Oakland, FL Homes for Sale with Garage

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  $370,000

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  1318 Painted Bunting Ave, Oakland, FL 34760

  One or more photo(s) has been virtually staged. You’re going to love this beautifully maintained 2-bedroom, 2.5-bath Townhome in the highly desirable Longleaf At Oakland which is perfectly located just a 1/2 mile from the Florida Turnpike, offering easy access to everything Central Florida has to offer. The entire interior was freshly painted in March 2026, giving the home a bright, fresh feel

  

  Randy Adams

  RE/MAX TOWN & COUNTRY REALTY

  (689) 399-4178

  1318 Painted Bunting Ave, Oakland, FL 34760
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  /24

  $894,000

  • 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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  /30

  $525,000 Open Sun 10AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,811 Sq Ft

  2660 Bobcat Chase Blvd, Oakland, FL 34760

  Welcome to your peaceful retreat in the heart of Oakland! Nestled within the highly sought-after Longleaf at Oakland community, this impeccably maintained 3-bedroom, 2 1/2-bathroom residence offers the perfect blend of 2020 construction and timeless Florida charm. Step inside to discover 1,811 square feet of bright, open-concept living space designed for both effortless entertaining and cozy

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (689) 336-3056

  2660 Bobcat Chase Blvd, Oakland, FL 34760
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  $635,000 New Construction

  • 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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  /69

  $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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  /4

  $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

  • 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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  /45

  $549,900

  • 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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  /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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  $725,000

  • 4 Beds
  • 3 Baths
  • 2,113 Sq Ft

  17936 Adrift Rd, Oakland, FL 34787

  This is an amazing one-story 4-bedroom, 3 bath lakeview, conservation area home with elegant exteriors and high end features in Waterleigh, Horizon West’s Premier Community! Desirable Horizon West, featuring resort-style amenities and thoughtful design minutes from Disney World Parks and resorts. Elegant 4 bedroom, 3-bath home offers 2,113 sq. ft. of single-story comfort, ideal for families or

  Stephen Hachey FLAT FEE MLS REALTY

  17936 Adrift Rd, Oakland, FL 34787
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  /57

  $990,000 Open Sun 12PM - 3PM

  • 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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  $649,900

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  5679 Orange Orchard Dr, Oakland, FL 34787

  Move-In Ready Home Near Hamlin Town Center with Open Layout and Private Backyard. Built in 2021 and located in the sought-after Wincey Groves community of Winter Garden, this beautifully maintained energy efficient 4-bedroom, 2.5-bath home offers thoughtfully designed living space with modern finishes and a functional open layout. The spacious main living area is filled with natural light and

  Helen Thompson RE/MAX SELECT GROUP

  5679 Orange Orchard Dr, Oakland, FL 34787
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  $974,300 Open Sun 12PM - 4PM

  • 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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  $579,000

  • 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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  $634,000 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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  /78

  $2,750,000

  • 5 Beds
  • 6 Baths
  • 4,373 Sq Ft

  812 Johns Point Dr, Oakland, FL 34787

  Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout.Designed for effortless entertaining, the open-concept layout

  Any Alves WRA BUSINESS & REAL ESTATE

  812 Johns Point Dr, Oakland, FL 34787
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  /58

  $1,785,000

  • 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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  /51

  $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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  /55

  $949,790 Open Sun 12PM - 4PM

  • 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 Open Sun 11AM - 2PM

  • 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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  /59

  $525,000

  • 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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  /25

  $693,240 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,147 Sq Ft

  3120 Namaste Dr, Oakland, FL 34787

  Under Construction. The Summerlin checks all your boxes! This breath taking two-story home features an expansive design with a convenient three-car garage. The first floor features an open-concept family room that complements a chef-ready kitchen and a cozy dining room, plus a private office and a spacious lanai. On the same level is the tranquil owner’s suite with an attached bathroom. Found

  Ben Goldstein LENNAR REALTY

  3120 Namaste Dr, Oakland, FL 34787
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  /55

  $819,000

  • 5 Beds
  • 4 Baths
  • 2,840 Sq Ft

  8807 Sonoma Coast Dr, Oakland, FL 34787

  Welcome to the beautiful community of Waterleigh in Winter Garden! This meticulously maintained home features 5 bedrooms, 4 bathrooms, and a second floor laundry and bonus/game room. This thoughtfully designed open-concept home offers functionality and space for all. The spacious foyer invites you into the great room filled with natural light and overlooks the pond. The kitchen features stainless

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  8807 Sonoma Coast Dr, Oakland, FL 34787
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  /19

  $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

  $399,000

  • 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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  /55

  $1,949,000 Open Sun 12PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft

  511 Briley Ave, Oakland, FL 34787

  Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space.Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy

  Carolina Dumit CORCORAN PREMIER REALTY

  511 Briley Ave, Oakland, FL 34787
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  /4

  $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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  $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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  /3

  $548,000 New Construction

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

  12911 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. 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

  Dayene Grubert ORLANDO TBI REALTY LLC

  12911 Westhaven Oak Dr, Oakland, FL 34787
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  $599,000

  • 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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  /55

  $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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  /46

  $898,000

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

  9409 Emerald Berry Dr, Oakland, FL 34787

  Nestled on a premium homesite with no rear neighbors in the exclusive Summerlake Reserve enclave, this beautifully designed home blends comfort, functionality, and thoughtful upgrades throughout. The home offers 4 bedrooms, 3.5 bathrooms, a private office with barn doors, a spacious loft, and an extended covered lanai ideal for indoor-outdoor living. The gourmet kitchen is both elegant and

  Manuella Espinosa LA ROSA REALTY LLC

  9409 Emerald Berry Dr, Oakland, FL 34787
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  /29

  $390,000

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

  2120 Gopher Tortoise Terrace, Oakland, FL 34787

  Welcome to 2120 Gopher Tortoise Terrace in charming Oakland, Florida, a beautifully maintained 3 bedroom, 2.5 bathroom townhome that offers comfort, style, and an incredible opportunity for qualified buyers to assume the seller’s low 2.75 percent mortgage rate, subject to lender approval, potentially providing significant monthly savings compared to today’s interest rates. From the moment you

  Richard Aybar KELLER WILLIAMS ADVANTAGE III

  2120 Gopher Tortoise Terrace, 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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  $364,900 Open Sun 12PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  2117 Gopher Tortoise Terrace, Oakland, FL 34787

  Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining. The kitchen, where matching marble countertops and cabinetry create a clean and cohesive look. A charming office nook on the first floor provides the perfect spot for working from home or managing daily tasks while staying connected to the living areas.

  Mary Herrod De Boer SERHANT

  2117 Gopher Tortoise Terrace, Oakland, FL 34787

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