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Winter Park, FL 55+ active adult communities & homes for sale
90 communities near Winter Park
2,487 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $1Ms
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
$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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.
$100Ks
- $500Ks
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
- $300Ks
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
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
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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
- $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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
Download the Ultimate 55+ Homebuying Guide
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$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
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
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$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
- $700Ks
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
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
- $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
- $600Ks
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
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
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Questions? Call us:
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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
1 rating (1 reviews)
![Sullivan Ranch]()
$300Ks
- $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Heritage Hills
![3788 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,672 sq ft
|House
3788 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6350932 • LPT REALTY, LLC, Manuela Leon
Grand Haven
![455 RIVERFRONT DR UNIT A104, PALM COAST,..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,167 sq ft
|Condo
455 RIVERFRONT DR UNIT A104, PALM COAST,...
Community: Grand Haven
MLS FC313284 • COASTAL GATEWAY REAL ESTATE GR, Ma...
Stonecrest
![17355 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,179 sq ft
|House
17355 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5098071 • BLACK TIE REALTY, INC., Mark Dyer
Royal Highlands
![20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,070 sq ft
|House
20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
MLS G5095688 • VANGIE BERRY SIGNATURE REALTY, Ang...
Latitude Margaritaville
![237 BLUE STARFISH PL, DAYTONA BEACH, FL,..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,681 sq ft
|House
237 BLUE STARFISH PL, DAYTONA BEACH, FL,...
Community: Latitude Margaritaville
MLS O6344382 • EXP REALTY LLC, Todd Schroth
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The Villages®
![15102 SANDALWOOD DR # 102, WILDWOOD, FL,..., Wildwood, FL 34785]()
3 beds
|2 baths
|1,474 sq ft
|Condo
15102 SANDALWOOD DR # 102, WILDWOOD, FL,...
Community: The Villages®
MLS G5100208 • DOWN HOME REALTY, LLLP, Melanie Mo...
Twin Lakes
![2516 PICKETT AVE, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
2516 PICKETT AVE, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5106768 • GODWIN REALTY GROUP, Melissa Godwi...
Venetian Bay
![2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,536 sq ft
|House
2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA...
Community: Venetian Bay
MLS V4943580 • REALTY PROS ASSURED, James Brodick
Latitude Margaritaville
![614 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
614 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1217136 • Bob Hodges and Sons Realty, Kelley ...
Plantation at Leesburg
![4552 PEACH TREE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,709 sq ft
|House
4552 PEACH TREE ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS OM707194 • BOARDWALK REALTY ASSOCIATES LLC, P...
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.
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...
Plantation at Leesburg
![5062 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,021 sq ft
|House
5062 EL DESTINO DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS S5116631 • COLDWELL BANKER SOLOMON, Susy Orti...
American Village
![31 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
4 beds
|2 baths
|1,986 sq ft
|House
31 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC313292 • DR HORTON REALTY INC., Charlie Rog...
Venetian Bay
![3361 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,440 sq ft
|House
3361 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1085451 • OCEAN PROPERTIES & MANAGEMENT, Ev...
Plantation at Leesburg
![3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,664 sq ft
|House
3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Community: Plantation at Leesburg
MLS G5102758 • CENTURY 21 MYERS REALTY, Mary Jane...
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Plantation at Leesburg
![4745 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,988 sq ft
|House
4745 TARA VIEW RD, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5101070 • CENTURY 21 MYERS REALTY, Mary Jane...
Plantation at Leesburg
![25102 MERIWEATHER RD, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|2,271 sq ft
|House
25102 MERIWEATHER RD, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5099607 • CENTURY 21 MYERS REALTY, Dawn Broo...
The Villages®
![9230 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162]()
2 beds
|2 baths
|1,148 sq ft
|House
9230 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
MLS O6342467 • HOUWZER INC, Daniel Robinson
Plantation Bay Golf & Country Club
![1245 HAMPSTEAD LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,870 sq ft
|House
1245 HAMPSTEAD LN, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1218649 • Deuces Realty, Mark Polakovich
The Villages®
![13103 SANDALWOOD DR # 13103, WILDWOOD, F..., Wildwood, FL 34785]()
2 beds
|1 baths
|1,000 sq ft
|Condo
13103 SANDALWOOD DR # 13103, WILDWOOD, F...
Community: The Villages®
MLS G5089886 • FLAMINGO REAL ESTATE & MNGMT, Kody...
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.
Breakaway Trails
![6 BLACK PINE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,289 sq ft
|House
6 BLACK PINE WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
MLS FC311606 • REALTY EXECUTIVES OCEANSIDE, Eric ...
Compass Pointe
![839 DANVILLE CIR, MELBOURNE, FL, 32904, Melbourne, FL 32904]()
3 beds
|2 baths
|1,976 sq ft
|House
839 DANVILLE CIR, MELBOURNE, FL, 32904
Community: Compass Pointe
MLS 1053141 • RE/MAX Aerospace Realty, Rick S Cap...
Highland Lakes
![5606 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5102950 • FLORIDA PLUS REALTY, LLC, Claire B...
Solivita
![507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,302 sq ft
|House
507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS TB8429298 • NHR BROKERAGE LLC, Madalina Tat
The Villages®
![1737 LAUREN LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
1737 LAUREN LN, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5102847 • FLAMINGO REAL ESTATE & MNGMT, Robb...
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Stonecrest
![10882 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,616 sq ft
|House
10882 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
MLS OM710659 • RE/MAX PREMIER REALTY LADY LK, Jay...
Venetian Bay
![3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,174 sq ft
|House
3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1084688 • THE KEYES COMPANY, Lesley Lounsbu...
Plantation Bay Golf & Country Club
![875 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
875 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC313186 • OLIVE GROVE REAL ESTATE, Sean Tabo...
Solivita
![346 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5129606 • ARISTA REALTY GROUP, LLC, Douglas ...
Solivita
![555 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,610 sq ft
|House
555 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5121580 • ARISTA REALTY GROUP, LLC, Douglas ...
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.
Harbor Hills Country Club
![5252 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,844 sq ft
|House
5252 GROVE MNR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS R4909778 • BLACK TIE REAL ESTATE PROFESSIONAL...
The Villages®
![1042 AVENIDA SONOMA, LADY LAKE, FL, 3215..., Lady Lake, FL 32159]()
3 beds
|3 baths
|2,271 sq ft
|House
1042 AVENIDA SONOMA, LADY LAKE, FL, 3215...
Community: The Villages®
MLS O6330934 • EXP REALTY LLC, Mark Ramey
The Villages®
![2123 HEATHER HILL LOOP, THE VILLAGES, FL..., The Villages, FL 32162]()
3 beds
|2 baths
|1,565 sq ft
|House
2123 HEATHER HILL LOOP, THE VILLAGES, FL...
Community: The Villages®
MLS G5102956 • ERA GRIZZARD REAL ESTATE, Lori Dav...
The Villages®
![4406 CREIGHTON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|2,061 sq ft
|House
4406 CREIGHTON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5100580 • WORTH CLARK REALTY, Nathan Piotrow...
Stonecrest
![17867 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,597 sq ft
|House
17867 SE 115TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS GC532918 • WATSON REALTY CORP, Faylene Welcom...
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(888) 625-4885
The Villages®
![278 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,966 sq ft
|House
278 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5095422 • HOMESMART, Maria Czarnecki
Carmel Condominium
![1420 HUNTINGTON LN 2405, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,008 sq ft
|Condo
1420 HUNTINGTON LN 2405, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS 1048708 • Coldwell Banker Realty, Galina K. R...
Kings Ridge
![4021 NEWLAND ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS OM706308 • REMAX/PREMIER REALTY, Eugene Gadou...
Plantation at Leesburg
![25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,737 sq ft
|House
25333 RIVER CREST DR, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5096317 • CENTURY 21 MYERS REALTY, Mary Jane...
The Country Club of Mount Dora
![1521 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|3 baths
|3,028 sq ft
|House
1521 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6339213 • UNITED REAL ESTATE PREFERRED, Kay ...
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2,487
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near Winter Park
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REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
This application does not include information on all of the properties available for sale at this time.
