paver driveway. Step inside to impressive tall ceilings, enhancing the natural light and creating a bright,

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  13278 Serene Glade Rd, Winter Garden, FL 34787
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  /30

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft

  14501 Grove Resort Ave Unit 1617, Winter Garden, FL 34787

  Complete turnkey unit with prime views to the lake, pool and Disney parks area. One of the few units that allow to enjoy the nightly fireworks from the balcony. The Grove Resort & Water Park, Orlando's newest luxury vacation home community offers owners privacy and convenience with a full suite of amenities including multiple bars and restaurants, full service spa, water park, breathtaking

  Marco Rangel CENTURY 21 Tenace Realty

  14501 Grove Resort Ave Unit 1617, Winter Garden, FL 34787
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  /45

  $439,900

  • 3 Beds
  • 2.5 Baths
  • 1,829 Sq Ft

  16154 Treadwell St, Winter Garden, FL 34787

  Step inside this Winter Garden stunner and feel your shoulders drop. Everything about this upgraded and move in ready, 3 bedroom, 2.5-bath Hawksmoor townhome whispers comfort, style, and ease. Just bring your clothes. The furnishings are included! The moment you enter, sunlight pours across the upgraded luxury vinyl plank floors, and the entire main living space feels warm and inviting. The

  Addie Owens TOUCHSTONE REAL ESTATE

  16154 Treadwell St, Winter Garden, FL 34787
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  /28

  $400,000

  • 4 Beds
  • 3 Baths
  • 2,037 Sq Ft

  11018 Hanlon Terrace Aly, Winter Garden, FL 34787

  Beautiful 2019 built townhome located in sought after Winding Bay Preserve. Located just 10 minutes south of Hamlin area’s shopping, dining and movie theater. Beautiful resort style amenities! Pool, playground, dog park and fitness park provide year round entertainment. The home features a first floor bedroom. Perfect for guests or in-laws. The first floor continues into the open common areas.

  Dane Moore KELLER WILLIAMS SUBURBAN TAMPA

  11018 Hanlon Terrace Aly, Winter Garden, FL 34787
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  /72

  $420,000

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  14501 Grove Resort Ave Unit 2407, Winter Garden, FL 34787

  Experience the ultimate resort lifestyle at The Grove Resort & Water Park!This luxurious 3-bedroom, 2-bathroom fully furnished condo is more than a home – it’s a vacation destination and an incredible investment opportunity. Located just minutes from Walt Disney World®, this unit offers a spacious layout, elegant finishes, and breathtaking resort amenities.Indulge in Surfari Water Park

  Nancy Gittens De Jimenez BARTO REAL ESTATE LLC

  14501 Grove Resort Ave Unit 2407, Winter Garden, FL 34787
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  /36

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,751 Sq Ft

  5685 New Independence Pkwy, Winter Garden, FL 34787

  Welcome to this newly UPDATED and uniquely UPGRADED 3-bedroom, 2.5-bath END-UNIT townhome in the highly sought-after New Independence/Signature Lakes community of Winter Garden, where thoughtful improvements, stylish finishes, and an unbeatable location come together to say WELCOME HOME! Major updates begin with a newly PAINTED EXTERIOR (2024) and continue inside with FRESH INTERIOR PAINT (2024),

  Jennifer Wemert WEMERT GROUP REALTY LLC

  5685 New Independence Pkwy, Winter Garden, FL 34787
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  /77

  $450,000

  • 4 Beds
  • 3 Baths
  • 1,853 Sq Ft

  15479 Sugar Citrus Dr, Winter Garden, FL 34787

  Motivated Seller, bring all offers! Recent price reduction just taken. This vacant, move-in ready townhome is an incredible opportunity—schedule your private tour today and make it yours! For questions or to arrange a showing, call or text the owner/agent directly. This beautifully renovated 4-bedroom, 3-bath townhome in Hamlin Reserve offers the perfect blend of city living, comfort, and

  Ivelisse Gonzalez Almanzar, PA ALLIANCE REALTY ENTERPRISES INC

  15479 Sugar Citrus Dr, Winter Garden, FL 34787
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  /44

  $460,000

  • 3 Beds
  • 3 Baths
  • 1,544 Sq Ft

  14501 Grove Resort Ave Unit 2101, Winter Garden, FL 34787

  Experience resort-style living and exceptional investment potential with this luxurious first floor condo located in The Grove Resort & Water Park, Orlando’s premier vacation destination. Ideally situated just 5 minutes from Walt Disney World, this fully furnished, turnkey residence offers a perfect combination of elegance, comfort, and convenience. Notice the Soaring Ceilings in this beautiful

  Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

  14501 Grove Resort Ave Unit 2101, Winter Garden, FL 34787
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  /24

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,154 Sq Ft

  711 Burch Ave, Winter Garden, FL 34787

  Welcome to this lovely 3-bedroom, 2-bath home, just minutes from the heart of Downtown Winter Garden. Freshly painted inside and out, with a brand-new kitchen countertop, it feels fresh, modern, and move-in ready. The layout is cozy and practical—perfect for families or anyone looking to enjoy all the charm and convenience of Winter Garden living.One great bonus is the additional room with

  Carina Davis LAKESIDE REALTY WINDERMERE INC

  711 Burch Ave, Winter Garden, FL 34787
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  /57

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 1,655 Sq Ft

  14971 Apollo Bond Dr, Winter Garden, FL 34787

  This luxurious townhouse, built in 2019, is located in the Watermark Community in Horizon West, known for its top-rated A schools. The home has an open floor plan with tile flooring, kitchen with 42" cabinets, granite countertops, and a butler's pantry. Upstairs, you'll find three bedrooms, including a master suite with dual sinks, a walk-in shower, and a walk-in closet. A private bricked lanai

  Adriana Lima WRA BUSINESS & REAL ESTATE

  14971 Apollo Bond Dr, Winter Garden, FL 34787
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  /36

  $456,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  9428 Bolshoi Aly, Winter Garden, FL 34787

  Under Construction. Discover this stunning new construction townhome at 9428 Bolshoi Alley in Winter Garden! This thoughtfully designed home features 3 bedrooms, 2.5 bathrooms, a flex room, a 2-car detached garage, and more. This townhome's design emphasizes functionality and comfort throughout. The open-concept living area creates seamless transitions between spaces, making it ideal for both

  Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

  9428 Bolshoi Aly, Winter Garden, FL 34787
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  /10

  $472,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  Lila II Plan at Osprey Ranch - 32'/40' Single Family, Winter Garden, FL 34787

  Private primarysuite with bath and walk-in closet. Beautiful kitchen with plenty of counterspace for entertaining. Open dining area and great room near kitchen. Covered lanai off dining area for enjoying outdoors. Rear 2-car garage with access to laundry room.

  K. Hovnanian Homes Builder

  15221 Blue Peacock Ln Unit 36450266, Winter Garden, FL 34787
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  /6

  $429,990

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft

  15066 Book Club Rd, Winter Garden, FL 34787

  Beautiful move in ready 3 Bedroom 2.5 Bathroom Townhome in Storey Grove. Ground floor features formal living and dining areas with beautiful soft grey walls and easy care tile. The guest bathroom features modern cabinets, solid surface countertops and storage closet. The family room is just off the kitchen which has modern cabinets, solid surface countertops, custom tile backsplash and stainless

  Lidia Barberini AGENT TRUST REALTY CORPORATION

  15066 Book Club Rd, Winter Garden, FL 34787
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  /42

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft

  15412 Amberbeam Blvd, Winter Garden, FL 34787

  Welcome to your future beautifully updated home in Stoneybrook West—one of the most sought-after communities in the Winter Garden area! This cozy home sits directly on the golf course, offering peaceful views and a lifestyle that blends comfort, recreation, and convenience. Located within a 24-hour guard-gated community, residents enjoy an impressive array of amenities, including private lake

  Jasmine Abdallah PREFERRED REAL ESTATE BROKERS II

  15412 Amberbeam Blvd, Winter Garden, FL 34787
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  /6

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  10534 Tribute Dr, Winter Garden, FL 34787

  This stunning and spacious townhome will exceed all expectations! Built in 2023 and designed with modern living in mind, this 3-bedroom, 2.5-bath home feels like a model property and offers the perfect blend of style, comfort, and investment potential. The first floor showcases an open-concept design with upgraded tile flooring, a beautifully appointed kitchen featuring solid-surface countertops,

  Solon Potenciano Silva, Jr LEGACY PLUS REALTY

  10534 Tribute Dr, Winter Garden, FL 34787
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  /59

  $489,000

  • 3 Beds
  • 3 Baths
  • 1,955 Sq Ft

  14010 Scarlet Aster Aly, Winter Garden, FL 34787

  Experience modern luxury in this beautifully crafted like new townhome by RockWell Homes. The Edison floor plan offers three spacious bedrooms, three stylish bathrooms, and a two car garage. Thoughtfully designed for comfort and outdoor enjoyment, it includes a welcoming front porch, a covered balcony, a rear patio, and an inviting outdoor living area with a beautiful view of the pond and nightly

  Ana Afshin GERMEROTH REALTY LLC

  14010 Scarlet Aster Aly, Winter Garden, FL 34787
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  /36

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft

  6108 Lewis And Clark Ave, Winter Garden, FL 34787

  AMAZING HOME in WINTER GARDEN, set in Signature Lakes, within the INDEPENDENCE COMMUNITY of Horizon West. This single-story residence was recently remodeled and is move-in ready, with new laminate flooring in all three bedrooms, fresh interior and exterior paint, a new irrigation system and new garage door springs. The location is excellent, in South Winter Garden, just minutes from Hamlin, where

  Marilu Drummond AMG INTERNATIONAL REALTY

  6108 Lewis And Clark Ave, Winter Garden, FL 34787
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  /20

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,874 Sq Ft

  2337 Farnham Dr, Ocoee, FL 34761

  One of the best locations in Ocoee! Fantastic one level newer single-family home with 3 bedrooms plus office or possible 4 th bedroom in beautiful, nicely maintained gated community of Preserve at Crown Pointe. All stainless appliances stay!Nice storage and open concept floorplan with large stone counter for bar chair option. This home sits on one of the few almost 1/3 acre CUL DE SAC PRIME lots

  Brigitte Knott CHARLES RUTENBERG REALTY ORLANDO

  2337 Farnham Dr, Ocoee, FL 34761
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  /14

  $420,000

  • Land
  • 0.26 Acre
  • $1,615,385 per Acre

  1161 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

  1161 Prado Ln, Oakland, FL 34787

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