Oakland, FL Homes for Sale

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  $993,000

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

  624 Hull Island Dr, Oakland, FL 34787

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

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 449-7661

  624 Hull Island Dr, Oakland, FL 34787
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  $659,000 Open Sun 10AM - 12PM

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

  16186 Honey Harvest St, Oakland, FL 34787

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

  

  Nicole Rader

  MAINFRAME REAL ESTATE

  (689) 303-5944

  16186 Honey Harvest St, Oakland, FL 34787
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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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  $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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  $829,346 New Construction

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

  15075 Tea Tree Dr, Oakland, FL 34787

  The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

  Dream Finders Homes Builder

  15075 Tea Tree Dr, Oakland, FL 34787
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  $505,990 New Construction

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

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

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

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36487507, Oakland, FL 34787
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  $375,000 Open Fri 1PM - 5PM

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

  2100 Gopher Tortoise Terrace, Oakland, FL 34787

  Imagine coming home to a space that feels open, comfortable, and perfectly placed for everyday life. This corner-unit townhome in the desirable Longleaf at Oakland community offers added privacy, abundant natural light, and a thoughtfully designed layout that truly works for today’s lifestyle. Inside, the home features a clean, modern feel with plank vinyl flooring, granite countertops, and

  Stiliany Collado LLC MARKET CONNECT REALTY LLC

  2100 Gopher Tortoise Terrace, Oakland, FL 34787
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  $560,000

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

  2065 White Feather Loop, Oakland, FL 34787

  Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential

  Denis Bochkov PINK MIAMI

  2065 White Feather Loop, Oakland, FL 34787
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  $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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  $990,000 Open Sat 12PM - 4PM

  • 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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  $824,950

  • 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 + Office, 2 1/2 Bath 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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  $817,745 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,005 Sq Ft

  12916 Westhaven Oak Dr, Oakland, FL 34787

  The Ormond's welcoming covered porch and entry flow into the inviting foyer, opening to the spacious great room, beautiful dining room, and desirable large covered lanai beyond. The well-designed kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and roomy pantry. The lovely primary bedroom suite is complete with dual walk-in closets and spa-like

  Toll Brothers, Inc. Builder

  12916 Westhaven Oak Dr, Oakland, FL 34787
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  $780,000 New Construction

  • 4 Beds
  • 3 Baths
  • 3,076 Sq Ft

  5808 Dancing Willow St, Oakland, FL 34787

  TAKE FULL ADVANTAGE OF THIS GREAT OPPORTUNITY! This stunning brand new home is part of the first phase of the Parkside Trails development, so it features over $100,000 in upgrades and is for sale at a very attractive price. If you compare it to other new homes of the same model in regular homesites offered by the builder, you will quickly see that this is a real opportunity. When you buy this

  Tisa Sa Barreto SELECTA REALTY LLC

  5808 Dancing Willow St, Oakland, FL 34787
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  $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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  $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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  /2

  $898,000

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft

  9409 Emerald Berry Dr, Oakland, FL 34787

  This beautifully upgraded Baldwin floorplan by Hartizen Homes offers 4 bedrooms, 3.5 bathrooms, a private office with barn doors, loft space, and an extended covered lanai on a premium homesite with no rear neighbors.The gourmet kitchen features built-in oven and microwave, smooth cooktop with vent hood, soft-close cabinetry, 42” upper cabinets, contrasting island cabinetry, quartz

  Manuella Espinosa LA ROSA REALTY LLC

  9409 Emerald Berry Dr, Oakland, FL 34787
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  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,406 Sq Ft

  607 E Oakland Ave, Winter Garden, FL 34787

  Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home office PLUS upstairs bonus room, flexible living spaces make this home work for you. This is 607 E. Oakland Ave - where classic Old-Florida charm meets modern luxury and unbeatable location. Tile flooring and refined tray ceilings flow throughout the home, while the gourmet kitchen with premium upgrades is

  Kristine McKinley RE/MAX TOWN & COUNTRY REALTY

  607 E Oakland Ave, Winter Garden, FL 34787
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  $789,999

  • 5 Beds
  • 4.5 Baths
  • 3,682 Sq Ft

  3351 Current Ave, Oakland, FL 34787

  Welcome to this stunning two-story Tortola floor plan by Taylor Morrison, ideally located in the gated community of Lakeview Preserve in Winter Garden. Perfectly positioned on an oversized 75-foot-wide corner homesite with no rear neighbors, this home offers exceptional privacy, beautiful rear views, and a welcoming front porch that sets the tone from the moment you arrive. The elegant

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  3351 Current Ave, Oakland, FL 34787
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  /57

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,909 Sq Ft

  9611 Lost Creek Dr, Oakland, FL 34787

  No rear neighbors! Situated on a premium conservation lot with lake views, this fully furnished 4-bedroom, 3-bathroom two-story home in the desirable Waterleigh community offers privacy, upgrades, and true move-in-ready convenience. Exceptional curb appeal features a brick paver driveway and welcoming front porch. Inside, enjoy wood-look tile throughout the main living areas, a flexible formal

  Mariana Micheti M2M REALTY

  9611 Lost Creek Dr, Oakland, FL 34787
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  $794,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  4653 Golden Birch Ave, Oakland, FL 34787

  Stunning 3-bedroom, 2.5-bath home with soaring ceilings, a versatile front room, a gourmet kitchen. This is the beautiful Mahogany Estate Floor plan By Pulte, lots of upgrades Slide into this beautiful home, starting with a flexible front room—perfect as an office, study, or formal living space—welcoming you right at the entry. Just beyond, the high-end gourmet kitchen is a showstopper, featuring

  Armando Torres POWERHOUSE REAL ESTATE NETWORK

  4653 Golden Birch Ave, Oakland, FL 34787
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  $796,000

  • 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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  $725,000

  • 5 Beds
  • 4.5 Baths
  • 4,440 Sq Ft

  3387 Current Ave, Oakland, FL 34787

  Gorgeous home at Winter Garden gated community LakeView Preserve, San Benita model with upgrade of extended lanai and a lot of home improvement, Gourmet Kitchen, open floor plan, engineer wood flooring, NO CARPET in the house, crown molding, study room, dining room, and huge game room in second floor, first floor master bedroom suite, second floor with another bedroom suite. Ceiling fans with

  Li Xue AGENT GROUP REALTY

  3387 Current Ave, Oakland, FL 34787
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  $615,120 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,142 Sq Ft

  12915 Westhaven Oak Dr, Oakland, FL 34787

  Charming contemporary living. The Montpelier's welcoming porch and entry reveal the inviting foyer and views to the spacious great room, dining room, and desirable covered lanai beyond. The well-designed gourmet kitchen is equipped with a large center island with breakfast bar, plenty of counter and cabinet space, and sizable walk-in pantry. The private primary bedroom suite is highlighted by a

  Toll Brothers, Inc. Builder

  12915 Westhaven Oak Dr, Oakland, FL 34787
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  $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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  $557,845 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  12911 Westhaven Oak Dr, Oakland, FL 34787

  Superior contemporary design. The Liston's welcoming covered porch and entry open immediately onto the expansive great room, with views to the lovely dining room and desirable large covered lanai beyond. The well-equipped gourmet kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and generous walk-in pantry. The gorgeous primary bedroom suite is

  Toll Brothers, Inc. Builder

  12911 Westhaven Oak Dr, Oakland, FL 34787
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  $610,000

  • 5 Beds
  • 3.5 Baths
  • 3,248 Sq Ft

  1490 Stone Arrow Ct, Oakland, FL 34787

  This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters,

  Eric Jia NUMBER 1 BROKER, LLC

  1490 Stone Arrow Ct, 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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  $663,655 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  12919 Westhaven Oak Dr, Oakland, FL 34787

  Superior contemporary design. The Liston's welcoming covered porch and entry open immediately onto the expansive great room, with views to the lovely dining room and desirable large covered lanai beyond. The well-equipped gourmet kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and generous walk-in pantry. The gorgeous primary bedroom suite is

  Toll Brothers, Inc. Builder

  12919 Westhaven Oak Dr, Oakland, FL 34787
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  $1,809,000

  • 4 Beds
  • 4 Baths
  • 3,784 Sq Ft

  906 Allendale Ln, Winter Garden, FL 34787

  Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for

  Jurgita Blake CENTURY 21 CARIOTI

  906 Allendale Ln, Winter Garden, FL 34787
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  $580,000 Open Sun 12PM - 3PM

  • 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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  $695,000

  • 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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  $545,000

  • 4 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  2259 White Feather Loop, Oakland, FL 34787

  INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by

  Chuck Burt YOUNG REAL ESTATE

  2259 White Feather Loop, Oakland, FL 34787
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  $639,000

  • 4 Beds
  • 2.5 Baths
  • 2,473 Sq Ft

  2606 Bobcat Chase Blvd, Oakland, FL 34787

  *** Back on market after being temporarily off while the Seller moved (~45 days). *** Stunning former MODEL HOME on a premium CORNER lot – loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both comfort and

  Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
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  $519,000

  • 4 Beds
  • 2 Baths
  • 2,046 Sq Ft

  1270 Stationside Dr, Oakland, FL 34787

  Sellers motivated

  Ky Lam HOME INVEST REALTY INC

  1270 Stationside Dr, Oakland, FL 34787
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  /50

  $409,000

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

  2208 Gopher Tortoise Terrace, Oakland, FL 34760

  Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere.The large open kitchen offers a large island with seating for four, granite

  Fred Mansfield ORLANDO PROP MGMNT RLTY LLC

  2208 Gopher Tortoise Terrace, Oakland, FL 34760
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  $508,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Newbury Plan at Serenade at Ovation - Bungalow, 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

  $639,500

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

  847 Cura Ct, Oakland, FL 34787

  Located within the exclusive gated waterfront community of John’s Landing, this residence offers the perfect balance of Florida lifestyle, privacy, and everyday convenience, just minutes from Downtown Winter Garden and the scenic John’s Lake Chain. Set on an oversized lot at the end of a quiet cul-de-sac, the home features multiple living spaces, a bonus room / optional 5th bedroom, and a Florida

  Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  847 Cura Ct, Oakland, FL 34787
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  /62

  $1,799,000

  • 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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  $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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