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Winter Park, FL 55+ active adult communities & homes for sale - Page 55
90 communities near Winter Park
2,377 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $2Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
4.7 rating (18 reviews)
![Solivita]()
$100Ks
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300Ks
- $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$200Ks
- $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$200Ks
- $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
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5 rating (2 reviews)
![Plantation at Leesburg]()
$100Ks
- $500Ks
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
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 homes
5 rating (7 reviews)
![Kings Ridge]()
$200Ks
- $400Ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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
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
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
$100Ks
- $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $400Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (1 reviews)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
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5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $800Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200Ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
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)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$400Ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
5 rating (1 reviews)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
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5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$200Ks
- $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200Ks
- $500Ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$300Ks
- $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 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.
$200Ks
- $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
$400Ks
- $800Ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$400Ks
- $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
4 rating (2 reviews)
![Harbor Hills Country Club]()
$200Ks
- $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
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4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $300Ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$300Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
5 rating (2 reviews)
![Bridgewater at Viera]()
$300Ks
- $800Ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 homes
$200Ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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.
4.1 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
3.9 rating (7 reviews)
![Summit Greens]()
$300Ks
- $400Ks
Summit Greens, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2019
|
769 homes
5 rating (1 reviews)
![Royal Harbor]()
$300Ks
- $400Ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$200Ks
- $500Ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Heritage Isle
![3130 LE CONTE ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,394 sq ft
|Townhouse
3130 LE CONTE ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1058050 • Blue Marlin Real Estate, Sarah Reka...
Kings Ridge
![4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,968 sq ft
|House
4202 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5100062 • REALTY PROFESSIONALS OF FL,LLC, Ma...
Lake Ashton
![4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,083 sq ft
|House
4488 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4934805 • LAKE ASHTON REALTY INC., Candra Al...
Venetian Bay
![3020 KING PALM DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,179 sq ft
|House
3020 KING PALM DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1086490 • FLORIDA LIFE REAL ESTATE GROUP, S...
Solivita
![448 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6336931 • EXP REALTY LLC, Amy Moline
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Harbor Hills Country Club
![39634 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,579 sq ft
|House
39634 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Community: Harbor Hills Country Club
MLS O6359806 • IDEAL REALTY GLOBAL, Roseli Pereir...
Solivita
![722 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135961 • PELLEGO, LLC, Diane Cisek
The Villages®
![1161 DEL TORO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|House
1161 DEL TORO DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM713307 • KELLER WILLIAMS CORNERSTONE RE, St...
Carillon Lakes
![4268 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
3 beds
|2 baths
|2,117 sq ft
|House
4268 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
MLS L4957151 • S & D REAL ESTATE SERVICE LLC, Mat...
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.
Grand Haven
![14 EGRET DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313955 • CHAD AND SANDY REAL ESTATE GRP, Ch...
Four Seasons at Orlando
![2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747]()
3 beds
|2 baths
|2,042 sq ft
|House
2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Community: Four Seasons at Orlando
MLS O6311232 • LA ROSA REALTY PREMIER LLC, Andres...
Plantation Bay Golf & Country Club
![945 STONE LAKE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,910 sq ft
|House
945 STONE LAKE DR, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC313035 • VENTURE DEVELOPMENT REALTY,INC, El...
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...
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Lakes of Mount Dora
![2331 WAKEFIELD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,478 sq ft
|House
2331 WAKEFIELD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
MLS G5103414 • ATKINS REALTY OF LAKE COUNTY, BJ A...
Venetian Bay
![3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,644 sq ft
|House
3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS 1219853 • Oceans Luxury Realty Full Service L...
Spruce Creek South
![10551 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,690 sq ft
|House
10551 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM711058 • ROBERTS REAL ESTATE INC, Melissa B...
Spruce Creek Country Club
![13721 SE 87TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,342 sq ft
|House
13721 SE 87TH TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM708780 • JUDY L. TROUT REALTY, Jennifer Tra...
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.
Pennbrooke Fairways
![321 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,894 sq ft
|House
321 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5093172 • REAL BROKER, LLC, Mary Bell
Del Webb Minneola
![2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715]()
2 beds
|2 baths
|1,943 sq ft
|House
2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
MLS O6345393 • SERHANT, Silvia Kinkela
The Country Club of Mount Dora
![1641 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|3,813 sq ft
|House
1641 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5103973 • MORRIS REALTY AND INVESTMENTS, Cra...
The Villages®
![280 EMMALEE PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|House
280 EMMALEE PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6359310 • TOLARIS REALTY GROUP LLC, Debbie Z...
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Spruce Creek South
![17920 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,707 sq ft
|House
17920 SE 100TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM713087 • JUDY L. TROUT REALTY, Tom Campbell
The Villages®
![7935 SE 174TH LUDLOW PL, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
7935 SE 174TH LUDLOW PL, THE VILLAGES, F...
Community: The Villages®
MLS OM712551 • FL HOME SALES & DEV, Michelle Dink...
The Villages®
![939 KOLLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,880 sq ft
|House
939 KOLLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6350238 • REAL PROPERTY INTERNATIONAL, Bob L...
The Villages®
![870 HENDERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,375 sq ft
|House
870 HENDERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101221 • CENTURY 21 MYERS REALTY, Marion De...
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.
Grand Haven
![19 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313909 • COASTAL GATEWAY REAL ESTATE GROUP,...
Highland Lakes
![26030 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,293 sq ft
|Villa
26030 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5097059 • ERA GRIZZARD REAL ESTATE, Craig Yo...
Venetian Bay
![3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,460 sq ft
|House
3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS V4944025 • COLDWELL BANKER COAST REALTY, Ron ...
The Villages®
![3158 RAVEN CROFT TER, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|2 baths
|1,860 sq ft
|House
3158 RAVEN CROFT TER, THE VILLAGES, FL, ...
Community: The Villages®
MLS OM712749 • RE/MAX PREMIER REALTY LADY LK, Don...
Lakes of Mount Dora
![8167 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,613 sq ft
|House
8167 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5096620 • FLORIDA PLUS REALTY, LLC, Claire B...
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Royal Harbor
![3305 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|3 baths
|2,108 sq ft
|House
3305 BALTIC SEA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5104064 • ERA GRIZZARD REAL ESTATE, Christin...
The Villages®
![1222 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|1 baths
|936 sq ft
|Manufactured Home
1222 ZAPATA PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM712295 • LEGACY REALTY & ASSOCIATES, Mailyn...
Venetian Bay
![424 LUNA BELLA LN 432, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,753 sq ft
|Condo
424 LUNA BELLA LN 432, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS V4944450 • EXP REALTY LLC, Ali Partovi
Halifax Plantation
![3078 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,914 sq ft
|House
3078 SILVERMINES AVE, ORMOND BEACH, FL, ...
Community: Halifax Plantation
MLS FC313426 • NEVER 6 PERCENT REALTY INC., Peter...
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
![420 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
5 beds
|7 baths
|5,151 sq ft
|House
420 WINGSPAN DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1213407 • Florida Property Experts Inc, Fay S...
Solivita
![1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,543 sq ft
|House
1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
MLS TB8368866 • NHR BROKERAGE LLC, Madalina Tat
Plantation Bay Golf & Country Club
![1216 HAMPSTEAD LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,973 sq ft
|House
1216 HAMPSTEAD LN, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC312756 • VENTURE DEVELOPMENT REALTY,INC, El...
Harbor Hills Country Club
![39911 BAYVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,120 sq ft
|House
39911 BAYVIEW DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS OM710713 • LPT REALTY, LLC, Gary Martin
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Harbor Hills Country Club
![5435 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,821 sq ft
|House
5435 GROVE MNR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS NS1086097 • REAL BROKER, LLC, Michael Lowe
The Villages®
![2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,257 sq ft
|House
2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5093055 • BHHS FLORIDA REALTY, DeLite Bowden
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2,377
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REIN updates its listings on a daily basis. Data last updated: Jan 11, 2026.
This application does not include information on all of the properties available for sale at this time.
