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Winter Park, FL 55+ active adult communities & homes for sale - Page 43
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 (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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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
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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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.
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
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
$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
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
$300ks
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 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
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.
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
$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:
(888) 625-4885
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
The Villages®
![503 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,467 sq ft
|House
503 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105651 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![2473 BUTTONWOOD RUN, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,463 sq ft
|House
2473 BUTTONWOOD RUN, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5105650 • REALTY EXECUTIVES IN THE VILLAGES,...
Grand Haven
![14 SANDPIPER CT, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|1,868 sq ft
|House
14 SANDPIPER CT, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC314803 • RE/MAX SELECT PROFESSIONALS, DOUGL...
Pelican Bay Daytona Beach
![196 GRAY DOVE CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,833 sq ft
|Townhouse
196 GRAY DOVE CT, DAYTONA BEACH, FL, 321...
Community: Pelican Bay Daytona Beach
MLS 1221002 • Best Way Realty of Volusia LLC, Jim...
The Villages®
![1399 HOLLY HILL AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1399 HOLLY HILL AVE, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5105712 • RE/MAX SELECT PARTNERS, Edwin Budd
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Tohoqua Reserve
![1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|3 baths
|2,175 sq ft
|House
1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6367917 • MARK SPAIN REAL ESTATE, Jamey Bris...
Heritage Hills
![3201 SONESTA CT A, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3201 SONESTA CT A, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5105573 • KELLER WILLIAMS ELITE PARTNERS III...
Spruce Creek Country Club
![8516 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,296 sq ft
|House
8516 SE 137TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM715250 • RE/MAX PREMIER REALTY LADY LK, Jay...
The Villages®
![17766 SE 91ST POPLAR TER, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
17766 SE 91ST POPLAR TER, THE VILLAGES, ...
Community: The Villages®
MLS G5105669 • REALTY EXECUTIVES IN 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.
The Villages®
![304 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,360 sq ft
|House
304 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5104042 • RE/MAX PREMIER REALTY LADY LK, Cin...
VillageWalk at Lake Nona
![12077 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
5 beds
|4 baths
|4,093 sq ft
|House
12077 ULETA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6367880 • EXP REALTY LLC, Lissette Sanchez
Heritage Isle
![6531 INGALLS ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,806 sq ft
|House
6531 INGALLS ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1064566 • Coastal Life Properties LLC, Kane S...
The Villages®
![3468 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,182 sq ft
|Villa
3468 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5105647 • REALTY EXECUTIVES IN THE VILLAGES,...
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Four Seasons at Orlando
![7661 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
7661 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Community: Four Seasons at Orlando
MLS O6368190 • VIVA ORLANDO REALTY INC., Susan Ri...
Twin Lakes
![4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
MLS O6367771 • DIAMOND REAL ESTATE GROUP, George ...
The Villages®
![2403 ST GEORGE AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
2403 ST GEORGE AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5105582 • RE/MAX PREMIER REALTY, Guy William...
Spruce Creek Country Club
![9685 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,873 sq ft
|House
9685 SE 136TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM715214 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D...
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®
![926 LONG LEAF LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,541 sq ft
|House
926 LONG LEAF LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105619 • ERA GRIZZARD REAL ESTATE, Melissa ...
The Villages®
![1514 CERVANTES PL, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
3 beds
|2 baths
|2,308 sq ft
|House
1514 CERVANTES PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5105546 • REALTY EXECUTIVES IN THE VILLAGES,...
Royal Harbor
![6170 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,535 sq ft
|House
6170 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5105601 • EXP REALTY LLC, Taylor Kerr
Halifax Plantation
![3101 INISHMORE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,583 sq ft
|Villa
3101 INISHMORE DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS V4946303 • KELLER WILLIAMS RLTY FL. PARTN, Ch...
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The Villages®
![995 JOINER PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,521 sq ft
|House
995 JOINER PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5105542 • REALTY EXECUTIVES IN THE VILLAGES,...
Heritage Isle
![7248 BRODERICK DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|3 baths
|1,988 sq ft
|House
7248 BRODERICK DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1064363 • Brevard County Realty LLC, John Sta...
Park Place
![76 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,786 sq ft
|House
76 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
MLS FC314722 • KELLER WILLIAMS REALTY ATLANTIC PA...
Spruce Creek Country Club
![9921 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,872 sq ft
|House
9921 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM714926 • MARTY & HUGGINS REALTY, Ella Torre...
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
![1130 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,551 sq ft
|Townhouse
1130 HANSBERRY CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC314666 • VENTURE DEVELOPMENT REALTY,INC, El...
The Villages®
![10105 TURNBERRY LN, LEESBURG, FL, 34788, Leesburg, FL 34788]()
4 beds
|3 baths
|2,070 sq ft
|House
10105 TURNBERRY LN, LEESBURG, FL, 34788
Community: The Villages®
MLS S5140262 • AXEN REALTY, LLC, Stephanie Morale...
Arlington Ridge
![26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748]()
2 beds
|2 baths
|2,282 sq ft
|House
26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5105520 • FLORIDA PLUS REALTY, LLC, Simon Am...
Lake Ashton
![5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,677 sq ft
|House
5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4937220 • LAKE ASHTON REALTY INC., Lori Raat...
Solivita
![270 ADDISON DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5140151 • BORCHINI REALTY, Patricia Plumstea...
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(888) 625-4885
The Villages®
![509 DEL MAR DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,314 sq ft
|House
509 DEL MAR DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS OM714731 • CHARLES RUTENBERG REALTY INC, Glor...
The Villages®
![1234 DUSTIN DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,392 sq ft
|Manufactured Home
1234 DUSTIN DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5105245 • REALTY EXECUTIVES IN THE VILLAGES,...
Sandpiper Golf & Country Club
![664 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,456 sq ft
|House
664 EAGLE RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4957907 • COLDWELL BANKER REALTY, Ginger Qui...
Plantation at Leesburg
![25501 MAUREPAS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|2,945 sq ft
|House
25501 MAUREPAS LN, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5105507 • EXIT REALTY TRI-COUNTY, Steven Boo...
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.
Del Webb Sunbridge
![2445 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,401 sq ft
|House
2445 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6366682 • CHARLES RUTENBERG REALTY ORLANDO, ...
Grand Haven
![200 RIVERFRONT DR D201, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,167 sq ft
|Condo
200 RIVERFRONT DR D201, PALM COAST, FL, ...
Community: Grand Haven
MLS FC314697 • GRAND LIVING REALTY, Cindy Tetreau...
Sullivan Ranch
![30409 TOKARA TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,550 sq ft
|House
30409 TOKARA TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5105450 • WATSON REALTY CORP, Nancy McCloske...
Twin Lakes
![2487 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
2 beds
|2 baths
|1,351 sq ft
|Halfplex
2487 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS S5140190 • WEICHERT REALTORS HALLMARK PRO, Sh...
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(888) 625-4885
The Villages®
![17600 SE 88TH COVINGTON CIR, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|2,580 sq ft
|House
17600 SE 88TH COVINGTON CIR, THE VILLAGE...
Community: The Villages®
MLS G5105489 • CENTURY 21 ALTON CLARK, Regina Rod...
Trilogy® Orlando
![189 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|2 baths
|1,820 sq ft
|House
189 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6366813 • THE REAL ESTATE COLLECTION LLC, Er...
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2,513
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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.
