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Winter Park, FL 55+ active adult communities & homes for sale - Page 36
90 communities near Winter Park
2,398 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
- $3Ms
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
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $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)
![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)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - 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
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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]()
$200Ks
- $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
Highland Lakes
![6033 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5099864 • FLORIDA PLUS REALTY, LLC, Garnet E...
Gatherings of Lake Nona
![7565 LAUREATE BLVD UNIT 3304, ORLANDO, F..., Orlando, FL 32827]()
2 beds
|2 baths
|1,486 sq ft
|Condo
7565 LAUREATE BLVD UNIT 3304, ORLANDO, F...
Community: Gatherings of Lake Nona
MLS O6366432 • SERHANT, Sophia Rogers
VillageWalk at Lake Nona
![11863 FIORE DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
2 beds
|2 baths
|1,582 sq ft
|Halfplex
11863 FIORE DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6370397 • KELLER WILLIAMS WINTER PARK, Betsy...
Esplanade at Highland Ranch
![2640 MARIOTTA RDG, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|2 baths
|1,610 sq ft
|House
2640 MARIOTTA RDG, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5105853 • COLDWELL BANKER REALTY, Kelly Sutt...
Plantation at Leesburg
![25125 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|936 sq ft
|Manufactured Home
25125 BELLEVUE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5104233 • CENTURY 21 MYERS REALTY, Sheryl Mo...
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The Villages®
![7326 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,490 sq ft
|House
7326 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
MLS G5102766 • MVP PREMIER REALTY, LLC, Michael P...
Summit Greens
![1063 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,900 sq ft
|House
1063 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
MLS G5090006 • KELLER WILLIAMS ELITE PARTNERS III...
Heritage Isle
![3140 LE CONTE ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,407 sq ft
|Townhouse
3140 LE CONTE ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1038080 • Kimco Real Estate, Kim Forbes Stewa...
Highland Fairways
![3535 SADDLEBROOK WAY, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|2,145 sq ft
|House
3535 SADDLEBROOK WAY, LAKELAND, FL, 3381...
Community: Highland Fairways
MLS L4957644 • REGAL REAL ESTATE LLC, Debbie Ward...
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.
Four Seasons at Orlando
![7916 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|3 baths
|2,470 sq ft
|House
7916 HANSON BAY PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6368824 • KRESSLER REAL ESTATE, Andre Kressl...
Four Seasons at Orlando
![2031 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
2031 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS G5105687 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
Solivita
![634 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6309515 • SMOOTH LANDINGS REAL ESTATE, Misty...
Plantation Bay Golf & Country Club
![1109 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|3 baths
|1,604 sq ft
|Townhouse
1109 HANSBERRY CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1219767 • The Barnett Group Inc., Sally LaCla...
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The Villages®
![8195 SE 174TH ROWLAND ST, THE VILLAGES, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,208 sq ft
|Villa
8195 SE 174TH ROWLAND ST, THE VILLAGES, ...
Community: The Villages®
MLS G5097857 • SALLY LOVE REAL ESTATE, Donna Pull...
Lake James
![7953 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,990 sq ft
|House
7953 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4954430 • REMAX EXPERTS, Lorrie Clark
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...
The Villages®
![2466 SOPER ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,148 sq ft
|Villa
2466 SOPER ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5099735 • SALLY LOVE REAL ESTATE, Donna Pull...
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.
Spruce Creek Country Club
![9175 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,488 sq ft
|House
9175 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM713534 • ALL FLORIDA HOMES REALTY LLC, Nich...
Trilogy® Orlando
![115 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|3 baths
|2,111 sq ft
|House
115 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5104599 • COMMUNITY ELITE REALTY, Nancy Aitk...
Trilogy® Orlando
![135 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736]()
3 beds
|2 baths
|1,651 sq ft
|House
135 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5095104 • COMMUNITY ELITE REALTY, Nancy Aitk...
Sullivan Ranch
![30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,851 sq ft
|House
30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS O6319648 • LPT REALTY, LLC, Tony Tate
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Halifax Plantation
![2889 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,040 sq ft
|House
2889 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC313007 • BERKSHIRE HATHAWAY HOMESERVICE, Le...
Solivita
![429 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5124646 • PELLEGO, LLC, Stan Wilson
Twin Lakes
![5081 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
5081 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6330863 • CHARLES RUTENBERG REALTY ORLANDO, ...
VillageWalk at Lake Nona
![8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,..., Orlando, FL 32827]()
3 beds
|3 baths
|1,830 sq ft
|Townhouse
8681 LOWER VILLAGEWALK CIR, ORLANDO, FL,...
Community: VillageWalk at Lake Nona
MLS O6369740 • RE/MAX VANTAGE, AnnMarie Vachala
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.
Summer Trees
![6 LAKEPOINT CIR, PORT ORANGE, FL, 32128, Port Orange, FL 32128]()
2 beds
|2 baths
|1,406 sq ft
|House
6 LAKEPOINT CIR, PORT ORANGE, FL, 32128
Community: Summer Trees
MLS V4946457 • LPT REALTY, LLC, Ron Wysocarski
Cresswind at Victoria Gardens
![1653 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724]()
2 beds
|2 baths
|1,928 sq ft
|House
1653 VICTORIA GARDENS DR, DELAND, FL, 32...
Community: Cresswind at Victoria Gardens
MLS O6369685 • BETTER HOMES AND GARDENS REAL ESTA...
The Villages®
![18101 SANDALWOOD DR, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
1 beds
|1 baths
|872 sq ft
|Condo
18101 SANDALWOOD DR, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5105357 • RE/MAX PREMIER REALTY, Hope Wilson
Sullivan Ranch
![30308 LIPIZZAN TER, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,769 sq ft
|Villa
30308 LIPIZZAN TER, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
MLS G5100916 • COLDWELL BANKER VANGUARD EDGE, Mic...
Ridgehaven
![167 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,454 sq ft
|House
167 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6361163 • MERITAGE HOMES OF FL REALTY, Tatia...
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Ridgehaven
![1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,190 sq ft
|House
1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
MLS O6358258 • MERITAGE HOMES OF FL REALTY, Tatia...
Ridgehaven
![165 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,572 sq ft
|House
165 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6363528 • MERITAGE HOMES OF FL REALTY, Tatia...
Ridgehaven
![433 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,487 sq ft
|House
433 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6360549 • MERITAGE HOMES OF FL REALTY, Tatia...
Twin Lakes
![2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6296889 • EXP REALTY LLC, Dawn Grigsby
Download the Ultimate 55+ Homebuying Guide
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Palms at Serenoa
![17478 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
2 beds
|2 baths
|1,822 sq ft
|House
17478 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS O6369709 • ORLANDO REGIONAL REALTY, Kimberley...
Stonecrest
![17824 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,483 sq ft
|House
17824 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS TB8458785 • ANN LEE REALTY INC, Vicki Sommer
The Villages®
![706 JASON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
MLS OM713337 • KELLER WILLIAMS CORNERSTONE RE, Ci...
Grand Isle
![1703 KEYS GATE DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,668 sq ft
|House
1703 KEYS GATE DR, MELBOURNE, FL, 32940
Community: Grand Isle
MLS 1041641 • RE/MAX Aerospace Realty, Teresa Fer...
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Cresswind at Victoria Gardens
![1612 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,905 sq ft
|House
1612 LINCOLNSHIRE DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6354231 • BETTER HOMES AND GARDENS REAL ESTA...
Royal Harbor
![3592 TROPICAL SEAS LOOP, TAVARES, FL, 32..., Tavares, FL 32778]()
2 beds
|2 baths
|1,452 sq ft
|House
3592 TROPICAL SEAS LOOP, TAVARES, FL, 32...
Community: Royal Harbor
MLS G5103892 • ERA GRIZZARD REAL ESTATE, Tammy Ki...
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2,398
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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.
