15

Oakland, FL Homes for Sale under $500,000

Section Image Section Image
  • /50

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,685 Sq Ft

    9357 Jaywood Rd, Oakland, FL 34787

    Welcome to this charming single story home in Waterleigh, offering 3 bedrooms, 2 bathrooms, and a bright, open concept layout designed for comfortable living and effortless entertaining. The well appointed kitchen overlooks the spacious family room and features stainless steel appliances, generous preparation space, a walk in pantry, and a large center island ideal for casual dining and

    Javin Lopez AVANTI WAY REALTY LLC

    9357 Jaywood Rd, Oakland, FL 34787
  • /34

    $379,990

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft

    16931 Reseda Aly, Oakland, FL 34787

    JUST REDUCED - BEST PRICED TOWNHOME IN WATERLEIGH, WINTER GARDEN! This beautifully maintained 3-bedroom, 2.5-bath townhome features a bright open-concept floor plan designed for comfortable living and entertaining. The spacious kitchen offers granite countertops, stainless steel appliances, ample cabinet space, and A WHOLE-HOUSE WATER FILTRATION SYSTEM IS INCLUDED, providing added value and peace

    Leticia Mena MY REALTY GROUP, LLC.

    16931 Reseda Aly, Oakland, FL 34787
  • /37

    $435,000

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft

    521 W Herriott Ave, Oakland, FL 34760

    Virtually Staged. UPDATED 9/6/26 - Motivated Seller - Accepting Reasonable Offers! The home has recently been entirely staged in the property - come tour this beauty!NOTE: to add extra space, in replacement of a garage/storage - a (large shed) can be added onto the property within the sale of the home.Welcome to this brand-new construction home in the heart of Oakland! This

    Adam DeVito REAL BROKER, LLC

    521 W Herriott Ave, Oakland, FL 34760
  • /30

    $445,000

    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    10660 Words Dr, Oakland, FL 34787

    Welcome to 10660 Words Drive, Winter Garden, FL, a beautifully maintained home featuring a spacious and thoughtfully designed floor plan for comfortable everyday living.The open-concept layout includes a bright living area, a modern kitchen with ample cabinetry and countertop space, a dining area, and generously sized bedrooms that provide comfort and privacy.The primary suite serves as a

    Ashley Porto GLASSTONE GROUP INC

    10660 Words Dr, Oakland, FL 34787
  • /33

    $364,500

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

    1511 Sweet Apple St, Oakland, FL 34787

    Welcome to 1511 Sweet Apple Street, a well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect

    Ali Yche SOUTHERN PRESTIGE REALTY INC

    1511 Sweet Apple St, Oakland, FL 34787
  • /3

    $409,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,715 Sq Ft

    Porter Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36452383, Oakland, FL 34787
  • /2

    $449,900

    • Land
    • 16,117 Sq Ft
    • $1,215,946 per Acre

    2012 N Old Killarny St, Winter Garden, FL 34787

    Discover the perfect blend of luxury and natural beauty with these stunning lakefront lots in the Lake Apopka Sound subdivision. Set along the shores of scenic Lake Apopka, these spacious homesites offer breathtaking water views, serene sunsets, and access to one of Central Florida’s most picturesque settings. Lake Apopka Sound provides the ideal backdrop for your custom dream home. With close

    Chris Kaminski FLORIDAY PROPERTIES INC

    2012 N Old Killarny St, Winter Garden, FL 34787
  • /22

    $449,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft

    14014 Scarlet Aster Aly, Oakland, FL 34787

    ***** PRICE REDUCED *****Rare Dual Owner's Suite Townhome — Priced to Move, Near DisneyThis 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months

    Jarrett Brown LPT REALTY, LLC

    14014 Scarlet Aster Aly, Oakland, FL 34787
  • /4

    $498,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    Brantley Plan at Serenade at Ovation - Bungalows, Oakland, FL 34787

    Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36498626, Oakland, FL 34787
  • /25

    $468,000

    $22K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    14099 Lochend Way, Oakland, FL 34787

    Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining

    Anahi C Rosario INTERNATIONAL REAL ESTATE LLC

    14099 Lochend Way, Oakland, FL 34787
  • /3

    $411,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,729 Sq Ft

    Sage Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36488308, Oakland, FL 34787
  • /45

    $418,500

    $1K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,636 Sq Ft

    10648 Words Dr, Winter Garden, FL 34787

    Storey Grove **YES IT HAS A BACKYARD!!*BACKS TO GREENSPACE!!** 2023 built ** Open floorplan * Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING

    Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

    10648 Words Dr, Winter Garden, FL 34787
  • /17

    $401,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft

    Harbor Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36477638, Oakland, FL 34787
  • /28

    $433,000

    Open Mon 9AM - 7PM
    • 4 Beds
    • 2 Baths
    • 1,778 Sq Ft

    17802 Jefferson St, Oakland, FL 34787

    Virtually Staged. Step into 17802 Jefferson St, a residence presenting a refreshed exterior appeal from fresh exterior paint and modernized interior amenities. The kitchen is fully equipped with all stainless steel appliances, establishing a contemporary culinary space, while a central fireplace provides warmth and a welcoming ambiance in the living area. Updated style and comfort are ready for

    Karen Albright OPENDOOR BROKERAGE LLC

    17802 Jefferson St, Oakland, FL 34787
  • /42

    $379,000

    • 3 Beds
    • 2.5 Baths
    • 1,737 Sq Ft

    1424 Scarlet Oak Loop, Winter Garden, FL 34787

    Welcome to your beautifully updated home in the gated community of Winter Garden. This charming residence offers 3 bedrooms, 2.5 baths, 2-car garage, and approximately 1,737 sq. ft. of comfortable living space.In 2025, this home underwent a $53K renovation, featuring a modern kitchen with 42” shaker white cabinets with undermount lighting and quartz counters, stainless steel appliances,

    Paula Hemani TEAMCONNECT REALTY LLC

    1424 Scarlet Oak Loop, Winter Garden, FL 34787

Home Price Trends

Median Sale Price
$683,500
Median Single Family Sale Price
$752,500
Median Townhouse Sale Price
$382,000
Median 2 Bedroom Sale Price
$369,500
Average Price Per Sq Ft
$316
Number of Homes for Sale
29
Last 12 months Home Sales
108
Months of Supply
3.20
Median List Price
$737,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home