Oakland, FL Homes

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  $505,990

  New Construction

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

  Cooper Plan at Serenade at Ovation - Bungalows, 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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  $3,500 Per Month

  • 4 Beds
  • 3 Baths
  • 2,181 Sq Ft
  • **Charming Upgraded 4-Bedroom Home for Rent in Waterleigh Community**

  16707 Oakboro St, Oakland, FL 34787

  Welcome to 16707 Oakboro Street, a beautifully maintained 4-bedroom, 3-bathroom single-family home located in the highly desirable Waterleigh community of Winter Garden. Built in 2021, this spacious one-story residence offers approximately 2,181 square feet of thoughtfully designed living space, combining modern finishes, an inviting open-concept layout, and the comfort and convenience today's

  16707 Oakboro St, Oakland, FL 34787
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  /2

  $768,700

  Sold Oct 28, 2025

  5780 Dancing Willow St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,575 Sq Ft
  • Built 2025

  Last Sold Summary

  • $215/SF

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

  5780 Dancing Willow St, Oakland, FL 34787
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  Not Listed For Sale

  5832 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Built 2025

  5832 Meditation Dr, Oakland, FL 34787

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $1,495,000

  Open Sat 12AM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,620 Sq Ft

  137 Petris Ave, Oakland, FL 34760

  FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking in the peaceful surroundings and views of the West Orange Trail just beyond your front door.Step inside to soaring spaces, abundant natural light, and architectural details that immediately make an impression. A grand

  Alexis Anderson REGENCY REAL ESTATE LLC

  137 Petris Ave, Oakland, FL 34760
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  /26

  $2,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft
  • House for Rent

  13742 Werrington Dr, Oakland, FL 34787

  Jensen Model Home come with 3 bedrooms, 2 ½ baths, and a detached alley-loaded 2-car garage. Enjoy the wide-open space of this Horizon West, where the family room and kitchen flow harmoniously. The sizable family room offers plenty of natural light with lots of windows. The kitchen features a large island with overhang for seating, the perfect spot for prepping dinner and for meals on the go. The

  Jiu Feng Wei AAA GLOBAL VENTURES PA

  13742 Werrington Dr, Oakland, FL 34787
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  /2

  $617,500

  Sold Aug 25, 2026

  3351 Hanging Tide St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,741 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $225/SF
  • 29 Days On Market

  Current Estimated Value $647,878

  Last Listing Agent Devon Sobers KELLER WILLIAMS ADVANTAGE III

  3351 Hanging Tide St, Oakland, FL 34787
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  Est $882,745

  Not Listed For Sale

  5320 Citrus Leaf Blvd, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2025

  5320 Citrus Leaf Blvd, Oakland, FL 34787

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Tatiana Souza DAVILA HOMES
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  /43

  $825,000

  $20K PRICE DROP Under Contract

  • 5 Beds
  • 4 Baths
  • 4,240 Sq Ft

  14001 Rugby St, Oakland, FL 34787

  Under contract-accepting backup offers. Virtually Staged. Price improved and ready for its next owner, this beautifully maintained pool home in the sought-after Verde Park community offers more than 4,240 square feet of thoughtfully designed living space on a beautiful 0.26-acre corner lot in one of Winter Garden’s most beloved communities. With 5 bedrooms and 4 bathrooms, the home delivers an

  Ann Mertens KELLER WILLIAMS ELITE PARTNERS III REALTY

  14001 Rugby St, Oakland, FL 34787
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  /20

  $2,750 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Townhouse for Rent

  12295 Bracco St, Winter Garden, FL 34787

  Energy-efficient home for rent in the desirable Highland Ridge community! This stunning 3-bedroom, 2.5-bathroom house offers 1,788 square feet of modern living space. The open kitchen boasts a large island that seamlessly flows into the spacious dining and family room, perfect for entertaining. Upstairs, you'll find a versatile loft area ideal for a home office or playroom. Split floor plan,

  12295 Bracco St, Winter Garden, FL 34787
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  $495,000

  Sold Aug 12, 2026

  1937 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,069 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $239/SF
  • 52 Days On Market

  Current Estimated Value $486,742

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  1937 Standing Rock Cir, Oakland, FL 34787
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  Not Listed For Sale

  2915 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft
  • Built 2025

  2915 Transformation Way, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $990,000

  $110K PRICE DROP Pending

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9849 Lost Creek Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Virtually Staged. ACCEPTING BACK UP OFFERS. Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience. From the moment

  Jennifer Ibarra REAL BROKER, LLC

  9849 Lost Creek Dr, Oakland, FL 34787
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  $3,350 Per Month

  • 4 Beds
  • 3 Baths
  • 2,117 Sq Ft
  • House for Rent

  16284 Admirals Cove Ln, Oakland, FL 34787

  Welcome home, this beautiful Single Story house is located at the highly desired Waterleigh neighborhood. The well kept like new home has a tall ceiling, 4 bedrooms, 3 full bathrooms with a 2 car garage, a screened in back patio. There is no carpet at the property. Publix super market is right outside of the main community entrance, Flamingo crossings, Hamlin Town Center is within 5min drive.

  Ping Song SUNSHINE GROUP USA, INC

  16284 Admirals Cove Ln, Oakland, FL 34787
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  /2

  $430,000

  Sold Mar 23, 2026

  2201 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $245/SF
  • 6 Days On Market

  Current Estimated Value $435,204

  Last Listing Agent Christine Anthony CHARLES RUTENBERG REALTY ORLANDO

  2201 Standing Rock Cir, Oakland, FL 34787
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  Not Listed For Sale

  2907 Transformation Way, Oakland, FL 34787

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

  2907 Transformation Way, Oakland, FL 34787

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $1,049,000

  $246K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,469 Sq Ft

  250 N Walker St, Oakland, FL 34760

  Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak

  Alaina DiMare COAST TO COAST REAL ESTATE PRO

  250 N Walker St, Oakland, FL 34760
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  $4,595 Per Month

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

  9240 Sylvan Wds St, Oakland, FL 34787

  Spectacular 5/4 with 3 car garage home. This home has all the bells and whistles for your enjoyment, Modern kitchen with open floor plan to family/living room and access to large screened in patio. Fenced backyard. Upstairs has a large Loft and 4 bedrooms including the spacious master bedroom/master bathroom. This home is a must see located in Watermark Sub-division with to many features to

  9240 Sylvan Wds St, Oakland, FL 34787
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  /2

  $710,000

  Sold Nov 04, 2025

  1301 Johns Cove Ln, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,495 Sq Ft
  • Built 2003

  Last Sold Summary

  • 14% Below List Price
  • $285/SF
  • 124 Days On Market

  Current Estimated Value $697,797

  Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

  1301 Johns Cove Ln, Oakland, FL 34787
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  Not Listed For Sale

  2883 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2025

  2883 Transformation Way, Oakland, FL 34787

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $550,000

  New Construction $47K PRICE DROP Pending

  • 3 Beds
  • 3.5 Baths
  • 2,149 Sq Ft

  14736 Field Daisy Dr, Oakland, FL 34787

  Under Construction. What's Special: Close to Amenities | Close to Trails | North Facing Lot | Popular Plan | Covered Extended Lanai. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Newberry at 14736 Field Daisy Drive in Harvest at Ovation! The Newberry bungalow floor plan is a true representation of modern living and the perfect space for all of

  Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  14736 Field Daisy Dr, 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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  $550,000

  Sold May 22, 2026

  1490 Stone Arrow Ct, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,248 Sq Ft
  • Built 2019

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 96 Days On Market

  Current Estimated Value $564,760

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  1490 Stone Arrow Ct, Oakland, FL 34787
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  Est $1,489,667

  Not Listed For Sale

  410 Briley Ave, Oakland, FL 34787

  • 6 Beds
  • 5.5 Baths
  • 6,428 Sq Ft
  • Built 2026

  410 Briley Ave, Oakland, FL 34787

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC
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  $879,999

  • 4 Beds
  • 3 Baths
  • 2,931 Sq Ft

  17882 Adrift Rd, Oakland, FL 34787

  Virtually Staged. Welcome to Waterleigh! This beautiful 2023-built, 4-bedroom, 3-bath home sits on a spacious lotwith a peaceful natural lake view from the backyard. Featuring an open-concept layout, modernkitchen, versatile loft, and private owner’s suite. Enjoy resort-style pools, clubhouses, fitnesscenters, tennis courts, trails, and playgrounds. Publix is conveniently located at

  Winnie Tam FLORIDA REALTY INVESTMENTS

  17882 Adrift Rd, Oakland, FL 34787
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  $2,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  2140 Standing Rock Cir, Winter Garden, FL 34787

  Beautiful, modern, and meticulously maintained home in the welcoming Oakland Trails community. Featuring an open-concept floor plan with 3 bedrooms, 2 full bathrooms, and 1 half bathroom, this home offers comfortable and stylish living spaces. The well-appointed kitchen features wood cabinetry, ample counter space, and a spacious island, creating the perfect setting for everyday living and

  Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

  2140 Standing Rock Cir, Winter Garden, FL 34787
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  /34

  $535,000

  Sold Sep 14, 2026

  1808 Western Trailway Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 2019

  Last Sold Summary

  • 11% Below List Price
  • $288/SF
  • 34 Days On Market

  Current Estimated Value $590,579

  Last Listing Agent Susan Koptieff FLORIDA IN MOTION REALTY INC

  1808 Western Trailway Dr, Oakland, FL 34787
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  Not Listed For Sale

  5884 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Built 2025

  5884 Meditation Dr, Oakland, FL 34787

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  /24

  $617,990

  New Construction

  • 3 Beds
  • 3 Baths
  • 2,278 Sq Ft

  Lexington w/ Bonus Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 3 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36473362, Oakland, FL 34787
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  /23

  $2,600 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,567 Sq Ft
  • Townhouse for Rent

  9496 Bauer Aly, Oakland, FL 34787

  Waterleigh Subdivision 3/2.5 Town Home For Rent in Winter Garden, Fl. 34787. Range, Refrigerator, D/W, Disposal, Central Heat and A/C, Call to schedule a showing. Brand New Construction, townhouse for rent, energy efficient , 3 bedroom, 2.5 bathrooms. 1 Car Garage and large driveway. Spacious 1,567 SqFt.; Features include laundry room, walk-in closet, linen closet, blinds, ceiling fans, dual sink

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  9496 Bauer Aly, Oakland, FL 34787
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  $449,990

  Sold Nov 13, 2025

  17687 Japonica Bloom Dr, Oakland, FL 34787

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

  Move in Ready Sold Summary

  • $265/SF
  • 15 Days On Market

  Ashton Woods Northlake at Ovation - Estate

  17687 Japonica Bloom Dr, Oakland, FL 34787
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  Not Listed For Sale

  6678 Juneberry Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,846 Sq Ft
  • Built 2025

  6678 Juneberry Way, Oakland, FL 34787

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Adam Schott DRB GROUP REALTY, LLC
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  /57

  $499,900

  $20K PRICE DROP Pending

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

  2766 Bobcat Chase Blvd, Oakland, FL 34787

  Welcome to Longleaf at Oakland by Pulte! Built in 2020, this move-in-ready three-bedroom, 2.5-bath home offers 1,811 square feet of stylish living space featuring brand-new luxury vinyl plank flooring throughout, fresh interior paint, quartz countertops, stainless steel appliances and an open-concept layout designed for comfortable everyday living and effortless entertaining. Located less than

  Andrea Endlein PREMIER SOTHEBYS INT'L REALTY

  2766 Bobcat Chase Blvd, Oakland, FL 34787
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  $2,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,994 Sq Ft
  • House for Rent

  13075 Spring Grove Way, Oakland, FL 34787

  Welcome to the heart of Horizon West where location, lifestyle, and low-maintenance living come together! This home features an open-concept main floor, which features sleek ceramic plank flooring throughout, giving the space a modern, polished feel that's perfect for everyday living. With a serene pond located in front of the home, you'll love waking up to the peaceful water view right outside

  Rodrigo Barbosa PREMIER FLAT FEE REALTY LLC

  13075 Spring Grove Way, Oakland, FL 34787
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  $500,000

  Sold Jul 21, 2026

  1264 Ridge Lake Way, Oakland, FL 34760

  • Land
  • 10,454 Sq Ft
  • $2,083,333 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1264 Ridge Lake Way, Oakland, FL 34760
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  Not Listed For Sale

  5860 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2025

  5860 Meditation Dr, Oakland, FL 34787

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $925,990

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 3,498 Sq Ft

  15184 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15184 Tea Tree Dr, Oakland, FL 34787
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  $5,500 Per Month

  • 5 Beds
  • 4.5 Baths
  • 3,653 Sq Ft
  • House for Rent

  15511 Shorebird Ln, Oakland, FL 34787

  Welcome to this open plan 5 Bedroom, 4 and a half bathroom water front home including a 3 car garage.Flooring includes tile, laminate and carpet. You will never run out of storage with the abundance of cabinets. Chef's kitchen include upgraded appliances and wall oven. Large sliders allow plenty of light and gorgeous water view and open to a covered lanai. Some of the amenities include a

  Mark Volchko REALTY WORLD PREFERRED

  15511 Shorebird Ln, Oakland, FL 34787
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  /2

  $446,340

  Sold Feb 25, 2026

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft
  • Built 2026

  Last Sold Summary

  • $204/SF

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

  Unlisted Address
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  Not Listed For Sale

  5307 Citrus Leaf Blvd, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2025

  5307 Citrus Leaf Blvd, Oakland, FL 34787

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Tatiana Souza DAVILA HOMES

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