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Winter Garden, FL Homes for Sale in a Senior Community

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  • /42

    $449,000

    • 3 Beds
    • 2.5 Baths
    • 1,853 Sq Ft

    8156 Wood Sage Dr, Winter Garden, FL 34787

    Winter Garden – Rare, immaculate end-unit townhome in highly sought-after Summerlake, fully updated and truly MOVE-IN READY. Step onto the charming front porch—perfect for morning coffee as the neighborhood comes to life—and then into a bright, open interior with soaring ceilings, a freshly painted interior, and an inviting floor plan.The chef’s kitchen features abundant real wood cabinetry,

    Agent Photo

    Kathy Aparo-Griffin

    APARO-GRIFFIN PROPERTIES INC

    (321) 384-8375

    8156 Wood Sage Dr, Winter Garden, FL 34787
  • /43

    $699,000

    • 5 Beds
    • 4.5 Baths
    • 3,747 Sq Ft

    3407 Current Ave, Winter Garden, FL 34787

    Five bedrooms, four and a half baths, and a three-car split garage inside a gated waterfront community on Johns Lake. This 2020-built home in Lakeview Preserve is built around space and flexibility. The kitchen anchors the main living area with stainless appliances, a large center island, and an open sightline into the family room and dining space. A downstairs primary suite sits privately off

    Brad Young HOMEVEST REALTY

    3407 Current Ave, Winter Garden, FL 34787
  • /11

    $75,000

    • 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
  • /41

    $876,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,943 Sq Ft

    13043 Sandcastle Dr, Winter Garden, FL 34787

    Experience the perfect blend of luxury and convenience with the Palmary dream home. Formerly a model home, this stunning one-story residence showcases a thoughtfully designed layout with 3 spacious bedrooms, 2 full bathrooms, and a 2-car garage. Enjoy your private outdoor oasis featuring an in-ground pool with a sun shelf and a covered lanai pre-plumbed for an outdoor kitchen. Step inside to the

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    13043 Sandcastle Dr, 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
  • /5

    $119,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    950 Hyde Park Cir Unit 147, Winter Garden, FL 34787

    PRICE REDUCED for this Spacious home in our 55+ land leased community is a later model that features a split plan and a lovely location in our golf-cart friendly neighborhood. There is no carpeting and all flooring is easy care and attractive. bedrooms are large and offer many storage options for your convenience. Come out today to explore the possibilities in our lovely community.

    Sandra Bergman Cove Communities

    950 Hyde Park Cir Unit 147, Winter Garden, FL 34787
  • /10

    $135,000

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

    904 Royal View Cir Unit 395, Winter Garden, FL 34787

    This meticulous home in our 55+ land leased community is a must see. Great split and open floorplan for your enjoyment. All appliances will stay with the home and they are upgraded. beautiful luxury vinyl flooring and pleasing natural light are featured in all rooms. In addition there is an ample all seasons porch for entertaining and peaceful reflection. Tour this home today.

    Sandra Bergman Cove Communities

    904 Royal View Cir Unit 395, Winter Garden, FL 34787
  • /12

    $149,900

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

    790 Hyde Park Cir W Unit 381, Winter Garden, FL 34787

    This is a beautifully maintained Palm Harbor home in our 55+, land leased community. The storage is phenomenal and countless upgrades are offered. The roof is new and the HVAC is recent. The Kitchen features abundant workspace with newer black appliances. The bedrooms are spacious with a stunning custom built closet for your needs. The Corner lot is lovely with lush landscaping and a pleasing

    Sandra Bergman Cove Communities

    790 Hyde Park Cir W Unit 381, Winter Garden, FL 34787
  • /10

    $100,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    1012 Royal Citrus Ct Unit 441, Winter Garden, FL 34787

    PRICE REDUCTION ON this Beautiful home in our 55+ land leased community. The home sits on a cul de sac with a unique view of one of our ponds. Very quiet and serene setting. The floorplan is split and excellent for entertaining guests. Roof is in great condition and the A/C was installed this year. There is a double wide driveway for convenient parking. Lovely laminate flooring in main living

    Sandra Bergman Cove Communities

    1012 Royal Citrus Ct Unit 441, Winter Garden, FL 34787
  • /8

    $65,000

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

    765 White Chapel Rd Unit 307, Winter Garden, FL 34787

    This is a great value in our 55+ land leased community. Very attractive curb appeal with a fantastic view of the pond from several rooms of the home. The rooms are spacious and there is excellent storage throughout this floorplan. Come view this home today.

    Sandra Bergman Cove Communities

    765 White Chapel Rd Unit 307, Winter Garden, FL 34787
  • /70

    $880,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2 Baths
    • 2,049 Sq Ft

    15162 Canopy Cover Dr, Winter Garden, FL 34787

    This exceptional Mystique model by Pulte showcases one of the most impressive outdoor living spaces within Del Webb Oasis, a boutique 55+ resort-style community just minutes from Orlando’s top attractions. Situated on a premium conservation lot, this home offers privacy, tranquility, and unobstructed natural views—an ideal setting for those seeking an elevated and peaceful living experience. With

    Angela Camacho LA ROSA REALTY LLC

    15162 Canopy Cover Dr, Winter Garden, FL 34787
  • /9

    $95,000

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

    856 Royal View Cir Unit 391, Winter Garden, FL 34787

    New Listing in our 55+ land leased community. Discover this beautifully upgraded and unique mobile home that combines comfort, style and value. This home features 2 spacious bedrooms and baths with many modern upgrades and stylish finishes. Enjoy outdoor living with custom touches throughout the yard space. This is truly one of a kind. Make your appointment today.

    Sandra Bergman Cove Communities

    856 Royal View Cir Unit 391, Winter Garden, FL 34787
  • /8

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft

    604 White Chapel Rd Unit 281, Winter Garden, FL 34787

    Great floorplan in our 55+, land leased community. Recent roof and newer A/C unit and ductwork. The guest bath has been remodeled with a comfort height commode. All rooms have ceiling fans. The Kitchen has ample storage and beautiful finishes. Come out to see this one today.

    Sandra Bergman Cove Communities

    604 White Chapel Rd Unit 281, Winter Garden, FL 34787
  • /62

    $585,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    13360 Sunny Retreat Ln, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family and villa homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around

    Alan Martin FRONTLINE FLORIDA REALTY, INC.

    13360 Sunny Retreat Ln, Winter Garden, FL 34787
  • /15

    $78,500

    • 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
  • /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
  • /23

    $55,900

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    750 Hyde Park Cir W Unit 377, Winter Garden, FL 34787

    Charming 2BR, 2BA home with approximately 1,000 SqFt located in the desirable 55 plus gated community of Hyde Park Village. Major upgrades already completed: NEW Roof, 2023, and NEW AC 2023, giving you peace of mind and added value. Bonus Savings! The new owner will benefit from grandfathered lot rent of $1,034.01 a month for the remainder of the year, creating immediate savings. Ideally located

    Isabel Dalgleish Four Star Homes, Inc.

    750 Hyde Park Cir W Unit 377, 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
  • /35

    $675,000

    • 5 Beds
    • 3 Baths
    • 2,834 Sq Ft

    15403 Murcott Harvest Loop, Winter Garden, FL 34787

    Live the golf course lifestyle in the highly desirable Summerlake Groves community at Orange County National Golf Center and Lodge in beautiful Winter Garden.This thoughtfully designed 2 story home offers 5 bedrooms and 3 bathrooms, with a bright open concept layout that makes everyday living and entertaining effortless. The spacious kitchen flows seamlessly into the living and dining areas,

    Andre Kressler KRESSLER REAL ESTATE

    15403 Murcott Harvest Loop, Winter Garden, FL 34787
  • /11

    $135,000

    • 2 Beds
    • 2 Baths
    • 1,430 Sq Ft

    620 Hyde Park Cir W Unit 364, Winter Garden, FL 34787

    Thoughtfully updated home in our 55+ land leased community in beautiful Winter Garden. Step into this stunning, fully upgraded home that blends modern luxury with comfort and convenience. Open floorplan is spacious and inviting with beautiful seamless ceramic tile throughout. Stainless steel appliances will stay with home and the updated Kitchen is impressive. Lovely Bonus Room to utilize as

    Sandra Bergman Cove Communities

    620 Hyde Park Cir W Unit 364, Winter Garden, FL 34787
  • /51

    $649,900

    • 2 Beds
    • 2.5 Baths
    • 2,108 Sq Ft

    13846 Fresh Ivy St, Winter Garden, FL 34787

    Welcome to 13846 Fresh Ivy Street, nestled in the highly desirable Winter Garden area, just minutes away from world-famous Orlando attractions. This home is easy on the eyes and offers the perfect blend of comfort, convenience, and luxury living.This beautifully designed two-bedroom, two-and-a-half-bath home features over 2,100 square feet of living space. With spacious interiors, thoughtful

    Ken Pozek REAL BROKER, LLC

    13846 Fresh Ivy St, 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
  • /41

    $419,490

    • 3 Beds
    • 2.5 Baths
    • 1,617 Sq Ft

    5637 Water Rose Rd, Winter Garden, FL 34787

    ***WINDERMERE HIGH SCHOOL*** Price improvement – great opportunity in Signature Lakes / Winter Garden.Enjoy the best of Florida living in this beautiful townhome located in the highly desirable Signature Lakes / Independence community in Winter Garden. This well-maintained 3-bedroom, 2.5-bath home offers a functional layout with comfortable living spaces and plenty of natural light. The

    Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

    5637 Water Rose Rd, Winter Garden, FL 34787
  • /8

    $100,000

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

    680 Queensbury Loop Unit 207, Winter Garden, FL 34787

    This is a lovely home in our 55+, land leased community. The Kitchen is large and features ample cabinetry and counter space. Natural light is abundant and includes all appliances. The carpet is new and a lovely neutral color. The extra large Florida Room is great for entertaining or morning coffee. This carefully maintained home is a must see in our golf-cart friendly community.

    Sandra Bergman Cove Communities

    680 Queensbury Loop Unit 207, Winter Garden, FL 34787
  • /17

    $9,999

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    1025 Highgate Blvd, Winter Garden, FL 34787

    MOTIVATED SELLER ONLY $9,999 - ALL OFFERS WELCOME! Don't miss this incredible opportunity to own this 2-bedroom, 2-bathroom home is located in a desirable 55+ gated, golf cart-friendly community in Winter Garden, FL, and due to unforeseen circumstances, the seller must sell immediately and is ready to consider any offer ASAP. The home features a spacious master bedroom with two walk-in closets

    Stephanie Thompson USA Mobile & Manufactured Home Sales, LLC.

    1025 Highgate Blvd, Winter Garden, FL 34787
  • /14

    $85,000

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

    1035 Highgate Blvd Unit 18, Winter Garden, FL 34787

    GOLF CART INCLUDED with 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
  • /35

    $975,000

    • 3 Beds
    • 2.5 Baths
    • 2,270 Sq Ft

    15078 Canopy Cover Dr, Winter Garden, FL 34787

    This is it—the one buyers wait for and rarely catch in time. One of the final opportunities to own in Del Webb Oasis, a highly sought-after 55+ community by Pulte Homes, where lifestyle isn’t an upgrade—it’s built in. This extended Stardom Echelon isn’t just a home—it’s a fully dialed-in experience. Thoughtfully expanded and meticulously upgraded, it offers a private heated pool and extended

    David Weiss COLDWELL BANKER REALTY

    15078 Canopy Cover Dr, Winter Garden, FL 34787

Home Trends in Winter Garden, FL

Housing Trends

Median Sale Price
$575,000
Median Single Family Sale Price
$625,000
Median Townhouse Sale Price
$449,990
Median 2 Bedroom Sale Price
$229,997
Median 1 Bedroom Sale Price
$227,500
Average Price Per Sq Ft
$270
Number of Homes for Sale
709
Last 12 months Home Sales
1,898
Months of Supply
4.50
Median List Price
$599,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
0%
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