Oakland, FL Homes

• 

  

  

  /25

  $645,990

  New Construction

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

  Anna Maria w/ Bonus Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36501514, Oakland, FL 34787
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• 

  

  

  /17

  $3,800 Per Month

  • 5 Beds
  • 4.5 Baths
  • 2,861 Sq Ft
  • House for Rent

  15030 Summer Harvest St, Oakland, FL 34787

  Nestled in the sought-after Harvest at Ovation community in Horizon West/Winter Garden, this beautifully appointed single-family home offers the perfect combination of comfort, style, and location. Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, the home includes a desirable first-floor suite—ideal for guests or multi-generational living. Enjoy the convenience of being just minutes from

  Cristiane Leon KICANTO REALTY

  15030 Summer Harvest St, Oakland, FL 34787
• 

  

  /2

  $430,000

  Sold Mar 23, 2026

  2201 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $245/SF
  • 6 Days On Market

  Current Estimated Value $429,405

  Last Listing Agent Christine Anthony CHARLES RUTENBERG REALTY ORLANDO

  2201 Standing Rock Cir, Oakland, FL 34787
• 

  

  /2

  Est $573,750

  Not Listed For Sale

  11015 Bostwick Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 2023

  11015 Bostwick Aly, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /3

  $649,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  Biscayne Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36496529, Oakland, FL 34787
• 

  

  /29

  $2,595 Per Month

  • 4 Beds
  • 2 Baths
  • 1,778 Sq Ft
  • House for Rent

  17802 Jefferson St, Oakland, FL 34787

  Spacious 4 Bedroom, 2 Bath Split Plan Lake View House with Oversized Corner Lot. Owner has recently updated Home. New Paint on Interior. Tile throughout Home. Fireplace has Granite Hearth and Travertine Facing. Newer Custom Kitchen with granite tops, tumbled marble back splash with decorative tiles. Newer Stainless Steel Appliances. Master bath has Frameless Shower Door. No Sewer Bill. No Water

  Barry Stephens MAINFRAME REAL ESTATE

  17802 Jefferson St, Oakland, FL 34787
• 

  /2

  $710,000

  Sold Nov 04, 2025

  1301 Johns Cove Ln, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,495 Sq Ft
  • Built 2003

  Last Sold Summary

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

  Current Estimated Value $697,621

  Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

  1301 Johns Cove Ln, Oakland, FL 34787
• 

  /2

  Est $1,054,347

  Not Listed For Sale

  1112 Sarah Mathews Dr, Oakland, FL 34787

  • 5 Beds
  • 6 Baths
  • 3,956 Sq Ft
  • Built 2025

  1112 Sarah Mathews Dr, Oakland, FL 34787

  Last Sold Summary

  • 0 Days On Market
• 

  

  /3

  $603,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  Anna Maria Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36464429, Oakland, FL 34787
• 

  

  /19

  $2,800 Per Month

  • 4 Beds
  • 3 Baths
  • 1,847 Sq Ft
  • Townhouse for Rent

  4580 Maple Waltz, Oakland, FL 34787

  Welcome to this brand-new 4-bedroom, 3-bathroom townhome located in the highly desirable Parkside Trails community in Clermont. Featuring an open-concept floor plan filled with natural light, this home offers a modern kitchen with quartz countertops, stainless steel appliances, and ample cabinet space. One bedroom and a full bathroom are conveniently located on the first floor, perfect for guests

  Marta Faustino DTB FLORIDA REALTY, INC.

  4580 Maple Waltz, Oakland, FL 34787
• 

  /2

  $990,900

  Sold Jul 09, 2025

  1180 Riverway Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,796 Sq Ft
  • Built 2025

  Last Sold Summary

  • $354/SF

  Current Estimated Value $1,010,825

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

  1180 Riverway Dr, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  16465 Hamlin View St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • Built 2025

  16465 Hamlin View St, Oakland, FL 34787

  Last Sold Summary

  • 0 Days On Market
• 

  

  /57

  $990,000

  $110K PRICE DROP Pending

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9849 Lost Creek Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Virtually Staged. ACCEPTING BACK UP OFFERS. Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience. From the moment

  Jennifer Ibarra REAL BROKER, LLC

  9849 Lost Creek Dr, Oakland, FL 34787
• 

  

  /23

  $2,600 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,567 Sq Ft
  • Townhouse for Rent

  9496 Bauer Aly, Oakland, FL 34787

  Waterleigh Subdivision 3/2.5 Town Home For Rent in Winter Garden, Fl. 34787. Range, Refrigerator, D/W, Disposal, Central Heat and A/C, Call to schedule a showing. Brand New Construction, townhouse for rent, energy efficient , 3 bedroom, 2.5 bathrooms. 1 Car Garage and large driveway. Spacious 1,567 SqFt.; Features include laundry room, walk-in closet, linen closet, blinds, ceiling fans, dual sink

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  9496 Bauer Aly, Oakland, FL 34787
• 

  /2

  $550,000

  Sold May 22, 2026

  1490 Stone Arrow Ct, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,248 Sq Ft
  • Built 2019

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 96 Days On Market

  Current Estimated Value $573,118

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  1490 Stone Arrow Ct, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  16459 Hamlin View St, Oakland, FL 34787

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

  16459 Hamlin View St, Oakland, FL 34787

  Last Sold Summary

  • 26 Days On Market
• 

  

  /5

  $2,353,078

  New Construction Pending

  • 4 Beds
  • 6 Baths
  • 3,902 Sq Ft

  1204 Water Maple Dr, Oakland, FL 34760

  Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living

  Alexis Anderson REGENCY REAL ESTATE LLC

  1204 Water Maple Dr, Oakland, FL 34760
• 

  

  /32

  $3,100 Per Month

  • 4 Beds
  • 3 Baths
  • 1,897 Sq Ft
  • Townhouse for Rent

  12851 Westhaven Oak Dr, Oakland, FL 34787

  **AVAILABLE STARTING June 25, 2026** Welcome to this stunning townhome in the highly desirable Winter Garden area. Designed with modern living in mind, this home offers the perfect blend of style, comfort, and convenience. The open-concept floor plan creates a bright and inviting atmosphere, featuring a spacious family room, dining area, and a beautifully appointed kitchen with modern appliances

  Ricardo Molina TALENT REALTY SOLUTIONS

  12851 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  /37

  $449,990

  Sold Nov 13, 2025

  17687 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,696 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $265/SF
  • 15 Days On Market

  Ashton Woods Northlake at Ovation - Townhomes

  17687 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  Est $416,331

  Not Listed For Sale

  16926 Reseda Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2020

  16926 Reseda Aly, Oakland, FL 34787

  Last Sold Summary

  • 63 Days On Market
• 

  

  /76

  $1,145,000

  $150K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,469 Sq Ft

  250 N Walker St, Oakland, FL 34760

  SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property

  Alaina DiMare COAST TO COAST REAL ESTATE PRO

  250 N Walker St, Oakland, FL 34760
• 

  

  /37

  $2,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,687 Sq Ft
  • Townhouse for Rent

  9109 Legado Dr, Oakland, FL 34787

  Welcome to your new home in one of Central Florida’s most desirable communities! This beautiful residence offers the perfect blend of comfort, convenience, and resort-style living just minutes from the magic of Disney World. Step inside this corner unit, ideally positioned with no neighbors on one side, and discover a spacious, open-concept layout designed for modern living. The gourmet kitchen

  George Berry, III DIAMOND REAL ESTATE GROUP

  9109 Legado Dr, Oakland, FL 34787
• 

  /2

  $446,340

  Sold Feb 25, 2026

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft
  • Built 2026

  Last Sold Summary

  • $204/SF

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

  Unlisted Address
• 

  /2

  Est $853,266

  Not Listed For Sale

  932 Tilden Oaks Trail, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,362 Sq Ft
  • Built 2021

  932 Tilden Oaks Trail, Winter Garden, FL 34787

  Last Sold Summary

  • 6 Days On Market
• 

  

  /3

  $919,000

  New Construction $30K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 3,894 Sq Ft

  12940 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a

  Dayene Grubert ORLANDO TBI REALTY LLC

  12940 Westhaven Oak Dr, 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

  $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 $1,402,544

  Last Listing Agent Matthew Matin CLOCK TOWER REALTY

  141 Millholland St, Oakland, FL 34760
• 

  /2

  Not Listed For Sale

  3119 Armstrong Ave, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 1,867 Sq Ft
  • Built 2025

  3119 Armstrong Ave, Oakland, FL 34787

  Last Sold Summary
• 

  

  /43

  $550,000

  New Construction $47K PRICE DROP Pending

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

  14736 Field Daisy Dr, Oakland, FL 34787

  Under Construction. What's Special: Close to Amenities | Close to Trails | North Facing Lot | Popular Plan | Covered Extended Lanai. New Construction - August Completion! Built by America's Most Trusted Home Builder. 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

  Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  14736 Field Daisy Dr, Oakland, FL 34787
• 

  

  /24

  $3,350 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,450 Sq Ft
  • House for Rent

  15006 Summer Harvest St, Oakland, FL 34787

  Welcome to this beautiful 4-bedroom, 3.5-bath single-family bungalow located in the highly desirable Harvest at Ovation community in Winter Garden. This spacious home offers a thoughtfully designed floor plan featuring a first-floor bedroom with a full bathroom, perfect for guests, multigenerational living, or a private home office. The second floor includes 3 bedrooms, 2 full baths and a

  Tati Nagamine de Almeida TALENT REALTY SOLUTIONS

  15006 Summer Harvest 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

  Current Estimated Value $744,046

  Last Listing Agent Jennifer Coon LAKESIDE REALTY WINDERMERE INC

  2340 Standing Rock Cir, Winter Garden, FL 34787
• 

  /2

  Est $430,671

  Not Listed For Sale

  13311 Pontoon Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2023

  13311 Pontoon Rd, Oakland, FL 34787

  Last Sold Summary

  • 12 Days On Market
• 

  

  /53

  $974,300

  New Construction $46K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 4,271 Sq Ft

  4608 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

  4608 Golden Birch Ave, Oakland, FL 34787
• 

  

  /34

  $2,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,873 Sq Ft
  • Townhouse for Rent

  6069 Zen Way, Oakland, FL 34787

  Beautiful and brand-new corner-unit townhome in the highly desirable Wellness Ridge community! Ideally located just steps from the clubhouse and resort-style amenities, including a pool, playground, tennis courts, and basketball courts. This 3-bedroom, 2.5-bath home features an open-concept layout, a modern kitchen with stainless steel appliances, a spacious primary suite with a walk-in closet,

  Denise Simoes DELUX MIAMI GROUP, LLC.

  6069 Zen Way, Oakland, FL 34787
• 

  /2

  $519,000

  Sold May 22, 2026

  2618 Bobcat Chase Blvd, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft
  • Built 2020

  Last Sold Summary

  • $332/SF
  • 7 Days On Market

  Current Estimated Value $506,929

  Last Listing Agent Elena Santiago THE REAL ESTATE COLLECTION LLC

  2618 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $1,019,757

  Not Listed For Sale

  210 Hammock Preserve Loop, Oakland, FL 34787

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

  210 Hammock Preserve Loop, Oakland, FL 34787

  Last Sold Summary

  • 47 Days On Market
• 

  

  /5

  $1,295,000

  • Land
  • 1.26 Acres
  • $1,027,778 per Acre

  556 Walker St, Oakland, FL 34760

  Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your oasis—a timeless farmhouse, a classic Southern estate, or a

  Matthew Burks CORCORAN PREMIER REALTY

  556 Walker St, Oakland, FL 34760
• 

  

  /34

  $3,900 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft
  • House for Rent

  2501 Sky Stone Ct, Oakland, FL 34787

  Beautifully maintained home in the desirable Oakland Trails community, ideally located on a quiet dead-end street withpeaceful preserve views and no rear neighbors. The open layout features natural light, a spacious living area, a modernkitchen, and large, comfortable bedrooms. Enjoy community amenities, including a pool, playground, and walking paths,with direct access to the West

  Lisa Reed ENGEL & VOLKERS CLERMONT

  2501 Sky Stone Ct, Oakland, FL 34787
• 

  /2

  $470,000

  Sold Feb 14, 2026

  17562 Northlake Grove Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF

  Current Estimated Value $471,000

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

  17562 Northlake Grove Dr, Oakland, FL 34787
• 

  /2

  Est $484,115

  Not Listed For Sale

  16257 Prairie School Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft
  • Built 2021

  16257 Prairie School Dr, Oakland, FL 34787

  Last Sold Summary

  • 54 Days On Market

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