Oakland, FL Homes

• 

  

  /2

  Est $858,970

  Not Listed For Sale

  896 Tilden Oaks Trail, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,268 Sq Ft
  • Built 2022

  896 Tilden Oaks Trail, Winter Garden, FL 34787

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Rema Perras CORCORAN PREMIER REALTY
• 

  

  

  /3

  $411,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,729 Sq Ft

  Sage Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

  The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36488308, Oakland, FL 34787
• 

  

  /2

  $849,000

  Sold Jun 23, 2026

  624 Hull Island Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,708 Sq Ft
  • Built 1983

  Last Sold Summary

  • 15% Below List Price
  • $314/SF
  • 186 Days On Market

  Current Estimated Value $842,684

  Last Listing Agent Carmelo Nuccio RE/MAX EXCLUSIVE COLLECTION

  624 Hull Island Dr, Oakland, FL 34787
• 

  

  /2

  Est $769,884

  Not Listed For Sale

  9517 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft
  • Built 2024

  9517 Emerald Berry Dr, Oakland, FL 34787

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
• 

  

  

  /39

  $796,000

  $4K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,528 Sq Ft

  1970 Standing Rock Cir, Oakland, FL 34787

  Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1970 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  $785,000

  Sold Oct 24, 2025

  16152 Point Rock Dr, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $274/SF
  • 48 Days On Market

  Current Estimated Value $834,000

  Last Listing Agent Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16152 Point Rock Dr, Oakland, FL 34787
• 

  /2

  Est $576,954

  Not Listed For Sale

  15006 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,450 Sq Ft
  • Built 2024

  15006 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

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

  

  /57

  $585,000

  $45K PRICE DROP

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

  16186 Honey Harvest St, Oakland, FL 34787

  Move right into one of the most sought-after floor plans in Harvest at Ovation. This just-completed Taylor Morrison Baldwin model offers the rare opportunity to skip the build timeline and step into a never fully lived-in home loaded with designer upgrades and timeless style. Originally purchased as a long-term move, the sellers had a change of plans, creating an incredible opportunity for the

  Ken Pozek REAL BROKER, LLC

  16186 Honey Harvest St, Oakland, FL 34787
• 

  

  /52

  $580,000

  Sold Oct 31, 2025

  2642 Bobcat Chase Blvd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $320/SF
  • 38 Days On Market

  Current Estimated Value $573,333

  Last Listing Agent Johna Jennings Coastal Life Properties LLC

  2642 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $436,946

  Not Listed For Sale

  13461 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  13461 Princess St, Oakland, FL 34787

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
• 

  /2

  $3,399,000

  New Construction Pending

  • 5 Beds
  • 7 Baths
  • 5,092 Sq Ft

  515 N Nixon St, Oakland, FL 34787

  Set within the picturesque Briley Farm community in Oakland, Florida, this exceptional 5-bedroom, 7-bath estate offers an extraordinary blend of timeless design, spacious living, and resort-style amenities. Situated on an expansive 0.52-acre homesite, the residence encompasses approximately 5,092 square feet of beautifully designed living space, creating an ideal setting for both everyday living

  Alexis Anderson REGENCY REAL ESTATE LLC

  515 N Nixon St, Oakland, FL 34787
• 

  /2

  $420,000

  Sold Apr 30, 2026

  1227 Ridge Lake Way, Winter Garden, FL 34787

  • Land
  • 12,196 Sq Ft
  • $1,500,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 69 Days On Market

  Last Listing Agent Dawn Pickard THE C SMITH REAL ESTATE GROUP LLC

  1227 Ridge Lake Way, Winter Garden, FL 34787
• 

  /2

  Est $1,235,977

  Not Listed For Sale

  914 Tilden Oaks Trail, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,803 Sq Ft
  • Built 2022

  914 Tilden Oaks Trail, Winter Garden, FL 34787

  Last Sold Summary

  • 114 Days On Market

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC
• 

  

  /56

  $619,000

  New Construction $130K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  38 S Pollard St, Oakland, FL 34760

  NEW PRICE IMPROVEMENT! Seller incentive available!Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and

  Cassia Barros MS LAND & BUILDING LLC

  38 S Pollard St, Oakland, FL 34760
• 

  /2

  $1,200,000

  Sold Mar 10, 2026

  1120 Civitas Way, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,563 Sq Ft
  • Built 2022

  Last Sold Summary

  • $468/SF
  • 4 Days On Market

  Current Estimated Value $1,193,920

  Last Listing Agent Ashlen Hayward OAK AVENUE REAL ESTATE LLC

  1120 Civitas Way, Winter Garden, FL 34787
• 

  /2

  Est $651,690

  Not Listed For Sale

  14219 Spring Garden Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,179 Sq Ft
  • Built 2024

  14219 Spring Garden Dr, Oakland, FL 34787

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /13

  $2,615,320

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 4,658 Sq Ft

  1152 Prado Ln, Winter Garden, FL 34787

  Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own

  Alexis Anderson REGENCY REAL ESTATE LLC

  1152 Prado Ln, Winter Garden, FL 34787
• 

  /2

  $914,390

  Sold Nov 25, 2025

  4649 Golden Birch Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2025

  Last Sold Summary

  • $214/SF

  Current Estimated Value $927,546

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

  4649 Golden Birch Ave, Oakland, FL 34787
• 

  /2

  Est $1,252,321

  Not Listed For Sale

  15281 Arcadia Bluff Loop, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,115 Sq Ft
  • Built 2020

  15281 Arcadia Bluff Loop, Oakland, FL 34787
• 

  

  /3

  $1,032,000

  New Construction $23K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 3,894 Sq Ft

  12904 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026 The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a

  Dayene Grubert ORLANDO TBI REALTY LLC

  12904 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  /98

  $1,050,000

  Sold Sep 10, 2026

  806 Johns Point Dr, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 3,552 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $296/SF
  • 26 Days On Market

  Current Estimated Value $1,040,216

  Last Listing Agent Laura Romot GILKEY REAL ESTATE

  806 Johns Point Dr, Oakland, FL 34787
• 

  

  /9

  Est $423,993

  Not Listed For Sale

  10665 Words Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Built 2023

  10665 Words Dr, Oakland, FL 34787

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY
• 

  

  /31

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft

  14123 Frasier St, Oakland, FL 34787

  SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon

  Yornelly Sanchez Manrique LEVO REAL ESTATE LLC

  14123 Frasier St, Oakland, FL 34787
• 

  

  /36

  $751,000

  Sold Oct 03, 2025

  16041 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $265/SF
  • 26 Days On Market

  Taylor Morrison Harvest at Ovation

  16041 Honey Harvest St, Oakland, FL 34787
• 

  /2

  Est $436,876

  Not Listed For Sale

  6519 Glory Bower Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft
  • Built 2021

  6519 Glory Bower Dr, Oakland, FL 34787

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Michael McCourt EPOCH HOMES
• 

  /2

  $919,000

  New Construction Pending

  • 5 Beds
  • 4.5 Baths
  • 3,894 Sq Ft

  12940 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a

  Toll Brothers, Inc. Builder

  12940 Westhaven Oak Dr, Oakland, FL 34787
• 

  /2

  $695,000

  Sold Sep 22, 2025

  1281 Ridge Lake Way, Winter Garden, FL 34787

  • Land
  • 16,988 Sq Ft
  • $1,782,051 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 99 Days On Market

  Last Listing Agent Samantha Andrade KELLER WILLIAMS ELITE PARTNERS III REALTY

  1281 Ridge Lake Way, Winter Garden, FL 34787
• 

  /2

  Est $705,515

  Not Listed For Sale

  13234 Spring Grove Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • Built 2021

  13234 Spring Grove Way, Oakland, FL 34787

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Erica Diaz HOMEVEST REALTY
• 

  /2

  $858,120

  New Construction Pending

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

  15142 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

  15142 Tea Tree Dr, Oakland, FL 34787
• 

  /2

  $860,000

  Sold Jun 08, 2026

  9409 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $294/SF
  • 53 Days On Market

  Current Estimated Value $852,774

  Last Listing Agent Manuella Espinosa LA ROSA REALTY LLC

  9409 Emerald Berry Dr, Oakland, FL 34787
• 

  /2

  Est $521,777

  Not Listed For Sale

  14086 Frasier St, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2024

  14086 Frasier St, Oakland, FL 34787

  Last Sold Summary

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

  

  /78

  $2,700,000

  $150K PRICE DROP

  • 7 Beds
  • 6.5 Baths
  • 6,400 Sq Ft

  15522 Shorebird Ln, Oakland, FL 34787

  Welcome to an extraordinary estate in Lakeshore Preserve, this exceptional lakefront estate represents a rare convergence of scale, sophistication, and resort-inspired living. Crafted by Toll Brothers, this expanded Santa Bella model stands as one of the largest and most distinguished residences in the community, offering over 6,400 square feet, 7 bedrooms, and 6.5 bathrooms. A stately tile roof

  Jack Zhao EAST PEARL REALTY

  15522 Shorebird Ln, Oakland, FL 34787
• 

  /2

  $385,000

  Sold Mar 31, 2026

  8167 Mosaic Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,860 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $207/SF
  • 49 Days On Market

  Current Estimated Value $394,987

  Last Listing Agent Simon Colak USCO CAPITAL GROUP

  8167 Mosaic Ln, Oakland, FL 34787
• 

  /2

  Est $886,901

  Not Listed For Sale

  9122 Sonoma Coast Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,334 Sq Ft
  • Built 2021

  9122 Sonoma Coast Dr, Oakland, FL 34787

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Carla Trine MAINFRAME REAL ESTATE
• 

  

  /57

  $535,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  17167 Writing Aly, Oakland, FL 34787

  Under contract-accepting backup offers. Located in the heart of Horizon West, 17167 Writing Aly offers the space, flexibility, and location buyers are looking for in Winter Garden. Just minutes from Hamlin Town Center, the 429, Disney, and Downtown Winter Garden, this home is positioned in one of Central Florida’s fastest-growing areas while still offering a true neighborhood feel with community

  Ken Pozek REAL BROKER, LLC

  17167 Writing Aly, Oakland, FL 34787
• 

  /2

  $2,275,000

  Sold Nov 24, 2025

  530 Largovista Dr, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,798 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $474/SF
  • 110 Days On Market

  Current Estimated Value $2,273,761

  Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

  530 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $433,648

  Not Listed For Sale

  13460 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  13460 Princess St, Oakland, FL 34787

  Last Sold Summary

  • 159 Days On Market

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
• 

  

  /34

  $430,000

  New Construction

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

  11367 Great Rock St, Oakland, FL 34787

  Virtually Staged. **Virtually Staged | Tenant Occupied | Great Investment Opportunity**Beautiful two-story home in the desirable Storey Grove community in Winter Garden, currently rented for the full year—ideal for investors seeking immediate rental income.This home offers 3 bedrooms, 2.5 bathrooms, approximately 1,717 sq. ft. of living space, peaceful pond views, and a detached two-car

  Valquiria Gomes Pidgeon FLORIDA 360 REALTY LLC

  11367 Great Rock St, Oakland, FL 34787
• 

  /2

  $464,000

  Sold Oct 29, 2025

  2163 White Feather Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,744 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $266/SF
  • 65 Days On Market

  Current Estimated Value $465,918

  Last Listing Agent Joshua Earley EQUITY RENTAL MANAGEMENT

  2163 White Feather Loop, Winter Garden, FL 34787
• 

  /2

  Est $428,152

  Not Listed For Sale

  15169 Aqua Sol Ln, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  15169 Aqua Sol Ln, Oakland, FL 34787

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

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