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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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 (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
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
$300Ks
- $800Ks
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
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 (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 (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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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
- $600Ks
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
The Villages®
![2475 LAUREL BAY LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|House
2475 LAUREL BAY LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5104110 • RE/MAX PREMIER REALTY LADY LK, Guy...
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...
Tohoqua Reserve
![1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|2,056 sq ft
|House
1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS TB8445148 • MIHARA & ASSOCIATES INC., Raymond...
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
Plantation Bay Golf & Country Club
![24 GALE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,118 sq ft
|House
24 GALE LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC313835 • REALTY EXECUTIVES OCEANSIDE, Catri...
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Plantation at Leesburg
![4849 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,607 sq ft
|House
4849 SABLE RIDGE CT, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5103986 • CENTURY 21 MYERS REALTY, Mary Jane...
Spruce Creek Country Club
![9910 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,025 sq ft
|House
9910 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM713203 • RE/MAX PREMIER REALTY LADY LK, Jay...
Pelican Bay Daytona Beach
![156 KINGBIRD CIR 2120, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,562 sq ft
|Halfplex
156 KINGBIRD CIR 2120, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS V4945837 • DR PROPERTIES OF VOLUSIA COUNTY LL...
The Villages®
![2690 SUFFOLK ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2690 SUFFOLK ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103248 • REALTY EXECUTIVES IN THE VILLAGES,...
Carmel Condominium
![1410 HUNTINGTON LN 1203, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,008 sq ft
|Condo
1410 HUNTINGTON LN 1203, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS 1060366 • Realty World Curri Properties, Eile...
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®
![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®
![1421 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159]()
2 beds
|1 baths
|768 sq ft
|Manufactured Home
1421 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5103416 • EXP REALTY LLC, Michael Barbier
Trilogy® Orlando
![100 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,808 sq ft
|House
100 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6327214 • MARK SPAIN REAL ESTATE, Vickie Rey...
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...
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Stonecrest
![10952 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,476 sq ft
|House
10952 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5099613 • RE/MAX PREMIER REALTY, Pamalla Cra...
Heritage Isle
![6528 VAN NESS DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,006 sq ft
|House
6528 VAN NESS DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1050114 • Real Broker, LLC, Elizabeth Ann San...
Spruce Creek Country Club
![13485 SE 93RD COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,826 sq ft
|House
13485 SE 93RD COURT RD, SUMMERFIELD, FL,...
Community: Spruce Creek Country Club
MLS G5103746 • RE/MAX PREMIER REALTY LADY LK, Dia...
Venetian Bay
![3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
5 beds
|3 baths
|2,405 sq ft
|House
3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS 2117248 • HOMECOIN.COM, JONATHAN MINERICK
Solivita
![151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,356 sq ft
|House
151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
MLS O6295181 • WATSON REALTY CORP, Maritza Jimene...
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,...
The Villages®
![1506 DELLANO WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,782 sq ft
|House
1506 DELLANO WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS TB8436860 • DIVINE ESTATES REALTY LLC, Nehad ...
The Villages®
![4346 HELENA TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,295 sq ft
|House
4346 HELENA TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6358106 • THE AGENCY ORLANDO, Cassidy McWher...
Pelican Bay Daytona Beach
![148 BOB WHITE CT 1480, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,189 sq ft
|Condo
148 BOB WHITE CT 1480, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS NS1086326 • RE/MAX SIGNATURE, Chris Leon
The Villages®
![2454 MONROE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,927 sq ft
|House
2454 MONROE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6342169 • REAL BROKER, LLC, Ken Pozek
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Highland Lakes
![5609 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,251 sq ft
|House
5609 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5103638 • COLDWELL BANKER REALTY, Sara Suthe...
The Villages®
![6126 MULLIGAN RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|2,930 sq ft
|House
6126 MULLIGAN RUN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5094310 • RE/MAX PREMIER REALTY LADY LK, Lar...
Venetian Bay
![703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,226 sq ft
|House
703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS TB8410526 • ASHTON WOODS FLORIDA REALTY LLC, ...
Spruce Creek Country Club
![9203 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,870 sq ft
|House
9203 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM713135 • JUDY L. TROUT REALTY, Judy Trout
Legacy of Leesburg
![27302 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,478 sq ft
|House
27302 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
MLS G5097889 • CHARLES RUTENBERG REALTY ORLANDO, ...
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 Lakes at Harmony
![3428 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,474 sq ft
|House
3428 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5126461 • CORCORAN CONNECT LLC, Jeanine Corc...
Highland Lakes
![26608 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,499 sq ft
|House
26608 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5097058 • ERA GRIZZARD REAL ESTATE, Craig Yo...
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...
Solivita
![803 JASMINE CREEK RD, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
3 beds
|3 baths
|2,427 sq ft
|House
803 JASMINE CREEK RD, KISSIMMEE, FL, 347...
Community: Solivita
MLS O6347223 • REAL BROKER, LLC, Nick Carroll
Breakaway Trails
![2 SILVER LAKE WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,330 sq ft
|House
2 SILVER LAKE WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
MLS V4945279 • KELLER WILLIAMS RLTY FL. PARTN, Br...
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Plantation Bay Golf & Country Club
![55 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,790 sq ft
|House
55 BAY POINTE DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC313984 • NEVER 6 PERCENT REALTY INC., Peter...
Latitude Margaritaville
![208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,482 sq ft
|House
208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1218561 • LoKation, Aimee Aballo
The Villages®
![712 JASON DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,292 sq ft
|Manufactured Home
712 JASON DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102567 • IM REALTY, Ira Miller
VillageWalk at Lake Nona
![11731 EAGLE RAY LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|2 baths
|2,005 sq ft
|House
11731 EAGLE RAY LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6356279 • RE/MAX VANTAGE, Annia Torres PA
Venetian Bay
![2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,034 sq ft
|House
2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
MLS V4943028 • COLDWELL BANKER COAST REALTY, Ron ...
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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.
