Oakland, FL Homes

• 

  

  /2

  $840,000 Sold Aug 29, 2025

  413 MacChi Ave, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,290 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • $255/SF
  • 80 Days On Market

  Current Estimated Value $817,869

  Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

  413 MacChi Ave, Oakland, FL 34787
• 

  

  /2

  Not Listed For Sale

  6259 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • Built 2024

  6259 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $197/SF
  • 0 Days On Market

  • Last Sold Price $482,675
  • Oct 31, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
• 

  

  

  /52

  $416,900

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft

  2222 Gopher Tortoise Terrace, Oakland, FL 34787

  YOU Must see this absolutely Gorgeous 3BEDS,3 FULL BATH Townhouse in Oakland. located Between Winter Garden and Clermont..Great amenities for you enjoy the best of Florida lifestyle..This Property is the LARGEST SQ FT in the community and Best Floor Plan : Open floor concept ,that integrate Living space, Kitchen and Dinner space. Surrounded with sunlight windows. Engineering floor, granite

  Wagner ferreira LPT REALTY, LLC

  2222 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  

  /2

  $1,525,000 Sold Apr 06, 2026

  15722 E Oakland Ave, Oakland, FL 34760

  • 3 Beds
  • 2 Baths
  • 3,340 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $457/SF
  • 4 Days On Market

  Current Estimated Value $1,348,515

  Last Listing Agent Matt Erickson RE/MAX PRIME PROPERTIES

  15722 E Oakland Ave, Oakland, FL 34760
• 

  

  /2

  Est $408,631 Not Listed For Sale

  17005 Volume Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft
  • Built 2020

  17005 Volume Aly, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $248/SF
  • 39 Days On Market

  • Last Sold Price $425,000
  • Aug 16, 2024

  Last Listing Agent Abby Anderson Hayes REAL BROKER, LLC
• 

  

  /78

  $1,499,000

  • 4 Beds
  • 4.5 Baths
  • 3,613 Sq Ft

  1412 Johns Cove Ln, Oakland, FL 34787

  Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! Pristine views of John's Chain, and full access from your incredible Boat House with dual power lifts. This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely

  Betsey West NEXT RESIDENCE REALTY LLC

  1412 Johns Cove Ln, Oakland, FL 34787
• 

  /2

  $950,000 Sold Sep 23, 2025

  100 Demens St, Oakland, FL 34760

  • 4 Beds
  • 3 Baths
  • 3,025 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $314/SF
  • 100 Days On Market

  Current Estimated Value $948,321

  Last Listing Agent David Dorman CENTURY 21 CARIOTI

  100 Demens St, Oakland, FL 34760
• 

  /2

  Not Listed For Sale

  6301 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,043 Sq Ft
  • Built 2024

  6301 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $164/SF
  • 12 Days On Market

  • Last Sold Price $497,880
  • Oct 18, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
• 

  

  /47

  $875,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  8 Winters Landing Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), and drain field (2024), located in the heart of Oakland is just minutes from downtown Winter Garden.From the

  Danielle Norvell REGENCY REAL ESTATE LLC

  8 Winters Landing Dr, Oakland, FL 34787
• 

  /2

  $660,000 Sold Jun 12, 2025

  13672 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $349/SF
  • 96 Days On Market

  Current Estimated Value $669,810

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13672 Fresh Ivy St, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  6253 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • Built 2024

  6253 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $197/SF
  • 35 Days On Market

  • Last Sold Price $484,110
  • Aug 30, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
• 

  

  /24

  $1,099,000

  • 5 Beds
  • 4 Baths
  • 3,951 Sq Ft

  219 Largovista Dr, Oakland, FL 34787

  Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home features, 2 of the bedrooms is a suite, high-end finishes, and a seamless modern design throughout.Porcelain tile flooring, a stunning gourmet kitchen with island with quartz countertops, custom cabinetry and a premium

  Durval Da Rocha NOVARE REAL ESTATE LLC

  219 Largovista Dr, Oakland, FL 34787
• 

  /2

  $460,000 Sold Sep 23, 2025

  17055 Wynford Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,345 Sq Ft
  • Built 2021

  Last Sold Summary

  • 16% Below List Price
  • $196/SF
  • 160 Days On Market

  Current Estimated Value $478,262

  Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  17055 Wynford Ln, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  6379 Blissful St, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,023 Sq Ft
  • Built 2024

  6379 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $222/SF
  • 4 Days On Market

  • Last Sold Price $449,999
  • Aug 23, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
• 

  

  /3

  $409,990 New Construction

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

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

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36452383, Oakland, FL 34787
• 

  /2

  $580,109 Sold Dec 23, 2025

  17597 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 2025

  Last Sold Summary

  • $324/SF

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

  17597 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  6391 Blissful St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  6391 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $241/SF
  • 4 Days On Market

  • Last Sold Price $429,099
  • Oct 25, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
• 

  

  /76

  $1,299,500 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,911 Sq Ft

  8978 Sonoma Coast Dr, Oakland, FL 34787

  Under contract-accepting backup offers. LUXURY POOL HOME on PREMIUM LAKE FRONT LOT! Unique Opportunity to Enjoy an Outdoor PARADISE with STUNNING LAKE, CONSERVATION & SUNSET Views! The HOA is Allowing Docks on these Special Lots – Relax, Fish or Kayak! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3

  JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

  8978 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  $860,990 Sold Apr 20, 2026

  4628 Golden Birch Ave, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,379 Sq Ft
  • Built 2026

  Last Sold Summary

  • $362/SF

  Current Estimated Value $884,000

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

  4628 Golden Birch Ave, Oakland, FL 34787
• 

  /2

  Est $412,414 Not Listed For Sale

  15805 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 1,688 Sq Ft
  • Built 2024

  15805 Tollington Aly, Oakland, FL 34787

  Last Sold Summary

  • 4% Above List Price
  • $234/SF

  • Last Sold Price $394,810
  • May 30, 2024

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
• 

  

  /13

  $550,000 New Construction

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

  14736 Field Daisy Dr, Oakland, FL 34787

  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 your entertainment needs and desires. The 2149 sq. ft. two-story home with 3 bedrooms, 3.5 bathrooms and a 2-car detached garage presents prospective homebuyers with both the basic features and intricate details that

  Taylor Morrison Builder

  14736 Field Daisy Dr, Oakland, FL 34787
• 

  /2

  $88,000 Sold Apr 29, 2026

  406 W Herriott Ave, Oakland, FL 34760

  • Land
  • 3,920 Sq Ft
  • $977,778 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 36 Days On Market

  Current Estimated Value $157,016

  Last Listing Agent Migdalia Ramos V PROPERTIES INC

  406 W Herriott Ave, Oakland, FL 34760
• 

  /2

  Est $415,854 Not Listed For Sale

  15811 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,691 Sq Ft
  • Built 2024

  15811 Tollington Aly, Oakland, FL 34787

  Last Sold Summary

  Last Listing Agent Carlinhos Fregonezi TALENT REALTY SOLUTIONS
• 

  

  /23

  $395,000

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

  2228 Gopher Tortoise Terrace, Oakland, FL 34787

  This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, fans new carpet and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling.

  Leslie Anne Campasano ASANO REAL ESTATE LLC

  2228 Gopher Tortoise Terrace, 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 $786,000

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

  16152 Point Rock Dr, Oakland, FL 34787
• 

  /2

  Est $578,316 Not Listed For Sale

  15153 Summer Harvest St, Oakland, FL 34787

  • 3 Beds
  • 4 Baths
  • 2,149 Sq Ft
  • Built 2024

  15153 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  Last Listing Agent Carlinhos Fregonezi TALENT REALTY SOLUTIONS
• 

  

  /49

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 3,583 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to

  Subhas C Sawh LIBERTY HOME SALES INC

  729 Strihal Loop, 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 $564,243

  Last Listing Agent Johna Jennings Coastal Life Properties LLC

  2642 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $422,324 Not Listed For Sale

  2315 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,663 Sq Ft
  • Built 2018

  2315 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $253/SF
  • 35 Days On Market

  • Last Sold Price $420,000
  • Aug 08, 2024

  Last Listing Agent Dana Gold RE/MAX
• 

  

  /4

  $1,975,000 Open Mon 11AM - 4PM

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  1106 Sarah Mathews Dr, Oakland, FL 34787

  Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living

  Heather Spirazza REGENCY REAL ESTATE LLC

  1106 Sarah Mathews Dr, 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 $619,271 Not Listed For Sale

  1540 Stone Arrow Ct, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,248 Sq Ft
  • Built 2018

  1540 Stone Arrow Ct, Winter Garden, FL 34787

  Last Sold Summary

  • 5% Above List Price
  • $182/SF
  • 44 Days On Market

  • Last Sold Price $590,000
  • Aug 02, 2024

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC
• 

  

  /30

  $489,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  1051 Stationside Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 3-bath home in the heart of Oakland, where everyday living feels connected, convenient, and just a little more elevated. This home enjoys amazing views of the Oakland Nature Preserve. Ideally located within walking distance to the West Orange Trail and just minutes from the charm of downtown Oakland and

  Steve Healy CORCORAN PREMIER REALTY

  1051 Stationside Dr, Oakland, FL 34787
• 

  /2

  $900,000 Sold Sep 12, 2025

  619 Largovista Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,728 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $241/SF
  • 52 Days On Market

  Current Estimated Value $867,341

  Last Listing Agent Farhad Haniff EXP REALTY LLC

  619 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $545,768 Not Listed For Sale

  13037 Tollcross Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft
  • Built 2024

  13037 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $249/SF
  • 189 Days On Market

  • Last Sold Price $537,500
  • Mar 06, 2025

  Last Listing Agent Michele Drebes Weiand WRA BUSINESS & REAL ESTATE
• 

  

  /4

  $498,990 New Construction

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

  Brantley Plan at Serenade at Ovation - Bungalow, Oakland, FL 34787

  Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36498626, Oakland, FL 34787
• 

  /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 $1,107,068

  Last Listing Agent Ashlen Hayward THE AGENCY FL

  1120 Civitas Way, Winter Garden, FL 34787
• 

  /2

  Est $515,461 Not Listed For Sale

  13025 Tollcross Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft
  • Built 2024

  13025 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $294/SF
  • 91 Days On Market

  • Last Sold Price $540,000
  • Sep 24, 2024

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /17

  $2,238,120 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,204 Sq Ft

  1173 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Alexis Anderson REGENCY REAL ESTATE LLC

  1173 Prado Ln, Oakland, 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 $917,009

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

  4649 Golden Birch Ave, Oakland, FL 34787

Showing Results 241 - 280, Page 7 of 18