Oakland, FL Homes

• 

  

  

  /39

  $370,000

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  1318 Painted Bunting Ave, Oakland, FL 34760

  One or more photo(s) has been virtually staged. You’re going to love this beautifully maintained 2-bedroom, 2.5-bath Townhome in the highly desirable Longleaf At Oakland which is perfectly located just a 1/2 mile from the Florida Turnpike, offering easy access to everything Central Florida has to offer. The entire interior was freshly painted in March 2026, giving the home a bright, fresh feel

  

  Randy Adams

  RE/MAX TOWN & COUNTRY REALTY

  (689) 399-4178

  1318 Painted Bunting Ave, Oakland, FL 34760
• 

  

  

  /20

  $2,400 per month

  • 3 Beds
  • 3 Baths
  • 1,647 Sq Ft
  • House for Rent

  6080 Zen Way, Oakland, FL 34787

  Beatiful home located in a desirable Clermont community. This property offers a functional floor plan with comfortable living spaces, a bright kitchen, and spacious bedrooms, conveniently located near US-27, shopping, dining, and major attractions, with easy access to Orlando and surrounding areas. A mandatory Resident Benefit Package of $50/month is required and includes renters insurance (up to

  

  Juliana Garcia Moraes

  PRISTINE INTERNATIONAL REALTY LLC

  (321) 321-7380

  6080 Zen Way, Oakland, FL 34787
• 

  

  /2

  $440,000 Sold Apr 01, 2025

  13461 Princess St, Oakland, FL 34787

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

  Last Sold Summary

  • 12% Below List Price
  • $279/SF
  • 61 Days On Market

  Current Estimated Value $449,105

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13461 Princess St, Oakland, FL 34787
• 

  

  /2

  Est $853,507 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

  • 2% Above List Price
  • $355/SF
  • 6 Days On Market

  Last Sold Price $837,500

  Last Listing Agent Tony Marino REAL LIVING R E SOLUTIONS
• 

  

  

  /24

  $993,000

  • 4 Beds
  • 2 Baths
  • 2,708 Sq Ft

  624 Hull Island Dr, Oakland, FL 34787

  Discover a rare opportunity to own a private estate property in one of West Orange County’s most desirable corridors. Situated in Oakland, this 2.55-acre parcel offers space, privacy, and future potential just minutes from the conveniences of West Colonial Drive, Florida Turnpike (Exit 275), Clermont, and the vibrant districts of Oakland and Downtown Winter Garden. Properties like this are

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 449-7661

  624 Hull Island Dr, Oakland, FL 34787
• 

  

  /16

  $1,392 - $2,884 per month

  AVENUE ON OAKLAND

  Studio - 3 Beds

  751 W Oakland Ave, Oakland, FL 34787

  Perfectly located in Oakland, Florida with easy access to the West Orange bike trail and minutes from the historic downtown Winter Garden and the Florida Turnpike. The Avenue offers unparalleled amenities and an exquisite collection of studios, one, two- and three-bedroom apartment homes.

  751 W Oakland Ave, Oakland, FL 34787
• 

  /2

  $360,000 Sold Feb 06, 2026

  507 W Oakland Ave, Oakland, FL 34760

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $269/SF
  • 50 Days On Market

  Current Estimated Value $364,595

  Last Listing Agent Jennifer Ibarra REAL BROKER, LLC

  507 W Oakland Ave, Oakland, FL 34760
• 

  /2

  Est $444,674 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

  • $245/SF
  • 12 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Ken Pozek REAL BROKER, LLC
• 

  

  /30

  $525,000 Open Sun 10AM - 2PM

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

  2660 Bobcat Chase Blvd, Oakland, FL 34760

  Welcome to your peaceful retreat in the heart of Oakland! Nestled within the highly sought-after Longleaf at Oakland community, this impeccably maintained 3-bedroom, 2 1/2-bathroom residence offers the perfect blend of 2020 construction and timeless Florida charm. Step inside to discover 1,811 square feet of bright, open-concept living space designed for both effortless entertaining and cozy

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (689) 336-3056

  2660 Bobcat Chase Blvd, Oakland, FL 34760
• 

  

  /9

  $1,600 per month

  • 1 Bed
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  1996 N Old Killarney St, Winter Garden, FL 34787

  Beautiful one-bedroom, like new apartment with all utilities included, perfectly positioned along the tranquil shores of Lake Apopka. Enjoy peaceful living just moments from the West Orange trail, great for biking, walking or skating, the trail offers direct access into Historic Winter Garden. Conveniently located near state Road 50 and the Florida Turnpike, with easy access to major attractions

  Heidi Pfeffer-Morgan DALTON WADE INC

  1996 N Old Killarney St, Winter Garden, FL 34787
• 

  /2

  $672,590 Sold Mar 05, 2026

  4743 Forest Haven Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,946 Sq Ft
  • Built 2026

  Last Sold Summary

  • $228/SF
  • 0 Days On Market

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

  4743 Forest Haven Way, Oakland, FL 34787
• 

  /2

  Est $666,896 Not Listed For Sale

  13636 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 2024

  13636 Fresh Ivy St, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $358/SF
  • 3 Days On Market

  Last Sold Price $695,000

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
• 

  

  /92

  $2,100,000 Pending

  • 5 Beds
  • 5 Baths
  • 4,934 Sq Ft

  9008 Morgana Ct, Oakland, FL 34787

  Under contract-accepting backup offers. Set along the shoreline of Lake Hickorynut in Avalon Cove, this 2022-built lakefront residence blends refined design with the ease of modern Florida living. Positioned on a cul-de-sac corner lot of approximately 0.35 acres, the home offers long, open-water views and a lifestyle centered around indoor–outdoor connection, afternoon breezes off the lake, and

  

  Bent Danholm

  DANHOLM COLLECTION

  (321) 290-8436

  9008 Morgana Ct, Oakland, FL 34787
• 

  

  /20

  $3,550 per month

  • 4 Beds
  • 3 Baths
  • 2,113 Sq Ft
  • House for Rent

  8851 Sonoma Coast Dr, Oakland, FL 34787

  Property Id: 1303402Experience the perfect blend of comfort and style in this stunning 4-bedroom, 3-bathroom home, available for $3,550 a month. With a sleek kitchen featuring quartz countertops, a spacious primary suite, and elegant wide plank tile flooring, this home is designed for modern living. Nestled in a vibrant community near top-rated schools, parks, and a brand-new Publix, it’s

  8851 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  $625,000 Sold Aug 20, 2025

  2390 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft
  • Built 2018

  Last Sold Summary

  • 11% Below List Price
  • $303/SF
  • 39 Days On Market

  Current Estimated Value $605,993

  Last Listing Agent Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC

  2390 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  Est $626,890 Not Listed For Sale

  13648 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,707 Sq Ft
  • Built 2024

  13648 Fresh Ivy St, Oakland, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $363/SF
  • 13 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
• 

  

  /34

  $635,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,445 Sq Ft

  16186 Honey Harvest St, Oakland, FL 34787

  Move-In Ready Luxury in Harvest at Ovation — Taylor Morrison Popular Baldwin Floor Plan. Sellers had change of plans. Brand new home available for immediate move-in! Why wait months to build when this stunning, just-completed Taylor Morrison Baldwin floor plan is ready for you right now? Located in the highly sought-after Harvest at Ovation community in Orlando, this exceptional 4-bedroom,

  

  Nicole Rader

  MAINFRAME REAL ESTATE

  (689) 303-5944

  16186 Honey Harvest St, Oakland, FL 34787
• 

  

  /13

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • House for Rent

  6032 Zen Way, Oakland, FL 34787

  Beautiful newer construction home for rent in the highly desirable Wellness Ridge community in Clermont. This Lennar-built property offers approximately 1,782 square feet of heated living space with a modern open-concept floor plan, featuring 3 bedrooms, 2.5 bathrooms, and a two-car garage. The home features a spacious primary suite, comfortable secondary bedrooms, and a bright living and dining

  Mariana Haddad LA ROSA REALTY LLC

  6032 Zen Way, Oakland, FL 34787
• 

  /2

  $578,310 Sold Feb 12, 2026

  4759 Forest Haven Way, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 1,882 Sq Ft
  • Built 2025

  Last Sold Summary

  • $307/SF

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

  4759 Forest Haven Way, Oakland, FL 34787
• 

  

  /8

  Est $1,247,232 Not Listed For Sale

  1080 Canyon Creek Trail, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,852 Sq Ft
  • Built 2024

  1080 Canyon Creek Trail, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $327/SF
  • 15 Days On Market

  Last Sold Price $1,259,910

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

  

  /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

  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,648 Sq Ft
  • Townhouse for Rent

  17514 Northlake Grv Dr, Oakland, FL 34787

  This property is available. Please inquire on this site to schedule a showing. Welcome to your new home at 17514 Northlake Grove Drive, Oakland, FL 34787. This beautifully designed property boasts a contemporary exterior with inviting curb appeal, featuring a charming front porch and well-maintained landscaping. Inside, you'll find a spacious open-concept living area with sleek wood

  17514 Northlake Grv Dr, Oakland, FL 34787
• 

  /2

  $862,000 Sold Jun 25, 2025

  13133 Sunny Retreat Ln, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,808 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $307/SF
  • 47 Days On Market

  Last Listing Agent Roo Klaers COLDWELL BANKER REALTY

  13133 Sunny Retreat Ln, Oakland, FL 34787
• 

  

  /21

  Est $445,425 Not Listed For Sale

  2261 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft
  • Built 2019

  2261 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • $254/SF
  • 136 Days On Market

  Last Sold Price $446,000

  Last Listing Agent tulsi sharma WATSON REALTY CORP
• 

  

  /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
• 

  

  /28

  $2,245 per month

  • 3 Beds
  • 2.5 Baths
  • 1,834 Sq Ft
  • Townhouse for Rent

  6005 Zen Way, Oakland, FL 34787

  Brand New and Never Lived In! Located in one of Clermont’s most peaceful and desirable neighborhoods of Wellness Ridge in Clermont. This new two-story 3 bedrooms and 2.5 bathrooms townhome opens to an inviting dining room with shared access to a well-equipped kitchen. The open-concept kitchen flows into the living area, with granite countertops and modern cabinetry — ideal for entertaining or

  Mo Jabr RE/MAX 200 REALTY

  6005 Zen Way, Oakland, FL 34787
• 

  /2

  $980,000 Sold Jul 08, 2025

  1206 Civitas, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,765 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $354/SF
  • 6 Days On Market

  Current Estimated Value $962,607

  Last Listing Agent Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  1206 Civitas, Oakland, FL 34787
• 

  /2

  Est $464,418 Not Listed For Sale

  14034 Scarlet Aster Aly, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,941 Sq Ft
  • Built 2024

  14034 Scarlet Aster Aly, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $241/SF
  • 256 Days On Market

  Last Sold Price $467,000

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
• 

  

  /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
• 

  

  /23

  $2,550 per month

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

  9133 Mellow Coral St, Oakland, FL 34787

  This beautiful townhome offers 3 bedrooms, 2 full bathrooms, and 1 half bath. The home features stainless steel appliances, including a contemporary refrigerator, creating a modern and elegant kitchen space. On the second floor, you will find the spacious primary suite, two additional bedrooms, and a convenient laundry room equipped with a washer and dryer. Ideally located just steps from the

  Viviane Rocha WRA BUSINESS & REAL ESTATE

  9133 Mellow Coral St, Oakland, FL 34787
• 

  /2

  $1,010,000 Sold Mar 31, 2025

  1175 Celadon St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,751 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $367/SF
  • 8 Days On Market

  Current Estimated Value $1,014,164

  Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

  1175 Celadon St, Oakland, FL 34787
• 

  /2

  Est $970,622 Not Listed For Sale

  126 Hammock Preserve Loop, Oakland, FL 34787

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

  126 Hammock Preserve Loop, Oakland, FL 34787

  Last Sold Summary

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

  Last Sold Price $980,000

  Last Listing Agent Jenna Palmero COLDWELL BANKER REALTY
• 

  $829,346 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,718 Sq Ft

  15075 Tea Tree Dr, 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

  15075 Tea Tree Dr, Oakland, FL 34787
• 

  

  /23

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • House for Rent

  17651 Japonica Bloom Dr, Oakland, FL 34787

  Beautiful, brand-new 3-bedroom, 2-bath single-family home situated on a desirable corner lot, offering 1,788 sq ft of living space. This modern home features an open-concept layout with a contemporary kitchen equipped with stainless steel appliances, granite countertops, and a spacious island. Tile flooring runs throughout the entire home, including all bedrooms, providing a clean and cohesive

  Leidy Sanquiz ROMAN'S PRO REALTY LLC

  17651 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  $404,990 Sold Jul 29, 2025

  2907 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,647 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $246/SF
  • 18 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2907 Transformation Way, Oakland, FL 34787
• 

  /2

  Est $840,858 Not Listed For Sale

  3220 Sailing Pier Ave, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,363 Sq Ft
  • Built 2020

  3220 Sailing Pier Ave, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $372/SF
  • 116 Days On Market

  Last Sold Price $880,000

  Last Listing Agent Andrea Pointon POINTON REALTY INC
• 

  

  /4

  $505,990 New Construction

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

  Cooper Plan at Serenade at Ovation - Bungalow, Oakland, FL 34787

  Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36487507, Oakland, FL 34787
• 

  

  /23

  $2,900 per month

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Townhouse for Rent

  11043 Bookmark Ln, Oakland, FL 34787

  Beautiful townhome 4 bedrooms/ 2.5 bathrooms. Master suite on the first floor, beautiful upgraded tile floor. Great private area on the back all covered with bricks and two cars garage. Clubhouse is under construction, which will have an incredible swimming pool, splash zone, fitness center, basketball court and a beautiful sunset! Minutes away from Orlando theme parks, entertainment, shops and

  Isabel Sirizzotti SUNNY 365 REALTY GROUP

  11043 Bookmark 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

  Current Estimated Value $461,979

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  2023 White Feather Loop, Oakland, FL 34787
• 

  

  /49

  Est $568,649 Not Listed For Sale

  2550 Standing Rock Cir, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,638 Sq Ft
  • Built 2018

  2550 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 137 Days On Market

  Last Sold Price $580,000

  Last Listing Agent Monica Restrepo UNITED REALTY GROUP INC

Showing Results 1 - 40, Page 1 of 18