Oakland, FL Homes for Sale

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  /14

  $385,000

  • Land
  • 0.29 Acre
  • $1,327,586 per Acre

  610 Simeon Rd, Oakland, FL 34787

  Presenting a rare opportunity to purchase a 0.29-acre residential lot in the highly sought-after Town of Oakland. This unincorporated property offers exceptional flexibility, no HOA restrictions and agricultural zoning. Conveniently located just steps from the scenic West Orange Trail, the Oakland Nature Preserve, and downtown Oakland. Enjoy the peaceful surroundings amongst the oak trees and

  Blaine Dooley REGENCY REAL ESTATE LLC

  610 Simeon Rd, Oakland, FL 34787
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  /26

  $649,900

  • 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
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  /28

  $1,775,000

  • 5 Beds
  • 4.5 Baths
  • 3,991 Sq Ft

  854 Tilden Oaks Trail, Winter Garden, FL 34787

  This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offering a fifth bedroom, full bath, wet bar, office, and walk-in closet—an ideal setup for extended

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  854 Tilden Oaks Trail, Winter Garden, FL 34787
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  /60

  $990,000

  • 5 Beds
  • 3 Baths
  • 3,275 Sq Ft

  8162 Sayings Dr, Oakland, FL 34787

  Excellent opportunity for investors!Stunning home for sale in the coveted Storey Grove community, currently renting for $4,950 per month, guaranteeing excellent passive income from day one! Located in a prime area, close to top-notch schools and with easy access to Disney parks, this charming 5-bedroom, 3-bathroom residence offers the perfect balance of comfort, sophistication, and

  Adriana Franzoi WRA BUSINESS & REAL ESTATE

  8162 Sayings Dr, Oakland, FL 34787
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  /40

  $610,000 Open Sat 11AM - 1:30PM

  • 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
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  /46

  $745,000

  • 5 Beds
  • 4.5 Baths
  • 3,725 Sq Ft

  3294 Hanging Tide St, Oakland, FL 34787

  Step into this stunning two-story home in the popular gated community of Lakeview Preserve, where elegance meets functionality. Sitting on a larger homesite with a 4-foot garage extension, EV car charger, and beautiful stone-accented exterior, this home is as striking on the outside as it is inside. The Yorkshire floorplan by Pulte Homes offers 5 spacious bedrooms, 4.5 bathrooms, a large upstairs

  Amy Kidwell PREFERRED REAL ESTATE BROKERS

  3294 Hanging Tide St, Oakland, FL 34787
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  /35

  $585,000 Open Sat 12:30PM - 2:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  2090 Standing Rock Cir, Oakland, FL 34787

  Price reduced to $585,000 on this Stunning Home in Oakland Trails!This immaculate 3-bedroom, 2.5 bath home blends thoughtful upgrades with a warm, inviting layout. From the moment you walk in, pride of ownership is evident. The bright, open living area features built-in HEOS speakers, perfect for entertainment. The chef’s kitchen will impress with 42" wood cabinetry, granite countertops,

  Tim Boon CREEGAN GROUP

  2090 Standing Rock Cir, Oakland, FL 34787
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  /19

  $489,000

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft

  12748 Brodlove Ln, Oakland, FL 34787

  Seller Motivated! Live or invest in Encore at Ovation—a top Horizon West community in Winter Garden, Central Florida. This move-in ready home blends modern design, comfort, and everyday functionality—ideal as a primary residence or a Florida investment property. Move-in ready BUNGALOW-Style:• 3 bedrooms | 2.5 bathrooms• Bright open-concept living with abundant natural light• Modern

  Mayra Rivas Acevedo CASA SOL REALTY LLC

  12748 Brodlove Ln, Oakland, FL 34787
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  /13

  $500,000

  • Land
  • 0.47 Acre
  • $1,063,830 per Acre

  522 N Nixon St, Winter Garden, FL 34787

  As Central Florida's newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm, you will have the

  Chocky Burks CORCORAN PREMIER REALTY

  522 N Nixon St, Winter Garden, FL 34787
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  /47

  $525,000

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

  2375 Standing Rock Cir, Oakland, FL 34787

  Welcome to your perfect blend of serenity and convenience! This stunning 3-bedroom, 2.5-bath home offers over 2,000 square feet of living space and more than 3,200 square feet total. Situated on a corner lot, built in 2018, with a recently re-painted exterior and paid off solar panels, this home has curb appeal. The beautifully maintained property sits just steps from the West Orange Trail and

  

  Jarred Denison

  POP REALTY POWERED BY SELLSTATE

  (321) 415-7083

  2375 Standing Rock Cir, Oakland, FL 34787
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  /21

  $575,000

  • Land
  • 0.52 Acre
  • $1,105,769 per Acre

  520 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 24 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,

  Heather Spirazza REGENCY REAL ESTATE LLC

  520 N Pollard St, Winter Garden, FL 34787
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  /21

  $610,000

  • 5 Beds
  • 4 Baths
  • 3,903 Sq Ft

  219 Largovista Dr, Oakland, FL 34787

  Investor Special! Located in the highly desirable, gated lakefront community of Johns Landing. This spacious 5-bedroom, 4-bathroom pool home offers nearly 4,000 sq. ft. of living space (excluding garage) and features two upstairs primary suites, additional bedrooms with a loft and bathroom, plus a downstairs guest/in-law suite. The layout also includes formal living and dining rooms, an open

  Gnesa Fray INTERMIX REAL ESTATE INC

  219 Largovista Dr, Oakland, FL 34787
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  /14

  $475,000

  • Land
  • 0.37 Acre
  • $1,283,784 per Acre

  506 N Pollard St, Winter Garden, FL 34787

  As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

  Matthew Burks CORCORAN PREMIER REALTY

  506 N Pollard St, Winter Garden, FL 34787
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  /23

  $500,000

  • Land
  • 0.45 Acre
  • $1,111,111 per Acre

  514 N Pollard St, Winter Garden, FL 34787

  As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

  Alexis Anderson REGENCY REAL ESTATE LLC

  514 N Pollard St, Winter Garden, FL 34787
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  /40

  $455,000

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

  2023 White Feather Loop, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has Partial flooring replacement in some areas. Discover a bright interior tied together with a neutral color palette. You'll love cooking in this kitchen, complete with a spacious center island and a sleek backsplash. Relax in your primary suite with a walk in closet included. The primary bathroom

  Karen Albright OPENDOOR BROKERAGE LLC

  2023 White Feather Loop, Oakland, FL 34787
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  /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
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  /60

  $670,000

  • 5 Beds
  • 3 Baths
  • 2,916 Sq Ft

  3318 Current Ave, Oakland, FL 34787

  HOME WARRANTY INCLUDED + APPRAISAL COVERED IF BUYER USES SELLER’S PREFERRED LENDER! Welcome to your dream home in the highly sought-after Lakeview Preserve, a gated community nestled near the shores of Johns Lake in Winter Garden. This beautifully appointed residence offers spacious and flexible living with 5 bedrooms and 3 full bathrooms, including a convenient guest suite or office on the first

  Geoffrey Lopez II RADIUS REALTY GROUP LLC

  3318 Current Ave, Oakland, FL 34787
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  /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
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  /29

  $478,000

  • 4 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  2435 Standing Rock Cir, Oakland, FL 34787

  Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the

  Celestino De Cicco CENTRAL FLORIDA REALTY

  2435 Standing Rock Cir, Oakland, FL 34787
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  /24

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  14099 Lochend Way, Oakland, FL 34787

  Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining

  Anahi C Rosario INTERNATIONAL REAL ESTATE LLC

  14099 Lochend Way, Oakland, FL 34787
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  /33

  $504,995

  • 3 Beds
  • 2.5 Baths
  • 1,822 Sq Ft

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland community, where you'll find a modern 3-bedroom home with a bonus room—built in 2020, filled with upgrades and situated on a quiet cul-du-sac street. Located in Oakland, one of Central Florida’s most quaint and desirable small towns, 2755 Bobcat Chase offers a rare blend of peaceful living with unbeatable

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (321) 495-8074

  2755 Bobcat Chase Blvd, Oakland, FL 34787
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  /39

  $499,999

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  651 Regina Cir, Oakland, FL 34787

  ***SELLER SAYS SELL! BEST priced home in the community!*** Welcome to John’s Landing, a gated lakefront community in the charming town of Oakland, offering private lake access and a community dock on Johns Lake. Step inside this spacious 4-bedroom, 3-bathroom home with a 3-car garage and make it your own. The thoughtfully designed split floor plan includes a family room, formal living room,

  

  Savina Delgado Rodriguez

  THE PROPERTY FIRM

  (321) 495-8335

  651 Regina Cir, Oakland, FL 34787
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  /3

  $407,990 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
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  /16

  $999,563 New Construction

  • 4 Beds
  • 3 Baths
  • 2,686 Sq Ft

  Mabel Plan at Oakland Park - Park Series, Winter Garden, FL 34787

  David Weekley Homes Builder

  884 Tilden Oaks Trail Unit 36446359, Winter Garden, FL 34787
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  /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
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  /17

  $399,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

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

  The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36477638, Oakland, FL 34787
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  /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
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  /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
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  /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
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  $1,975,000 New Construction

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

  The Clementine Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36498057, Oakland, FL 34760
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  /4

  $505,990 New Construction

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

  Cooper Plan at Serenade at Ovation, 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
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  $2,175,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,433 Sq Ft

  The Citrus Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36480892, Oakland, FL 34760
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  /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
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  /3

  $409,990 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
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  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  The Hamlin Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36487597, Oakland, FL 34760
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  /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
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  /4

  $498,990 New Construction

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

  Brantley Plan at Serenade at Ovation, 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
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  /25

  $645,990 New Construction

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

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

  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  The Blossom Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36481095, Oakland, FL 34760
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  /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

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