About Winding Hollow
Market Summary
Avg. List Price
Current Listings
Avg. Active Days on Market
Historic
Civic engagement
Healthy foods
Late-night leisure
Animal advocates
Sites to see
Hops & brews
Farm culture
Shopping
Vehicle enthusiasts
market snapshot
We’ve gathered the latest market data to help you better understand what’s happening in Winding Hollow.
Recently Sold Avg.
Avg. Days on Market
Recently Sold
Avg. Price/Area
Properties in Winding Hollow
All
Sold
New - 1,599 Hours
Open House





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••••••
4 bd
3 ba
729 TIMBERWILDE AVENUE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: KELLER WILLIAMS ELITE PARTNERS III REALTY, 321-527-5111, Ken Pozek
Sold
New - 161 Hours
Open House





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••••••
4 bd
3 ba
712 TIMBERWILDE AVENUE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CHARLES RUTENBERG REALTY ORLANDO, 407-622-2122, Roberta Shoopman
Sold
New - 3,390 Hours
Open House





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••••••
4 bd
3 ba
1042 WINDING WATERS CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: RE/MAX TOWN & COUNTRY REALTY, 407-695-2066, Rob Breese, III
Sold
New - 6,056 Hours
Open House


••
865 E STATE ROAD 434, WINTER SPRINGS, FL 32708
Listing Courtesy Of: RCI REAL ESTATE INC., 407-256-0123, Devin Greene
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Active
Sold
New - 161 Hours
Open House





View listing to see more images.
••••••
4 bd
3 ba
712 TIMBERWILDE AVENUE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CHARLES RUTENBERG REALTY ORLANDO, 407-622-2122, Roberta Shoopman
Sold
New - 6,056 Hours
Open House


••
865 E STATE ROAD 434, WINTER SPRINGS, FL 32708
Listing Courtesy Of: RCI REAL ESTATE INC., 407-256-0123, Devin Greene
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Pending
Sold
New - 1,599 Hours
Open House





View listing to see more images.
••••••
4 bd
3 ba
729 TIMBERWILDE AVENUE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: KELLER WILLIAMS ELITE PARTNERS III REALTY, 321-527-5111, Ken Pozek
Sold
New - 3,390 Hours
Open House





View listing to see more images.
••••••
4 bd
3 ba
1042 WINDING WATERS CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: RE/MAX TOWN & COUNTRY REALTY, 407-695-2066, Rob Breese, III
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No matching listings
Recently Sold
Sold
- Feb 11, 2025
New - 3,344 Hours
Open House





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••••••
4 bd
3 ba
1229 WINDING CHASE BOULEVARD, WINTER SPRINGS, FL 32708
Listing Courtesy Of: EXP REALTY LLC, 888-883-8509, Jason Asa
Sold
- Jan 31, 2025
New - 6,988 Hours
Open House





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••••••
4 bd
3 ba
377 TWELVE OAKS DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: KELLER WILLIAMS LEGACY REALTY, 407-855-2222, Alisson Fernandes
Sold
- Jan 23, 2025
New - 3,201 Hours
Open House





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••••••
4 bd
3 ba
704 TIMBERWILDE AVENUE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CENTURY 21 INTEGRA, 407-474-0844, Kristin Vogt
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Nearby Schools
Public
Private
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Grade
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Precisely
and subject to change.
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Transit & Commute
Estimated commute times from Winding Hollow
Car-Dependent
Walkable
Very Walkable
Nearby Neighborhoods
Casselberry Estates
Greenbriar
4
Current Listings
Fox Hollow
11
Current Listings
Tuscawilla Chelsea Park
1
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Wildwood
2
Current Listings
Bear Creek- Winter Spring
1
Current Listings
Whites Landing
1
Current Listings
Reserves at Lake Irene
Castlewood
1
Current Listings
Harbor Winds
2
Current Listings
Hanover Place
2
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Lake Jessup
4
Current Listings
Lake Kathren
Spicewood
Hearth Place
Autumn Chase
Lake Jesup Woods
2
Current Listings
Lake Kathryn
2
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Country Club Village
Tuska Reserve
1
Current Listings
Davenport & Carrington
Eagles Point
1
Current Listings
Fox Ridge
3
Current Listings
Lake Glen Dr
1
Current Listings
Sanford
3
Current Listings
Eagles Glen
2
Current Listings
Kings Point
Oak Bend
1
Current Listings
Amherst
1
Current Listings
Sterling Park
1
Current Listings
Greens at Tuscawilla
Deer Pointe
Tuscawilla Forest
Seminole Heights
Wyndham Woods/Wil O Wik
4
Current Listings
Crystal Bowl
13
Current Listings
Seven Oaks
Williamson Heights
2
Current Listings
Howell Creek & Eagles Watch
Legends Winter Springs
Hacienda Village
Winter Springs Village
1
Current Listings
Trotwood / Sybilwood
Moss Cove
5
Current Listings
Deersong
1
Current Listings
Oak Forest
2
Current Listings
Seville Chase
3
Current Listings
Orange Avenue
Jesups Landing Townhomes
6
Current Listings
Mt Greenwood
4
Current Listings
Mosswood
Bear Springs Dr
5
Current Listings
The Springs
1
Current Listings
Jesups Reserve Townhomes
6
Current Listings
Avery Park
Tuskawilla Trails
Parkstone
4
Current Listings
Heritage Park Townhomes
2
Current Listings
North Orlando Estates
8
Current Listings
The Landings At Parkst
Tuscawilla
1
Current Listings
Wedgewood
Winter Springs
9
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Creeks Run
Whitesand Cove
The Highlands
19
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Lake Tuscawilla
1
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Brookside
Tuskawilla Springs
Vienna Woods
1
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Stone Gable
1
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Georgetowne
9
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Legacy Park
4
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Tuscawilla
1
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North Orlando Terrace
The Ranchlands
4
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Edgemon
1
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Casa Park Villas
1
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The Ranchlands
St John's Landing
1
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