Oakland, FL Homes

• 

  

  

  /55

  $499,990

  Sold Feb 20, 2026

  17621 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 9% Below List Price
  • $279/SF
  • 50 Days On Market

  Current Estimated Value $506,000

  17621 Japonica Bloom Dr, Oakland, FL 34787
• 

  

  /2

  Est $648,132

  Not Listed For Sale

  2214 Bay Line Rd, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,278 Sq Ft
  • Built 2020

  2214 Bay Line Rd, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  

  /2

  $510,880

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Amelia floor plan offers the ease of one-story living with a smart and stylish layout featuring three bedrooms, two bathrooms, and a two-car garage. A spacious great room flows effortlessly into the dining and kitchen areas, making entertaining and everyday living a breeze. The private primary suite is tucked away

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  Oakland, FL 34787
• 

  

  /2

  $395,000

  Sold Sep 30, 2025

  13298 Pontoon Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2023

  Last Sold Summary

  • 6% Below List Price
  • $252/SF
  • 51 Days On Market

  Current Estimated Value $393,501

  Last Listing Agent Cindy Brads COLDWELL BANKER REALTY

  13298 Pontoon Rd, Oakland, FL 34787
• 

  

  /2

  Est $1,798,322

  Not Listed For Sale

  625 Cheekwood Aly, Winter Garden, FL 34787

  • 6 Beds
  • 4.5 Baths
  • 3,796 Sq Ft
  • Built 2022

  625 Cheekwood Aly, Winter Garden, FL 34787

  Last Sold Summary

  • 17 Days On Market
• 

  

  /98

  $1,075,000

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

  806 Johns Point Dr, Oakland, FL 34787

  Mediterranean Elegance Meets Lakeside Luxury on John's Lake! Welcome to your own private paradise, nestled in the exclusive, small gated waterfront enclave of John’s Cove. Step inside this gorgeous, custom-built estate and be instantly captivated by soaring 25-30 foot vaulted ceilings, a dramatic winding staircase, elegant Roman-style arches and columns and abundant natural light. In this

  Laura Romot GILKEY REAL ESTATE

  806 Johns Point Dr, Oakland, FL 34787
• 

  /2

  $420,000

  Sold Jul 09, 2025

  709 Strihal Loop, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,621 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $259/SF
  • 24 Days On Market

  Current Estimated Value $424,510

  Last Listing Agent Jessica Stone CENTURY 21 CARIOTI

  709 Strihal Loop, Oakland, FL 34787
• 

  /2

  Est $457,330

  Not Listed For Sale

  14018 Scarlet Aster Aly, Oakland, FL 34787

  • 2 Beds
  • 2.5 Baths
  • 1,785 Sq Ft
  • Built 2024

  14018 Scarlet Aster Aly, Oakland, FL 34787

  Last Sold Summary

  • 115 Days On Market
• 

  /2

  $699,970

  New Construction Pending

  • 5 Beds
  • 4.5 Baths
  • 3,122 Sq Ft

  17162 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model by Dream Finders Homes. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage,

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17162 Ingram Hills Aly, Oakland, FL 34787
• 

  /2

  $604,000

  Sold Sep 19, 2025

  410 E Gulley Ave, Oakland, FL 34760

  • 5 Beds
  • 3 Baths
  • 2,458 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $246/SF
  • 30 Days On Market

  Current Estimated Value $668,560

  Last Listing Agent Keith Packey RE/MAX TITANIUM GROUP

  410 E Gulley Ave, Oakland, FL 34760
• 

  

  /11

  Est $903,799

  Not Listed For Sale

  13259 Tollcross Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,318 Sq Ft
  • Built 2025

  13259 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 25 Days On Market
• 

  /2

  $1,675,000

  New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  AR Homes Builder

  166 Hammock Preserve Loop, Oakland, FL 34787
• 

  /2

  $652,316

  Sold Nov 14, 2025

  16108 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft
  • Built 2025

  Last Sold Summary

  • $267/SF

  Current Estimated Value $662,000

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

  16108 Honey Harvest St, Oakland, FL 34787
• 

  /2

  Est $447,647

  Not Listed For Sale

  9030 Wading Walk Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2020

  9030 Wading Walk Ln, Oakland, FL 34787

  Last Sold Summary

  • 23 Days On Market
• 

  

  /17

  $2,130,760

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-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

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, FL 34787
• 

  /2

  $730,000

  Sold Jun 01, 2026

  5715 Orange Orchard Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 2021

  Last Sold Summary

  • $326/SF
  • 1 Day On Market

  Current Estimated Value $721,890

  Last Listing Agent Caroline De Castro Marcellini COMPASS FLORIDA, LLC

  5715 Orange Orchard Dr, Oakland, FL 34787
• 

  /2

  Est $890,452

  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
• 

  

  /47

  $669,900

  Open Sat 12PM - 3PM $10K PRICE INCREASE

  • 5 Beds
  • 4 Baths
  • 3,285 Sq Ft

  710 Regina Cir, Oakland, FL 34787

  Welcome to this exceptional pool home located in the sought-after gated lakefront community of Johns Landing. Situated on an oversized 13,000+ square-foot corner lot with a mostly fenced backyard, this spacious home offers over 3,000 square feet of thoughtfully designed living space.Featuring 4 bedrooms, 4 full bathrooms, a dedicated office, media room, and spacious loft, this home provides

  Brenda Anglada COLDWELL BANKER REALTY

  710 Regina Cir, Oakland, FL 34787
• 

  /2

  $2,675,000

  Sold Oct 30, 2025

  1179 Prado Ln, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 4,561 Sq Ft
  • Built 2026

  Last Sold Summary

  • $586/SF

  Current Estimated Value $2,628,000

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

  1179 Prado Ln, Oakland, FL 34787
• 

  /2

  Est $762,824

  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
• 

  

  /36

  $360,000

  Open Sat 11AM - 2PM $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,497 Sq Ft

  2117 Gopher Tortoise Terrace, Oakland, FL 34787

  PRICE Improvement PLUS seller concessions of HOA dues paid for the first year for the new buyer. Be sure to ask about a lender provided reduced rate offering a rate buy down to help reduce your monthly payment and/or closing costs. Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining. The kitchen, where

  Mary Herrod De Boer SERHANT

  2117 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  /2

  $57,000

  Sold Apr 29, 2026

  121 S Nixon St, Oakland, FL 34760

  • Land
  • 4,791 Sq Ft
  • $518,182 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 181 Days On Market

  Current Estimated Value $65,425

  Last Listing Agent Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

  121 S Nixon St, Oakland, FL 34760
• 

  /2

  Est $433,013

  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
• 

  

  /62

  $1,499,000

  $151K PRICE DROP

  • 6 Beds
  • 7.5 Baths
  • 5,614 Sq Ft

  620 N Tubb St, Oakland, FL 34760

  PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty

  Jennifer Wilson OAKSTRAND REALTY

  620 N Tubb St, Oakland, FL 34760
• 

  

  /37

  $449,990

  Sold Nov 07, 2025

  17681 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,577 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $285/SF
  • 9 Days On Market

  Current Estimated Value $607,000

  Ashton Woods Northlake at Ovation - Townhomes

  17681 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  Est $1,229,896

  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
• 

  

  /78

  $865,000

  $34K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,399 Sq Ft

  505 E Gulley Ave, Oakland, FL 34787

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **$10,000 towards closing costs**Welcome to this truly exceptional home offering space,flexibility & an unbeatable location!This beautiful,expansive residence features 4 spacious bedrooms,3.5 bathrooms,plus a versatile upstairs BONUS ROOM that can easily serve as a 5th bedrm—complete with closet & half bath

  Sandy Jones CLOCK TOWER REALTY

  505 E Gulley Ave, Oakland, FL 34787
• 

  /2

  $390,000

  Sold Jul 31, 2025

  121 W Oakland Ave, Oakland, FL 34760

  • 3 Beds
  • 1 Bath
  • 1,159 Sq Ft
  • Built 1935

  Last Sold Summary

  • $336/SF
  • 7 Days On Market

  Current Estimated Value $370,058

  Last Listing Agent Sheri Loiacono WINDSOR REALTY GROUP INC

  121 W Oakland Ave, Oakland, FL 34760
• 

  /2

  Est $648,610

  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
• 

  

  /3

  $594,000

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 2,143 Sq Ft

  12915 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is

  Dayene Grubert ORLANDO TBI REALTY LLC

  12915 Westhaven Oak Dr, Oakland, FL 34787
• 

  /2

  $607,690

  Sold Mar 27, 2026

  3088 Namaste Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,911 Sq Ft
  • Built 2026

  Last Sold Summary

  • 5% Below List Price
  • $209/SF
  • 20 Days On Market

  Current Estimated Value $608,366

  Last Listing Agent Ben Goldstein LENNAR REALTY

  3088 Namaste Dr, Oakland, FL 34787
• 

  /2

  Est $1,257,064

  Not Listed For Sale

  15281 Arcadia Bluff Loop, Oakland, FL 34787

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

  15281 Arcadia Bluff Loop, Oakland, FL 34787

  Last Sold Summary

  • 80 Days On Market
• 

  

  /31

  $414,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft

  1321 Planted Pine St, Oakland, FL 34760

  Under contract-accepting backup offers. Nestled in the highly desirable community of Longleaf at Oakland, this exquisite townhome is a blend of elegance and functionality. The open floor plan bathes the interior in natural light, creating a warm and inviting atmosphere. The kitchen, a modern culinary space, features stainless steel appliances, sleek granite countertops, and ample cabinet space.

  Justin Cabral PROPERTY LOGIC RE

  1321 Planted Pine St, Oakland, FL 34760
• 

  /2

  $583,380

  Sold Nov 18, 2025

  4652 Golden Birch Ave, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,199 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $265/SF
  • 7 Days On Market

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  4652 Golden Birch Ave, Oakland, FL 34787
• 

  

  /9

  Est $428,991

  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
• 

  

  /62

  $689,000

  • 4 Beds
  • 3.5 Baths
  • 2,686 Sq Ft

  15174 Field Daisy Dr, Oakland, FL 34787

  Welcome to this beautiful bungalow-style home in the highly desirable Osprey Ranch community in Winter Garden! Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, this thoughtfully designed residence offers comfort, style, and functionality for the whole family.Located just minutes from Disney, shopping, dining, and major highways, this home combines convenience with a peaceful

  Guilherme Garcia Cavalcante REALTY ONE GROUP INSPIRATION

  15174 Field Daisy Dr, Oakland, FL 34787
• 

  /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 $843,002

  Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

  413 MacChi Ave, Oakland, FL 34787
• 

  /2

  Est $426,919

  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
• 

  

  /6

  $2,210,000

  New Construction Pending

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

  1164 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to one of the most anticipated new builds at Grove at the Harvest District — the Sunburst Plan by Davila Homes, a luxury new construction masterpiece designed for those who prioritize space, style, and lifestyle.Spanning 4,204 livable square feet with 5,665 total square feet, this stunning 5-bedroom, 5.5-bath estate is thoughtfully designed from the

  Alexis Anderson REGENCY REAL ESTATE LLC

  1164 Prado Ln, Oakland, FL 34787
• 

  /2

  $599,990

  Sold May 28, 2026

  2982 Good Vibes Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,011 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Below List Price
  • $199/SF
  • 57 Days On Market

  Current Estimated Value $625,745

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2982 Good Vibes Way, Oakland, FL 34787

Showing Results 201 - 240, Page 6 of 18