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

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

3,648 homes near Winter Garden

Sort by:

Relevance

Relevance

5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 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
3.8 rating (14 reviews) Sun City Center
<$100k - $500Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $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
3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 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
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
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 - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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 (3 reviews) Stonecrest
<$100k - $500Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $600Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$300Ks - $2Ms
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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $500Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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 (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
No reviews yet Breakaway Trails
$300Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Royal Highlands 4528 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$425,000

2 beds

|

2 baths

|

2,200 sq ft

|

House

4528 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
Oak Run 8152 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$182,500

2 beds

|

2 baths

|

1,119 sq ft

|

House

8152 SW 108TH LOOP, OCALA, FL, 34481
Community: Oak Run
Sun City Center 668 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$299,000

3 beds

|

2 baths

|

1,568 sq ft

|

Villa

668 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Cresswind at Victoria Gardens 213 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$367,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

213 OLD MOSS CIR, DELAND, FL, 32724
Cherrywood 6084 SW 105TH PL, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

6084 SW 105TH PL, OCALA, FL, 34476
Community: Cherrywood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 12163 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$525,000

3 beds

|

2 baths

|

2,645 sq ft

|

House

12163 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Ridgehaven 171 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$320,575

3 beds

|

2 baths

|

1,572 sq ft

|

House

171 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
Spruce Creek Country Club 13430 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$284,999

2 beds

|

2 baths

|

1,575 sq ft

|

House

13430 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Royal Highlands 4950 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

2 baths

|

2,065 sq ft

|

House

4950 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 1402 CONCHAS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$359,900

2 beds

|

2 baths

|

1,146 sq ft

|

Villa

1402 CONCHAS DR, THE VILLAGES, FL, 32162
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.
Sandpiper Golf & Country Club 6143 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$289,900

2 beds

|

2 baths

|

1,216 sq ft

|

House

6143 CRANE DR, LAKELAND, FL, 33809
Spruce Creek Country Club 13660 SE 90TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$410,000

2 beds

|

2 baths

|

2,109 sq ft

|

House

13660 SE 90TH TER, SUMMERFIELD, FL, 3449...
The Villages® 2942 SILK TREE TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$539,900

3 beds

|

2 baths

|

2,274 sq ft

|

House

2942 SILK TREE TER, THE VILLAGES, FL, 32...
Community: The Villages®
Spruce Creek Country Club 9073 SE 136TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$215,000

2 beds

|

2 baths

|

1,136 sq ft

|

House

9073 SE 136TH LOOP, SUMMERFIELD, FL, 344...
Spruce Creek Country Club 12792 SE 90TH COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,598 sq ft

|

House

12792 SE 90TH COURT RD, SUMMERFIELD, FL,...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$498,500

3 beds

|

2 baths

|

1,830 sq ft

|

House

458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Spruce Creek Country Club 13544 SE 89TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$399,500

3 beds

|

2 baths

|

1,958 sq ft

|

House

13544 SE 89TH TERRACE RD, SUMMERFIELD, F...
Spruce Creek Country Club 8789 SE 136TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$335,900

3 beds

|

2 baths

|

2,029 sq ft

|

House

8789 SE 136TH LN, SUMMERFIELD, FL, 34491
Del Webb Orlando 300 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$438,900

2 beds

|

2 baths

|

1,728 sq ft

|

House

300 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek North 6473 SW 108TH ST, OCALA, FL, 34476, Ocala, FL 34476
$169,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

6473 SW 108TH ST, OCALA, FL, 34476
Community: Spruce Creek North
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.
The Villages® 1137 SUMMERTON ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$470,000

3 beds

|

2 baths

|

1,407 sq ft

|

Villa

1137 SUMMERTON ST, THE VILLAGES, FL, 321...
Community: The Villages®
Sun City Center 823 FOX HILLS DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$274,900

2 beds

|

2 baths

|

1,852 sq ft

|

House

823 FOX HILLS DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Marco Polo Village 4910 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$335,000

4 beds

|

2 baths

|

1,716 sq ft

|

House

4910 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
Del Webb Orlando 672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$389,900

2 beds

|

2 baths

|

1,956 sq ft

|

House

672 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Lakes at Harmony 3415 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$285,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

3415 SAGEBRUSH ST, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Orlando 136 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$419,900

3 beds

|

3 baths

|

1,982 sq ft

|

House

136 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek Country Club 9543 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$529,000

3 beds

|

2 baths

|

2,806 sq ft

|

House

9543 SE 137TH STREET RD, SUMMERFIELD, FL...
The Villages® 1268 CAMERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$309,900

2 beds

|

2 baths

|

1,248 sq ft

|

House

1268 CAMERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 919 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159
$435,000

3 beds

|

2 baths

|

1,634 sq ft

|

House

919 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
Spruce Creek Country Club 13320 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$459,000

2 beds

|

3 baths

|

2,346 sq ft

|

House

13320 SE 97TH TERRACE RD, SUMMERFIELD, F...
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.
Royal Highlands 6307 BERKSHIRE PASS, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,748 sq ft

|

House

6307 BERKSHIRE PASS, LEESBURG, FL, 34748
Community: Royal Highlands
Spruce Creek North 10967 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$199,999

2 beds

|

2 baths

|

1,248 sq ft

|

House

10967 SW 65TH AVE, OCALA, FL, 34476
Community: Spruce Creek North
Royal Highlands 4814 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748
$309,000

3 beds

|

2 baths

|

1,728 sq ft

|

House

4814 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
Spruce Creek Country Club 11728 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$310,000

2 beds

|

2 baths

|

1,575 sq ft

|

House

11728 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Del Webb Minneola 2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$479,500

2 beds

|

2 baths

|

1,405 sq ft

|

House

2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 8961 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$389,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

8961 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Spruce Creek Country Club 13968 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$384,900

3 beds

|

2 baths

|

2,120 sq ft

|

House

13968 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Royal Highlands 4712 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$250,000

3 beds

|

2 baths

|

1,615 sq ft

|

House

4712 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Royal Highlands 20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$389,000

3 beds

|

3 baths

|

2,224 sq ft

|

House

20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Spruce Creek Country Club 9894 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$429,000

3 beds

|

2 baths

|

2,267 sq ft

|

House

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344...

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
3,648 homes near Winter Garden
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.
© 2025 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: Nov 05, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top