Oakland, FL Homes

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  /2

  Est $473,387 Not Listed For Sale

  9267 Gran Teatro Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft
  • Built 2024

  9267 Gran Teatro Dr, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $264/SF
  • 82 Days On Market

  Last Sold Price $484,990

  Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY
• 

  $634,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  12919 Westhaven Oak Dr, Oakland, FL 34787

  Superior contemporary design. The Liston's welcoming covered porch and entry open immediately onto the expansive great room, with views to the lovely dining room and desirable large covered lanai beyond. The well-equipped gourmet kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and generous walk-in pantry. The gorgeous primary bedroom suite is

  Toll Brothers, Inc. Builder

  12919 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  /2

  $980,000 Sold Apr 14, 2025

  210 Hammock Preserve Loop, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,070 Sq Ft
  • Built 2023

  Last Sold Summary

  • 18% Below List Price
  • $319/SF
  • 47 Days On Market

  Current Estimated Value $1,005,278

  Last Listing Agent Matthew Sutton BERGER REALTY & INVESTMENTS

  210 Hammock Preserve Loop, Oakland, FL 34787
• 

  

  /2

  Est $998,967 Not Listed For Sale

  1056 Sadler Oaks Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,711 Sq Ft
  • Built 2024

  1056 Sadler Oaks Way, Oakland, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $387/SF
  • 129 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY
• 

  

  

  /58

  $1,785,000

  • 4 Beds
  • 4 Baths
  • 3,784 Sq Ft

  906 Allendale Ln, Winter Garden, FL 34787

  Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for

  Jurgita Blake CENTURY 21 CARIOTI

  906 Allendale Ln, Winter Garden, FL 34787
• 

  /2

  $444,590 Sold Jul 29, 2025

  6678 Juneberry Way, Oakland, FL 34787

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

  Last Sold Summary

  • $241/SF
  • 39 Days On Market

  Current Estimated Value $447,105

  Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

  6678 Juneberry Way, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 5 Baths
  • 3,794 Sq Ft
  • Built 2025

  Unlisted Address

  Last Sold Summary

  • $470/SF

  Last Sold Price $1,783,268

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
• 

  

  /55

  $949,790 Open Sat 10AM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 4,313 Sq Ft

  4632 Golden Birch Ave, Oakland, FL 34787

  Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Introducing the exquisite

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  4632 Golden Birch Ave, Oakland, FL 34787
• 

  /2

  $395,000 Sold Feb 19, 2026

  321 E Gulley Ave, Oakland, FL 34760

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

  Last Sold Summary

  • 8 Days On Market

  Current Estimated Value $424,879

  Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

  321 E Gulley Ave, Oakland, FL 34760
• 

  /2

  Est $582,570 Not Listed For Sale

  13007 Tollcross Way, Oakland, FL 34787

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

  13007 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $290/SF

  Last Sold Price $626,549

  Last Listing Agent Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY
• 

  

  /40

  $580,000 Open Thu 12PM - 3:30PM

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

  13732 Fresh Ivy St, Oakland, FL 34787

  Not your average Del Webb home—this nearly new, designer-upgraded retreat offers rare touches and nightly neighborhood Disney fireworks views. Why wait to build? This home is just under a year old and move-in ready, located in the vibrant 55+ community of Del Webb Oasis, where resort-style amenities include a clubhouse, zero-entry pool with cabanas, tennis, pickleball, and more. The open-concept

  Ken Pozek REAL BROKER, LLC

  13732 Fresh Ivy St, Oakland, FL 34787
• 

  /2

  $688,000 Sold Aug 28, 2025

  2901 Haze Rd, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,385 Sq Ft
  • Built 2025

  Last Sold Summary

  • $203/SF

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

  2901 Haze Rd, Oakland, FL 34787
• 

  /2

  Est $799,984 Not Listed For Sale

  9462 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft
  • Built 2024

  9462 Emerald Berry Dr, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $251/SF
  • 62 Days On Market

  Last Sold Price $804,990

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
• 

  

  /43

  $695,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,163 Sq Ft

  2450 Standing Rock Cir, Oakland, FL 34787

  Under contract-accepting backup offers. Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or

  Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  2450 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  $535,000 Sold Feb 24, 2026

  9029 Sonoma Coast Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • Built 2021

  Last Sold Summary

  • $266/SF
  • 64 Days On Market

  Current Estimated Value $527,021

  Last Listing Agent Abraham Mendez NONA LEGACY POWERED BY LA ROSA

  9029 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  Est $841,549 Not Listed For Sale

  5590 Orange Orchard Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,853 Sq Ft
  • Built 2021

  5590 Orange Orchard Dr, Oakland, FL 34787

  Last Sold Summary

  • 10% Below List Price
  • $328/SF
  • 3 Days On Market

  Last Sold Price $935,000

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS
• 

  /2

  $606,440 Pending

  • 4 Beds
  • 3 Baths
  • 2,102 Sq Ft

  17156 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17156 Ingram Hills Aly, Oakland, FL 34787
• 

  /2

  $387,900 Sold Jul 17, 2025

  1509 Sweet Apple St, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $214/SF
  • 144 Days On Market

  Current Estimated Value $381,252

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  1509 Sweet Apple St, Oakland, FL 34787
• 

  /2

  Est $724,704 Not Listed For Sale

  1404 High Springs Ln, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,059 Sq Ft
  • Built 2020

  1404 High Springs Ln, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $239/SF
  • 92 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Kaitlin LaMacchia DENIZ REALTY PARTNERS LLC
• 

  

  /59

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  2259 White Feather Loop, Oakland, FL 34787

  INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by

  Chuck Burt YOUNG REAL ESTATE

  2259 White Feather Loop, Oakland, FL 34787
• 

  /2

  $585,000 Sold Aug 20, 2025

  15114 Field Daisy Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 2025

  Last Sold Summary

  • $273/SF

  Current Estimated Value $571,622

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

  15114 Field Daisy Dr, Oakland, FL 34787
• 

  /2

  Est $808,391 Not Listed For Sale

  9516 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft
  • Built 2024

  9516 Emerald Berry Dr, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $261/SF
  • 13 Days On Market

  Last Sold Price $837,210

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
• 

  

  /86

  $629,000

  • 4 Beds
  • 2.5 Baths
  • 2,473 Sq Ft

  2606 Bobcat Chase Blvd, Oakland, FL 34787

  *** Back on the market after being temporarily off while the Seller moved (~45 days).*** NEW PRICE *** MOTIVATED *** Stunning former MODEL HOME on a premium CORNER lot (FENCING is allowed)– loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful

  Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  $455,000 Sold Jun 11, 2025

  13418 Princess St, Oakland, FL 34787

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

  Last Sold Summary

  • 1% Above List Price
  • $288/SF
  • 185 Days On Market

  Current Estimated Value $459,897

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13418 Princess St, Oakland, FL 34787
• 

  /2

  Est $591,062 Not Listed For Sale

  12891 Westhaven Oak Dr, Oakland, FL 34787

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

  12891 Westhaven Oak Dr, Oakland, FL 34787

  Last Sold Summary

  • 9% Below List Price
  • $340/SF

  Last Sold Price $649,233

  Last Listing Agent Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY
• 

  

  /25

  $693,240 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,147 Sq Ft

  3120 Namaste Dr, Oakland, FL 34787

  Under Construction. The Summerlin checks all your boxes! This breath taking two-story home features an expansive design with a convenient three-car garage. The first floor features an open-concept family room that complements a chef-ready kitchen and a cozy dining room, plus a private office and a spacious lanai. On the same level is the tranquil owner’s suite with an attached bathroom. Found

  Ben Goldstein LENNAR REALTY

  3120 Namaste Dr, Oakland, FL 34787
• 

  /2

  $954,900 Sold Oct 09, 2025

  4637 Golden Birch Ave, Oakland, FL 34787

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

  Last Sold Summary

  • $224/SF
  • 0 Days On Market

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

  4637 Golden Birch Ave, Oakland, FL 34787
• 

  /2

  Est $581,561 Not Listed For Sale

  2050 Standing Rock Cir, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,596 Sq Ft
  • Built 2019

  2050 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $231/SF
  • 5 Days On Market

  Last Sold Price $599,000

  Last Listing Agent Scott Swinson, Jr CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /55

  $819,000

  • 5 Beds
  • 4 Baths
  • 2,840 Sq Ft

  8807 Sonoma Coast Dr, Oakland, FL 34787

  Welcome to the beautiful community of Waterleigh in Winter Garden! This meticulously maintained home features 5 bedrooms, 4 bathrooms, and a second floor laundry and bonus/game room. This thoughtfully designed open-concept home offers functionality and space for all. The spacious foyer invites you into the great room filled with natural light and overlooks the pond. The kitchen features stainless

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  8807 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  $430,000 Sold Jul 16, 2025

  1113 Prado Ln, Oakland, FL 34787

  • Land
  • 0.37 Acre
  • $1,162,162 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  1113 Prado Ln, Oakland, FL 34787
• 

  /2

  Est $458,041 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

  • $257/SF
  • 115 Days On Market

  Last Sold Price $459,175

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
• 

  

  /19

  $519,000

  • 4 Beds
  • 2 Baths
  • 2,046 Sq Ft

  1270 Stationside Dr, Oakland, FL 34787

  Sellers motivated

  Ky Lam HOME INVEST REALTY INC

  1270 Stationside Dr, Oakland, FL 34787
• 

  /2

  $449,490 Sold Jul 22, 2025

  2915 Transformation Way, Oakland, FL 34787

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

  Last Sold Summary

  • $250/SF
  • 4 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2915 Transformation Way, Oakland, FL 34787
• 

  

  /11

  Est $891,190 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

  • 1% Below List Price
  • $271/SF
  • 25 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  

  /39

  $600,000 Pending

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

  1119 Bobcat Chase Blvd, Oakland, FL 34760

  Prepare to be captivated by this enchanting 4-bedroom, 2.5-bath pool home, nestled amidst mature oaks that lend an air of timeless charm. Located in the idyllic community of Long Leaf, this home boasts the best lot in the neighborhood—complete with a cozy fire pit that begs for evening gatherings under the stars.Step inside to discover a kitchen adorned with tasteful taupe cabinetry,

  Erica Diaz HOMEVEST REALTY

  1119 Bobcat Chase Blvd, Oakland, FL 34760
• 

  /2

  $380,000 Sold Jul 25, 2025

  2203 Gopher Tortoise Terrace, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $235/SF
  • 57 Days On Market

  Current Estimated Value $372,529

  Last Listing Agent Dawn Thomas KELLER WILLIAMS REALTY AT THE LAKES

  2203 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  /2

  Est $447,107 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

  • 7% Below List Price
  • $264/SF
  • 23 Days On Market

  Last Sold Price $479,000

  Last Listing Agent Brooke Barlow REAL BROKER, LLC
• 

  

  /50

  $399,000

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

  2208 Gopher Tortoise Terrace, Oakland, FL 34760

  Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere.The large open kitchen offers a large island with seating for four, granite

  Fred Mansfield ORLANDO PROP MGMNT RLTY LLC

  2208 Gopher Tortoise Terrace, Oakland, FL 34760
• 

  /2

  $525,000 Sold Oct 22, 2025

  233 Largovista Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 93 Days On Market

  Current Estimated Value $512,800

  Last Listing Agent Rachael Segarra EXP REALTY LLC

  233 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $756,093 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

  • 3% Below List Price
  • $266/SF
  • 39 Days On Market

  Last Sold Price $776,710

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP

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