Call us at (888) 625-4885 to learn more about active adult communities in Winter Park

Winter Park, FL 55+ active adult communities & homes for sale - Page 16

2,377 homes near Winter Park

Sort by:

Relevance

Relevance

4 rating (17 reviews) The Villages®
<$100k - $2Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
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
5 rating (1 reviews) Plantation Bay Golf &...
$200Ks - $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (3 reviews) Stonecrest
$200Ks - $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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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.
Grand Haven
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Heritage Isle
$200Ks - $500Ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Del Webb at Viera
$400Ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 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 Park? 55places can help!
Questions? Call us: (888) 625-4885
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 - $400Ks
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) 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.
Halifax Plantation
$200Ks - $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
Breakaway Trails
$400Ks - $800Ks
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 Park? 55places can help!
Questions? Call us: (888) 625-4885
4.8 rating (6 reviews) Highland Lakes
$100Ks - $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
5 rating (2 reviews) Bridgewater at Viera
$300Ks - $800Ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes
The Country Club of Mount...
$200Ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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.
4.1 rating (9 reviews) Indian River Colony Club
$200Ks - $400Ks
Indian River Colony Club, Melbourne, FL
New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes
3.9 rating (7 reviews) Summit Greens
$300Ks - $400Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
5 rating (1 reviews) Royal Harbor
$300Ks - $400Ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Lakeside Landings
$200Ks - $500Ks
Lakeside Landings, Oxford, FL
New and Resale | Age-targeted | Built 2005 - present | 700 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
1 rating (1 reviews) Sullivan Ranch
$200Ks - $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Highland Fairways
$100Ks - $300Ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Halifax Plantation 2885 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$485,000

4 beds

|

3 baths

|

2,115 sq ft

|

House

2885 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
Venetian Bay 349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$379,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Plantation at Leesburg 5140 DESOTO WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$179,900

2 beds

|

2 baths

|

1,224 sq ft

|

Manufactured Home

5140 DESOTO WAY, LEESBURG, FL, 34748
Stonecrest 11019 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,324 sq ft

|

House

11019 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Traditions at Lake Ruby 3986 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$399,900

4 beds

|

3 baths

|

2,320 sq ft

|

House

3986 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Country Club of Mount Dora 9071 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$275,000

2 beds

|

2 baths

|

1,494 sq ft

|

House

9071 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Cresswind at Victoria Gardens 104 OVERTON GARDENS LN, DELAND, FL, 3272..., Deland, FL 32724
$385,000

3 beds

|

2 baths

|

1,820 sq ft

|

House

104 OVERTON GARDENS LN, DELAND, FL, 3272...
The Villages® 334 JUAREZ WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,248 sq ft

|

House

334 JUAREZ WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Four Seasons at Orlando 2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$625,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747
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.
New Plantation Bay Golf & Country Club 844 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$394,900

2 beds

|

2 baths

|

1,526 sq ft

|

House

844 PINEWOOD DR, ORMOND BEACH, FL, 32174
New The Timbers at Everlands 1273 BLESSED ISLES DR NW, PALM BAY, FL, ..., Palm Bay, FL 32907
$475,990

3 beds

|

3 baths

|

2,601 sq ft

|

House

1273 BLESSED ISLES DR NW, PALM BAY, FL, ...
Del Webb at Viera 8870 SHORELINE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$739,982

3 beds

|

3 baths

|

2,171 sq ft

|

House

8870 SHORELINE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
New Spruce Creek Country Club 9479 SE 130TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$469,000

3 beds

|

3 baths

|

2,346 sq ft

|

House

9479 SE 130TH STREET RD, SUMMERFIELD, FL...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Foxwood Lake Estates 1570 HEATHER HILL DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$209,900

3 beds

|

2 baths

|

1,630 sq ft

|

Manufactured Home

1570 HEATHER HILL DR, LAKELAND, FL, 3381...
New Foxwood Lake Estates 4815 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810
$183,000

2 beds

|

2 baths

|

1,312 sq ft

|

Manufactured Home

4815 FOXWOOD BLVD, LAKELAND, FL, 33810
New Lake Henry Estates 516 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$244,990

2 beds

|

2 baths

|

1,393 sq ft

|

House

516 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
New Colonnades 1678 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$215,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

1678 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
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.
New Solivita 2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$329,500

2 beds

|

2 baths

|

1,703 sq ft

|

House

2285 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
New Baytree 239 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$235,000

2 beds

|

2 baths

|

1,228 sq ft

|

House

239 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
New Ridgehaven 442 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$500,000

4 beds

|

3 baths

|

2,487 sq ft

|

House

442 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
New Plantation at Leesburg 4802 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748
$385,000

3 beds

|

3 baths

|

2,162 sq ft

|

House

4802 SUMMERBRIDGE CIR, LEESBURG, FL, 347...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New The Country Club of Mount Dora 9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$350,000

3 beds

|

2 baths

|

1,587 sq ft

|

House

9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
New The Villages® 1426 LA HERMOSA DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$424,900

3 beds

|

2 baths

|

1,892 sq ft

|

House

1426 LA HERMOSA DR, THE VILLAGES, FL, 32...
Community: The Villages®
Bridgewater at Viera 1563 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$460,900

3 beds

|

2 baths

|

1,598 sq ft

|

House

1563 GREAT BELT CIR, MELBOURNE, FL, 3294...
Heritage Isle 3386 BANCROFT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$330,000

3 beds

|

2 baths

|

1,315 sq ft

|

Townhouse

3386 BANCROFT DR, MELBOURNE, FL, 32940
Community: Heritage Isle
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.
Sullivan Ranch 30118 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$435,000

4 beds

|

2 baths

|

1,955 sq ft

|

House

30118 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
The Villages® 1514 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$234,500

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1514 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
The Villages® 17285 SE 85TH WILLOWICK CIR, THE VILLAGE..., The Villages, FL 32162
$419,000

3 beds

|

2 baths

|

2,003 sq ft

|

House

17285 SE 85TH WILLOWICK CIR, THE VILLAGE...
Community: The Villages®
Latitude Margaritaville 519 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$424,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

519 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Solivita 469 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$499,000

3 beds

|

4 baths

|

2,616 sq ft

|

House

469 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3109 ARCHER AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$465,000

3 beds

|

2 baths

|

1,600 sq ft

|

Villa

3109 ARCHER AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Grand Haven 63 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$1,700,000

3 beds

|

3 baths

|

3,296 sq ft

|

House

63 FRONT ST, PALM COAST, FL, 32137
Community: Grand Haven
Spruce Creek Country Club 13194 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$268,000

2 beds

|

2 baths

|

1,283 sq ft

|

House

13194 SE 93RD TERRACE RD, SUMMERFIELD, F...
Carillon Lakes 4220 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$335,000

3 beds

|

2 baths

|

1,735 sq ft

|

House

4220 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon 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.
Sullivan Ranch 30409 TOKARA TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$544,500

4 beds

|

3 baths

|

2,550 sq ft

|

House

30409 TOKARA TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Latitude Margaritaville 1032 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$470,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

1032 SEA SHELL CT, DAYTONA BEACH, FL, 32...
The Villages® 5562 LANSING DR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$125,000

2 beds

|

2 baths

|

784 sq ft

|

Mobile Home

5562 LANSING DR, WILDWOOD, FL, 34785
Community: The Villages®
Del Webb Minneola 2763 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$417,500

2 beds

|

2 baths

|

1,395 sq ft

|

House

2763 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New The Villages® 105 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$164,500

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

105 CYPRESS RD, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 917 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$765,000

3 beds

|

2 baths

|

2,082 sq ft

|

House

917 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®

Want more information about active adult communities around Winter Park?

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 Park?

Call us: (888) 625-4885
2,377 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: Jan 11, 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