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Winter Park, FL 55+ active adult communities & homes for sale - Page 58
90 communities near Winter Park
2,513 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
$100ks
- $1Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$100ks
- $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
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3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300ks
- $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 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 (1 reviews)
![Plantation Bay Golf &...]()
$400ks
- $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
5 rating (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
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3.8 rating (4 reviews)
![Spruce Creek South]()
$100ks
- $200ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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 (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
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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.
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
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4 rating (2 reviews)
![Harbor Hills Country Club]()
$300ks
- $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200ks
- $400ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (2 reviews)
![Heritage Isle]()
$300ks
- $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.
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
3.8 rating (5 reviews)
![Traditions at Lake Ruby]()
$200ks
- $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
552 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$200ks
- $500ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 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
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
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
Lakes of Mount Dora
![8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,811 sq ft
|House
8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS O6328646 • FLORIDA HOME TEAM REALTY LLC, Kris...
Cresswind at Victoria Gardens
![1677 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724]()
3 beds
|2 baths
|1,512 sq ft
|House
1677 VICTORIA GARDENS DR, DELAND, FL, 32...
Community: Cresswind at Victoria Gardens
MLS O6331891 • SAND DOLLAR REALTY GROUP INC, Tamm...
Gatherings of Lake Nona
![7565 LAUREATE BLVD 3308, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,368 sq ft
|Condo
7565 LAUREATE BLVD 3308, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6330795 • REAL BROKER, LLC, Peter Luu
Grand Haven
![8 HIDDEN LAKE WAY, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|2,183 sq ft
|House
8 HIDDEN LAKE WAY, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC311515 • COASTAL GATEWAY REAL ESTATE GROUP,...
The Villages®
![375 SIMPSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,887 sq ft
|House
375 SIMPSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS P4935705 • HUT REALTY, LLC, Daniel Hut
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Carillon Lakes
![3913 SERENADE LN 4, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,722 sq ft
|Condo
3913 SERENADE LN 4, LAKELAND, FL, 33811
Community: Carillon Lakes
MLS L4954498 • KELLER WILLIAMS REALTY SMART, Joe ...
Solivita
![525 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131724 • FAIRWAY REALTY OF SOLIVITA, Bonnie...
Halifax Plantation
![1317 MIDDLE LAKE DR, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
5 beds
|3 baths
|2,528 sq ft
|House
1317 MIDDLE LAKE DR, ORMOND BEACH, FL, 3...
Community: Halifax Plantation
MLS FC311514 • REALTY PROS ASSURED, Marvin Adams
High Vista at Ridgewood Lakes
![457 GOLF VISTA CIR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
4 beds
|3 baths
|2,211 sq ft
|House
457 GOLF VISTA CIR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6330032 • VESTI LLC, Natalie Rivera
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.
Kings Ridge
![4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,968 sq ft
|House
4202 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5100062 • REALTY PROFESSIONALS OF FL,LLC, Ma...
Plantation Bay Golf & Country Club
![856 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,562 sq ft
|Townhouse
856 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1216088 • Venture Development Realty, Inc, De...
Latitude Margaritaville
![595 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
595 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1216079 • Bob Hodges and Sons Realty, Kelley ...
Solivita
![313 SANTA BARBARA LN, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
2 beds
|3 baths
|2,343 sq ft
|House
313 SANTA BARBARA LN, KISSIMMEE, FL, 347...
Community: Solivita
MLS S5131195 • PELLEGO, LLC, Stan Wilson
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Spruce Creek Country Club
![11977 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,720 sq ft
|House
11977 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM706021 • JUDY L. TROUT REALTY, Judy Trout
Indian River Colony Club
![1198 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940]()
3 beds
|3 baths
|2,304 sq ft
|House
1198 CONTINENTAL AVE, MELBOURNE, FL, 329...
Community: Indian River Colony Club
MLS 1052685 • Four Star Real Estate LLC, Robin St...
Del Webb Oasis
![15084 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787]()
3 beds
|3 baths
|2,270 sq ft
|House
15084 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
MLS O6328280 • REAL BROKER, LLC, Ken Pozek
Lake Ashton
![4124 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,682 sq ft
|House
4124 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4935581 • LAKE ASHTON REALTY INC., Candra Al...
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®
![919 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159]()
3 beds
|2 baths
|1,634 sq ft
|House
919 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
MLS G5099866 • GODFREY REALTY GROUP, INC., Joe Go...
The Villages®
![8544 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,481 sq ft
|House
8544 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
MLS OM705783 • ENGEL & VOLKERS OCALA, TaMara York
Highland Lakes
![6033 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5099864 • FLORIDA PLUS REALTY, LLC, Garnet E...
Huntington at Hunter's Ridge
![6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,637 sq ft
|House
6 FOX LAIR CT, ORMOND BEACH, FL, 32174
Community: Huntington at Hunter's Ridge
MLS FC311356 • REALTY PROS ASSURED, Tyler Renick
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The Villages®
![1117 PARADISE DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,383 sq ft
|Manufactured Home
1117 PARADISE DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS A4659524 • FLATFEE.COM, Cliff Glansen
Carmel Condominium
![1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,008 sq ft
|Condo
1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS 1052313 • Ellingson Properties, Gregory Ellin...
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...
Pelican Bay Daytona Beach
![220 SURF SCOOTER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,760 sq ft
|Townhouse
220 SURF SCOOTER DR, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1215672 • Simply Real Estate, Geraldine Westf...
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.
Halifax Plantation
![2983 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,106 sq ft
|House
2983 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC311194 • REALTY EXCHANGE, LLC, Deidre Vlass...
The Timbers at Everlands
![853 ANTIBES CT, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|3 baths
|2,182 sq ft
|House
853 ANTIBES CT, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1051806 • Blue Marlin Real Estate, Jason Bist...
The Timbers at Everlands
![2223 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|4 baths
|1,710 sq ft
|House
2223 ANTARUS DR NW, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1051805 • Blue Marlin Real Estate, Jason Bist...
The Villages®
![220 ESTRADA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,121 sq ft
|Villa
220 ESTRADA PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099622 • EXP REALTY LLC, Debbie Gentry
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
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Lake Ashton
![5384 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,682 sq ft
|House
5384 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
MLS P4935506 • LAKE ASHTON REALTY INC., Candra Al...
Spruce Creek South
![10185 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|3 baths
|1,982 sq ft
|House
10185 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS O6325610 • COLDWELL BANKER REALTY, Bob Paulso...
Grand Haven
![23 CREEKSIDE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
4 beds
|3 baths
|2,633 sq ft
|House
23 CREEKSIDE DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC311160 • FLORIDA DREAMS PROPERTIES INC, Ale...
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...
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.
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 1215517 • Realty Pros Assured, James Brodick
Tohoqua Reserve
![2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|2,054 sq ft
|House
2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5130256 • LA ROSA REALTY KISSIMMEE, Sal Mala...
Latitude Margaritaville
![422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,922 sq ft
|House
422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS V4943508 • COLDWELL BANKER REALTY, Edit Perez
Colonnades
![4805 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
4805 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS G5099299 • FLORIDA REALTY MARKETPLACE, Cathy ...
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The Villages®
![1802 PETUNIA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,434 sq ft
|Manufactured Home
1802 PETUNIA LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099228 • COLDWELL BANKER VANGUARD LIFESTYLE...
Spruce Creek Country Club
![13944 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,120 sq ft
|House
13944 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5099176 • MORRIS REALTY AND INVESTMENTS, Ken...
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2,513
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
