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Winter Park, FL 55+ active adult communities & homes for sale - Page 56
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
Download the Ultimate 55+ Homebuying Guide
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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
Solivita
![154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
3 beds
|4 baths
|2,616 sq ft
|House
154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347...
Community: Solivita
MLS S5133904 • PELLEGO, LLC, Stan Wilson
Plantation Bay Golf & Country Club
![46 LONGRIDGE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,529 sq ft
|Townhouse
46 LONGRIDGE LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1217630 • Venture Development Realty, Inc, Co...
Solivita
![157 SAND PIPER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS P4936191 • KELLER WILLIAMS REALTY SMART 1, Da...
Heritage Isle
![3664 GURRERO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,061 sq ft
|House
3664 GURRERO DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1056444 • RE/MAX Aerospace Realty, Ellie M Ch...
The Country Club of Mount Dora
![1521 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
2 beds
|3 baths
|3,028 sq ft
|House
1521 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6339213 • UNITED REAL ESTATE PREFERRED, Kay ...
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Del Webb Sunbridge
![2928 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
3 beds
|3 baths
|1,854 sq ft
|Townhouse
2928 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6339451 • CENTURY 21 CARIOTI, Ketan Patel
Sullivan Ranch
![30113 JUTLAND CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
5 beds
|4 baths
|3,320 sq ft
|House
30113 JUTLAND CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5101223 • COLDWELL BANKER VANGUARD EDGE, Mic...
Plantation Bay Golf & Country Club
![1283 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,029 sq ft
|House
1283 ROYAL POINTE LN, ORMOND BEACH, FL, ...
Community: Plantation Bay Golf & Country Club
MLS FC312406 • VENTURE DEVELOPMENT REALTY,INC, De...
The Villages®
![12406 NE 50TH VW, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|2,096 sq ft
|House
12406 NE 50TH VW, OXFORD, FL, 34484
Community: The Villages®
MLS OM708816 • EXP REALTY LLC, Garrett Huffman
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®
![1705 STAUNTON ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
1705 STAUNTON ST, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101292 • REALTY EXECUTIVES IN THE VILLAGES,...
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 ...
Halifax Plantation
![3026 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,232 sq ft
|House
3026 ADRIAN DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC312375 • LPT REALTY LLC (PALM COAST), Danie...
Latitude Margaritaville
![154 GYPSY PALACE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
154 GYPSY PALACE, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1217405 • Fathom Realty FL LLC, Adrienne Smit...
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The Villages®
![913 SOLEDAD WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,982 sq ft
|House
913 SOLEDAD WAY, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5101526 • LPT REALTY, LLC, Jenna Wood
Sandpiper Golf & Country Club
![6222 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,318 sq ft
|House
6222 CRANE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS TB8422739 • HOMESMART, Cynthia Fannan
Stonecrest
![17520 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,402 sq ft
|House
17520 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5101380 • CHARLES RUTENBERG REALTY ORLANDO, ...
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...
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.
VillageWalk at Lake Nona
![11887 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
2 beds
|2 baths
|1,708 sq ft
|House
11887 DELFINA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS TB8422156 • SOUTH EARTH REALTY LLC, Ting Li
Del Webb Orlando
![418 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,713 sq ft
|House
418 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5133545 • KELLER WILLIAMS REALTY AT THE LAKE...
Grand Haven
![6 SCARLET OAK CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|3 baths
|2,465 sq ft
|House
6 SCARLET OAK CIR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC312207 • GRAND LIVING REALTY, Rochele Harri...
Halifax Plantation
![3124 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,717 sq ft
|House
3124 BAILEY ANN DR, ORMOND BEACH, FL, 32...
Community: Halifax Plantation
MLS 1217281 • Realty Pros Assured, Buzzy Porter
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Stonecrest
![17076 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,752 sq ft
|House
17076 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS G5101399 • RE/MAX PREMIER REALTY LADY LK, Cur...
Pennbrooke Fairways
![32716 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,370 sq ft
|House
32716 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5101176 • ERA GRIZZARD REAL ESTATE, Sharon W...
Latitude Margaritaville
![553 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,161 sq ft
|House
553 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS FC312280 • REALTY EXCHANGE, LLC, Daniel Shapk...
The Villages®
![421 ALDAMA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
421 ALDAMA AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5101240 • MAXREV LLC, Jayne Marvin
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.
Del Webb Orlando
![507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
4 beds
|3 baths
|2,616 sq ft
|House
507 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS P4936042 • LA ROSA REALTY PRESTIGE, Keith St....
The Villages®
![335 LOGAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,266 sq ft
|Villa
335 LOGAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM708038 • RE/MAX PREMIER REALTY, Cory Freili...
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
Cresswind at Victoria Gardens
![115 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,773 sq ft
|House
115 HERON POINT WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS A11865319 • A. Leon Realty Inc., Adolfo Quint...
Pelican Bay Daytona Beach
![150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,365 sq ft
|Condo
150 BLUE HERON DR B, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1217166 • EXP Realty LLC, Debbie Ellis
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Lake Ashton
![5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,031 sq ft
|House
5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4936039 • LAKE ASHTON REALTY INC., Candra Al...
Lake Ashton
![4496 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,312 sq ft
|House
4496 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4936036 • LAKE ASHTON REALTY INC., Candra Al...
Pennbrooke Fairways
![642 GLEN OAKS DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,632 sq ft
|House
642 GLEN OAKS DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5100872 • MAXREV LLC, Jayne Marvin
Tohoqua Reserve
![1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|1,559 sq ft
|Villa
1873 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5133310 • EXP REALTY LLC, Carlos Nolte
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
![9343 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|3 baths
|2,324 sq ft
|House
9343 SE 124TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM707460 • JUDY L. TROUT REALTY, Judy Trout
Solivita
![159 CASAVISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5132415 • PELLEGO, LLC, Stan Wilson
Stonecrest
![17789 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,463 sq ft
|House
17789 SE 113TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM707848 • KELLER WILLIAMS CORNERSTONE RE, Al...
Stonecrest
![17409 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,700 sq ft
|House
17409 SE 111TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM707769 • KELLER WILLIAMS CORNERSTONE RE, Ci...
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Lake Ashton
![6212 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,175 sq ft
|House
6212 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
MLS P4935966 • LAKE ASHTON REALTY INC., Lori Raat...
Spruce Creek South
![9667 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
9667 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM707768 • KELLER WILLIAMS CORNERSTONE RE, Ci...
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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.
