Oakland, FL Homes for Sale with Pool

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  /39

  $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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  /34

  $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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  /58

  $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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  /44

  $737,000

  • 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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  $528,000 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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  /48

  $579,999

  • 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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  $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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  /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 Sat 10AM - 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 Thu 12PM - 3:30PM

  • 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

  $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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  /86

  $629,000

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

  2606 Bobcat Chase Blvd, Oakland, FL 34787

  *** Back on the market after being temporarily off while the Seller moved (~45 days).*** NEW PRICE *** MOTIVATED *** Stunning former MODEL HOME on a premium CORNER lot (FENCING is allowed)– 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

  Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
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  /25

  $688,240 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 Sat 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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  $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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  /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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  /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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  /3

  $594,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,143 Sq Ft

  12915 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is

  DeVahn Powell ORLANDO TBI REALTY LLC

  12915 Westhaven Oak Dr, Oakland, FL 34787
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  /76

  $1,275,000

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  1156 Civitas Way, Winter Garden, FL 34787

  Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes

  Heidi Pfeffer-Morgan DALTON WADE INC

  1156 Civitas Way, Winter Garden, FL 34787
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  /45

  $865,000

  • 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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  /3

  $1,998,000 New Construction

  • 4 Beds
  • 4 Baths
  • 4,557 Sq Ft

  1258 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The

  Chris Herlihy NEW HOMES REAL ESTATE, INC.

  1258 Ridge Lake Way, Winter Garden, FL 34787
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  /52

  $416,900

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft

  2222 Gopher Tortoise Terrace, Oakland, FL 34787

  YOU Can't miss this Gorgeous 3beds,3 full Bath townhouse in Oakland . near Winter Garden and Clermont..Perfect amenities for you enjoy the best of Florida lifestyle..This Property have absolutely the Best Floor Plan : Open floor concept ,that integrate Living space, Kitchen and Dinner space. Surrounded with sunlight windows. Engineering floor, granite counters, stainless appliances. Perfect for

  Wagner ferreira LPT REALTY, LLC

  2222 Gopher Tortoise Terrace, Oakland, FL 34787
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  /78

  $1,588,000

  • 4 Beds
  • 4.5 Baths
  • 3,613 Sq Ft

  1412 Johns Cove Ln, Oakland, FL 34787

  Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely reinvented since the current owners purchased it. Renovations include, a kitchen with all new appliances

  Betsey West NEXT RESIDENCE REALTY LLC

  1412 Johns Cove Ln, Oakland, FL 34787
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  /33

  $539,990 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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  /13

  $596,832 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,149 Sq Ft

  14736 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Newberry at 14736 Field Daisy Drive in Harvest at Ovation! The Newberry bungalow floor plan is a true representation of modern living and the perfect space for all of your entertainment needs and desires. The 2149 sq. ft. two-story home with 3 bedrooms, 3.5 bathrooms and a 2-car detached garage presents prospective homebuyers with both the basic features and intricate details that

  Taylor Morrison Builder

  14736 Field Daisy Dr, Oakland, FL 34787
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  /23

  $395,000

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

  2228 Gopher Tortoise Terrace, Oakland, FL 34787

  This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling. Community

  Leslie Anne Campasano ASANO REAL ESTATE LLC

  2228 Gopher Tortoise Terrace, Oakland, FL 34787
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  /63

  $759,000

  • 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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  /49

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 3,583 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to

  Subhas Sawh LIBERTY HOME SALES INC

  729 Strihal Loop, Oakland, FL 34787
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  /4

  $1,975,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  1106 Sarah Mathews Dr, Oakland, FL 34787

  Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living

  Heather Spirazza REGENCY REAL ESTATE LLC

  1106 Sarah Mathews Dr, 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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  /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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  /11

  $1,295,000

  • Land
  • 1.26 Acres
  • $1,027,778 per Acre

  556 Walker St, Oakland, FL 34760

  LAST DEVELOPER OWNED LOT IN BILEY PHASE 1. Lakefront homesite with the ability to add your own private dock. 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

  Chocky Burks CORCORAN PREMIER REALTY

  556 Walker St, Oakland, FL 34760
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  /32

  $510,000

  • 3 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  15220 Blue Peacock Ln, Oakland, FL 34787

  Welcome to this beautiful home featuring an open floor plan that blends comfort, style, and functionality. Filled with natural light, the spacious layout is perfect for both everyday living and entertaining. The inviting living area offers a warm setting for gatherings, while the modern kitchen boasts stainless steel appliances, abundant cabinetry, and generous counter space for the home chef.

  DENILEY VALDES TALENT REALTY SOLUTIONS

  15220 Blue Peacock Ln, Oakland, FL 34787
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  /38

  $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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