Call us at (888) 625-4885 to learn more about active adult communities near Winter Park
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
Summer Trees
![128 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,268 sq ft
|House
128 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS V4944401 • ADAMS, CAMERON & CO., REALTORS, Ma...
Venetian Bay
![424 LUNA BELLA LN APT 330, NEW SMYRNA BE..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,953 sq ft
|Condo
424 LUNA BELLA LN APT 330, NEW SMYRNA BE...
Community: Venetian Bay
MLS V4943469 • LANE REALTY SERVICES, LLC, Pam Dea...
Del Webb Sunbridge
![2698 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
3 beds
|3 baths
|2,080 sq ft
|House
2698 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6322425 • REAL LIVING R E SOLUTIONS, Ladd Ts...
Plantation Bay Golf & Country Club
![642 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,873 sq ft
|House
642 ELK RIVER DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC308480 • VENTURE DEVELOPMENT REALTY,INC, De...
The Villages®
![766 ARTESIA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
766 ARTESIA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6337827 • NETWORTH REALTY OF ORLANDO, LLC, W...
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Spruce Creek South
![10683 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,620 sq ft
|House
10683 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
MLS G5096056 • HANSON REAL ESTATE GROUP, INC., Je...
Heritage Hills
![3512 BELLAND CIR B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3512 BELLAND CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5094587 • COLDWELL BANKER HUBBARD HANSEN, Ji...
Grand Haven
![67 EASTLAKE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC312796 • PALM COAST REAL ESTATE COMPANY, JE...
Traditions at Lake Ruby
![3667 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
3 beds
|3 baths
|2,562 sq ft
|House
3667 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS S5136779 • CORCORAN CONNECT LLC, Amy Berland
Sullivan Ranch
![30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,452 sq ft
|House
30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
MLS O6351059 • LA ROSA REALTY PREMIER LLC, Tavis ...
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.
Heritage Isle
![3624 SANSOME CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,006 sq ft
|House
3624 SANSOME CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1044432 • Blue Marlin Real Estate, Ania H Boo...
Plantation at Leesburg
![25233 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,751 sq ft
|House
25233 LOST OAK CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5103743 • CENTURY 21 MYERS REALTY, Dawn Broo...
Heritage Isle
![3386 BANCROFT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,315 sq ft
|Townhouse
3386 BANCROFT DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1059176 • EXP Realty, LLC, Eugene Crockett Jr...
Sullivan Ranch
![30304 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
6 beds
|4 baths
|3,499 sq ft
|House
30304 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5099259 • ROBIN MITCHELL REALTY, Kimberly Re...
Twin Lakes
![2606 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
2606 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6349312 • GILLISPIE TEAM REAL ESTATE BUY AND...
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Solivita
![651 HIGHLANDS HAMMOCK DR, POINCIANA, FL,..., Poinciana, FL 34759]()
2 beds
|3 baths
|1,800 sq ft
|House
651 HIGHLANDS HAMMOCK DR, POINCIANA, FL,...
Community: Solivita
MLS S5121218 • BORCHINI REALTY, Yamile Osorio Var...
Solivita
![3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5130722 • BORCHINI REALTY, Yamile Osorio Var...
Royal Highlands
![22125 DRAW BRIDGE DR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,200 sq ft
|House
22125 DRAW BRIDGE DR, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS G5099045 • VANGIE BERRY SIGNATURE REALTY, Ang...
Royal Highlands
![5518 QUEEN VICTORIA DR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,757 sq ft
|House
5518 QUEEN VICTORIA DR, LEESBURG, FL, 34...
Community: Royal Highlands
MLS O6343470 • KELLER WILLIAMS ADVANTAGE III, Ern...
The Villages®
![17096 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
17096 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS OM692931 • REALTY ONE GROUP EPIC, Michael Mil...
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.
Twin Lakes
![2600 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,935 sq ft
|House
2600 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6346165 • LPT REALTY, LLC, Jessica Snyder
Arlington Ridge
![26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748]()
4 beds
|3 baths
|2,318 sq ft
|House
26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5103238 • WATSON REALTY CORP, Nancy McCloske...
Highland Fairways
![3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,210 sq ft
|House
3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS TB8407029 • LAND MERCHANTS REAL ESTATE SERVIC...
Lakeside Landings
![10274 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,616 sq ft
|House
10274 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
MLS TB8399387 • LA ROSA REALTY LLC, Adriana Olive...
The Villages®
![16914 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
16914 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS G5090816 • EXP REALTY LLC, Denise Nabinger
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Plantation at Leesburg
![25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,653 sq ft
|House
25800 BELLE HELENE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096683 • SCATES REALTY & INVESTMENT PRO, Ei...
The Villages®
![16846 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,906 sq ft
|House
16846 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
MLS OM706331 • COLDWELL BANKER VANGUARD LIFESTYLE...
Spruce Creek South
![17855 SE 99TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
17855 SE 99TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM689620 • JUDY L. TROUT REALTY, Jennifer Tra...
The Villages®
![805 ROYAL PALM AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159]()
2 beds
|2 baths
|984 sq ft
|Manufactured Home
805 ROYAL PALM AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5099231 • REALTY EXECUTIVES IN THE VILLAGES,...
Plantation Bay Golf & Country Club
![801 ARBOR GLEN CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,569 sq ft
|House
801 ARBOR GLEN CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS V4943501 • REALTY PROS ASSURED, Mary Maholias
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
![9573 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,708 sq ft
|House
9573 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5101394 • RE/MAX PREMIER REALTY LADY LK, Rob...
Silver Lakes
![6320 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,857 sq ft
|House
6320 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
MLS L4956195 • XCELLENCE REALTY, INC, Bill Madlin
Huntington at Hunter's Ridge
![23 HERON WING DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|3 baths
|1,549 sq ft
|Villa
23 HERON WING DR, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS FC312484 • APPROVED PATRIOT REALTY LLC, Chris...
Spruce Creek South
![17807 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
17807 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5094339 • TEAM WYN REALTY LLC, Gloria Wyning...
Stonecrest
![17784 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,832 sq ft
|Villa
17784 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5100473 • RE/MAX PREMIER REALTY LADY LK, Cin...
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Breakaway Trails
![5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,204 sq ft
|House
5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174
Community: Breakaway Trails
MLS 1210077 • Florida Realty Plus LLC, Suzana Pet...
The Villages®
![2912 BARBOZA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2912 BARBOZA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103511 • SELLSTATE SUPERIOR REALTY, Heather...
Lake James
![8152 LAKE JAMES DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|2,175 sq ft
|House
8152 LAKE JAMES DR, LAKELAND, FL, 33810
Community: Lake James
MLS TB8439726 • REMAX EXPERTS, Adam Smith
Pelican Bay Daytona Beach
![224 BOB WHITE CT # 224, DAYTONA BEACH, F..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,668 sq ft
|Condo
224 BOB WHITE CT # 224, DAYTONA BEACH, F...
Community: Pelican Bay Daytona Beach
MLS NS1086334 • REALTY PROS ASSURED, Bryan Morfor...
Cresswind at Victoria Gardens
![123 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,894 sq ft
|House
123 AVENHAM DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4945564 • COLDWELL BANKER COAST REALTY, Jaso...
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2,487
homes
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.
