Oakland, FL Homes

• 

  

  /2

  $649,000 Sold Mar 09, 2026

  2169 Bay Line Rd, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,274 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $285/SF
  • 14 Days On Market

  Current Estimated Value $619,786

  Last Listing Agent Mariana Wartella LPT REALTY, LLC

  2169 Bay Line Rd, Oakland, FL 34787
• 

  

  /2

  Est $499,856 Not Listed For Sale

  14114 Frasier St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,985 Sq Ft
  • Built 2024

  14114 Frasier St, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $254/SF
  • 105 Days On Market

  Last Sold Price $505,000

  Last Listing Agent Aline Duda V ENTERPRISES LLC
• 

  

  

  /23

  $575,000

  • Land
  • 0.45 Acre
  • $1,277,778 per Acre

  514 N Pollard St, Winter Garden, FL 34787

  Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

  Alexis Anderson REGENCY REAL ESTATE LLC

  514 N Pollard St, Winter Garden, FL 34787
• 

  

  /2

  $395,000 Sold Feb 19, 2026

  329 E Gulley Ave, Oakland, FL 34760

  • Land
  • 0.28 Acre
  • $1,410,714 per Acre

  Last Sold Summary

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

  329 E Gulley Ave, Oakland, FL 34760
• 

  

  /2

  Est $507,622 Not Listed For Sale

  14078 Frasier St, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,114 Sq Ft
  • Built 2024

  14078 Frasier St, Oakland, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $237/SF
  • 0 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Asher Chen AAA GLOBAL VENTURES PA
• 

  

  /30

  $704,118 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,441 Sq Ft

  14780 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

  Taylor Morrison Builder

  14780 Field Daisy Dr, Oakland, FL 34787
• 

  /2

  $571,000 Sold Apr 29, 2025

  201 W Briley Ave, Oakland, FL 34760

  • 3 Beds
  • 2 Baths
  • 1,790 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Above List Price
  • $319/SF
  • 4 Days On Market

  Current Estimated Value $572,260

  Last Listing Agent Kari Fleck THE REAL ESTATE COLLECTION LLC

  201 W Briley Ave, Oakland, FL 34760
• 

  /2

  Est $1,449,552 Not Listed For Sale

  100 Millholland St, Oakland, FL 34760

  • 5 Beds
  • 5 Baths
  • 3,747 Sq Ft
  • Built 2015

  100 Millholland St, Oakland, FL 34760

  Last Sold Summary

  • 9% Below List Price
  • $427/SF
  • 137 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Chris Pixley ENGEL & VOLKERS NEW SMYRNA
• 

  

  /3

  $409,990 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

  $1,440,000 Sold Mar 28, 2025

  816 Johns Point Dr, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 3,450 Sq Ft
  • Built 2020

  Last Sold Summary

  • 9% Below List Price
  • $417/SF
  • 37 Days On Market

  Current Estimated Value $1,345,265

  Last Listing Agent Marc Harris LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  816 Johns Point Dr, Oakland, FL 34787
• 

  /2

  Est $509,377 Not Listed For Sale

  14387 Braemar St, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,094 Sq Ft
  • Built 2024

  14387 Braemar St, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $249/SF

  Last Sold Price $521,995

  Last Listing Agent Eileen Scates SCATES REALTY & INVESTMENT PRO
• 

  

  /27

  $625,000

  • 5 Beds
  • 3.5 Baths
  • 3,007 Sq Ft

  2451 Sky Stone Ct, Oakland, FL 34787

  THIS ONE IS A MUST SEE! Upgrades on upgrades on upgrades! Welcome to Oakland Trails in the charming City of Oakland. This spacious 5-bedroom, 3.5-bath home offers a flexible layout perfect for today’s lifestyle. Enjoy a cozy Great Room, formal Dining Room, and a stunning modern staircase that leads into an open-concept Living Room and beautifully upgraded Kitchen featuring ample cabinetry,

  Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

  2451 Sky Stone Ct, Oakland, FL 34787
• 

  /2

  $425,990 Sold Nov 26, 2025

  17496 Northlake Grove Dr, Oakland, FL 34787

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

  Last Sold Summary

  • $270/SF

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

  17496 Northlake Grove Dr, Oakland, FL 34787
• 

  /2

  Est $801,207 Not Listed For Sale

  1221 Wilder Oaks Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 2024

  1221 Wilder Oaks Way, Oakland, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $352/SF
  • 162 Days On Market

  Last Sold Price $788,500

  Last Listing Agent Jasmine Martz OLYMPUS EXECUTIVE REALTY INC
• 

  

  /30

  $474,990 Pending

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

  2135 Standing Rock Cir, Oakland, FL 34787

  Under contract-accepting backup offers. ASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home located in the charming town of Oakland, FL. Offering 3 bedrooms, 2.5 bathrooms, and 2,078 square feet of thoughtfully designed living space, this home features an open floor plan that’s perfect for both everyday living and entertaining. The spacious layout is

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  2135 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  $1,660,000 Sold Oct 23, 2025

  102 Hammock Preserve Loop, Oakland, FL 34787

  • 6 Beds
  • 5 Baths
  • 3,911 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $424/SF
  • 102 Days On Market

  Current Estimated Value $1,641,978

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  102 Hammock Preserve Loop, Oakland, FL 34787
• 

  

  /56

  Est $769,881 Not Listed For Sale

  5633 Orange Orchard Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft
  • Built 2021

  5633 Orange Orchard Dr, Oakland, FL 34787

  Last Sold Summary

  • 6% Below List Price
  • $305/SF
  • 13 Days On Market

  Last Sold Price $820,000

  Last Listing Agent Rema Perras CORCORAN PREMIER REALTY
• 

  

  /49

  $899,900

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft

  13343 Sunny Retreat Ln, Oakland, FL 34787

  The neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the

  John Hart ENGEL & VOLKERS ORLANDO DR PHILLIPS

  13343 Sunny Retreat Ln, Oakland, FL 34787
• 

  /2

  $409,040 Sold Aug 27, 2025

  5832 Meditation Dr, Oakland, FL 34787

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

  Last Sold Summary

  • $233/SF
  • 15 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  5832 Meditation Dr, Oakland, FL 34787
• 

  /2

  Est $521,428 Not Listed For Sale

  13031 Tollcross Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft
  • Built 2024

  13031 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $283/SF
  • 141 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  

  /51

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft

  8708 Sonoma Coast Dr, Oakland, FL 34787

  Nestled in Phase 3 of Waterleigh in Horizon West, this stunning single-story home offers 4 bedrooms and 3.5 bathrooms on a premium .41-acre lot with no rear neighbors, providing both privacy and tranquility. Situated on a quiet cul-de-sac, the home features beautiful views and a peaceful setting, just a short stroll from a charming community green space with a pavilion and picnic area. Inside,

  Linda Sirois LONDON FOSTER REALTY

  8708 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  $645,954 Sold Nov 21, 2025

  17579 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft
  • Built 2025

  Last Sold Summary

  • $303/SF

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

  17579 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  Est $602,414 Not Listed For Sale

  13109 Tollcross Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,182 Sq Ft
  • Built 2024

  13109 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $298/SF
  • 42 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  

  /14

  $385,000

  • Land
  • 0.29 Acre
  • $1,327,586 per Acre

  610 Simeon Rd, Oakland, FL 34787

  Presenting a rare opportunity to purchase a 0.29-acre residential lot in the highly sought-after Town of Oakland. This unincorporated property offers exceptional flexibility, no HOA restrictions and agricultural zoning. Conveniently located just steps from the scenic West Orange Trail, the Oakland Nature Preserve, and downtown Oakland. Enjoy the peaceful surroundings amongst the oak trees and

  Blaine Dooley REGENCY REAL ESTATE LLC

  610 Simeon Rd, Oakland, FL 34787
• 

  /2

  $300,000 Sold Jun 24, 2025

  380 Jefferson St, Oakland, FL 34760

  • Land
  • 0.27 Acre
  • $1,111,111 per Acre

  Last Sold Summary

  Current Estimated Value $760,000

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

  380 Jefferson St, Oakland, FL 34760
• 

  

  /34

  Est $406,347 Not Listed For Sale

  9085 Legado Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,513 Sq Ft
  • Built 2020

  9085 Legado Dr, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $278/SF
  • 1 Day On Market

  Last Sold Price $421,000

  Last Listing Agent ALLISON JOHNSTON MAINSTAY BROKERAGE LLC
• 

  

  /15

  $614,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,149 Sq Ft

  14748 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Newberry at 14748 Field Daisy Drive in Harvest at Ovation. The Newberry Bungalow offers modern living with a layout designed for both everyday comfort and effortless entertaining. Step through the foyer into a spacious great room, passing a secondary bedroom and full bath along the way. The designer kitchen overlooks the main living area and flows seamlessly to the bright, inviting

  Taylor Morrison Builder

  14748 Field Daisy Dr, Oakland, FL 34787
• 

  /2

  $512,500 Sold Dec 08, 2025

  1787 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft
  • Built 2017

  Last Sold Summary

  • 8% Below List Price
  • $238/SF
  • 155 Days On Market

  Current Estimated Value $504,185

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1787 White Feather Loop, Oakland, FL 34787
• 

  /2

  Est $559,674 Not Listed For Sale

  15169 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,338 Sq Ft
  • Built 2024

  15169 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $245/SF

  Last Sold Price $572,240

  Last Listing Agent Antonio Cardoso Desmarais TALENT REALTY SOLUTIONS
• 

  

  /17

  $449,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft

  8937 Matriarca Aly, Oakland, FL 34787

  Price adjustment! Move in ready! Freshly painted last year in “North Star” inside, and luxury vinyl plank flooring (no carpets) in this end townhouse just minutes away from theme parks and great shopping at Legado community in Windermere. 3 spacious bedrooms, and 2.5 bathrooms combine with generous living space in this 2-story townhome. Designed for entertaining, the "Minneola" features a large

  Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

  8937 Matriarca Aly, Oakland, FL 34787
• 

  /2

  $701,000 Sold May 02, 2025

  3394 Buoy Cir, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,747 Sq Ft
  • Built 2021

  Last Sold Summary

  • 13% Below List Price
  • $187/SF
  • 453 Days On Market

  Current Estimated Value $726,535

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  3394 Buoy Cir, Oakland, FL 34787
• 

  /2

  Est $622,810 Not Listed For Sale

  3303 Buoy Cir, Oakland, FL 34787

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

  3303 Buoy Cir, Oakland, FL 34787

  Last Sold Summary

  • $226/SF
  • 128 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Kyle Madorin UPWELL REALTY LLC
• 

  $829,346 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft

  15075 Tea Tree Dr, Oakland, FL 34787

  Opportunity in Avalon Woods! Welcome to the Biscayne, a spacious two-story single-family home designed with both style and functionality in mind. The 20-foot ceiling entryway creates a stunning first impression, leading into a bright and open main living area. A guest bedroom with full bath downstairs provides comfort and flexibility for visitors or multi-generational living. The beautifully

  Dream Finders Homes Builder

  15075 Tea Tree Dr, Oakland, FL 34787
• 

  /2

  $591,290 Sold Jan 09, 2026

  2823 Haze Rd, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 2,201 Sq Ft
  • Built 2025

  Last Sold Summary

  • $269/SF
  • 0 Days On Market

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

  2823 Haze Rd, Oakland, FL 34787
• 

  

  /31

  Est $438,586 Not Listed For Sale

  16287 Prairie School Dr, Oakland, FL 34787

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

  16287 Prairie School Dr, Oakland, FL 34787

  Last Sold Summary

  • 6% Below List Price
  • $257/SF
  • 6 Days On Market

  Last Sold Price $467,500

  Last Listing Agent Thomas Moffett BHHS FLORIDA REALTY
• 

  

  /33

  $587,990 Pending

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  2930 Good Vibes Way, Oakland, FL 34787

  Under Construction. The Jagger has it all! This sleek new two-story home features a convenient game room on the second level, perfect for entertaining, relaxation and more. The first floor is host to an inviting open-concept layout shared between a modern kitchen, elegant dining room and comfortable family room. Three secondary bedrooms boast a private space near the front of the home off the

  Ben Goldstein LENNAR REALTY

  2930 Good Vibes Way, Oakland, FL 34787
• 

  /2

  $540,000 Sold Apr 25, 2025

  16459 Hamlin View St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,078 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Below List Price
  • $260/SF
  • 26 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  16459 Hamlin View St, Oakland, FL 34787
• 

  

  /11

  Est $501,780 Not Listed For Sale

  2035 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2018

  2035 White Feather Loop, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $250/SF
  • 7 Days On Market

  Last Sold Price $520,000

  Last Listing Agent James Goodyear COMPASS FLORIDA LLC
• 

  /2

  $908,676 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  15099 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15099 Tea Tree Dr, Oakland, FL 34787
• 

  /2

  $819,006 Sold Sep 17, 2025

  16125 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2024

  Last Sold Summary

  • $289/SF
  • 0 Days On Market

  Current Estimated Value $821,000

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

  16125 Honey Harvest St, Oakland, FL 34787

Showing Results 321 - 360, Page 9 of 18