Oakland, FL Homes

• 

  

  

  /3

  $649,990 New Construction

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

  Biscayne Plan at Serenade at Ovation - Single Family Homes, 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
• 

  

  

  /20

  $2,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft
  • House for Rent

  12748 Brodlove Ln, Oakland, FL 34787

  Welcome to Encore at Ovation in Horizon West! Charming BUNGALOW-style 3BR/2.5BA rental featuring a bright, open-concept layout with abundant natural light. Modern kitchen with quality cabinetry, quartz countertops, and stainless-steel appliances. Spacious primary suite with walk-in closet and private bath. Immediate availability. Community amenities include a resort-style pool, fitness center,

  Mayra Rivas Acevedo Casa Sol Realty LLC

  12748 Brodlove Ln, Oakland, FL 34787
• 

  

  /2

  $455,000 Sold Dec 23, 2025

  2023 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $218/SF
  • 123 Days On Market

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  2023 White Feather Loop, Oakland, FL 34787
• 

  

  /2

  Est $670,527 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 2,861 Sq Ft

  15014 Summer Harvest St, Oakland, FL 34787

  15014 Summer Harvest St, Oakland, FL 34787
• 

  

  

  /69

  $785,000

  • 4 Beds
  • 3 Baths
  • 2,909 Sq Ft

  9062 Sonoma Coast Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Special Financing Available — Ask for Details!Experience resort-style living in the highly desirable Waterleigh community of Winter Garden. This one-of-a-kind home sits on a rare, oversized lot with no rear neighbors, offering ultimate privacy and tranquility — perfect for families or anyone seeking a private retreat in one of Central Florida’s

  Asher Chen AAA GLOBAL VENTURES PA

  9062 Sonoma Coast Dr, Oakland, FL 34787
• 

  

  /20

  $3,410 per month

  • 4 Beds
  • 2.5 Baths
  • 2,441 Sq Ft
  • House for Rent

  12767 Harvest Rain Ave, Oakland, FL 34787

  Be the first to live in this brand-new home just delivered by the builder!Located in one of Winter Garden’s most desirable areas, surrounded by top-rated A schools, this property offers luxury, comfort, and flexibility. This beautiful residence features 4 bedrooms, including one room on the first floor that can serve as a bedroom, office, playroom, or whatever best fits your family’s needs.

  Natalia Romanelli Mourao MS LAND & BUILDING LLC

  12767 Harvest Rain Ave, Oakland, FL 34787
• 

  /2

  $465,597 Sold Dec 22, 2025

  17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787

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

  Last Sold Summary

  • $275/SF
  • 20 Days On Market

  Last Listing Agent Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787
• 

  /2

  Est $1,776,174 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,020 Sq Ft

  1243 Civitas Way, Winter Garden, FL 34787

  1243 Civitas Way, Winter Garden, FL 34787
• 

  

  /3

  $603,990 New Construction

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

  Anna Maria Plan at Serenade at Ovation - Single Family Homes, 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
• 

  

  /17

  $2,800 per month

  • 4 Beds
  • 2 Baths
  • 2,196 Sq Ft
  • House for Rent

  15238 Blue Peacock Ln, Oakland, FL 34787

  Step into 15238 Blue Peacock Ln—your next place to call home. This comfortable 4-bedroom, 3-bath rental is available for $2,900/month and offers 2,196 sq ft of bright, open living space ideal for everyday living and hosting guests. With a convenient first-floor bedroom, a cozy patio, and a 2-car garage, the home is designed for easy, practical living. Located just a short drive from Disney and

  Mariana Nossa WRA BUSINESS & REAL ESTATE

  15238 Blue Peacock Ln, Oakland, FL 34787
• 

  /2

  $1,000,000 Sold Feb 03, 2025

  13229 Tollcross Way, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,894 Sq Ft
  • Built 2024

  Last Sold Summary

  • 13% Below List Price
  • $257/SF
  • 161 Days On Market

  Current Estimated Value $1,005,713

  Last Listing Agent Dayene S. Grubert ORLANDO TBI REALTY LLC

  13229 Tollcross Way, Oakland, FL 34787
• 

  /2

  Est $526,947 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  14091 Frasier St, Oakland, FL 34787

  14091 Frasier St, Oakland, FL 34787
• 

  

  /48

  $364,900

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  507 W Oakland Ave, Oakland, FL 34760

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location!Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland

  Jennifer Ibarra REAL BROKER, LLC

  507 W Oakland Ave, Oakland, FL 34760
• 

  

  /18

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft
  • Townhouse for Rent

  17705 Japonica Bloom Dr, Oakland, FL 34787

  Beautiful Corner Townhome for Rent in One of Winter Garden’s Best Communities!Welcome to this bright and spacious 3-bedroom corner townhome, perfectly located in an exceptional Winter Garden condominium. This home offers comfort, style, and convenience and best of all, it features NO carpet throughout, making it modern, clean, and easy to maintain. Enjoy the extra windows and natural light

  Margot Villacinda Chavez WRA BUSINESS & REAL ESTATE

  17705 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  $768,700 Sold Oct 28, 2025

  5780 Dancing Willow St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,575 Sq Ft
  • Built 2025

  Last Sold Summary

  • $215/SF

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

  5780 Dancing Willow St, Oakland, FL 34787
• 

  /2

  Est $641,603 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 2,861 Sq Ft

  15030 Summer Harvest St, Oakland, FL 34787

  15030 Summer Harvest St, Oakland, FL 34787
• 

  

  /57

  $990,000

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

  9849 Lost Creek Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Big Price Reduction!!!!!! 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 you arrive,

  Jennifer Ibarra REAL BROKER, LLC

  9849 Lost Creek Dr, Oakland, FL 34787
• 

  

  /29

  $2,900 per month

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • House for Rent

  3017 Good Vibes Way, Oakland, FL 34787

  Quick facts: - End unit with large lawn- Lawn care INCLUDED- 1.2 Gb optic fiber internet INCLUDED- Pool, fitness center, tennis, pickle, and basket ball courts- Attached Garage, no rushing in the rain or burning in the sun from the garage. - Guest room on the first floor Welcome to this beautiful newly built home featuring great room connected with open kitchen. Being the end

  Steven Xu AMERICAN HOME DREAM

  3017 Good Vibes Way, Oakland, FL 34787
• 

  /2

  $1,224,660 Sold Feb 10, 2025

  15252 Canopy Cover Dr, Oakland, FL 34787

  • 4 Beds
  • 5 Baths
  • 3,653 Sq Ft
  • Built 2024

  Last Sold Summary

  • $335/SF
  • 0 Days On Market

  Current Estimated Value $1,215,734

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  15252 Canopy Cover Dr, Oakland, FL 34787
• 

  /2

  Est $491,147 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,833 Sq Ft

  9231 Gran Teatro Dr, Oakland, FL 34787

  9231 Gran Teatro Dr, Oakland, FL 34787
• 

  

  /51

  $719,900

  • 4 Beds
  • 4.5 Baths
  • 2,908 Sq Ft

  15133 Summer Harvest St, Oakland, FL 34787

  **1% lender credit with preferred lender** Better than new construction! This sought-after Baldwin floor plan from Taylor Morrison’s Bungalow Series sits on a premium first-phase pond-view lot. Featuring numerous upgrades and a rare detached garage with private den, this home offers the perfect blend of charm, functionality, and value. This versatile space includes a wet bar, full bathroom, and

  Nick Whitehouse RE/MAX PRIME PROPERTIES

  15133 Summer Harvest St, Oakland, FL 34787
• 

  

  /26

  $2,900 per month

  • 4 Beds
  • 2.5 Baths
  • 2,114 Sq Ft
  • House for Rent

  12337 Bracco St, Oakland, FL 34787

  Welcome to this stunning 2023 single-family home, perfectly situated on an oversized lot with no rear neighbors—offering privacy, space, and a serene outdoor area ideal for relaxing, walking, or grilling.Inside, the open-concept layout features a chef’s kitchen designed for entertaining and hosting family gatherings. All four bedrooms are conveniently located on the second floor, along with a

  Janet Quinones MAGNUS REALTY GROUP LLC

  12337 Bracco St, Oakland, FL 34787
• 

  /2

  $620,000 Sold May 12, 2025

  1215 Johns Cove Ln, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,811 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $221/SF
  • 124 Days On Market

  Current Estimated Value $636,426

  Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

  1215 Johns Cove Ln, Oakland, FL 34787
• 

  /2

  Est $656,479 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,743 Sq Ft

  12742 Lavender Bloom Aly, Oakland, FL 34787

  12742 Lavender Bloom Aly, Oakland, FL 34787
• 

  

  /54

  $999,300 New Construction

  • 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
• 

  

  /39

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,817 Sq Ft
  • Townhouse for Rent

  13118 Bounty Ave, Oakland, FL 34787

  PERFECT Location in PERFECT Waterleigh Community at Winter Garden! CORNER LOT! 3 bedroom + Loft/Office Upstairs + 2.5 baths. Rent includes lawn maintenance and all appliance and ALL 4 community amenities access. Great school district. Waterleigh is an amazing community, tons of amenities, including TWO large resort style clubhouses, TWO resort style pools and 3rd pool amenity, and 4th amenity is

  Jacky Liu YORK MILLS REALTY LLC

  13118 Bounty Ave, 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

  Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

  1301 Johns Cove Ln, Oakland, FL 34787
• 

  /2

  Est $494,766 Not Listed For Sale

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

  14015 Lochend Way, Oakland, FL 34787

  14015 Lochend Way, Oakland, FL 34787
• 

  

  /11

  $895,000

  • Land
  • 1.03 Acres
  • $868,932 per Acre

  529 N Pollard St, Winter Garden, FL 34787

  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

  Matthew Burks CORCORAN PREMIER REALTY

  529 N Pollard St, Winter Garden, FL 34787
• 

  

  /10

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 480 Sq Ft
  • Apartment for Rent

  5652 Lemon Grass St Unit B, Oakland, FL 34787

  BRAND NEW HOUSE IN WELLNESS RIDGE!Experience modern living in this beautifully designed private suite, crafted for comfort and convenience. Enjoy your own private entrance, a bright and spacious bedroom, and a luxurious bathroom featuring high-end finishes and a large shower. The well-equipped kitchenette includes a cooktop, refrigerator, microwave, dishwasher, and sink—everything you need

  Tiago Ferreira MANAGER PROP

  5652 Lemon Grass St Unit B, 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 $968,809

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

  1180 Riverway Dr, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,685 Sq Ft

  6343 Blissful St, Oakland, FL 34787

  6343 Blissful St, Oakland, FL 34787
• 

  

  /3

  $655,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

  Captiva Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490537, Oakland, FL 34787
• 

  

  /25

  $3,650 per month

  • 4 Beds
  • 3 Baths
  • 2,170 Sq Ft
  • House for Rent

  14213 Spring Garden Dr, Oakland, FL 34787

  For Rent 14213 Spring Garden Dr, Winter Garden, FL 34787 Brand-New Luxury One-Story Home | 4 Bedrooms | 3 Full Bathrooms | 2-Car Garage | Premium Upgrades Throughout Welcome to this stunning brand-new luxury home located in the highly sought-after Winter Garden area, just 5 minutes from Disney's Western Gate. Built by a top national builder(Toll Brother), this spacious single-story residence

  Qinghe Meng AAA GLOBAL VENTURES PA

  14213 Spring Garden Dr, Oakland, FL 34787
• 

  /2

  $1,200,000 Sold Jan 09, 2025

  914 Tilden Oaks Trail, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,803 Sq Ft
  • Built 2022

  Last Sold Summary

  • 11% Below List Price
  • $316/SF
  • 114 Days On Market

  Current Estimated Value $1,224,343

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC

  914 Tilden Oaks Trail, Winter Garden, FL 34787
• 

  /2

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,097 Sq Ft

  17971 Hither Hills Cir, Winter Garden, FL 34787

  17971 Hither Hills Cir, Winter Garden, FL 34787
• 

  /2

  $617,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,278 Sq Ft

  Lexington w/ Bonus Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 2 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36473362, Oakland, FL 34787
• 

  

  /41

  $3,100 per month

  • 3 Beds
  • 2.5 Baths
  • 2,206 Sq Ft
  • House for Rent

  14111 Frasier St, Oakland, FL 34787

  Be the first to live in this brand new Meritage Home that perfectly combines comfort, style, and energy efficiency. The open concept floor plan features a modern kitchen with a large island overlooking the great room, dining area, and patio, ideal for relaxing or entertaining. Enjoy beautiful finishes throughout, including quartz countertops, stylish tile flooring, and a detached two-car garage

  Denise Batista ALLUX REAL ESTATE LLC

  14111 Frasier St, Oakland, FL 34787
• 

  /2

  $628,000 Sold Dec 26, 2024

  15049 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,830 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $222/SF
  • 10 Days On Market

  Current Estimated Value $642,019

  Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  15049 Summer Harvest St, Oakland, FL 34787
• 

  /2

  Est $846,160 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,562 Sq Ft

  14384 Wabasso Loop, Oakland, FL 34787

  14384 Wabasso Loop, Oakland, FL 34787

Showing Results 41 - 80, Page 2 of 18