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Winter Park, FL 55+ active adult communities & homes for sale - Page 24
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®
![8645 SE 177TH GRASSMERE ST, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|3,085 sq ft
|House
8645 SE 177TH GRASSMERE ST, THE VILLAGES...
Community: The Villages®
MLS G5108514 • RE/MAX PREMIER REALTY LADY LK, Rob...
Gatherings of Lake Nona
![7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,445 sq ft
|Condo
7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6383756 • KELLER WILLIAMS ADVANTAGE REALTY, ...
Gatherings of Lake Nona
![7557 LAUREATE BLVD 6401, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,368 sq ft
|Condo
7557 LAUREATE BLVD 6401, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6383767 • KELLER WILLIAMS ADVANTAGE REALTY, ...
Sandpiper Golf & Country Club
![6260 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,830 sq ft
|House
6260 CRANE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4959538 • COLDWELL BANKER REALTY, Ginger Qui...
The Villages®
![1305 LA ESTRELLITA WAY, THE VILLAGES, FL..., The Villages, FL 32162]()
3 beds
|2 baths
|1,817 sq ft
|House
1305 LA ESTRELLITA WAY, THE VILLAGES, FL...
Community: The Villages®
MLS G5107029 • BLU SEA DREAMS,LLC, Elizabeth Fox
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The Country Club of Mount Dora
![1500 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,484 sq ft
|House
1500 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6383176 • UNITED REAL ESTATE PREFERRED, Kay ...
The Villages®
![1462 PELICAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,715 sq ft
|House
1462 PELICAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108545 • WORTH CLARK REALTY, Chris Day
The Villages®
![242 JUAREZ WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,066 sq ft
|House
242 JUAREZ WAY, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5106248 • ERA GRIZZARD REAL ESTATE, Kaylyn H...
The Villages®
![5546 COTTRELL CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,809 sq ft
|Villa
5546 COTTRELL CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5108519 • LPT REALTY, LLC, Lena Morgan
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.
Sullivan Ranch
![20900 OLDENBURG LOOP, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
4 beds
|2 baths
|2,110 sq ft
|House
20900 OLDENBURG LOOP, MOUNT DORA, FL, 32...
Community: Sullivan Ranch
MLS G5108461 • KELLIE & CO REAL ESTATE, Kellie Wh...
Scottish Highlands
![2003 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,360 sq ft
|House
2003 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5108501 • ERA GRIZZARD REAL ESTATE, Cynthia ...
Summer Trees
![73 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,228 sq ft
|Townhouse
73 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS O6383307 • WEMERT GROUP REALTY LLC, Jenny Wem...
Twin Lakes
![2461 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Halfplex
2461 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
MLS S5144223 • KELLER WILLIAMS LEGACY REALTY, Ter...
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(888) 625-4885
Heritage Isle
![2700 CAMBERLY CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,394 sq ft
|Townhouse
2700 CAMBERLY CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS S5144286 • REAL BROKER, LLC, Jennifer Peters
Oakview
![1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,220 sq ft
|House
1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
MLS G5108372 • LPT REALTY, LLC, Vanessa Aybar Bad...
Venetian Bay
![3102 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,916 sq ft
|House
3102 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS FC316181 • REALTY EXCHANGE COMMERCIAL RESIDEN...
Spruce Creek South
![17587 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,652 sq ft
|House
17587 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM719019 • KELLER WILLIAMS CORNERSTONE RE, Ri...
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®
![17283 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,640 sq ft
|House
17283 SE 94TH COULTS CIR, THE VILLAGES, ...
Community: The Villages®
MLS G5108454 • CENTURY 21 ALTON CLARK, Regina Rod...
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...
The Villages®
![16715 SE 80TH CLOVERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,477 sq ft
|House
16715 SE 80TH CLOVERWOOD TER, THE VILLAG...
Community: The Villages®
MLS G5108215 • SALLY LOVE REAL ESTATE, Lee Harper
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...
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The Villages®
![2726 MONCAYO AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|1 baths
|1,034 sq ft
|Villa
2726 MONCAYO AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6384183 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![1134 SALIDO AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,542 sq ft
|House
1134 SALIDO AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108451 • REALTY EXECUTIVES IN THE VILLAGES,...
Venetian Bay
![3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,338 sq ft
|House
3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS 1223226 • RE/MAX Signature, Charles A Ottley
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...
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.
Scottish Highlands
![1605 SELKIRK DR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,284 sq ft
|House
1605 SELKIRK DR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5108482 • ERA GRIZZARD REAL ESTATE, Cynthia ...
Cresswind at Victoria Gardens
![304 STONINGTON WAY, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,480 sq ft
|House
304 STONINGTON WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6383140 • BETTER HOMES AND GARDENS REAL ESTA...
The Villages®
![16905 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,924 sq ft
|House
16905 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
MLS NS1087246 • ENGEL & VOLKERS NEW SMYRNA, Josep...
Grand Haven
![10 RIVER PARK DR N, PALM COAST, FL, 3213..., Palm Coast, FL 32137]()
2 beds
|2 baths
|1,828 sq ft
|Townhouse
10 RIVER PARK DR N, PALM COAST, FL, 3213...
Community: Grand Haven
MLS FC316308 • RE/MAX SELECT PROFESSIONALS, Cryst...
The Lakes at Harmony
![3204 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773]()
4 beds
|3 baths
|2,361 sq ft
|House
3204 OXBOW CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5144242 • TIE TEAM REALTY LLC, Chris Woeste
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The Villages®
![3500 COUNTRYSIDE PATH, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|2 baths
|1,531 sq ft
|House
3500 COUNTRYSIDE PATH, THE VILLAGES, FL,...
Community: The Villages®
MLS G5107040 • RE/MAX PREMIER REALTY, Matthew Rob...
The Villages®
![1994 ORANGEBURG TER, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
2 beds
|2 baths
|1,142 sq ft
|House
1994 ORANGEBURG TER, THE VILLAGES, FL, 3...
Community: The Villages®
MLS OM719204 • CB/ELLISON RLTY WEST, Brian McCart...
The Villages®
![1776 WAX BERRY CT, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,944 sq ft
|House
1776 WAX BERRY CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108343 • RE/MAX PREMIER REALTY, Tammy Freil...
The Villages®
![1469 SOTHELL ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1469 SOTHELL ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5108340 • DOWN HOME REALTY, LLLP, Damon Mort...
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.
Royal Harbor
![5279 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|1,713 sq ft
|House
5279 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS G5108034 • COLDWELL BANKER VANGUARD EDGE, Lor...
Plantation at Leesburg
![25045 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,188 sq ft
|Manufactured Home
25045 PINE HL, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5108405 • RE/MAX PREMIER REALTY, Brad Craycr...
Twin Lakes
![2682 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5144006 • WEICHERT REALTORS HALLMARK PRO, Sh...
Plantation Bay Golf & Country Club
![848 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,101 sq ft
|Townhouse
848 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC316285 • VENTURE DEVELOPMENT REALTY,INC, Ri...
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Lake Ashton
![4648 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,847 sq ft
|House
4648 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4937876 • CENTURY 21 MYERS REALTY LAKE WALES...
The Villages®
![17835 SE 88TH GRIMBALL AVE, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,608 sq ft
|House
17835 SE 88TH GRIMBALL AVE, THE VILLAGES...
Community: The Villages®
MLS G5107776 • WORTH CLARK REALTY, Joy Farenden
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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.
