Oakland, FL Homes for Sale

• 

  

  

  /16

  $2,130,760 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, FL 34787
• 

  

  

  /36

  $364,900

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

  2117 Gopher Tortoise Terrace, Oakland, FL 34787

  Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining. The kitchen, where matching marble countertops and cabinetry create a clean and cohesive look. A charming office nook on the first floor provides the perfect spot for working from home or managing daily tasks while staying connected to the living areas.

  Mary Herrod De Boer SERHANT

  2117 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  

  

  /62

  $1,499,000

  • 6 Beds
  • 7.5 Baths
  • 5,614 Sq Ft

  620 N Tubb St, Oakland, FL 34760

  PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty

  Jennifer Wilson OAKSTRAND REALTY

  620 N Tubb St, Oakland, FL 34760
• 

  

  

  /3

  $594,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,143 Sq Ft

  12915 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is

  DeVahn Powell ORLANDO TBI REALTY LLC

  12915 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  

  /76

  $1,275,000

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  1156 Civitas Way, Winter Garden, FL 34787

  Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes

  Heidi Pfeffer-Morgan DALTON WADE INC

  1156 Civitas Way, Winter Garden, FL 34787
• 

  

  /3

  $2,098,000 New Construction

  • 4 Beds
  • 4 Baths
  • 4,557 Sq Ft

  1258 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The

  Chris Herlihy NEW HOMES REAL ESTATE, INC.

  1258 Ridge Lake Way, Winter Garden, FL 34787
• 

  

  /52

  $416,900

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

  2222 Gopher Tortoise Terrace, Oakland, FL 34787

  YOU Must see this absolutely Gorgeous 3BEDS,3 FULL BATH Townhouse in Oakland. located Between Winter Garden and Clermont..Great amenities for you enjoy the best of Florida lifestyle..This Property is the LARGEST SQ FT in the community and Best Floor Plan : Open floor concept ,that integrate Living space, Kitchen and Dinner space. Surrounded with sunlight windows. Engineering floor, granite

  Wagner ferreira LPT REALTY, LLC

  2222 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  

  /78

  $1,499,000

  • 4 Beds
  • 4.5 Baths
  • 3,613 Sq Ft

  1412 Johns Cove Ln, Oakland, FL 34787

  Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! Pristine views of John's Chain, and full access from your incredible Boat House with dual power lifts. This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely

  Betsey West NEXT RESIDENCE REALTY LLC

  1412 Johns Cove Ln, Oakland, FL 34787
• 

  

  /47

  $885,000

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  8 Winters Landing Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), located in the heart of Oakland is just minutes from downtown Winter Garden.From the moment you step inside,

  Danielle Norvell REGENCY REAL ESTATE LLC

  8 Winters Landing Dr, Oakland, FL 34787
• 

  

  /3

  $409,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  Porter Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36452383, Oakland, FL 34787
• 

  

  /76

  $1,299,500

  • 5 Beds
  • 3.5 Baths
  • 3,911 Sq Ft

  8978 Sonoma Coast Dr, Oakland, FL 34787

  LUXURY POOL HOME on PREMIUM LAKE FRONT LOT! Unique Opportunity to Enjoy an Outdoor PARADISE with STUNNING LAKE, CONSERVATION & SUNSET Views! The HOA is Allowing Docks on these Special Lots – Relax, Fish or Kayak! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3 Car Garage. The OUTDOOR LIVING Space is

  JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

  8978 Sonoma Coast Dr, Oakland, FL 34787
• 

  

  /13

  $550,000 New Construction

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

  14736 Field Daisy Dr, Oakland, FL 34787

  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 your entertainment needs and desires. The 2149 sq. ft. two-story home with 3 bedrooms, 3.5 bathrooms and a 2-car detached garage presents prospective homebuyers with both the basic features and intricate details that

  Taylor Morrison Builder

  14736 Field Daisy Dr, Oakland, FL 34787
• 

  

  /23

  $395,000

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

  2228 Gopher Tortoise Terrace, Oakland, FL 34787

  This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, fans new carpet and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling.

  Leslie Anne Campasano ASANO REAL ESTATE LLC

  2228 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  

  /49

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 3,583 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to

  Subhas C Sawh LIBERTY HOME SALES INC

  729 Strihal Loop, Oakland, FL 34787
• 

  

  /4

  $1,975,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  1106 Sarah Mathews Dr, Oakland, FL 34787

  Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living

  Heather Spirazza REGENCY REAL ESTATE LLC

  1106 Sarah Mathews Dr, Oakland, FL 34787
• 

  

  /4

  $498,990 New Construction

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

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

  Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36498626, Oakland, FL 34787
• 

  

  /17

  $2,238,120 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,204 Sq Ft

  1173 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Alexis Anderson REGENCY REAL ESTATE LLC

  1173 Prado Ln, Oakland, FL 34787
• 

  

  /11

  $1,295,000

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

  556 Walker St, Oakland, FL 34760

  LAST DEVELOPER OWNED LOT IN BILEY PHASE 1. Lakefront homesite with the ability to add your own private dock. 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

  Chocky Burks CORCORAN PREMIER REALTY

  556 Walker St, Oakland, FL 34760
• 

  

  /32

  $510,000

  • 3 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  15220 Blue Peacock Ln, Oakland, FL 34787

  Welcome to this beautiful home featuring an open floor plan that blends comfort, style, and functionality. Filled with natural light, the spacious layout is perfect for both everyday living and entertaining. The inviting living area offers a warm setting for gatherings, while the modern kitchen boasts stainless steel appliances, abundant cabinetry, and generous counter space for the home chef.

  DENILEY VALDES TALENT REALTY SOLUTIONS

  15220 Blue Peacock Ln, Oakland, FL 34787
• 

  

  /24

  $607,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  3160 Namaste Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Under Construction. This lovely Riviera Next Gen® single-story home features an attached private suite with its own living room, kitchenette, bedroom and bathroom. In the main home is an open space layout in the kitchen, nook and family room, which extends to the covered patio through sliding glass doors for outdoor living. There is a flex space to

  Ben Goldstein LENNAR REALTY

  3160 Namaste Dr, Oakland, FL 34787
• 

  

  /18

  $895,000

  • Land
  • 0.89 Acre
  • $1,005,618 per Acre

  537 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 personal oasis—whether that’s a timeless farmhouse, a

  Blaine Dooley REGENCY REAL ESTATE LLC

  537 N Pollard St, Winter Garden, FL 34787
• 

  $1,032,585 New Construction

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

  12904 Westhaven Oak Dr, Oakland, FL 34787

  The Griffin's welcoming extended covered porch, and inviting covered entry and foyer, flow past the lovely dining room to the spacious great room and views of the desirable covered lanai beyond. The well-designed kitchen overlooks a bright casual dining area, and is highlighted by a large center island with breakfast bar, plenty of counter and cabinet space, and roomy walk-in pantry. The graceful

  Toll Brothers, Inc. Builder

  12904 Westhaven Oak Dr, Oakland, FL 34787
• 

  

  /64

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

  13067 Tollcross Way, Oakland, FL 34787

  Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  13067 Tollcross Way, Oakland, FL 34787
• 

  

  /21

  $647,690 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,911 Sq Ft

  3128 Namaste Dr, Oakland, FL 34787

  Under Construction. The Inverness is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s suite

  Ben Goldstein LENNAR REALTY

  3128 Namaste Dr, Oakland, FL 34787
• 

  

  /60

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft

  936 Kylee Aly, Winter Garden, FL 34787

  Move-in ready 3-bedroom, 2.5-bathroom single-family home in the Oakland Park community of Winter Garden, Florida. Built in 2022, turnkey condition, full appliance package included, and a low-maintenance 0.05-acre homesite designed for connected daily living without the upkeep. Oakland Park is one of those Winter Garden communities people move to on purpose. Tree-lined streets, walkable sidewalks,

  Nelson Cruz REAL BROKER, LLC

  936 Kylee Aly, Winter Garden, FL 34787
• 

  

  /34

  $565,000

  • 4 Beds
  • 3.5 Baths
  • 2,477 Sq Ft

  16140 Harbor Mist Aly, Oakland, FL 34787

  Priced to sell — don't miss this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community. Offering 2,477 sq ft, 4 bedrooms, and 3.5 bathrooms, this home is move-in ready with major updates already done. The open-concept main floor features a chef-ready kitchen with granite countertops, wood cabinetry, and stainless steel appliances, flowing into spacious

  Jeanine Louis-Alcime EXP REALTY LLC

  16140 Harbor Mist Aly, Oakland, FL 34787
• 

  

  /10

  $3,200,000

  • 41 Beds
  • 75 Baths
  • 17,021 Sq Ft

  15992 W Colonial Dr, Oakland, FL 34787

  15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily OpportunityExceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland.Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style

  Kyler Moreland REMAX SUNSTATE REALTY

  15992 W Colonial Dr, Oakland, FL 34787
• 

  

  /23

  $575,000

  • Land
  • 0.45 Acre
  • $1,277,778 per Acre

  514 N Pollard St, Winter Garden, FL 34787

  Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

  Alexis Anderson REGENCY REAL ESTATE LLC

  514 N Pollard St, Winter Garden, FL 34787
• 

  

  /30

  $700,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,441 Sq Ft

  14780 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

  Taylor Morrison Builder

  14780 Field Daisy Dr, Oakland, FL 34787
• 

  

  /3

  $411,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,729 Sq Ft

  Sage Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

  The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36488308, Oakland, FL 34787
• 

  

  /30

  $874,900

  • 4 Beds
  • 4.5 Baths
  • 3,134 Sq Ft

  1231 Foltz Loop, Oakland, FL 34787

  Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living

  Elisabeth Rusnak SOUTHERN REALTY GROUP LLC

  1231 Foltz Loop, Oakland, FL 34787
• 

  

  /49

  $899,900

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft

  13343 Sunny Retreat Ln, Oakland, FL 34787

  The neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the

  John Hart ENGEL & VOLKERS ORLANDO DR PHILLIPS

  13343 Sunny Retreat Ln, Oakland, FL 34787
• 

  

  /59

  $699,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  38 S Pollard St, Oakland, FL 34760

  Welcome to this beautifully crafted custom-built two-story home in the highly desirable Town of Oakland—offering the perfect blend of quality construction, modern design, and small-town charm with NO HOA.The thoughtfully designed floor plan features all main living areas on the first floor, including a spacious living room, dining area, and a well-appointed kitchen with high-quality

  Cassia Barros MS LAND & BUILDING LLC

  38 S Pollard St, Oakland, FL 34760
• 

  

  /38

  $729,900

  • 5 Beds
  • 4.5 Baths
  • 2,931 Sq Ft

  15070 Summer Harvest St, Oakland, FL 34787

  PRICED TO SELL! 5BR Corner Lot + Private In-Law Suite + Soaring Ceilings Near Amenities Rare opportunity to own a spacious 5-bedroom home with a private in-law suite above the garage. Located on a premium corner lot just steps from the amenity center, this home offers flexibility, privacy, and modern upgrades. Priced aggressively for a quick sale—this one will not last. Welcome to this

  Robert Benenati 365 REALTY, INC.

  15070 Summer Harvest St, Oakland, FL 34787
• 

  

  /3

  $577,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

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

  The Lexington floorplan is a spacious one-story design, featuring three comfortable bedrooms and two bathrooms, offering a total of 1,856 square feet. This home includes a versatile three-car garage with tandem space, perfect for extra storage or a workshop area. The open-concept layout connects the great room, cafe, and kitchen, creating a welcoming atmosphere for entertaining and everyday

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36464864, Oakland, FL 34787
• 

  

  /14

  $440,000

  • Land
  • 0.26 Acre
  • $1,692,308 per Acre

  1161 Prado Ln, Oakland, FL 34787

  Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal

  Alexis Anderson REGENCY REAL ESTATE LLC

  1161 Prado Ln, Oakland, FL 34787
• 

  

  /3

  $374,900

  • Land
  • 0.24 Acre
  • $1,562,083 per Acre

  1215 Ridge Lake Way, Winter Garden, FL 34787

  LOT 247: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1215 Ridge Lake Way, Winter Garden, FL 34787
• 

  

  /36

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft

  651 J W Jones Rd, Winter Garden, FL 34787

  Welcome Home! Bicyclists and nature lovers will appreciate being just minutes from West Orange Trail. Let the stresses of the day melt away as you step into this beautiful residence in the highly sought-after Winter Garden. Relax on the screened front porch as you soak in the peaceful atmosphere. Inside, the open-concept design makes entertaining effortless, with a spacious living area, a kitchen

  David Seeley EXIT REALTY TRI-COUNTY

  651 J W Jones Rd, Winter Garden, FL 34787

Showing Results 41 - 78, Page 2 of 2