Oakland, FL Homes

• 

  

  

  /52

  $410,000

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

  13293 Pontoon Rd, Oakland, FL 34787

  Sometimes the right home just feels easy. This 3-bedroom, 3-bath corner unit townhome was built in 2023 and sits in one of Winter Garden’s most sought-after neighborhoods, Waterleigh. From the moment you pull into the driveway, you’ll notice how clean, simple, and ready it feels. No projects. No waiting. Just move in and enjoy.Inside, natural light pours through every room, highlighting

  Mark Raumaker SERHANT

  13293 Pontoon Rd, Oakland, FL 34787
• 

  

  

  /30

  $2,990 per month

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • House for Rent

  2684 Bobcat Chase Blvd, Oakland, FL 34787

  $200.00 off the first month’s rent. LOCATION, LOCATION, LOCATION! Discover this beautifully constructed 4-bedroom, 2.5-bathroom home built in 2021, ideally located just minutes from downtown Winter Garden! The open-concept main floor features a modern kitchen with quartz countertops, solid wood cabinets, tile floors, a breakfast bar, and a closet pantry—perfect for cooking and entertaining. The

  Sarah Cohim MCO REALTY GROUP LLC

  2684 Bobcat Chase Blvd, Oakland, FL 34787
• 

  

  

  /37

  $449,990 Sold Nov 13, 2025

  • 1,696 Sq Ft
  • $265/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  17687 Japonica Bloom Dr, Oakland, FL 34787

  Welcome to The Regina II in Northlake at Ovation, where modern design meets everyday convenience. This thoughtfully crafted home offers spacious living areas perfect for both relaxing and entertaining. Nestled in the highly sought-after Winter Garden area, residents can enjoy great schools, scenic surroundings, and a true sense of community. Located just 37 minutes from Orlando International

  Ashton Woods

  17687 Japonica Bloom Dr, Oakland, FL 34787
• 

  

  /2

  Est $506,982 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft

  14011 Lochend Way, Oakland, FL 34787

  14011 Lochend Way, Oakland, FL 34787
• 

  

  

  /51

  $839,900

  • 3 Beds
  • 2.5 Baths
  • 2,348 Sq Ft

  9008 Sonoma Coast Dr, Oakland, FL 34787

  Welcome to your dream home! This beautifully decorated 3 Bedroom, 2 1/2 Bath + Office home where comfort meets style offers stunning lake views and a sleek tile roof. Upon entering you'll be greeted by architectural arches and a wide foyer entry. To your left, you will be greeted by architectural arches and a wide foyer entry. On your left you will find a Den/Study/Office with glass entry doors &

  Gary Berkson RE/MAX CENTRAL REALTY

  9008 Sonoma Coast Dr, Oakland, FL 34787
• 

  

  /41

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft
  • Townhouse for Rent

  4584 Maple Waltz, Oakland, FL 34787

  Welcome to 4584 Maple Waltz Alley, a pristine, never-lived-in new construction home perfectly situated between Clermont and Winter Garden. This thoughtfully designed floorplan offers an open-concept living area where the kitchen, dining, and family spaces flow seamlessly to maximize comfort and natural light. The bedrooms are arranged for privacy, with the primary suite tucked away featuring a

  Ashley Porto GLASSTONE GROUP INC

  4584 Maple Waltz, Oakland, FL 34787
• 

  /2

  $410,000 Sold Feb 07, 2025

  1171 Railside Way, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 1,759 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $233/SF
  • 13 Days On Market

  Current Estimated Value $411,472

  Last Listing Agent Mark D'Italia PROPERTY LOGIC RE

  1171 Railside Way, Oakland, FL 34787
• 

  /2

  Est $495,761 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft

  14047 Lochend Way, Oakland, FL 34787

  14047 Lochend Way, Oakland, FL 34787
• 

  

  /26

  $649,700

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft

  326 Largovista Dr, Oakland, FL 34787

  Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring ceilings, abundant natural light, and an open-concept layout ideal for both entertaining and everyday

  Chris Sanford EXP REALTY LLC

  326 Largovista Dr, Oakland, FL 34787
• 

  

  /45

  $3,750 per month

  • 5 Beds
  • 4 Baths
  • 2,700 Sq Ft
  • House for Rent

  12887 Westhaven Oak Dr, Oakland, FL 34787

  Amazing Property, Welcome to your Luxury dream home! This stunning 5 bedroom, 4 bathroom property boasts superior quality finishes andtop-of-the-line appliances throughout. From the moment you step inside, you'll be wowed by the open floor plan, 9’4” Ceilings and qualitycraftsmanship that is evident in every detail. The heart of the home is the beautiful gourmet kitchen, complete with

  Maria Elena EXP REALTY LLC

  12887 Westhaven Oak Dr, Oakland, FL 34787
• 

  /2

  $1,050,000 Sold Feb 14, 2025

  1056 Sadler Oaks Way, Oakland, FL 34787

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

  Last Sold Summary

  • 4% Below List Price
  • $387/SF
  • 129 Days On Market

  Current Estimated Value $1,042,482

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1056 Sadler Oaks Way, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

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

  Unlisted Address

  Unlisted Address
• 

  

  /51

  $849,000

  • 4 Beds
  • 4.5 Baths
  • 2,741 Sq Ft

  3375 Hanging Tide St, Oakland, FL 34787

  An Enchanting Suburban Gem Marries the appeal of small-town life with the allure of urban conveniences. 4 Bedroom, 4.5 Bathroom POOL Home situated within the Gated Community of the stylish Lakeview Preserve on beautiful Johns Lake. Sitting on a private cul-de-sac, this residence offers breathtaking sunset views over the pool and an inviting indoor-outdoor living experience. The heart of the home

  Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  3375 Hanging Tide St, Oakland, FL 34787
• 

  

  /9

  $2,449 per month

  • 3 Beds
  • 2.5 Baths
  • 1,451 Sq Ft
  • Condo for Rent

  12028 Holystone St, Oakland, FL 34787

  ATTENTION GOOD RENTERS!! COME TO SHOW THIS WONDERFUL OPORTUNITY FOR RENT YOUR DREAM TOWNHOUSE IN WINTER GARDEN. THE COMMUNITY IS BEAUTIFUL, GREAT SCHOOLS, GREAT AREAS FOR LIVING. ONCE YOU ENTER TO THE PROPERTY, YOU WILL FEEL LIKE YOU ARE AT HOME. THE DISTIBUTION ON FIRST FLOOR IS NICE BECAUSE YOU WILL SEE THE FAMILY ROM, DINING ROOM AND KITCHEN ALL INTEGRATED IN ONE OPEN SPACE. THE SECOND FLOOR

  Maria G Camacho ORLANDO KEY REALTY LLC

  12028 Holystone St, Oakland, FL 34787
• 

  /2

  $980,000 Sold Mar 17, 2025

  126 Hammock Preserve Loop, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,811 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $349/SF
  • 19 Days On Market

  Current Estimated Value $982,215

  Last Listing Agent Jenna Palmero COLDWELL BANKER REALTY

  126 Hammock Preserve Loop, Oakland, FL 34787
• 

  /2

  Est $597,213 Not Listed For Sale

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

  13007 Tollcross Way, Oakland, FL 34787

  13007 Tollcross Way, Oakland, FL 34787
• 

  

  /55

  $997,790 New Construction

  • 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
• 

  

  /41

  $3,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • House for Rent

  9588 Jacques Aly, Oakland, FL 34787

  Welcome to Waterleigh in the desirable area of Horizon West located in Winter Garden, FL. “Come Here and Stay” in this stunning community situated on over 1,400 acres of land with over a dozen lakes and ponds. Check out one of Waterleigh’s most popular bungalow floor-plans the Cordale offering 4 bedrooms, 2.5 bathrooms, and an attached 2 car garage. Enjoy the water view, while sitting on the

  Teresa Valdes VALSTAR REALTY LLC

  9588 Jacques Aly, Oakland, FL 34787
• 

  /2

  $1,400,000 Sold Jun 27, 2025

  141 Millholland St, Oakland, FL 34760

  • 4 Beds
  • 3.5 Baths
  • 3,497 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $400/SF
  • 72 Days On Market

  Current Estimated Value $1,394,602

  Last Listing Agent Matthew Matin CLOCK TOWER REALTY

  141 Millholland St, Oakland, FL 34760
• 

  /2

  Est $834,528 Not Listed For Sale

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

  5590 Orange Orchard Dr, Oakland, FL 34787

  5590 Orange Orchard Dr, Oakland, FL 34787
• 

  

  /38

  $709,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  2986 Good Vibes Way, Oakland, FL 34787

  Under Construction. Welcome to the Steely, an innovative two-story Next Gen® home. This home features a private suite with a separate entrance, living area, kitchenette, bedroom, bathroom and laundry, ideal for multigenerational households. The main home is host to an inviting open-concept layout that blends the kitchen, living and dining areas, while a luxe owner’s suite at the back of the home

  Ben Goldstein LENNAR REALTY

  2986 Good Vibes Way, Oakland, FL 34787
• 

  

  /76

  $5,500 per month

  • 5 Beds
  • 4.5 Baths
  • 3,653 Sq Ft
  • House for Rent

  15511 Shorebird Ln, Oakland, FL 34787

  Welcome to this open plan 5 Bedroom, 4 and a half bathroom water front home including a 3 car garage.Flooring includes tile, laminate and carpet. You will never run out of storage with the abundance of cabinets. Chef's kitchen include upgraded appliances and wall oven. Large sliders allow plenty of light and gorgeous water view and open to a covered lanai. Some of the amenities include a

  Mark Volchko REALTY WORLD PREFERRED

  15511 Shorebird Ln, Oakland, FL 34787
• 

  /2

  $700,000 Sold Jan 16, 2025

  930 Auction Aly, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,425 Sq Ft
  • Built 2022

  Last Sold Summary

  • 8% Below List Price
  • $289/SF
  • 76 Days On Market

  Current Estimated Value $718,685

  Last Listing Agent Sandy Jones CLOCK TOWER REALTY

  930 Auction Aly, Winter Garden, FL 34787
• 

  /2

  Est $827,799 Not Listed For Sale

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

  9516 Emerald Berry Dr, Oakland, FL 34787

  9516 Emerald Berry Dr, Oakland, FL 34787
• 

  

  /40

  $599,900

  • 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

  $735,000 Sold Oct 30, 2025

  2340 Standing Rock Cir, Winter Garden, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,493 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $210/SF
  • 112 Days On Market

  Last Listing Agent Jennifer Coon KELLER WILLIAMS WINTER PARK

  2340 Standing Rock Cir, Winter Garden, FL 34787
• 

  /2

  Est $625,252 Not Listed For Sale

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

  12891 Westhaven Oak Dr, Oakland, FL 34787

  12891 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  /43

  $714,500

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

  2450 Standing Rock Cir, Oakland, FL 34787

  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 relaxing with friends. Go outside to your

  Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  2450 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  $690,000 Sold May 13, 2025

  2157 Bay Line Rd, Oakland, FL 34787

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

  Last Sold Summary

  • 10% Below List Price
  • $303/SF
  • 69 Days On Market

  Current Estimated Value $682,021

  Last Listing Agent Jamie Stolinas Crame CENTURY 21 CARIOTI

  2157 Bay Line Rd, Oakland, FL 34787
• 

  /2

  Est $596,562 Not Listed For Sale

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

  2050 Standing Rock Cir, Oakland, FL 34787

  2050 Standing Rock Cir, Oakland, FL 34787
• 

  

  /32

  $1,450,000

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

  101 N Starr St, Oakland, FL 34760

  Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney.Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly.

  Evan Gfeller BHHS FLORIDA REALTY

  101 N Starr St, Oakland, FL 34760
• 

  /2

  $395,000 Sold Nov 21, 2025

  13322 Pontoon Rd, Oakland, FL 34787

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

  Last Sold Summary

  • 1% Below List Price
  • $252/SF
  • 46 Days On Market

  Last Listing Agent Denise Gregorie CLOCK TOWER REALTY

  13322 Pontoon Rd, Oakland, FL 34787
• 

  /2

  Est $480,735 Not Listed For Sale

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

  14018 Scarlet Aster Aly, Oakland, FL 34787

  14018 Scarlet Aster Aly, Oakland, FL 34787
• 

  

  /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

  $855,000 Sold Apr 10, 2025

  234 Hammock Preserve Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,255 Sq Ft
  • Built 2023

  Last Sold Summary

  • $379/SF
  • 6 Days On Market

  Current Estimated Value $863,284

  Last Listing Agent Lianna D'Angelo SOTERA LIVING

  234 Hammock Preserve Loop, Oakland, FL 34787
• 

  /2

  Est $456,701 Not Listed For Sale

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

  9030 Wading Walk Ln, Oakland, FL 34787

  9030 Wading Walk Ln, Oakland, FL 34787
• 

  

  /4

  $508,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Newbury Plan at Serenade at Ovation, Oakland, FL 34787

  Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490206, Oakland, FL 34787
• 

  /2

  $695,000 Sold Feb 03, 2025

  14219 Spring Garden Dr, Oakland, FL 34787

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

  Last Sold Summary

  • 11% Below List Price
  • $319/SF
  • 48 Days On Market

  Current Estimated Value $695,630

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO

  14219 Spring Garden Dr, Oakland, FL 34787
• 

  /2

  Est $769,333 Not Listed For Sale

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

  9517 Emerald Berry Dr, Oakland, FL 34787

  9517 Emerald Berry Dr, Oakland, FL 34787
• 

  

  /49

  $645,000

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  847 Cura Ct, Oakland, FL 34787

  Welcome to this beautifully maintained home located in the gated waterfront community of John’s Landing, nestled along the scenic 2,600-acre John’s Lake chain. This property offers a blend of upgraded features, generous living spaces, and an exceptional community lifestyle. A brand-new roof will be delivered at closing, as the replacement process is already underway through the insurance company.

  Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  847 Cura Ct, Oakland, FL 34787

Showing Results 81 - 120, Page 3 of 18