26

Winter Garden, FL Homes for Sale under $100,000

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  • /13

    $99,000

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    14816 Sugura Dr Unit 2111, Winter Garden, FL 34787

    This nicely maintained two-bedroom, two-bathroom home offers the perfect blend of comfort and convenience. Step inside to discover a spacious layout with a separate Florida room and plenty of natural light. The French doors open up to the main living space with built in cabinet and dining area. The spacious bedrooms are very comfortable for anyone. The screened in porch offers a lovely outdoor

    Kim Unger CFL PROPERTY GROUP

    14816 Sugura Dr Unit 2111, Winter Garden, FL 34787
  • /11

    $85,000

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    865 Highgate Blvd Unit 156, Winter Garden, FL 34787

    This Palm Harbor home sits on a beautifully wooded corner lot in our land leased 55+ community. Spacious Living Room and Dining Room area with ample storage options and plenty of natural light. The Kitchen is open and a good size suitable for Dining and features a large walk in Pantry. Guest Bath has been upgraded with a beautiful walk in shower. Adjacent to the living area is a super-sized three

    Sandra Bergman Cove Communities

    865 Highgate Blvd Unit 156, Winter Garden, FL 34787
  • /11

    $79,900

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    595 Royal Oak Dr N Unit 271, Winter Garden, FL 34787

    This is a wonderful opportunity in our 55+ land leased community. PRICE REDUCTION with New AC , New Range, NEW Dishwasher The washer and dryer 2 years old. Nice open floor plan with natural light throughout the home.. Expanded parking pad with plenty of room for several cars and a golf cart. Excellent storage in both Kitchen and Baths with upgraded appliances. Formal Dining space in addition to a

    Sandra Bergman Cove Communities

    595 Royal Oak Dr N Unit 271, Winter Garden, FL 34787
  • /11

    $95,000

    • 2 Beds
    • 2 Baths
    • 1,680 Sq Ft

    745 Queensbury Loop Unit 222, Winter Garden, FL 34787

    An excellent opportunity in our 55+, land leased golf cart community. This spacious home offers newer roof and A/C. The floorplan is an inviting open concept that is both functional and unique. The Kitchen flows seamlessly into the Dining space The Primary bedroom includes a generous closet and an ensuite for added privacy. Excellent opportunity to create your own dream home with some cosmetic

    Sandra Bergman Cove Communities

    745 Queensbury Loop Unit 222, Winter Garden, FL 34787
  • /14

    $92,900

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    14431 Huelva St Unit 3108, Winter Garden, FL 34787

    This spacious 3-bedroom, 2-bathroom residence, located in the highly desired Gated Resort-Style Community of Vista del Lago, offers the perfect blend of style, comfort, and functionality. Featuring a carport, storage shed, and a relaxing screen room, this property is designed for easy Florida living. Inside, you'll find hard flooring throughout, a stunning updated kitchen with quartz countertops,

    Kim Unger CFL PROPERTY GROUP

    14431 Huelva St Unit 3108, Winter Garden, FL 34787
  • /16

    $89,900

    • 2 Beds
    • 2 Baths
    • 1,196 Sq Ft

    14722 Sugura Dr Unit 2076, Winter Garden, FL 34787

    This well-kept home offers comfort and modern updates throughout. Features include: New carport and windows (2025) Updated vanities and toilets Finished drywall in the living room area Roof replaced in 2020 A/C installed in 2022 New water heater (2021) Move-in ready with thoughtful upgrades that provide peace of mind and lasting value. Features Finished Drywall in Main Living Area Laminate Wood

    Kim Unger CFL PROPERTY GROUP

    14722 Sugura Dr Unit 2076, Winter Garden, FL 34787
  • /21

    $32,500

    • 1 Bed
    • 1 Bath
    • 432 Sq Ft

    13905 W Colonial Dr Unit 200, Winter Garden, FL 34787

    Experience Florida living at its finest in this well-maintained park model home boasts an open floor plan that combines comfort, convenience, and charm in Winter Garden. featuring all-new vinyl plank flooring, all appliances, and a washer and dryer. Enjoy the outdoors in your screened-in room, relax on the back patio, and take advantage of the two storage sheds for extra space, also comes with a

    Crystal Brewer Four Star Homes, Inc.

    13905 W Colonial Dr Unit 200, Winter Garden, FL 34787
  • /26

    $58,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    14444 Vista Del Lago Blvd, Winter Garden, FL 34787

    Huge price drop of $17,0000. motivated seller. This charming fully 2-bedroom, 2-bath residence is heart of Vista Del Lago, one of Central Florida's most loved all-ages family communities! Minute walk to the clubhouse with a hot tub and pool. Perfectly located near Disney and a variety of shopping and dining options in the Four Corners area. Enjoy spacious master bedroom and an open floor plan for

    Gary DeMarigny USA Mobile & Manufactured Home Sales, LLC.

    14444 Vista Del Lago Blvd, Winter Garden, FL 34787
  • /2

    $59,000

    • Land
    • 0.1 Acre
    • $590,000 per Acre

    764 Klondike Ave, Winter Garden, FL 34787

    Excellent parcel in downtown Winter Garden. Great location.

    Fernanda Heidtmann Nobre WRA BUSINESS & REAL ESTATE

    764 Klondike Ave, Winter Garden, FL 34787
  • /15

    $88,500

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    1020 Hyde Park Cir Unit 140, Winter Garden, FL 34787

    Spacious 2 Bed, 2 Bath Manufactured Home. Do not miss this opportunity to own a well maintained, move in ready manufactured home in one of Winter Gardens most sought after 55plus gated Community! Features included Large 2 bedroom, 2 bathroom layout, well-maintained interior and exterior, move-in ready condition, located in a quiet, secure, pet-friendly, gated community, convenient to shopping,

    Isabel Dalgleish Four Star Homes, Inc.

    1020 Hyde Park Cir Unit 140, Winter Garden, FL 34787
  • /13

    $27,500

    • 1 Bed
    • 1 Bath
    • 396 Sq Ft

    14400 W Colonial Dr Unit 4, Winter Garden, FL 34787

    This quaint and quiet 1 bedroom 1 bathroom cottage located within the family friendly . Stage Stop Campground in Winter Garden Florida currently serves as an Airbnb with great rental history and is seeking a new loving owner. This home has been well maintained and is move in ready. Lot rent includes electric, water, lawn care and trash. Amenities feature a swimming pool, community center, and

    Scott Rankin Four Star Homes, Inc.

    14400 W Colonial Dr Unit 4, Winter Garden, FL 34787
  • /12

    $90,000

    • 2 Beds
    • 2 Baths
    • 1,680 Sq Ft

    740 Queensbury Loop Unit 213, Winter Garden, FL 34787

    Great price on this new listing in our 55+ land leased community. Spacious 2 Bedroom 2 Bath home in great condition with a practical floor plan and generous living space. Both bedrooms offer ample space and privacy. The two full bathrooms offer comfort and convenience. Very well maintained home that is MOVE IN READY. Perfect for year round living or a seasonal retreat.

    Sandra Bergman Cove Communities

    740 Queensbury Loop Unit 213, Winter Garden, FL 34787
  • /13

    $75,900

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    16738 Cordoba St Unit 3103, Winter Garden, FL 34787

    This 2 bedroom 2 bathroom home is priced to sell. It features wood laminate flooring throughout. The roof and water heater were both replaced in 2023 and the A/C in 2024 and offers a transferrable warranty.

    Kim Unger CFL PROPERTY GROUP

    16738 Cordoba St Unit 3103, Winter Garden, FL 34787
  • /22

    $95,000 Open House 2/21

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    14225 Canarias Dr, Winter Garden, FL 34787

    Welcome to this spacious and well-maintained 3-bedroom, 2-bath manufactured home located in Vista del Lago, a vibrant, family-friendly community offering resort-style amenities and a welcoming atmosphere. Recent updates include fresh interior and exterior paint for a bright, modern look, new vinyl flooring in the master bedroom, kitchen, and breakfast nook that is durable, stylish, and easy to

    Maria Orozco Four Star Homes, Inc.

    14225 Canarias Dr, Winter Garden, FL 34787
  • /11

    $39,000

    • 2 Beds
    • 2 Baths
    • 768 Sq Ft

    610 Royal Oak Dr N Unit 187, Winter Garden, FL 34787

    Neat and tidy home in our 55+ land leased community. Excellent curb appeal and a private rear yard for your enjoyment. Floors are laminate and ceramic tile in main living area. Nice natural light throughout the home and a lovely front porch to enjoy on those cooler days. Book a tour for this well priced home in our golf-cart community. .

    Sandra Bergman Cove Communities

    610 Royal Oak Dr N Unit 187, Winter Garden, FL 34787
  • /10

    $89,900

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    14217 Canarias Dr, Winter Garden, FL 34787

    Rare 3-bedroom opportunity at this price in the community! Located at the end of a quiet cul-de-sac, this bright and spacious 3BR/2BA home features a desirable split floorplan and skylights throughout. The updated primary bath includes a walk-in shower and soaking tub. Enjoy year-round comfort on the large screened patio with vinyl windows, overlooking a peaceful conservation area. Additional

    Kim Unger CFL PROPERTY GROUP

    14217 Canarias Dr, Winter Garden, FL 34787
  • /8

    $95,000

    • Land
    • 0.15 Acre
    • $633,333 per Acre

    1500 E Bay St, Winter Garden, FL 34787

    INVESTORS AND BUILDERS WANTED!!! Nearly half an acre between the two adjacent Lots in the heart of charming Winter Garden. The Lots add up to .40 Acre & offers an exceptional opportunity to build your dream home or investment property. This is a Rare opportunity to purchase a double lot in the city of Winter Garden! Zone R2, Utilities, water, sewer is also available. The lots are Designated &

    Jorge Barcelo LA ROSA REALTY LLC

    1500 E Bay St, Winter Garden, FL 34787
  • /11

    $72,000

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    1005 Hyde Park Cir Unit 136, Winter Garden, FL 34787

    SELLER MOTIVATED on this home that has so many great features in our 55+, land leased community. You will notice that the parking is ample with plenty of room for several cars and a golf cart. The landscaping is very attractive and is low maintenance. Beautiful oak trees in the rear of home provide lovely shade in the yard. The AC is newer and has been serviced regularly. The Kitchen is large and

    Sandra Bergman Cove Communities

    1005 Hyde Park Cir Unit 136, Winter Garden, FL 34787
  • /8

    $69,999

    • Land
    • 0.28 Acre
    • $249,996 per Acre

    0 Killarney Cove Dr, Winter Garden, FL 34787

    This is a group of 3 lots for sale; they can all be purchased or sold individually. They're side by side. The lots have canal access to Lake Apopka. They will need to be cleaned out due to the overgrowth. Right off of highway 50 just minutes to the turnpike onramp for quick access anywhere in the Orlando area. Tax ID 19 22 27 0000 00 043 is first on the left, middle Lot is Tax ID 19 22 27 0000 00

    Carl Mataushek REAL ESTATE FIRM OF ORLANDO

    0 Killarney Cove Dr, Winter Garden, FL 34787
  • /10

    $95,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    14714 Vista Del Lago Blvd Unit 5081, Winter Garden, FL 34787

    This charming cottage style 3-bedroom, 2-bathroom home located in the desired community of Vista del Lago offers comfort, convenience, and curb appeal in one perfect package. Enjoy the highly sought-after side-by-side parking under a covered carport, making everyday living easy and accessible. Step inside to find a welcoming layout with an indoor laundry room for added convenience. The screen

    Kim Unger CFL PROPERTY GROUP

    14714 Vista Del Lago Blvd Unit 5081, Winter Garden, FL 34787
  • /25

    $38,500

    • 1 Bed
    • 1 Bath
    • 480 Sq Ft

    14400 W Colonial Dr Unit 2, Winter Garden, FL 34787

    Family Park and Recreation! Close to all the parks Disney, Universal, Seaworld. This is the cutest home. One large Bedroom and one bath. Fully furnished and ready to stay in the winter! This home has been completely updated with outside porches to sit and enjoy the breeze. The park has a large pool to swim and relax after a long day at the parks. Affordable Park fees make this home a must see.

    Joanne Gauthier Four Star Homes, Inc.

    14400 W Colonial Dr Unit 2, Winter Garden, FL 34787
  • /8

    $45,000

    • 2 Beds
    • 2 Baths
    • 884 Sq Ft

    761 Royal Oak Dr E Unit 253, Winter Garden, FL 34787

    This is a great value in our 55+ land leased community. Cottage feel when you enter this well kept home. Natural light filtered through all rooms. There are good storage options and upgraded appliances. Nicely shaded lot with low maintenance landscaping for your enjoyment. Come see this gem today.

    Sandra Bergman Cove Communities

    761 Royal Oak Dr E Unit 253, Winter Garden, FL 34787
  • /20

    $32,900

    • 1 Bed
    • 1 Bath
    • 456 Sq Ft

    14400 W Colonial Dr Unit 28, Winter Garden, FL 34787

    1 Bedroom, 1 Bath Tiny Home, 12 wide PT, with open floor plan. One mile from vibrant downtown Winter Garden and walking distance to lots of misc. shopping. Recently updated with new shingle roof, flooring, cabinets, appliances. Huge porch on a concrete slab, extra storage with Washer and Dryer in attached workshop. HOA includes, Electric, Water, Sewer, Garbage, Lawn, Pool, Clubhouse, Internet and

    Larry Bruner Four Star Homes, Inc.

    14400 W Colonial Dr Unit 28, Winter Garden, FL 34787
  • /19

    $90,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    16641 Rialto Dr Unit 4295, Winter Garden, FL 34787

    This beautifully maintained three-bedroom, two-bathroom split plan home features wood laminate flooring in the living room area and ceramic tile in the kitchen. The home features side-by-side parking for extra convenience. The spacious kitchen is great for entertaining friends and family. It is located on a peaceful street. The home will have a new roof prior to closing

    Kim Unger CFL PROPERTY GROUP

    16641 Rialto Dr Unit 4295, Winter Garden, FL 34787
  • /12

    $85,000

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    1035 Highgate Blvd Unit 18, Winter Garden, FL 34787

    This home in our 55+ land leased community has been thoughtfully remodeled and is move in ready. The roof is brand new and the A/C is recent. Pleasing open floor plan with large rooms for your comfort. Ample parking and a nice sized shed for convenience. This home is within walking distance of the heated pool and other beautiful amenities. Come tour this home today.

    Sandra Bergman Cove Communities

    1035 Highgate Blvd Unit 18, Winter Garden, FL 34787
  • /17

    $84,900

    • 2 Beds
    • 2 Baths
    • 1,456 Sq Ft

    1197 Meadow Finch Dr, Winter Garden, FL 34787

    Move in at closing and make this your dream home with a little TLC Walk to many shopping choices, Publix, Aldi, misc. restaurants, Etc. 1 mile to vibrant downtown Winter Garden, access to Turnpike, 429, 408. GOLD standard Home Warranty with full price offer. $2,500 Discount for a CASH contract. Enjoy life in beautiful Central Florida.

    Larry Bruner Four Star Homes, Inc.

    1197 Meadow Finch Dr, Winter Garden, FL 34787

Home Trends in Winter Garden, FL

Housing Trends

Median Sale Price
$570,000
Median Single Family Sale Price
$620,000
Median Townhouse Sale Price
$443,000
Median 2 Bedroom Sale Price
$232,500
Median 1 Bedroom Sale Price
$122,000
Average Price Per Sq Ft
$267
Number of Homes for Sale
627
Last 12 months Home Sales
1,806
Months of Supply
4.20
Median List Price
$595,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-2%
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