Studio to 5 Bedroom Homes for Sale in Oakland, FL

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  $1,000,000

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

  624 Hull Island Dr, Oakland, FL 34787

  Find out about the unique chance to be the owner of a 2,700 sqft home which sits on 2.55 private acres which we think is the ideal setting for space, privacy, and great growth. This 1983 built home has been very well preserved in it’s original condition which makes it the perfect choice for buyers who are after land, character and the freedom to update the home to suit their own style. In the

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 449-7661

  624 Hull Island Dr, Oakland, FL 34787
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  /38

  $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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  /92

  $2,200,000

  • 5 Beds
  • 5 Baths
  • 5,143 Sq Ft

  9008 Morgana Ct, Oakland, FL 34787

  Set along the shoreline of Lake Hickorynut in the boutique community of Avalon Cove, this 2022-built lakefront residence combines modern design, thoughtful detail, and a lifestyle centered around light, space, and water. Positioned on a cul-de-sac corner lot of approximately 0.35 acres, the home captures long, open-water views and effortless indoor-outdoor living. Sunsets unfold across the lake

  

  Bent Danholm

  MAXIM Realty Orlando

  (321) 290-8436

  9008 Morgana Ct, Oakland, FL 34787
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  /52

  $535,000

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft

  9029 Sonoma Coast Dr, Oakland, FL 34787

  Experience modern Florida living in this stunning, move-in-ready home at 9029 Sonoma Coast Dr, Winter Garden. Built in 2020, this light-filled residence features 3 spacious bedrooms, 2.5 bathrooms, and an open-plan layout that blends comfort with contemporary style, offering over 2,000 square feet of thoughtfully designed living space.? Step inside to discover a beautifully updated interior with

  

  Abraham Mendez

  NONA LEGACY POWERED BY LA ROSA

  (321) 766-5509

  9029 Sonoma Coast Dr, Oakland, FL 34787
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  /33

  $500,000

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

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (321) 495-8074

  2755 Bobcat Chase Blvd, 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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  /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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  $830,266 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
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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
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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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  $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
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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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  /40

  $479,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft

  17526 Northlake Grove Dr, Oakland, FL 34787

  Discover exceptional living in this thoughtfully designed end-unit townhome, perfectly situated in the heart of Winter Garden. Just 37 minutes from Orlando International Airport and 20 minutes from world-famous Disney theme parks, this home offers unbeatable convenience paired with the charm and rich local history the area is known for. Inside, you’ll find a beautifully curated kitchen, living,

  Ashton Woods Builder

  17526 Northlake Grove Dr, Oakland, FL 34787
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  $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
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  /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
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  $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
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  /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
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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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  /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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  /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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  /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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  /26

  $649,700

  • 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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  /51

  $849,000

  • 4 Beds
  • 4.5 Baths
  • 2,741 Sq Ft

  3375 Hanging Tide St, Oakland, FL 34787

  An Enchanting Suburban Gem Marries the appeal of small-town life with the allure of urban conveniences. 4 Bedroom, 4.5 Bathroom POOL Home situated within the Gated Community of the stylish Lakeview Preserve on beautiful Johns Lake. Sitting on a private cul-de-sac, this residence offers breathtaking sunset views over the pool and an inviting indoor-outdoor living experience. The heart of the home

  Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  3375 Hanging Tide St, Oakland, FL 34787
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  /55

  $997,790 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,313 Sq Ft

  4632 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

  4632 Golden Birch Ave, Oakland, FL 34787
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  /38

  $709,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  2986 Good Vibes Way, Oakland, FL 34787

  Under Construction. Welcome to the Steely, an innovative two-story Next Gen® home. This home features a private suite with a separate entrance, living area, kitchenette, bedroom, bathroom and laundry, ideal for multigenerational households. The main home is host to an inviting open-concept layout that blends the kitchen, living and dining areas, while a luxe owner’s suite at the back of the home

  Ben Goldstein LENNAR REALTY

  2986 Good Vibes Way, Oakland, FL 34787
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  /40

  $599,900

  • 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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  /43

  $714,500

  • 5 Beds
  • 4 Baths
  • 3,163 Sq Ft

  2450 Standing Rock Cir, Oakland, FL 34787

  Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or relaxing with friends. Go outside to your

  Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  2450 Standing Rock Cir, 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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  /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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  /49

  $645,000

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  847 Cura Ct, Oakland, FL 34787

  Welcome to this beautifully maintained home located in the gated waterfront community of John’s Landing, nestled along the scenic 2,600-acre John’s Lake chain. This property offers a blend of upgraded features, generous living spaces, and an exceptional community lifestyle. A brand-new roof will be delivered at closing, as the replacement process is already underway through the insurance company.

  Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  847 Cura Ct, Oakland, FL 34787
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  /62

  $1,850,000

  • 6 Beds
  • 5 Baths
  • 4,104 Sq Ft

  1101 Eagles Pass Way, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two

  Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  1101 Eagles Pass Way, Oakland, FL 34787
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  /39

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,448 Sq Ft

  501 E Oakland Ave, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue

  Erica Diaz HOMEVEST REALTY

  501 E Oakland Ave, Winter Garden, FL 34787
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
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  /18

  $515,000

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

  13748 Werrington Dr, Oakland, FL 34787

  Seller offering concessions to compete with new construction in the area! 13748 Werrington Drive isn’t just a house — it’s your next chapter waiting to be written. Tucked inside the vibrant, amenity-rich community of Encore at Ovation, this stylish 3-bedroom, 2.5-bath gem offers the perfect mix of comfort, design, and location. From the moment you step through the door, you’ll fall in love with

  Kimberly Ann Zeidner, LLC CHARLES RUTENBERG REALTY ORLANDO

  13748 Werrington Dr, Oakland, FL 34787
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  $630,000

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

  12554 Westhaven Oak Dr, Oakland, FL 34787

  This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

  Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

  12554 Westhaven Oak Dr, Oakland, FL 34787
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  /60

  $997,000

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

  9549 Bolero Rd, Oakland, FL 34787

  The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen

  Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

  9549 Bolero Rd, 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 PA PREFERRED REAL ESTATE BROKERS

  3294 Hanging Tide St, Oakland, FL 34787
• 

  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  AR Homes Builder

  166 Hammock Preserve Loop, Oakland, FL 34787
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  /29

  $471,900

  • 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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  /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

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