not an image

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 13

2,259 homes near Winter Park

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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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 - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
5 rating (1 reviews) Plantation Bay Golf &...
$400ks - $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
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 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
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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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 Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 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
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
4.4 rating (16 reviews) Del Webb Orlando
$200ks - $500ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (1 reviews) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
Trilogy® Orlando 537 NARROW VIEW LN, GROVELAND, FL, 34736, Groveland, FL 34736
$400,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

537 NARROW VIEW LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 853 WINCHESTER CT, THE VILLAGES, FL, 321..., The Villages, FL 32162
$449,000

3 beds

|

2 baths

|

1,532 sq ft

|

Villa

853 WINCHESTER CT, THE VILLAGES, FL, 321...
Community: The Villages®
Venetian Bay 424 LUNA BELLA LN 416C, NEW SMYRNA BEACH..., New Smyrna Beach, FL 32168
$304,900

2 beds

|

2 baths

|

1,669 sq ft

|

Condo

424 LUNA BELLA LN 416C, NEW SMYRNA BEACH...
Community: Venetian Bay
Summer Trees 79 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$220,000

2 beds

|

2 baths

|

1,229 sq ft

|

Condo

79 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Del Webb at Viera 9013 BLISSFUL BREEZE TRL, MELBOURNE, FL,..., Melbourne, FL 32940
$409,210

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

9013 BLISSFUL BREEZE TRL, MELBOURNE, FL,...
Community: Del Webb at Viera
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Harbor Hills Country Club 6200 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$239,900

2 beds

|

2 baths

|

1,537 sq ft

|

Villa

6200 TOPSAIL RD, LADY LAKE, FL, 32159
Freedom Homes at Grand Reserve 5 CADDY CT, BUNNELL, FL, 32110, Bunnell, FL 32110
$299,900

4 beds

|

2 baths

|

1,778 sq ft

|

House

5 CADDY CT, BUNNELL, FL, 32110
Venetian Bay 424 LUNA BELLA LN 416, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$304,900

2 beds

|

2 baths

|

1,669 sq ft

|

Condo

424 LUNA BELLA LN 416, NEW SMYRNA BEACH,...
Community: Venetian Bay
Lakeside Landings 10339 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484
$385,000

3 beds

|

2 baths

|

2,003 sq ft

|

House

10339 ADDISON SHORE WAY, OXFORD, FL, 344...
Community: Lakeside Landings
Grand Haven 10 S WATERVIEW DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$769,000

3 beds

|

3 baths

|

2,643 sq ft

|

House

10 S WATERVIEW DR, PALM COAST, FL, 32137
Community: Grand Haven
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 Savannahs 4324 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904
$425,000

2 beds

|

2 baths

|

1,773 sq ft

|

House

4324 CALADIUM CIR, WEST MELBOURNE, FL, 3...
Community: The Savannahs
The Villages® 611 LISBON LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$357,800

2 beds

|

2 baths

|

1,721 sq ft

|

House

611 LISBON LN, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 842 PICKETT RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$525,000

3 beds

|

2 baths

|

1,939 sq ft

|

House

842 PICKETT RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 3419 CARRABELLE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$285,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3419 CARRABELLE CT, THE VILLAGES, FL, 32...
Community: The Villages®
Stonecrest 17424 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$279,000

3 beds

|

2 baths

|

1,446 sq ft

|

House

17424 SE 111TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Spruce Creek Country Club 13322 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$289,750

2 beds

|

2 baths

|

1,346 sq ft

|

House

13322 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1625 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$165,000

2 beds

|

2 baths

|

1,332 sq ft

|

Manufactured Home

1625 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
American Village 17 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$319,000

3 beds

|

2 baths

|

1,745 sq ft

|

House

17 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Venetian Bay 3365 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$439,900

4 beds

|

3 baths

|

2,307 sq ft

|

House

3365 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Royal Highlands 21830 KING EDWARD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$359,900

3 beds

|

2 baths

|

2,268 sq ft

|

House

21830 KING EDWARD CT, LEESBURG, FL, 3474...
Community: Royal Highlands
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.
Stonecrest 16887 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$439,000

3 beds

|

2 baths

|

2,100 sq ft

|

House

16887 SE 110TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
Pelican Bay Daytona Beach 140 GOLDEN EYE DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$194,900

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

140 GOLDEN EYE DR D, DAYTONA BEACH, FL, ...
Del Webb Oasis 15139 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787
$699,000

2 beds

|

2 baths

|

2,000 sq ft

|

House

15139 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
Spring Lake Towers 700 MIRROR TER 506, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$119,000

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 506, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
The Villages® 562 ALLENWOOD LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$490,000

3 beds

|

2 baths

|

1,906 sq ft

|

House

562 ALLENWOOD LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
Pelican Bay Daytona Beach 108 DUCK HAWK CIR 3020, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$229,900

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

108 DUCK HAWK CIR 3020, DAYTONA BEACH, F...
Kings Ridge 3675 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$309,900

2 beds

|

2 baths

|

1,713 sq ft

|

House

3675 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2446 HOPESPRING LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2446 HOPESPRING LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 321 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$369,000

2 beds

|

2 baths

|

1,478 sq ft

|

House

321 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 8201 SE 169TH PALOWNIA LOOP, THE VILLAGE..., The Villages, FL 32162
$225,000

2 beds

|

2 baths

|

1,163 sq ft

|

Villa

8201 SE 169TH PALOWNIA LOOP, THE VILLAGE...
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.
Legacy of Leesburg 5304 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$330,000

3 beds

|

2 baths

|

1,641 sq ft

|

House

5304 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
Kings Ridge 3786 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$359,000

2 beds

|

2 baths

|

1,645 sq ft

|

House

3786 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Pelican Bay Daytona Beach 141 GOLDEN EYE DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$197,500

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

141 GOLDEN EYE DR B, DAYTONA BEACH, FL, ...
The Villages® 1019 GOLDEN GROVE DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$289,500

2 beds

|

2 baths

|

1,142 sq ft

|

House

1019 GOLDEN GROVE DR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 919 WEEPING WILLOW AVE, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$226,000

2 beds

|

2 baths

|

1,392 sq ft

|

Manufactured Home

919 WEEPING WILLOW AVE, LADY LAKE, FL, 3...
Community: The Villages®
Alamanda Key 543 HEMING WAY, MELBOURNE, FL, 32901, Melbourne, FL 32901
$375,000

3 beds

|

2 baths

|

1,937 sq ft

|

House

543 HEMING WAY, MELBOURNE, FL, 32901
Community: Alamanda Key
The Villages® 1133 DEL TORO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$329,000

2 beds

|

2 baths

|

1,332 sq ft

|

House

1133 DEL TORO DR, LADY LAKE, FL, 32159
Community: The Villages®
Heritage Isle 7248 BRODERICK DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$415,000

4 beds

|

3 baths

|

1,988 sq ft

|

House

7248 BRODERICK DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Cresswind at Victoria Gardens 1383 LONGLEY PL, DELAND, FL, 32724, Deland, FL 32724
$350,000

2 beds

|

2 baths

|

1,433 sq ft

|

House

1383 LONGLEY PL, DELAND, FL, 32724
Summer Trees 6040 SPRUCE POINT CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$429,900

3 beds

|

2 baths

|

2,132 sq ft

|

House

6040 SPRUCE POINT CIR, PORT ORANGE, FL, ...
Community: Summer Trees
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 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
2,259 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: Jul 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