not an image

Call us at (689) 407-5757 to learn more about active adult communities in Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale - Page 29

3,497 homes near Winter Garden

Sort by:

Relevance

Relevance

4 rating (17 reviews) The Villages®
$100ks - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
3.8 rating (14 reviews) Sun City Center
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4 rating (56 reviews) On Top of the World
$100ks - $600ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
5 rating (2 reviews) Plantation at Leesburg
$100ks - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4 rating (2 reviews) Harbor Hills Country Club
$300ks - $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Lake Jovita Golf and Coun...
$400ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
12...3
Mirada 10274 ECHO DOCK LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$289,990

2 beds

|

3 baths

|

1,747 sq ft

|

Townhouse

10274 ECHO DOCK LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
The Villages® 1479 GEORGETOWN AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$369,000

3 beds

|

2 baths

|

House

1479 GEORGETOWN AVE, THE VILLAGES, FL, 3...
Community: The Villages®
Highland Fairways 2140 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$230,000

2 beds

|

2 baths

|

1,394 sq ft

|

House

2140 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
The Villages® 437 JARQUIN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$375,000

2 beds

|

2 baths

|

1,161 sq ft

|

Villa

437 JARQUIN WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Tampa Bay Golf and Country Club 9936 GAP WEDGE DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$359,900

3 beds

|

2 baths

|

1,707 sq ft

|

House

9936 GAP WEDGE DR, SAN ANTONIO, FL, 3357...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Tampa Bay Golf and Country Club 10312 OLD TAMPA BAY DR, SAN ANTONIO, FL,..., San Antonio, FL 33576
$339,900

3 beds

|

2 baths

|

1,682 sq ft

|

House

10312 OLD TAMPA BAY DR, SAN ANTONIO, FL,...
Spruce Creek Country Club 13524 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$369,000

3 beds

|

2 baths

|

1,998 sq ft

|

House

13524 SE 87TH CIR, SUMMERFIELD, FL, 3449...
Baytree 116 BAYTREE BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$260,000

3 beds

|

3 baths

|

1,581 sq ft

|

Villa

116 BAYTREE BLVD, TAVARES, FL, 32778
Community: Baytree
On Top of the World 9185 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$319,900

3 beds

|

2 baths

|

2,051 sq ft

|

House

9185 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 2082 SIFIELD GREENS WAY 3, SUN CITY CENT..., Sun City Center, FL 33573
$244,900

2 beds

|

2 baths

|

1,206 sq ft

|

Condo

2082 SIFIELD GREENS WAY 3, SUN CITY CENT...
Community: Sun City Center
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Stone Creek 8750 SW 59TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$480,000

3 beds

|

3 baths

|

2,110 sq ft

|

House

8750 SW 59TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
SummerGlen 16304 SW 12TH TER, OCALA, FL, 34473, Ocala, FL 34473
$282,500

3 beds

|

2 baths

|

1,836 sq ft

|

House

16304 SW 12TH TER, OCALA, FL, 34473
Community: SummerGlen
Quail Meadow 3498 NW 50TH CT, OCALA, FL, 34482, Ocala, FL 34482
$258,000

3 beds

|

2 baths

|

1,511 sq ft

|

House

3498 NW 50TH CT, OCALA, FL, 34482
Community: Quail Meadow
On Top of the World 8458 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$549,900

3 beds

|

3 baths

|

2,457 sq ft

|

House

8458 SW 97TH CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 16980 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$320,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

16980 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
The Villages® 2334 ROSE ARBOR ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$529,900

3 beds

|

2 baths

|

1,695 sq ft

|

Villa

2334 ROSE ARBOR ST, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9152 SW 85TH PL, OCALA, FL, 34481, Ocala, FL 34481
$529,000

2 beds

|

2 baths

|

2,104 sq ft

|

House

9152 SW 85TH PL, OCALA, FL, 34481
Community: On Top of the World
Cresswind at Victoria Gardens 115 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724
$299,900

3 beds

|

2 baths

|

1,687 sq ft

|

House

115 AVENHAM DR, DELAND, FL, 32724
The Villages® 1832 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$824,900

3 beds

|

2 baths

|

2,502 sq ft

|

House

1832 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1017 PINEWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$269,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1017 PINEWOOD PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Cresswind at Victoria Gardens 307 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$299,999

2 beds

|

2 baths

|

1,547 sq ft

|

House

307 HERON POINT WAY, DELAND, FL, 32724
Spruce Creek Country Club 9570 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$359,999

2 beds

|

2 baths

|

1,528 sq ft

|

House

9570 SE 136TH PL, SUMMERFIELD, FL, 34491
Esplanade at Wiregrass Ranch 4605 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$499,900

3 beds

|

2 baths

|

1,926 sq ft

|

House

4605 ROSATTI RD, WESLEY CHAPEL, FL, 3354...
The Villages® 1469 RAMON RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,562 sq ft

|

House

1469 RAMON RD, THE VILLAGES, FL, 32162
Community: The Villages®
The Lakes at Harmony 3113 SONGBIRD CIR, ST CLOUD, FL, 34773, St Cloud, FL 34773
$399,900

3 beds

|

2 baths

|

1,876 sq ft

|

House

3113 SONGBIRD CIR, ST CLOUD, FL, 34773
The Villages® 1306 DEBRA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$179,900

2 beds

|

2 baths

|

1,120 sq ft

|

Manufactured Home

1306 DEBRA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1982 SOMERSET AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,404 sq ft

|

House

1982 SOMERSET AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 6359 SW 117TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$249,900

2 beds

|

2 baths

|

1,368 sq ft

|

House

6359 SW 117TH LOOP, OCALA, FL, 34476
Community: Oak Run
High Vista at Ridgewood Lakes 53 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$325,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

53 HIGH VISTA DR, DAVENPORT, FL, 33837
Valencia Lakes 4972 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$329,900

2 beds

|

2 baths

|

1,648 sq ft

|

Villa

4972 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Sun City Center 2322 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$214,900

2 beds

|

2 baths

|

1,829 sq ft

|

Condo

2322 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Del Webb Orlando 519 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$300,000

2 beds

|

2 baths

|

1,358 sq ft

|

House

519 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Sun City Center 309 KNOTTWOOD CT 309, SUN CITY CENTER, F..., Sun City Center, FL 33573
$110,000

2 beds

|

2 baths

|

1,073 sq ft

|

Condo

309 KNOTTWOOD CT 309, SUN CITY CENTER, F...
Community: Sun City Center
Solivita 130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$369,000

3 beds

|

2 baths

|

2,141 sq ft

|

House

130 PRIMA DR, KISSIMMEE, FL, 34759
Community: Solivita
Spruce Creek Preserve 11273 SW 136TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$259,000

2 beds

|

2 baths

|

1,398 sq ft

|

House

11273 SW 136TH PL, DUNNELLON, FL, 34432
Marco Polo Village 5337 SW 111TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$489,900

4 beds

|

3 baths

|

2,675 sq ft

|

House

5337 SW 111TH LANE RD, OCALA, FL, 34476
Community: Marco Polo Village
The Villages® 1521 HOLLYBERRY PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$374,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

1521 HOLLYBERRY PL, THE VILLAGES, FL, 32...
Community: The Villages®
Lake Jovita Golf and Country Club 13539 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$800,000

4 beds

|

4 baths

|

3,217 sq ft

|

House

13539 CARRYBACK DR, DADE CITY, FL, 33525
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 8331 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$294,800

4 beds

|

2 baths

|

2,240 sq ft

|

Manufactured Home

8331 COUNTY RD 109, LADY LAKE, FL, 32159
Community: The Villages®
On Top of the World 9240 SW 90TH CT B, OCALA, FL, 34481, Ocala, FL 34481
$199,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

9240 SW 90TH CT B, OCALA, FL, 34481
Community: On Top of the World
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Frequently Asked Questions


Want more information about active adult communities around Winter Garden?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winter Garden?

Call us: (689) 407-5757
3,497 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top