25

Oakland, FL Homes for Sale under $900,000

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  • /41

    $850,000

    • 6 Beds
    • 4 Baths
    • 4,001 Sq Ft

    1603 Johns Cove Ln, Oakland, FL 34787

    Exceptional 6-bedroom, 4-bathroom home on a private cul-de-sac in the highly desirable gated community of Johns Cove. This spacious residence features formal living and dining rooms, a large family room, soaring vaulted ceilings, and a double staircase. The kitchen offers stainless steel appliances, granite countertops, a large island, abundant cabinetry, and a breakfast area with tranquil pond

    Agent Photo

    Yusuf Gencay

    RE/MAX Town & Country Realty

    1603 Johns Cove Ln, Oakland, FL 34787
  • /3

    $603,990

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

    Anna Maria Plan at Serenade at Ovation - 50' Collection, 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
  • /43

    $825,000

    $20K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 4,240 Sq Ft

    14001 Rugby St, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Price improved and ready for its next owner, this beautifully maintained pool home in the sought-after Verde Park community offers more than 4,240 square feet of thoughtfully designed living space on a beautiful 0.26-acre corner lot in one of Winter Garden’s most beloved communities. With 5 bedrooms and 4 bathrooms, the home delivers an exceptional

    Ann Mertens KELLER WILLIAMS ELITE PARTNERS III REALTY

    14001 Rugby St, Oakland, FL 34787
  • /25

    $645,990

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 2,688 Sq Ft

    Anna Maria w/ Bonus Plan at Serenade at Ovation - 50' Collection, 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
  • /3

    $649,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,689 Sq Ft

    Biscayne Plan at Serenade at Ovation - 50' Collection, 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
  • /3

    $655,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,843 Sq Ft

    Captiva Plan at Serenade at Ovation - 50' Collection, 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
  • /2

    $617,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,278 Sq Ft

    Lexington w/ Bonus Plan at Serenade at Ovation - 50' Collection, 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
  • /56

    $729,000

    $51K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,284 Sq Ft

    8114 Sayings Dr, Winter Garden, FL 34787

    Virtually Staged. Welcome to this beautifully maintained 5-bedroom, 3-bathroom home in the highly sought-after Storey Grove community of Winter Garden, one of Horizon West's most desirable neighborhoods. Offering approximately 3,300 square feet of thoughtfully designed living space, this exceptional home combines comfort, functionality, and an unbeatable location. Perfectly positioned on a

    Anna Shi LPT REALTY, LLC

    8114 Sayings Dr, Winter Garden, FL 34787
  • /12

    $799,999

    • 5 Beds
    • 3 Baths
    • 3,413 Sq Ft

    16 Oakland Pointe Cir, Oakland, FL 34760

    Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new

    Jack Keller JACK KELLER INC

    16 Oakland Pointe Cir, Oakland, FL 34760
  • /42

    $799,000

    • 4 Beds
    • 3 Baths
    • 2,117 Sq Ft

    9296 Bolero Rd, Oakland, FL 34787

    Welcome to this beautifully maintained 4-bedroom, 3-bath home built in 2020, ideally situated on a premium corner lot at the end of a quiet cul-de-sac in the highly desirable Waterleigh community. Offering an open-concept layout with luxury vinyl flooring, a spacious kitchen featuring a large island, modern finishes, and seamless living and dining areas, this home is perfect for everyday living

    Any Alves WRA BUSINESS & REAL ESTATE

    9296 Bolero Rd, Oakland, FL 34787
  • /80

    $739,000

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

    9152 Sonoma Coast Dr, Oakland, FL 34787

    Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home in the highly sought-after Winter Garden area! Perfectly positioned on a premium homesite, this home offers breathtaking water and conservation views with NO REAR NEIGHBORS, providing exceptional privacy and a peaceful backdrop. Designed for both comfort and functionality, the open floor plan features a private first-floor guest

    Yujie Jiang INTOP REALTY LLC

    9152 Sonoma Coast Dr, Oakland, FL 34787
  • /46

    $699,900

    $50K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,852 Sq Ft

    2017 Boss Hewett St, Oakland, FL 34787

    Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously maintained 2,852 sq ft home built in 2022, with owned rooftop solar that keeps utility costs well below the Florida norm for a home this size. Four bedrooms, four full baths, and a two-car garage, all just minutes from historic Winter Garden's shops, restaurants, and Saturday farmers market.All four

    Peter Biskup CHARLES RUTENBERG REALTY ORLANDO

    2017 Boss Hewett St, Oakland, FL 34787
  • /45

    $639,000

    • 4 Beds
    • 3 Baths
    • 2,650 Sq Ft

    529 Johns Landing Way, Oakland, FL 34787

    Welcome home to this stunning 4-bedroom, 3-bathroom pool home tucked inside a sought-after gated community! Offering 2,650 square feet of thoughtfully designed living space, this home is perfect for both everyday comfort and entertaining. The versatile 4th bedroom is ideal as a mother-in-law suite, guest quarters, or home office — perfect for multi-generational living. The spacious primary suite

    Denise Pellegrino REAL BROKER, LLC

    529 Johns Landing Way, Oakland, FL 34787
  • /47

    $669,900

    $10K PRICE INCREASE
    • 5 Beds
    • 4 Baths
    • 3,285 Sq Ft

    710 Regina Cir, Oakland, FL 34787

    Welcome to this exceptional pool home located in the sought-after gated lakefront community of Johns Landing. Situated on an oversized 13,000+ square-foot corner lot with a mostly fenced backyard, this spacious home offers over 3,000 square feet of thoughtfully designed living space.Featuring 4 bedrooms, 4 full bathrooms, a dedicated office, media room, and spacious loft, this home provides

    Brenda Anglada COLDWELL BANKER REALTY

    710 Regina Cir, Oakland, FL 34787
  • /62

    $689,000

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft

    15174 Field Daisy Dr, Oakland, FL 34787

    Welcome to this beautiful bungalow-style home in the highly desirable Osprey Ranch community in Winter Garden! Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, this thoughtfully designed residence offers comfort, style, and functionality for the whole family.Located just minutes from Disney, shopping, dining, and major highways, this home combines convenience with a peaceful

    Guilherme Garcia Cavalcante REALTY ONE GROUP INSPIRATION

    15174 Field Daisy Dr, Oakland, FL 34787
  • /25

    $780,000

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

    8807 Sonoma Coast Dr, Oakland, FL 34787

    Welcome to resort-style living in Waterleigh, one of Horizon West's most sought-after master-planned communities. This stunning 5-bedroom, 4-bathroom home offers the perfect blend of space, serenity, and lifestyle, all anchored by breathtaking pond views right from your own backyard. Step outside to your private patio and take in the tranquil water view, the ideal backdrop for morning coffee,

    Kerstin Crow LOKATION

    8807 Sonoma Coast Dr, Oakland, FL 34787
  • /57

    $765,000

    $95K PRICE DROP
    • 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

    Patricia Mendonca Garcia Cunha M2M REALTY

    9611 Lost Creek Dr, Oakland, FL 34787
  • /9

    $609,990

    New Construction $38K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,911 Sq Ft

    3128 Namaste Dr, Oakland, FL 34787

    Under Construction. The Inverness is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s suite

    Ben Goldstein LENNAR REALTY

    3128 Namaste Dr, Oakland, FL 34787
  • /30

    $643,000

    New Construction $61K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,441 Sq Ft

    14780 Field Daisy Dr, Oakland, FL 34787

    Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

    Taylor Morrison Builder
    14780 Field Daisy Dr, Oakland, FL 34787
  • /30

    $874,900

    • 4 Beds
    • 4.5 Baths
    • 3,134 Sq Ft

    1231 Foltz Loop, Oakland, FL 34787

    Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living

    Elisabeth Rusnak SOUTHERN REALTY GROUP LLC

    1231 Foltz Loop, Oakland, FL 34787
  • /39

    $796,000

    $4K PRICE DROP
    • 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
  • /57

    $610,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,445 Sq Ft

    16186 Honey Harvest St, Oakland, FL 34787

    Move right into one of the most sought-after floor plans in Harvest at Ovation. This just-completed Taylor Morrison Baldwin model offers the rare opportunity to skip the build timeline and step into a never fully lived-in home loaded with designer upgrades and timeless style. Originally purchased as a long-term move, the sellers had a change of plans, creating an incredible opportunity for the

    Ken Pozek REAL BROKER, LLC

    16186 Honey Harvest St, Oakland, FL 34787
  • /56

    $629,999

    New Construction $119K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,872 Sq Ft

    38 S Pollard St, Oakland, FL 34760

    Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current

    Cassia Barros MS LAND & BUILDING LLC

    38 S Pollard St, Oakland, FL 34760
  • /37

    $625,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,642 Sq Ft

    914 Trowman Aly, Winter Garden, FL 34787

    Looking for a move-in ready home in Winter Garden with modern upgrades, an ideal location, and a true sense of community? Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in the highly desirable Oakland Park neighborhood. Designed for today's lifestyle, this home features a bright open-concept floor plan, abundant natural light, spacious living areas, and a functional layout

    Erica Diaz HOMEVEST REALTY

    914 Trowman Aly, Winter Garden, FL 34787
  • /60

    $779,900

    • 4 Beds
    • 4 Baths
    • 2,831 Sq Ft

    944 Kylee Aly, Winter Garden, FL 34787

    Welcome to this exceptional 4-bedroom, 4-bath residence with a private office, expansive loft, and 2,831 square feet of beautifully designed living space in the highly sought-after McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. Perfectly positioned on a private corner end lot, this stunning home is complemented by a welcoming front porch and showcases

    Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

    944 Kylee Aly, Winter Garden, FL 34787

Home Price Trends

Median Sale Price
$680,000
Median Single Family Sale Price
$785,000
Median Townhouse Sale Price
$386,950
Median 2 Bedroom Sale Price
$384,900
Average Price Per Sq Ft
$310
Number of Homes for Sale
38
Last 12 months Home Sales
115
Months of Supply
4.00
Median List Price
$749,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
5%
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