Oakland, FL Homes for Sale with Pool

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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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  /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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  /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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  /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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  /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
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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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  /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
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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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  /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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  /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
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  $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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  /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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  /79

  $3,575,000 New Construction

  • 5 Beds
  • 7 Baths
  • 5,478 Sq Ft

  510 Briley Ave, Oakland, FL 34787

  Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two

  Alexis Anderson REGENCY REAL ESTATE LLC

  510 Briley Ave, 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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  /35

  $585,000

  • 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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  /24

  $1,250,000

  • Land
  • 0.82 Acre
  • $1,524,390 per Acre

  552 Walker St, Oakland, FL 34760

  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

  Alexis Anderson REGENCY REAL ESTATE LLC

  552 Walker St, Oakland, FL 34760
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  /33

  $569,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,175 Sq Ft

  2934 Good Vibes Way, Oakland, FL 34787

  Under Construction. This popular new Hendrix is a four-bedroom home with convenient single-story living. Three secondary bedrooms are located near the front of the home off the foyer, near a versatile flex space ready to be used as an office or studio. An open-concept floorplan blends the kitchen, living and dining areas with easy access to a covered patio, while a luxe owner’s suite is nestled

  Ben Goldstein LENNAR REALTY

  2934 Good Vibes Way, Oakland, FL 34787
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  /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
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  /4

  $800,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,101 Sq Ft

  16029 Honey Harvest St, Oakland, FL 34787

  New Construction - Ready Now! Built by Taylor Morrison, America's Most Trusted Homebuilder. Welcome to the Cumberland at 16029 Honey Harvest Street in Harvest at Ovation. This spacious two-story Cumberland offers 5 bedrooms, 4.5 bathrooms, and flexible living for every stage of life. The open-concept great room, dining area, and gourmet kitchen flow effortlessly together and open to an extended

  Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  16029 Honey Harvest St, Oakland, FL 34787
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  /38

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  12043 Holystone St, Oakland, FL 34787

  “The property is currently active for sale but is rented for $2500 monthly, with a lease valid until February 2026. The lease must be honored, so the property is best suited for investors looking for a rental income opportunity.”Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It

  Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

  12043 Holystone St, Oakland, FL 34787
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  /7

  $1,700,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,909 Sq Ft

  1207 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours

  Chris Herlihy NEW HOMES REAL ESTATE, INC.

  1207 Ridge Lake Way, Winter Garden, 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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  /47

  $700,000

  • 5 Beds
  • 3.5 Baths
  • 3,381 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Experience the height of Florida luxury in this stunningly renovated 5-bedroom pool home, nestled within an exclusive gated community featuring a private boat ramp and lake access. Boasting soaring ceilings, quartz countertops, and a striking panoramic landing, this residence blends architectural elegance with modern sophistication. Peace of mind is

  Dylan Stanley MARK SPAIN REAL ESTATE

  729 Strihal Loop, Oakland, FL 34787
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  /35

  $587,000

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

  16140 Harbor Mist Aly, Oakland, FL 34787

  Welcome to your dream home in Winter Garden! This stunning 2018-built residence offers 2,477 square feet of thoughtfully designed living space with four bedrooms and three and a half bathrooms. The open floor plan creates an inviting atmosphere perfect for both daily living and entertaining guests who might "accidentally" extend their stay. The first floor showcases beautiful tile flooring

  Jeanine Louis-Alcime EXP REALTY LLC

  16140 Harbor Mist Aly, Oakland, FL 34787
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  /84

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,857 Sq Ft

  1808 Western Trailway Dr, Oakland, FL 34787

  Welcome to this stunning, like-new 3-bedroom, 2-bath home in the charming Hull Island community of Oakland, just 0.5 miles from the West Orange Trail, 1.5 miles to Costco, and only 10 minutes from historic downtown Winter Garden. Recently updated and truly move-in ready, this split-plan residence shines with beautiful wood-look tile flooring throughout (no carpet anywhere!), fresh backyard turf

  Daniel McGrath UNLOCK REALTY GROUP INC

  1808 Western Trailway Dr, Oakland, FL 34787
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  /39

  $800,000

  • 5 Beds
  • 3 Baths
  • 3,528 Sq Ft

  1970 Standing Rock Cir, Oakland, FL 34787

  Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1970 Standing Rock Cir, Oakland, FL 34787
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  /17

  $460,000 New Construction

  • 4 Beds
  • 3 Baths
  • 1,847 Sq Ft

  4580 Maple Waltz, Oakland, FL 34787

  Exceptional investment opportunity! This stunning new townhome built by Pulte Homes is located in the desirable Park Side Trails community in Clermont, FL. The property is already leased starting November 28th with a 12-month contract at $2,800/month, offering immediate rental income and a great return potential.Featuring a bright and open floor plan with abundant natural light throughout,

  Marta Faustino DTB FLORIDA REALTY, INC.

  4580 Maple Waltz, Oakland, FL 34787

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