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Winter Garden, FL Homes for Sale in a Senior Community

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  • /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
  • /4

    $150,000 New Construction

    • Studio
    • 1 Bath
    • 350 Sq Ft

    15695 Grove Resort Ave Unit 4417, Winter Garden, FL 34787

    Enjoy this Beautiful Studio Condo within The Terraces at the Grove Resort & Water Park, the property has enough amenities that you wouldn't have to leave BUT Disney World is minutes away. The property boast a private retreat with Boutique/Hotel accommodations. As an Owner or a Guest you will enjoy the SURFING WATER PARK, WAVE POOL, FITNESS STUDIO, MIMI MARKET, SECLUDED INFINITY POOL with a

    Linda Levine CONDOMINIUM MARKETING LLC

    15695 Grove Resort Ave Unit 4417, 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
  • /11

    $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
  • /25

    $401,470 New Construction

    • 2 Beds
    • 2 Baths
    • 1,579 Sq Ft

    15873 Gem View St, Winter Garden, FL 34787

    Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    15873 Gem View St, 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
  • /70

    $885,000

    • 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
  • /50

    $994,295 New Construction

    • 3 Beds
    • 3 Baths
    • 2,902 Sq Ft

    13037 Sandcastle Dr, Winter Garden, FL 34787

    Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of resort-style amenities with social events and activities centered in the clubhouse and planned by a

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    13037 Sandcastle Dr, 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
  • /30

    $404,010 New Construction

    • 2 Beds
    • 2 Baths
    • 1,579 Sq Ft

    15837 Gem View St, Winter Garden, FL 34787

    Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    15837 Gem View St, Winter Garden, FL 34787
  • /30

    $679,240 New Construction

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

    15168 Canopy Cover Dr, Winter Garden, FL 34787

    Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    15168 Canopy Cover Dr, 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
  • /60

    $403,900

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    13615 Splashing Isla Dr, Winter Garden, FL 34787

    This is a one-of-a-kind opportunity to own the most unique Ellenwood Villa in the entire community. Standing in a class of its own, this pristine, move-in-ready residence features two bedrooms, two bathrooms, and a versatile flex space perfect for a home office or den. The interior is defined by an elegant, sun-drenched open concept with soaring ceilings and strategically placed high-wall windows

    Nanette Edmonds JAMIESON PROPERTIES, INC.

    13615 Splashing Isla Dr, 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
  • /30

    $399,590 Open Sat 10AM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,579 Sq Ft

    15831 Gem View St, Winter Garden, FL 34787

    Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    15831 Gem View St, Winter Garden, FL 34787
  • /30

    $397,580 New Construction

    • 2 Beds
    • 2 Baths
    • 1,579 Sq Ft

    15825 Gem View St, Winter Garden, FL 34787

    Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis offers an abundance of

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    15825 Gem View 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
  • /36

    $395,000

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    13562 Pearl Beach St, Winter Garden, FL 34787

    Price Reduced.....Incredible upgrades! Welcome to this stunning, bright, airy nearly new villa (occupied for only a few months), offering 2 bedrooms, 2 full bathrooms, and a den/office, in the highly sought-after 55+ community of DEL WEBB OASIS, nestled in the heart of Horizon West - just five minutes from the magical Mickey arches of Walt Disney World. This move-in ready home boasts an open

    Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

    13562 Pearl Beach St, Winter Garden, FL 34787
  • /35

    $715,000

    • 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

    $675,000

    • 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

    $425,000

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

    5637 Water Rose Rd, Winter Garden, FL 34787

    ***WINDERMERE HIGH SCHOOL***Welcome to one of the most upgraded and well-maintained townhomes in the community — and a rare opportunity zoned for highly desirable Windermere High School. Unlike many comparable units, this beautifully maintained 2016 property has been thoughtfully updated and is truly move-in ready. The home features upgraded flooring throughout, eliminating outdated carpet

    Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

    5637 Water Rose Rd, Winter Garden, FL 34787
  • /25

    $485,000

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

    14143 Title Way, Winter Garden, FL 34787

    Experience the perfect combination of modern upgrades, unbeatable convenience, and premium outdoor space in this stunning Winter Garden townhouse. Located in a highly sought-after, family-friendly neighborhood, this property offers a lifestyle of unmatched comfort and ease. Top-Tier Schools & WalkabilitySay goodbye to stressful morning drop-off lines! Nestled in an A-rated school district,

    Zhe Wang AAA GLOBAL VENTURES PA

    14143 Title Way, Winter Garden, FL 34787
  • /46

    $829,000

    • 4 Beds
    • 4.5 Baths
    • 2,766 Sq Ft

    15852 Shorebird Ln, Winter Garden, FL 34787

    Stunning 2-Story Home in Winter Garden – 4 Bedrooms, Solar Panels, and Exceptional Features This beautiful two-story home in the highly sought-after Winter Garden neighborhood offers everything you need for luxury living and modern convenience. With 4 spacious bedrooms, including a luxurious master suite complete with a walk-in closet, this home is designed to provide comfort and style for every

    Joao De Souza Freitas, Jr WRA BUSINESS & REAL ESTATE

    15852 Shorebird Ln, 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
  • /7

    $760,000

    • 5 Beds
    • 3.5 Baths
    • 3,074 Sq Ft

    15457 Murcott Harvest Loop, Winter Garden, FL 34787

    Enjoy golf course living in Summerlake Groves at Orange County National in Winter Garden. This two-story home offers 4 bedrooms and 3.5 baths with a bright, open-concept layout perfect for everyday living and entertaining. The kitchen features a large Silestone island, 42” cabinets with crown molding, stainless-steel appliances, and a walk-in pantry, overlooking the living and breakfast areas.

    Mariana Nossa WRA BUSINESS & REAL ESTATE

    15457 Murcott Harvest Loop, Winter Garden, FL 34787

Home Trends in Winter Garden, FL

Housing Trends

Median Sale Price
$570,011
Median Single Family Sale Price
$625,000
Median Townhouse Sale Price
$449,945
Median 2 Bedroom Sale Price
$230,000
Median 1 Bedroom Sale Price
$225,000
Average Price Per Sq Ft
$269
Number of Homes for Sale
672
Last 12 months Home Sales
1,848
Months of Supply
4.40
Median List Price
$599,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-1%
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