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Winter Park, FL 55+ active adult communities & homes for sale - Page 67
98 communities near Winter Park
2,698 homes near Winter Park
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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
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
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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
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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 (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
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 (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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
5 rating (8 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
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
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
Download the Ultimate 55+ Homebuying Guide
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2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
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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
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
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 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.
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 homes
$400ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$100ks
- $300ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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 Timbers at Everlands
![2223 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|4 baths
|1,710 sq ft
|House
2223 ANTARUS DR, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1051805 • Blue Marlin Real Estate, Jason Bist... • Blue Marlin Real Estate
Spruce Creek Country Club
![13944 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,120 sq ft
|House
13944 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5099176 • MORRIS REALTY AND INVESTMENTS, Ken... • MORRIS REALTY AND INVESTMENTS
Royal Highlands
![4738 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,892 sq ft
|House
4738 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
MLS O6323322 • CORCORAN PREMIER REALTY, Robert We... • CORCORAN PREMIER REALTY
Arlington Ridge
![3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,476 sq ft
|House
3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5099008 • WATSON REALTY CORP, Nancy McCloske... • WATSON REALTY CORP
Summer Trees
![79 CYPRESS POND RD 79, PORT ORANGE, FL, ..., Port Orange, FL 32128]()
2 beds
|2 baths
|888 sq ft
|Condo
79 CYPRESS POND RD 79, PORT ORANGE, FL, ...
Community: Summer Trees
MLS V4943507 • EXIT BEACH REALTY, Jan Baran • EXIT BEACH REALTY
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Pelican Bay Daytona Beach
![133 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,242 sq ft
|Condo
133 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS FC310736 • EXIT REALTY FIRST CHOICE, Kathy Ke... • EXIT REALTY FIRST CHOICE
Venetian Bay
![349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,520 sq ft
|House
349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1085211 • CENTURY 21 SUNDANCE REALTY, Bryan... • CENTURY 21 SUNDANCE REALTY
The Savannahs
![4464 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904]()
4 beds
|2 baths
|2,051 sq ft
|House
4464 CALADIUM CIR, WEST MELBOURNE, FL, 3...
Community: The Savannahs
MLS 1049631 • Seacoast Realty, Inc, Natalie Lawso... • Seacoast Realty, Inc
Highland Fairways
![3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,529 sq ft
|House
3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS B4901969 • LAND SOUTH REALTY, LLC, Ron Denney • LAND SOUTH REALTY, LLC
Del Webb Minneola
![2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,405 sq ft
|House
2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS O6319407 • RE/MAX SELECT GROUP, Mike Mondello • RE/MAX SELECT GROUP
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
![27328 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,894 sq ft
|House
27328 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5098428 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Lake James
![7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,990 sq ft
|House
7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4953716 • KELLER WILLIAMS REALTY, Joe Christ... • KELLER WILLIAMS REALTY
Cindy Certified
Plantation Bay Golf & Country Club
![829 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
829 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC310286 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Sandpiper Golf & Country Club
![5976 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,478 sq ft
|House
5976 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953367 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5970 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,582 sq ft
|House
5970 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953368 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
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Sandpiper Golf & Country Club
![5992 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,478 sq ft
|House
5992 TEAL TRL, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953369 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5987 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,478 sq ft
|House
5987 TEAL TRL, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953370 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5982 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,582 sq ft
|House
5982 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953366 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5914 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,321 sq ft
|House
5914 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953365 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
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
![5927 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,321 sq ft
|House
5927 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953362 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5926 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,640 sq ft
|House
5926 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953363 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5933 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,321 sq ft
|House
5933 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953361 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5921 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,640 sq ft
|House
5921 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4953359 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Sandpiper Golf & Country Club
![5909 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,640 sq ft
|House
5909 CORMORANT CT, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4952909 • REGAL REAL ESTATE LLC, Tammy Stori... • REGAL REAL ESTATE LLC
Venetian Bay
![2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,034 sq ft
|House
2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
MLS V4943028 • COLDWELL BANKER COAST REALTY, Ron ... • COLDWELL BANKER COAST REALTY
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Venetian Bay
![2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,754 sq ft
|House
2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS V4942853 • REALTY PROS ASSURED, Buzzy Porter • REALTY PROS ASSURED
Solivita
![619 TAPATIO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5122696 • FIVE STAR REALTY & INVESTMENT GROU... • FIVE STAR REALTY & INVESTMENT GROUP
Solivita
![537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS G5096869 • BACK PORCH REALTY, LLC, Jackie Rog... • BACK PORCH REALTY, LLC
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.
Plantation at Leesburg
![25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,653 sq ft
|House
25800 BELLE HELENE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096683 • SCATES REALTY & INVESTMENT PRO, Ei... • SCATES REALTY & INVESTMENT PRO
Plantation at Leesburg
![25339 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,765 sq ft
|House
25339 CRESTWATER DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096143 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Vienna Square
![1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,118 sq ft
|Villa
1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
MLS P4934564 • KELLER WILLIAMS REALTY SMART 1, Do... • KELLER WILLIAMS REALTY SMART 1
Plantation Bay Golf & Country Club
![1009 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|5 baths
|3,927 sq ft
|House
1009 SUDBURY LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS TB8375913 • ICI SELECT REALTY, Ali Kargar • ICI SELECT REALTY
Cindy Certified
Royal Highlands
![20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,070 sq ft
|House
20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
MLS G5095688 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Kings Ridge
![3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,552 sq ft
|House
3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5095074 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
Spruce Creek Country Club
![9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,126 sq ft
|House
9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM698604 • SELLSTATE NGR- SUMMERFIELD, Virgil... • SELLSTATE NGR- SUMMERFIELD
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Spruce Creek Country Club
![13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,760 sq ft
|House
13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS A4646770 • NEW DOOR REAL ESTATE LLC, Alicia A... • NEW DOOR REAL ESTATE LLC
The Wellington
![689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,050 sq ft
|Condo
689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,...
Community: The Wellington
MLS TB8360466 • RIVERA & ASSOCIATES REALTY, Maria... • RIVERA & ASSOCIATES REALTY
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
In Winter Park, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.
Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.
Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.
Want more information about active adult communities around Winter Park?
Want to learn more about 55+ communities in Winter Park?
2,698
homes
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© 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.
