Oakland, FL Homes for Sale with Garage

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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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  $2,100,000

  • 5 Beds
  • 5 Baths
  • 4,934 Sq Ft

  9008 Morgana Ct, Oakland, FL 34787

  Set along the shoreline of Lake Hickorynut in Avalon Cove, this 2022-built lakefront residence blends refined design with the ease of modern Florida living. Positioned on a cul-de-sac corner lot of approximately 0.35 acres, the home offers long, open-water views and a lifestyle centered around indoor–outdoor connection, afternoon breezes off the lake, and sunsets enjoyed from the covered balcony

  

  Bent Danholm

  MAXIM REALTY ORLANDO

  (321) 290-8436

  9008 Morgana Ct, Oakland, FL 34787
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  $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. Set

  

  Andrew Kincaid

  BHHS FLORIDA REALTY

  (321) 321-2133

  101 N Starr St, Oakland, FL 34760
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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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  /55

  $499,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft

  17621 Japonica Bloom Dr, Oakland, FL 34787

  Enjoy comfortable and convenient living in Northlake at Ovation, where this thoughtfully designed home features a private primary suite with a spacious walk-in closet, creating a peaceful retreat at the end of the day. Ideally located, the community offers easy access to everyday conveniences and popular destinations—just 37 minutes from Orlando International Airport, 20 minutes from world-famous

  Ashton Woods Builder

  17621 Japonica Bloom Dr, Oakland, 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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  $395,000

  • 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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  $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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  $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

  • 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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  /3

  $949,000 New Construction

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

  12940 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction Bronson Peak. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a covered lanai. The master bedroom/ on the second floor includes a large

  DeVahn Powell ORLANDO TBI REALTY LLC

  12940 Westhaven Oak Dr, Oakland, FL 34787
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  $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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  $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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  $620,000

  • 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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  $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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  $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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  $839,950

  • 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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  $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! Enjoy life in the award-winning Coral Grand home design by Pulte Homes, located on a very special lot with no rear neighbors, in a highly desirable area of the community where no more lots are available. This beautiful new home is part of the first phase of the Parkside Trails development, so it features over $110,000 in upgrades and is for sale at a

  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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  /40

  $580,000

  • 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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  $704,500

  • 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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  $645,900

  • 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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  $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, 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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  /21

  $445,999

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

  12748 Brodlove Ln, Oakland, FL 34787

  MOTIVATED SELLER — MUST SELL! — PRICED BELOW MARKET. Exceptionally maintained 2022 M/I Homes Baldwin floorplan in sought-after Encore at Ovation (Horizon West/Winter Garden). 3BD/2.5BA bungalow-style, move-in ready and turnkey with smart-home features (smart appliances/thermostat). Bright open-concept living with abundant natural light. Modern kitchen with quartz countertops, quality cabinetry,

  Mayra Rivas Acevedo CASA SOL REALTY LLC

  12748 Brodlove Ln, Oakland, FL 34787
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  $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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  $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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  $875,000

  • 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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  $568,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  13121 Tollcross Way, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion July 2025. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master

  Alicea Salgado ORLANDO TBI REALTY LLC

  13121 Tollcross Way, 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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  $2,350,000

  • 5 Beds
  • 4.5 Baths
  • 4,436 Sq Ft

  9014 Morgana Ct, Oakland, FL 34787

  This is more than a house ~ it is a fully furnished, turnkey lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare

  Jennifer Wemert WEMERT GROUP REALTY LLC

  9014 Morgana Ct, 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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  $642,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,011 Sq Ft

  2982 Good Vibes Way, Oakland, FL 34787

  Under Construction. The Dylan is all the rage! This stylish two-story home features a first-floor owner’s suite, offering a private retreat with a full bathroom and walk-in closet. An additional bedroom is located near the front of the home, steps from a full bathroom. A spacious and flexible open-concept layout blends the kitchen, living and dining areas, while a nearby flex space provides the

  Ben Goldstein LENNAR REALTY

  2982 Good Vibes Way, Oakland, FL 34787
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  /44

  $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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  /53

  $418,900

  • 3 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  8167 Mosaic Ln, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Gorgeous Townhouse located in Winter Garden at the great Ravenna Community, just 10 minutes drive from Disney World, close to good Winter Garden restaurants, new shopping malls, supermarkets, banks ext. This 3 bedroom 2/1 bathroom home with stunning features and open floor plan, separated dining room that is fully upgraded floor and cabinets and

  Simon Colak USCO CAPITAL GROUP

  8167 Mosaic Ln, Oakland, FL 34787
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  $665,000

  • 4 Beds
  • 3 Baths
  • 2,274 Sq Ft

  2169 Bay Line Rd, Oakland, FL 34787

  Welcome home to Hull Island, where refined design meets serene Florida living. This impeccably maintained 4-bedroom, 3-bath home offers the rare combination of conservation privacy, thoughtful upgrades, and resort-style community amenities—truly better than new. Backing to a protected nature preserve with no rear neighbors, the home provides a peaceful retreat while still being moments from

  Mariana Wartella LPT REALTY, LLC

  2169 Bay Line Rd, Oakland, FL 34787

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