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Winter Park, FL 55+ active adult communities & homes for sale - Page 3
90 communities near Winter Park
2,513 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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
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
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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
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 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)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
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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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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 (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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$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 (3 reviews)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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.
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
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
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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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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
5 rating (2 reviews)
![Heritage Isle]()
$300ks
- $500ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
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.
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
3.8 rating (5 reviews)
![Traditions at Lake Ruby]()
$200ks
- $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
552 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
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
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
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
New
The Villages®
![3273 RIVERTON RD, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,143 sq ft
|House
3273 RIVERTON RD, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110421 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
New
Bridgewater at Viera
![8904 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,132 sq ft
|House
8904 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1073739 • LPT Realty LLC, Kate Flack
New
Spruce Creek Country Club
![9210 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,575 sq ft
|House
9210 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM722246 • KELLER WILLIAMS CORNERSTONE RE, Cr...
New
Plantation Bay Golf & Country Club
![1106 OXBRIDGE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,165 sq ft
|House
1106 OXBRIDGE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC317472 • VENTURE DEVELOPMENT REALTY,INC, El...
New
The Villages®
![1537 DORAL CIR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,284 sq ft
|Manufactured Home
1537 DORAL CIR, LADY LAKE, FL, 32159
Community: The Villages®
MLS TB8494337 • SILVER DOOR REALTY LLC, Michelle ...
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New
The Villages®
![1626 GIBBES WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1626 GIBBES WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110521 • REALTY EXECUTIVES IN THE VILLAGES,...
New
Sandpiper Golf & Country Club
![6136 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,378 sq ft
|House
6136 MAGPIE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS R4911003 • DYW LLC, Yvonne Wherrett
New
Solivita
![2340 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6395972 • REAL BROKER, LLC, Brian Batiz Sala...
New
The Villages®
![930 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159]()
3 beds
|2 baths
|1,558 sq ft
|House
930 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
MLS G5110447 • RE/MAX PREMIER REALTY, Guy William...
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
The Villages®
![1929 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|2,693 sq ft
|House
1929 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
MLS TB8494065 • HOMECOIN.COM, Jonathan Minerick
New
Kings Ridge
![2246 BELSFIELD CIR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,985 sq ft
|House
2246 BELSFIELD CIR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5110402 • COLDWELL BANKER HUBBARD HANSEN, Je...
New
The Timbers at Everlands
![1571 MIRAFLORES TRL, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
2 beds
|2 baths
|1,308 sq ft
|Townhouse
1571 MIRAFLORES TRL, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1073897 • Lennar Realty, Inc., Jennifer Riche...
New
Cresswind at Victoria Gardens
![1177 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724]()
3 beds
|3 baths
|2,191 sq ft
|House
1177 AVERY MEADOWS WAY, DELAND, FL, 3272...
Community: Cresswind at Victoria Gardens
MLS O6395605 • BETTER HOMES AND GARDENS REAL ESTA...
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New
Lakes at Laurel Highlands
![2826 VAN AMBER CT, LAKELAND, FL, 33811, Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2826 VAN AMBER CT, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS TB8494252 • PROPERTY HOLDINGS REALTY GROUP, L...
New
Palms at Serenoa
![3449 TWIN FLOWER CT, CLERMONT, FL, 34714, Clermont, FL 34714]()
2 beds
|2 baths
|1,627 sq ft
|House
3449 TWIN FLOWER CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
MLS O6394746 • SOVERA REALTY GROUP, LLC, Gennifer...
New
Grand Haven
![455 RIVERFRONT DR A303, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|2 baths
|1,762 sq ft
|Condo
455 RIVERFRONT DR A303, PALM COAST, FL, ...
Community: Grand Haven
MLS FC317191 • COASTAL GATEWAY REAL ESTATE GROUP,...
New
The Villages®
![2418 HOPESPRING LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,611 sq ft
|House
2418 HOPESPRING LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS OM722166 • LPT REALTY, LLC, Brian Williams
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
![800 ARBOR GLEN CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,654 sq ft
|House
800 ARBOR GLEN CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC317317 • REAL BROKER, LLC, Claudia Haar
New
The Villages®
![5548 MILLICAN AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,633 sq ft
|Villa
5548 MILLICAN AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110603 • JACOBS PREMIER PROPERTIES, Daniel ...
New
The Country Club of Mount Dora
![3022 ANDOVER CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
2 beds
|2 baths
|1,444 sq ft
|House
3022 ANDOVER CT, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5110593 • FLORIDA LIFESTYLE REALTY GROUP, Ka...
New
The Villages®
![1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,388 sq ft
|House
1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS R4911000 • BLACK TIE REAL ESTATE PROFESSIONAL...
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New
The Villages®
![1424 WALNUT WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,337 sq ft
|House
1424 WALNUT WAY, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5110581 • SOUNDINGS, LLC, Lili Whittington
New
Plantation at Leesburg
![5225 CHANTICLEER DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,413 sq ft
|House
5225 CHANTICLEER DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6396046 • WATSON REALTY CORP, Beth Stoothoff
New
The Villages®
![1147 ELIZABETH CT, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,602 sq ft
|Villa
1147 ELIZABETH CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110344 • VISIONARY PROPERTIES INC, Judy Blu...
New
Solivita
![545 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6395202 • FLORIDA PLUS REALTY, LLC, Sarah Bo...
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
The Lakes at Harmony
![3273 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|3 baths
|1,955 sq ft
|House
3273 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6396010 • DALTON WADE INC, Maleisa Remsberg
New
The Villages®
![3984 MCDOWELL DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,926 sq ft
|House
3984 MCDOWELL DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110543 • WORTH CLARK REALTY, Chris Day
New
Traditions at Lake Ruby
![4040 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,599 sq ft
|House
4040 CARTERET DR, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS B4902225 • KLINE REAL ESTATE SERVICES, Scott ...
New
Pelican Bay Daytona Beach
![151 GREY WIDGEON CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,850 sq ft
|Townhouse
151 GREY WIDGEON CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS V4948241 • TOWN AND COUNTRY REALTY, Deborah D...
New
Sandpiper Golf & Country Club
![6357 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,121 sq ft
|House
6357 EGRET DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS R4910996 • DYW LLC, Yvonne Wherrett
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New
Plantation Bay Golf & Country Club
![1029 STONE LAKE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,575 sq ft
|House
1029 STONE LAKE DR, ORMOND BEACH, FL, 32...
Community: Plantation Bay Golf & Country Club
MLS FC317448 • KELLER WILLIAMS RLTY FL. PARTN, Wi...
New
Spruce Creek South
![17309 SE 98TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,536 sq ft
|House
17309 SE 98TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM722095 • EXP REALTY LLC, Garrett Huffman
New
Plantation Bay Golf & Country Club
![94 BAY LAKE DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,014 sq ft
|House
94 BAY LAKE DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC317439 • VENTURE DEVELOPMENT REALTY,INC, De...
New
Royal Harbor
![3292 SEVEN SEAS DR, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,870 sq ft
|House
3292 SEVEN SEAS DR, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5110508 • BEACON REAL ESTATE & ASSOC, Al Spr...
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
High Vista at Ridgewood Lakes
![232 OAK HAMMOCK DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,465 sq ft
|House
232 OAK HAMMOCK DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5147118 • KELLER WILLIAMS REALTY AT THE LAKE...
New
Pelican Bay Daytona Beach
![135 GREY WIDGEON CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,942 sq ft
|Townhouse
135 GREY WIDGEON CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS V4948320 • EXP REALTY LLC, Debbie Weller
New
The Villages®
![2912 ASHER PATH, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,133 sq ft
|House
2912 ASHER PATH, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6396066 • GAILEY ENTERPRISES REAL ESTATE, Ri...
New
Cresswind at Victoria Gardens
![188 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,507 sq ft
|House
188 OLD MOSS CIR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4948279 • LANE REALTY SERVICES, LLC, Pam Dea...
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(888) 625-4885
New
The Villages®
![2940 GULLEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,525 sq ft
|House
2940 GULLEY LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5110369 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
New
Stonecrest
![17335 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,829 sq ft
|House
17335 SE 111TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5110308 • RE/MAX PREMIER REALTY LADY LK, Cin...
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2,513
homes
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
