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Winter Park, FL 55+ active adult communities & homes for sale - Page 29
90 communities near Winter Park
2,398 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $2Ms
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
- $3Ms
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
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
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
$100Ks
- $400Ks
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
- $400Ks
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
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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
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
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
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 (8 reviews)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$400Ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 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
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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
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.
$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
- $800Ks
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
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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
- $800Ks
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
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.
4.1 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
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
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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
The Villages®
![5094 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|2,109 sq ft
|House
5094 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
MLS OM712430 • MEADOWS REALTY, LLC, Bert Meadows
Lakeside Landings
![5368 COMPASS PT # 202, OXFORD, FL, 34484, Oxford, FL 34484]()
2 beds
|2 baths
|1,402 sq ft
|Condo
5368 COMPASS PT # 202, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5099614 • ERA GRIZZARD REAL ESTATE, Felecia ...
The Villages®
![915 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|2,022 sq ft
|House
915 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5105852 • IM REALTY, Ira Miller
Grand Isle
![1611 LAGO MAR DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
MLS 1064280 • RE/MAX Aerospace Realty, Teresa Fer...
Grand Haven
![9 CREEKSIDE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313466 • VIRTUAL HOMES REALTY, Alina Pekars...
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Plantation at Leesburg
![24526 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,145 sq ft
|House
24526 BOCAGE WAY, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6368957 • LONDON FOSTER REALTY, Carrie Steve...
Arlington Ridge
![27106 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,436 sq ft
|House
27106 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6343489 • LPT REALTY, LLC, Raymond Reyes
Royal Harbor
![3001 LAKE HURON LN, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,920 sq ft
|House
3001 LAKE HURON LN, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5096992 • ERA GRIZZARD REAL ESTATE, Tammy Ki...
Solivita
![448 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8395602 • KELLER WILLIAMS SUBURBAN TAMPA, T...
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
![11735 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,413 sq ft
|House
11735 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM706900 • JUDY L. TROUT REALTY, Jennifer Tra...
Spruce Creek Country Club
![12546 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|2,119 sq ft
|House
12546 SE 92ND TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM712768 • RE/MAX FOXFIRE - SUMMERFIELD, Caro...
Palms at Serenoa
![17386 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
3 beds
|2 baths
|1,621 sq ft
|House
17386 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS G5095939 • LIST NOW REALTY, LLC, Matt Buttner
The Villages®
![3141 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,340 sq ft
|House
3141 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5100707 • RE/MAX PREMIER REALTY, Tammy Freil...
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The Villages®
![3359 ARLYN PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|1,905 sq ft
|House
3359 ARLYN PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102603 • RE/MAX PREMIER REALTY LADY LK, Mat...
Venetian Bay
![236 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,610 sq ft
|House
236 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS O6332615 • COLLADO REAL ESTATE, Sharon Snow
Foxwood Lake Estates
![1530 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,430 sq ft
|Manufactured Home
1530 LONGBOW DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5135663 • WATSON REALTY CORP, Lois Ann Cox
The Villages®
![8333 COUNTY ROAD 109A-1, LADY LAKE, FL, ..., Lady Lake, FL 32159]()
3 beds
|2 baths
|1,904 sq ft
|Manufactured Home
8333 COUNTY ROAD 109A-1, LADY LAKE, FL, ...
Community: The Villages®
MLS G5102517 • REAL BROKER, LLC, Denise Beserock
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.
Stonecrest
![11351 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,717 sq ft
|House
11351 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5105707 • CHARLES RUTENBERG REALTY ORLANDO, ...
Lakes of Mount Dora
![8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,156 sq ft
|House
8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS O6328646 • FLORIDA HOME TEAM REALTY LLC, Kris...
The Villages®
![2109 SUAREZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
2109 SUAREZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102011 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![100 VIZCAYA CT, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS TB8452171 • CHARLES RUTENBERG REALTY INC, Al ...
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Venetian Bay
![414 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,724 sq ft
|House
414 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS TB8447633 • ASHTON WOODS FLORIDA REALTY LLC, ...
Kings Ridge
![3562 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,713 sq ft
|House
3562 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5103088 • WATSON REALTY CORP., REALTORS, Mic...
Solivita
![251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
2 beds
|2 baths
|2,050 sq ft
|House
251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
MLS A11938835 • New Beginnings R.E. & Investm, Th...
Scottish Highlands
![15 ABERDEEN CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,224 sq ft
|House
15 ABERDEEN CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS O6344103 • 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.
Solivita
![1155 GLENDORA RD N, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS FC313946 • COASTAL GATEWAY REAL ESTATE GR, Cy...
Spruce Creek Country Club
![9074 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,672 sq ft
|House
9074 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM711457 • REALTY ONE GROUP DAVALLS, David St...
The Villages®
![1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159]()
2 beds
|2 baths
|936 sq ft
|Manufactured Home
1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5103522 • RE/MAX PREMIER REALTY, Tammy Freil...
The Lakes at Harmony
![3388 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|3 baths
|1,918 sq ft
|House
3388 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6351645 • RESORT REALTY GROUP LTD INC, David...
Lake Ashton
![4115 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,688 sq ft
|House
4115 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS O6344464 • KELLER WILLIAMS ADVANTAGE 2 REALTY...
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Heritage Isle
![6531 INGALLS ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,806 sq ft
|House
6531 INGALLS ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1064566 • Coastal Life Properties LLC, Kane S...
Summer Trees
![130 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,363 sq ft
|House
130 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1218501 • RE/MAX Signature, Amy Wilson
Sullivan Ranch
![21846 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
2 beds
|2 baths
|1,437 sq ft
|House
21846 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5103969 • COLDWELL BANKER STEVENS RE, Kyle L...
The Villages®
![8061 SE 167TH HILLTOP LOOP, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,513 sq ft
|House
8061 SE 167TH HILLTOP LOOP, THE VILLAGES...
Community: The Villages®
MLS G5105946 • RE/MAX PREMIER REALTY, Tammy Freil...
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.
Lake Ashton
![4120 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|4 baths
|2,968 sq ft
|House
4120 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS O6346784 • PREMIER SOTHEBYS INT'L REALTY, Ale...
The Villages®
![1142 W BOONE CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,120 sq ft
|House
1142 W BOONE CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5098404 • RE/MAX PREMIER REALTY, Tammy Freil...
Indian River Colony Club
![1329 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,616 sq ft
|House
1329 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1065420 • Four Star Real Estate LLC, Shellie ...
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
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Lake James
![7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,990 sq ft
|House
7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4953716 • KELLER WILLIAMS REALTY SMART, Joe ...
Spruce Creek Country Club
![12900 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,149 sq ft
|House
12900 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM708818 • SHEPPARD ASSOCIATES, LLC, Patrick ...
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2,398
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REIN updates its listings on a daily basis. Data last updated: Jan 11, 2026.
This application does not include information on all of the properties available for sale at this time.
