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Winter Park, FL 55+ active adult communities & homes for sale - Page 62
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
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.
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.
Park Place
![107 PARK PLACE CIR, PALM COAST, FL, 3216..., Palm Coast, FL 32164]()
3 beds
|2 baths
|1,759 sq ft
|House
107 PARK PLACE CIR, PALM COAST, FL, 3216...
Community: Park Place
MLS FC316256 • NEXTHOME NEW BEGINNINGS, Brianne N... • NEXTHOME NEW BEGINNINGS
Alamanda Key
![4220 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901]()
3 beds
|2 baths
|1,551 sq ft
|House
4220 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
MLS 1069103 • Lokation Real Estate, Cheryld T. Ha... • Lokation Real Estate
Lake Ashton
![5264 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|2,011 sq ft
|House
5264 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
MLS P4937885 • LAKE ASHTON REALTY INC., Lori Raat... • LAKE ASHTON REALTY INC.
Cindy Certified
The Villages®
![1194 MCDONOUGH PL, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
4 beds
|2 baths
|2,028 sq ft
|House
1194 MCDONOUGH PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5107637 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
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VillageWalk at Lake Nona
![11831 FAN TAIL LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
2 beds
|2 baths
|1,526 sq ft
|Halfplex
11831 FAN TAIL LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6375764 • LPT REALTY, LLC, Manuel Delgado • LPT REALTY, LLC
The Villages®
![17723 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,027 sq ft
|House
17723 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
MLS OM718904 • LPT REALTY, LLC, Gary Martin • LPT REALTY, LLC
Royal Highlands
![21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,074 sq ft
|House
21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5108275 • FLORIDA PLUS REALTY, LLC, Tonya Ti... • FLORIDA PLUS REALTY, LLC
Cindy Certified
Cindy Certified
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®
![9711 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
9711 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
MLS G5107046 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
Spruce Creek South
![9826 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,312 sq ft
|House
9826 SE 178TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5107726 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Plantation at Leesburg
![4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,979 sq ft
|House
4721 TARA VIEW RD, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6380183 • KELLER WILLIAMS HERITAGE REALTY, R... • KELLER WILLIAMS HERITAGE REALTY
Indian River Colony Club
![1311 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
4 beds
|3 baths
|1,859 sq ft
|House
1311 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1069235 • Four Star Real Estate LLC, Shellie ... • Four Star Real Estate LLC
Cindy Certified
Legacy of Leesburg
![5922 SAGE LEAF PL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,913 sq ft
|House
5922 SAGE LEAF PL, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5107713 • FLORIDA PLUS REALTY, LLC, Claire B... • FLORIDA PLUS REALTY, LLC
Want to learn more about 55+ communities in Winter Park?
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Harbor Hills Country Club
![5321 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,948 sq ft
|House
5321 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5107981 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Plantation Bay Golf & Country Club
![39 MAGNOLIA DR 39, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,300 sq ft
|Condo
39 MAGNOLIA DR 39, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC315963 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Spruce Creek South
![17952 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
17952 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS O6380283 • ALL FLORIDA PROPERTY GROUP,INC, Me... • ALL FLORIDA PROPERTY GROUP,INC
Cindy Certified
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 Bay Golf & Country Club
![39 MAGNOLIA DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,300 sq ft
|Condo
39 MAGNOLIA DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1222747 • Venture Development Realty, Inc, El... • Venture Development Realty, Inc
The Villages®
![3698 ROBERTSON WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,695 sq ft
|Villa
3698 ROBERTSON WAY, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5107870 • LPT REALTY, LLC, Genie Muldoon • LPT REALTY, LLC
Plantation at Leesburg
![25308 CASA DEL LAGO LN, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,344 sq ft
|Manufactured Home
25308 CASA DEL LAGO LN, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5107740 • LPT REALTY, LLC, Kelly Monroe • LPT REALTY, LLC
The Country Club of Mount Dora
![8032 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,949 sq ft
|House
8032 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5107406 • LPT REALTY, LLC, Kelly Monroe • LPT REALTY, LLC
Esplanade at Highland Ranch
![2639 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|2 baths
|1,732 sq ft
|House
2639 STARGRASS CIR, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS O6379731 • PREMIER SOTHEBYS INT'L REALTY, Aud... • PREMIER SOTHEBYS INT'L REALTY
Solivita
![140 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5143222 • RIGHT TRACK REALTY, Kelley Spear • RIGHT TRACK REALTY
The Villages®
![8337 SE 176TH LAWSON LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
8337 SE 176TH LAWSON LOOP, THE VILLAGES,...
Community: The Villages®
MLS OM717826 • WORTH CLARK REALTY, Celeste Dionne • WORTH CLARK REALTY
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Stonecrest
![11255 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,408 sq ft
|House
11255 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5107821 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Cindy Certified
Plantation Bay Golf & Country Club
![831 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
831 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC315021 • FLORIDA HOMES REALTY & MORTGAGE, T... • FLORIDA HOMES REALTY & MORTGAGE
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.
Solivita
![632 PORTOFINO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6379328 • PREMIER SOTHEBYS INT'L REALTY, Ari... • PREMIER SOTHEBYS INT'L REALTY
Park Place
![21 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,878 sq ft
|House
21 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
MLS 2128257 • UNITED REAL ESTATE GALLERY, JAMES H... • UNITED REAL ESTATE GALLERY
The Villages®
![758 MOORE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,642 sq ft
|House
758 MOORE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107698 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Four Seasons at Orlando
![7637 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
7637 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Community: Four Seasons at Orlando
MLS O6379571 • EXP REALTY LLC, Harold Olson • EXP REALTY LLC
Del Webb Sunbridge
![2434 N CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
2 beds
|2 baths
|1,584 sq ft
|Villa
2434 N CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS L4958972 • BETTER HOMES & GARDENS RE LIFESTYL... • BETTER HOMES & GARDENS RE LIFESTYLES
The Villages®
![13811 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|2 baths
|2,280 sq ft
|Manufactured Home
13811 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6379162 • THE PROPERTY PROS REAL ESTATE, INC... • THE PROPERTY PROS REAL ESTATE, INC
The Country Club of Mount Dora
![8013 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,256 sq ft
|House
8013 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5106558 • COLDWELL BANKER VANGUARD EDGE, Lyn... • COLDWELL BANKER VANGUARD EDGE
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Cindy Certified
Del Webb Minneola
![2750 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,409 sq ft
|House
2750 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS G5107474 • CENTURY 21 MYERS ROSE REALTY, Dawn... • CENTURY 21 MYERS ROSE 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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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.
