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 3

124 communities near Winter Garden

Sort by:

Relevance

Relevance

5 rating (2 reviews) Palms at Serenoa
$200ks - $400ks
Palms at Serenoa, Clermont, FL
New Construction | 55+ age-restricted | Built 2018 - present | 570 homes
1 rating (1 reviews) Windermere
$100ks - $200ks
Windermere, Inverness, FL
Resale Only | Age-targeted | Built 1989 - present | 180 homes
Esplanade Of Tampa
$500ks - $700ks
Esplanade Of Tampa, Tampa, FL
Resale Only | Age-targeted | Built 2015 - 2019 | 300 homes
Thunderbird Hill
$100ks - $200ks
Thunderbird Hill, Sebring, FL
Resale Only | 55+ age-restricted | Built 1984 - 2000 | 103 homes
Huntington at Hunter's Ri...
$300ks
Huntington at Hunter's Ri..., Ormond Beach, FL
New Construction | 55+ age-restricted | Built 2015 - present | 326 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
3.9 rating (7 reviews) Summit Greens
$300ks - $400ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
Lake James
$300ks
Lake James, Lakeland, FL
New and Resale | 55+ age-restricted | Built 2004 - present | 216 homes
Del Webb Catalina
$300ks - $1Ms
Del Webb Catalina, Lakewood Ranch, FL
New Construction | 55+ age-restricted | Built 2023 - present | 1,300 homes
Summit Chase Villas
$100ks
Summit Chase Villas, Tavares, FL
Resale Only | 55+ age-restricted | Built 1982 - 1989 | 60 homes
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
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 DeLand
$300ks - $500ks
Cresswind DeLand, DeLand, FL
New Construction | 55+ age-restricted | Built 2023 - present | 600 homes
Vienna Square
$100ks - $200ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Tarawood
$200ks
Tarawood, Floral City, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 150 homes
5 rating (4 reviews) Carillon Lakes
$200ks - $400ks
Carillon Lakes, Lakeland, FL
Resale Only | Age-targeted | Built 2000 - 2006 | 650 homes
Marco Polo Village
$200ks - $300ks
Marco Polo Village, Ocala, FL
New and Resale | 55+ age-restricted | Built 1998 - present | 261 homes
Cresswind at Hammock Oaks
$300ks - $500ks
Cresswind at Hammock Oaks, Lady Lake, FL
New and Resale | 55+ age-restricted | Built 2024 - 2025 | 141 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Alhambra Villas Condomini...
$100ks - $200ks
Alhambra Villas Condomini..., DeLand, FL
Resale Only | 55+ age-restricted | Built 1970 - 1972 | 60 homes
5 rating (1 reviews) Silver Lakes
$100ks - $300ks
Silver Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes
El Dorado
$400ks - $600ks
El Dorado, Ocala, FL
Resale Only | Age-targeted | Built 1978 - 2003 | 56 homes
Hidden Creek
$100ks - $200ks
Hidden Creek, Sebring, FL
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 55 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.
Encore at Fishhawk Ranch
$200ks - $500ks
Encore at Fishhawk Ranch, Lithia, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 240 homes
3 rating (1 reviews) Cormorant Point
$100ks - $200ks
Cormorant Point, Sebring, FL
Resale Only | 55+ age-restricted | Built 1981 - 2007 | 150 homes
Carlsberg Estates on Lake...
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Cresswind at Lake Harris
$300ks - $500ks
Cresswind at Lake Harris, Tavares, FL
New Construction | 55+ age-restricted | Built 2025 - present | 625 homes
Royal Palm
$200ks - $300ks
Royal Palm, Port Orange, FL
Resale Only | 55+ age-restricted | Built 2002 - 2016 | 458 homes
Villas On The Green
$200ks - $300ks
Villas On The Green, Riverview, FL
Resale Only | 55+ age-restricted | Built 1989 - 1992 | 105 homes
Baytree
$100ks - $300ks
Baytree, Tavares, FL
Resale Only | 55+ age-restricted | Built 1990 - 2003 | 221 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spring Lake Towers
$100ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
Lakes at Laurel Highlands
$200ks - $300ks
Lakes at Laurel Highlands, Lakeland, FL
New Construction | Age-targeted | Built 2017 - present | 65 homes
The Wellington
$100ks - $200ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 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.
Archers Mill
$300ks - $500ks
Archers Mill, Ormond Beach, FL
New Construction | Age-targeted | 94 homes
2 rating (1 reviews) Heritage Landings
$200ks - $300ks
Heritage Landings, Lakeland, FL
New Construction | 55+ age-restricted | Built 2017 - 2020 | 65 homes
Preserve at Lakeside Land...
$200ks - $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
Oakview
$100ks - $200ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Bridgewater Landing
$200ks - $300ks
Bridgewater Landing, Riverview, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 64 homes
Anand Nilay
$500ks - $700ks
Anand Nilay, Tampa, FL
New Construction | Age-targeted | Built 2025 - present | 105 homes
Poinsettia Heights
$100ks - $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
5 rating (1 reviews) Cypress Lakes
$100ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lennar at Sanctuary at We...
$300ks - $500ks
Lennar at Sanctuary at We..., Clermont, FL
New Construction | 55+ age-restricted | Built 2025 - 2026 | 203 homes
Fountain View
$300ks - $400ks
Fountain View, Ormond Beach, FL
New Construction | 55+ age-restricted | Built 2023 - present | 100 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.
The Villages® 1126 MIONA SHORES DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$949,900

3 beds

|

2 baths

|

2,680 sq ft

|

House

1126 MIONA SHORES DR, THE VILLAGES, FL, ...
Community: The Villages®
Sun City Center 1810 MILFORD CIR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$375,000

2 beds

|

2 baths

|

1,852 sq ft

|

House

1810 MILFORD CIR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Spruce Creek South 10701 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$279,900

3 beds

|

2 baths

|

1,668 sq ft

|

House

10701 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Latitude Margaritaville 294 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$358,888

2 beds

|

2 baths

|

1,308 sq ft

|

House

294 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
The Villages® 1075 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,258 sq ft

|

Villa

1075 BURNETTOWN PL, 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
The Villages® 2289 SWANSEA TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,612 sq ft

|

Villa

2289 SWANSEA TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Trilogy® Orlando 306 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$350,000

3 beds

|

2 baths

|

1,925 sq ft

|

House

306 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
On Top of the World 8533 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$645,000

3 beds

|

2 baths

|

2,969 sq ft

|

House

8533 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1507 BARRERA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$329,900

3 beds

|

2 baths

|

1,553 sq ft

|

House

1507 BARRERA CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1339 LAJOLLA CIR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$319,900

2 beds

|

2 baths

|

1,094 sq ft

|

Villa

1339 LAJOLLA CIR, THE VILLAGES, FL, 3215...
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.
On Top of the World 10075 SW 91ST PL, OCALA, FL, 34481, Ocala, FL 34481
$255,000

2 beds

|

2 baths

|

1,766 sq ft

|

House

10075 SW 91ST PL, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9947 SW 100TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481
$275,000

2 beds

|

2 baths

|

1,469 sq ft

|

House

9947 SW 100TH TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
Solivita 513 BARCELONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$295,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

513 BARCELONA DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1068 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$598,700

3 beds

|

2 baths

|

1,837 sq ft

|

Villa

1068 BURNETTOWN PL, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1606 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$260,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1606 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 9791 SW 82ND STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$525,000

3 beds

|

3 baths

|

2,893 sq ft

|

House

9791 SW 82ND STREET RD, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 7559 SW 97TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$329,000

2 beds

|

2 baths

|

1,865 sq ft

|

House

7559 SW 97TH AVE, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1930 RHETT RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,434 sq ft

|

Villa

1930 RHETT RD, THE VILLAGES, FL, 32163
Community: The Villages®
On Top of the World 9037 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$219,900

3 beds

|

2 baths

|

1,584 sq ft

|

House

9037 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Baytree 615 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$285,000

3 beds

|

2 baths

|

1,440 sq ft

|

House

615 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
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® 17648 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162
$299,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17648 SE 93RD BUTLER CT, THE VILLAGES, F...
Community: The Villages®
Stone Creek 9137 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$264,000

2 beds

|

2 baths

|

1,437 sq ft

|

House

9137 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1707 GOMEZ PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$269,900

2 beds

|

2 baths

|

1,344 sq ft

|

House

1707 GOMEZ PL, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 9343 SW 102ND AVENUE RD, OCALA, FL, 3448..., Ocala, FL 34481
$459,000

2 beds

|

2 baths

|

2,104 sq ft

|

House

9343 SW 102ND AVENUE RD, OCALA, FL, 3448...
Community: On Top of the World
Stone Creek 9534 SW 65TH PL, OCALA, FL, 34481, Ocala, FL 34481
$379,900

2 beds

|

2 baths

|

1,964 sq ft

|

House

9534 SW 65TH PL, OCALA, FL, 34481
Community: Stone Creek
Twin Lakes 2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$550,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
The Villages® 1214 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,146 sq ft

|

Villa

1214 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marion Landing 6185 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476
$218,000

3 beds

|

2 baths

|

1,682 sq ft

|

House

6185 SW 84TH ST, OCALA, FL, 34476
Community: Marion Landing
On Top of the World 9359 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$397,000

3 beds

|

2 baths

|

2,165 sq ft

|

House

9359 SW 94TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 4946 NE 124TH RD, OXFORD, FL, 34484, Oxford, FL 34484
$380,000

3 beds

|

3 baths

|

2,547 sq ft

|

House

4946 NE 124TH RD, OXFORD, FL, 34484
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.
Sun City Center 302 ANDOVER PL 167, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$95,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

302 ANDOVER PL 167, SUN CITY CENTER, FL,...
Community: Sun City Center
Breakaway Trails 1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$725,000

5 beds

|

3 baths

|

3,193 sq ft

|

House

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
The Villages® 1806 QUEENSBURY TER, THE VILLAGES, FL, 3..., The Villages, FL 32162
$269,900

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

1806 QUEENSBURY TER, THE VILLAGES, FL, 3...
Community: The Villages®
Stonecrest 12271 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$389,000

4 beds

|

3 baths

|

2,246 sq ft

|

House

12271 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Latitude Margaritaville 224 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$357,900

2 beds

|

2 baths

|

1,308 sq ft

|

House

224 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Cresswind at Victoria Gardens 1157 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724
$449,700

2 beds

|

2 baths

|

1,928 sq ft

|

House

1157 AVERY MEADOWS WAY, DELAND, FL, 3272...
Lake Jovita Golf and Country Club 13915 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,195,000

4 beds

|

3 baths

|

3,613 sq ft

|

House

13915 CARRYBACK DR, DADE CITY, FL, 33525
Lake Ashton 4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,058 sq ft

|

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 444 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$359,900

2 beds

|

2 baths

|

1,308 sq ft

|

House

444 LIME AVE, DAYTONA BEACH, FL, 32124
Mirada 10799 GABLE DIG LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$285,000

2 beds

|

3 baths

|

1,747 sq ft

|

Villa

10799 GABLE DIG LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
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 optout@55places.com. 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
124 communities
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: Oct 10, 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