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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
Want to learn more about 55+ communities in Winter Park?
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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
Legacy of Leesburg
![5304 FANTASY WAY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,087 sq ft
|House
5304 FANTASY WAY, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5104762 • RE/MAX TITANIUM GROUP, Darlene Mis...
Lake Ashton
![1124 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,113 sq ft
|House
1124 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
MLS P4934195 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Latitude Margaritaville
![519 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
519 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1219219 • Keller Williams Realty Florida Part...
The Villages®
![2924 FRENCH OAK AVE, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|1,723 sq ft
|House
2924 FRENCH OAK AVE, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5104564 • DOWN HOME REALTY, LLLP, Amber Byrn...
Foxwood Lake Estates
![1620 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,800 sq ft
|Manufactured Home
1620 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4955864 • DALTON WADE INC, Jarrod Nyland
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Heritage Isle
![6641 RINGOLD ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,861 sq ft
|House
6641 RINGOLD ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1056231 • RE/MAX Aerospace Realty, Teresa Fer...
The Villages®
![1615 NAVIDAD ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,143 sq ft
|Villa
1615 NAVIDAD ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5097226 • REALTY EXECUTIVES IN THE VILLAGES,...
Halifax Plantation
![2653 FERMOY DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,662 sq ft
|House
2653 FERMOY DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS O6353330 • PULTE REALTY OF NORTH FLORIDA LLC,...
The Villages®
![470 MONETTA LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,908 sq ft
|House
470 MONETTA LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5104823 • SALLY LOVE REAL ESTATE, Kim Coffer
The Villages®
![2940 GULLEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,525 sq ft
|Villa
2940 GULLEY LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5103430 • SALLY LOVE REAL ESTATE, Kim Coffer
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®
![3495 RESTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,203 sq ft
|House
3495 RESTON DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5100538 • SALLY LOVE REAL ESTATE, Kim Coffer
Venetian Bay
![661 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,748 sq ft
|House
661 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS A4667960 • TAYLOR MORRISON REALTY OF FLORIDA ...
Venetian Bay
![668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
5 beds
|4 baths
|3,221 sq ft
|House
668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6334879 • TAYLOR MORRISON REALTY OF FLORIDA ...
Venetian Bay
![672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,748 sq ft
|House
672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6334874 • TAYLOR MORRISON REALTY OF FLORIDA ...
Venetian Bay
![673 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
6 beds
|5 baths
|4,181 sq ft
|House
673 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6334591 • TAYLOR MORRISON REALTY OF FLORIDA ...
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Venetian Bay
![677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|3,221 sq ft
|House
677 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS A4659011 • TAYLOR MORRISON REALTY OF FLORIDA ...
Royal Harbor
![5138 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|1,889 sq ft
|House
5138 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS G5102936 • DOWN HOME REALTY, LLLP, Amber Byrn...
Heritage Hills
![3201 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3201 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5093860 • HOMESMART, Kevin Trout
The Villages®
![9089 SE 177TH BELMONT PL, THE VILLAGES, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,283 sq ft
|Villa
9089 SE 177TH BELMONT PL, THE VILLAGES, ...
Community: The Villages®
MLS G5102154 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![776 ALCOTT AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
776 ALCOTT AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102897 • COLDWELL BANKER REALTY, William Pe...
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.
Carillon Lakes
![4344 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
5 beds
|4 baths
|3,461 sq ft
|House
4344 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
MLS L4955562 • REAL BROKER, LLC, Briana Isidore
Halifax Plantation
![1405 NEWRY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,344 sq ft
|House
1405 NEWRY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS TB8421323 • LISTED SIMPLY, Sinan Zakaria
Spruce Creek Country Club
![13535 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,262 sq ft
|House
13535 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM705805 • JUDY L. TROUT REALTY, Judy Trout
Gatherings of Lake Nona
![7557 LAUREATE BLVD UNIT 6208, ORLANDO, F..., Orlando, FL 32827]()
2 beds
|2 baths
|1,445 sq ft
|Condo
7557 LAUREATE BLVD UNIT 6208, ORLANDO, F...
Community: Gatherings of Lake Nona
MLS O6204269 • KELLER WILLIAMS ADVANTAGE REALTY, ...
High Vista at Ridgewood Lakes
![100 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|2,051 sq ft
|House
100 MOSS LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5101667 • KELLER WILLIAMS REALTY AT THE LAKE...
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Grand Haven
![16 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313306 • COASTAL GATEWAY REAL ESTATE GROUP,...
Venetian Bay
![3054 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|4 baths
|1,847 sq ft
|Townhouse
3054 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1086008 • EXIT REAL ESTATE PROPERTY SOL, Ca...
Summer Trees
![55 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,775 sq ft
|House
55 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS V4944694 • COLDWELL BANKER COAST REALTY, Ron ...
Latitude Margaritaville
![110 SALT SHAKER ST, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
110 SALT SHAKER ST, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1219530 • LoKation, Aimee Aballo
Spruce Creek Country Club
![13883 SE 94TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,575 sq ft
|House
13883 SE 94TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM713497 • RE/MAX FOXFIRE - SUMMERFIELD, Caro...
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 at Leesburg
![24725 BRIGHTWATER CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,132 sq ft
|House
24725 BRIGHTWATER CT, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS TB8445644 • HOME SOLD REALTY LLC, Camilo Pere...
The Villages®
![1701 PALM AIRE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
1701 PALM AIRE DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5103112 • SELLSTATE SUPERIOR REALTY, Willi M...
Grand Haven
![12 RIVER POINT DR # 12, PALM COAST, FL, ..., Palm Coast, FL 32137]()
2 beds
|3 baths
|2,201 sq ft
|Townhouse
12 RIVER POINT DR # 12, PALM COAST, FL, ...
Community: Grand Haven
MLS FC313223 • COASTAL GATEWAY REAL ESTATE GROUP,...
Stonecrest
![12115 SE 175TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,074 sq ft
|House
12115 SE 175TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS G5103110 • FLORIDA ADVANTAGE REALTY GROUP, Ta...
Spruce Creek Country Club
![12176 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,120 sq ft
|House
12176 SE 91ST AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5103054 • KELLER WILLIAMS ELITE PARTNERS III...
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Spruce Creek Country Club
![13184 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,423 sq ft
|House
13184 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM709877 • REALTY ONE GROUP DAVALLS, Michael ...
Sandpiper Golf & Country Club
![6143 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,216 sq ft
|House
6143 CRANE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS R4909881 • DYW LLC, Yvonne Wherrett
Spruce Creek Country Club
![9333 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|2,148 sq ft
|House
9333 SE 124TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM708731 • JUDY L. TROUT REALTY, Judy Trout
Pelican Bay Daytona Beach
![100 BITTERN CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
4 beds
|3 baths
|3,140 sq ft
|House
100 BITTERN CT, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS G5101152 • WATSON REALTY CORP, Beth Stoothoff
Spruce Creek Country Club
![11800 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,346 sq ft
|House
11800 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM706841 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D...
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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.
