About Winding Woods
Market Summary
Avg. List Price
Current Listings
Avg. Active Days on Market
Dog lovers
Animal advocates
Athleisure wear
Fashion trending
Vehicle enthusiasts
Fitness oriented
Day-time leisure
Friendly community
Shopping
Hard working
market snapshot
We’ve gathered the latest market data to help you better understand what’s happening in Winding Woods.
Recently Sold Avg.
Avg. Days on Market
Recently Sold
Avg. Price/Area
Properties in Winding Woods
All
Sold
New - 57 Hours
Open House





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••••••
3 bd
2 ba
2646 BARKSDALE COURT, CLEARWATER, FL 33761
Listing Courtesy Of: IVY LEAGUE REALTY, 727-687-2088, Frank Foye, Jr.
Sold
New - 5 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #B102, CLEARWATER, FL 33761
Listing Courtesy Of: KELLER WILLIAMS REALTY- PALM H, 727-772-0772, Vanessa Leonard
Sold
New - 1,405 Hours
Open House





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••••••
3 bd
2 ba
2637 BARKSDALE COURT #2637, CLEARWATER, FL 33761
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Ed Karlander
Sold
New - 1,693 Hours
Open House





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••••••
3 bd
2 ba
2587 FOREST RUN COURT #141B, CLEARWATER, FL 33761
Listing Courtesy Of: OPENDOOR BROKERAGE LLC, Homes@opendoor.com, Greg Blackall
Sold
New - 28 Hours
Open House





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••••••
3 bd
2 ba
2572 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Kelly Hustedde
Sold
New - 310 Hours
Open House





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••••••
4 bd
3 ba
2665 LAKEBREEZE LANE N, CLEARWATER, FL 33759
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Mark Fazzini
Sold
New - 2,333 Hours
Open House





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••••••
3 bd
2 ba
2600 BARKSDALE COURT, CLEARWATER, FL 33761
Listing Courtesy Of: PREFERRED SHORE LLC, 941-999-1179, Anthony Rudolph
Sold
New - 1,526 Hours
Open House





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••••••
3 bd
2 ba
2736 HAVERHILL COURT #2736, CLEARWATER, FL 33761
Listing Courtesy Of: REMAX EXPERTS, 863-802-5262, Pavlina Blahova
Sold
New - 161 Hours
Open House





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••••••
2 bd
3 ba
2747 ENTERPRISE ROAD E #17, CLEARWATER, FL 33759
Listing Courtesy Of: RE/MAX ALLIANCE GROUP, 727-845-4321, Daphne Thomas
Sold
New - 1,431 Hours
Open House





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••••••
2 bd
2 ba
2650 BARKSDALE COURT #0, CLEARWATER, FL 33761
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Robert Kidwell
Sold
New - 336 Hours
Open House





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••••••
2 bd
2 ba
2632 ENTERPRISE ROAD E #A23, CLEARWATER, FL 33759
Listing Courtesy Of: FUTURE HOME REALTY INC, 813-855-4982, Michael Lauer
Sold
New - 239 Hours
Open House





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••••••
3 bd
2 ba
2610 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: LPT REALTY LLC, Andrew Duncan
Sold
New - 264 Hours
Open House
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #A207, CLEARWATER, FL 33761
Listing Courtesy Of: KELLER WILLIAMS REALTY- PALM H, 727-772-0772, Maria Hourdas
Sold
New - 545 Hours
Open House





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••••••
4 bd
3 ba
2510 CYPRESS BEND DRIVE E, CLEARWATER, FL 33761
Listing Courtesy Of: CAMELOT INC REALTORS, 727-791-8100, Patricia Vernon, PA
Sold
New - 1,857 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #A105, CLEARWATER, FL 33761
Listing Courtesy Of: REALTY ONE GROUP MVP, 800-896-8790, Brianna Beyer
Sold
New - 1,150 Hours
Open House





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••••••
3 bd
2 ba
2566 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: MANGROVE BAY REALTY LLC, 813-444-7440, Valarie Gerbus
Sold
New - 2,791 Hours
Open House





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••••••
2 bd
2 ba
2715 HAVERHILL COURT #2715, CLEARWATER, FL 33761
Listing Courtesy Of: FUTURE HOME REALTY INC, 813-855-4982, Penny Cooper
Sold
New - 3,496 Hours
Open House





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••••••
3 bd
2 ba
2747 SAND HOLLOW COURT, CLEARWATER, FL 33761
Listing Courtesy Of: FUTURE HOME REALTY INC, 813-855-4982, Ena Ebanks
Sold
New - 485 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #F209, CLEARWATER, FL 33761
Listing Courtesy Of: CHARLES RUTENBERG REALTY INC, 866-580-6402, Elena Kapetaneas
Sold
New - 1,405 Hours
Open House





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••••••
3 bd
2 ba
2722 SAND HOLLOW COURT #2722, CLEARWATER, FL 33761
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Nancy Leslie
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Active
Sold
New - 57 Hours
Open House





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••••••
3 bd
2 ba
2646 BARKSDALE COURT, CLEARWATER, FL 33761
Listing Courtesy Of: IVY LEAGUE REALTY, 727-687-2088, Frank Foye, Jr.
Sold
New - 5 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #B102, CLEARWATER, FL 33761
Listing Courtesy Of: KELLER WILLIAMS REALTY- PALM H, 727-772-0772, Vanessa Leonard
Sold
New - 1,405 Hours
Open House





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••••••
3 bd
2 ba
2637 BARKSDALE COURT #2637, CLEARWATER, FL 33761
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Ed Karlander
Sold
New - 1,693 Hours
Open House





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••••••
3 bd
2 ba
2587 FOREST RUN COURT #141B, CLEARWATER, FL 33761
Listing Courtesy Of: OPENDOOR BROKERAGE LLC, Homes@opendoor.com, Greg Blackall
Sold
New - 28 Hours
Open House





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••••••
3 bd
2 ba
2572 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Kelly Hustedde
Sold
New - 310 Hours
Open House





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••••••
4 bd
3 ba
2665 LAKEBREEZE LANE N, CLEARWATER, FL 33759
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Mark Fazzini
Sold
New - 2,333 Hours
Open House





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••••••
3 bd
2 ba
2600 BARKSDALE COURT, CLEARWATER, FL 33761
Listing Courtesy Of: PREFERRED SHORE LLC, 941-999-1179, Anthony Rudolph
Sold
New - 1,526 Hours
Open House





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••••••
3 bd
2 ba
2736 HAVERHILL COURT #2736, CLEARWATER, FL 33761
Listing Courtesy Of: REMAX EXPERTS, 863-802-5262, Pavlina Blahova
Sold
New - 161 Hours
Open House





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••••••
2 bd
3 ba
2747 ENTERPRISE ROAD E #17, CLEARWATER, FL 33759
Listing Courtesy Of: RE/MAX ALLIANCE GROUP, 727-845-4321, Daphne Thomas
Sold
New - 1,431 Hours
Open House





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••••••
2 bd
2 ba
2650 BARKSDALE COURT #0, CLEARWATER, FL 33761
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Robert Kidwell
Sold
New - 336 Hours
Open House





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••••••
2 bd
2 ba
2632 ENTERPRISE ROAD E #A23, CLEARWATER, FL 33759
Listing Courtesy Of: FUTURE HOME REALTY INC, 813-855-4982, Michael Lauer
Sold
New - 239 Hours
Open House





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••••••
3 bd
2 ba
2610 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: LPT REALTY LLC, Andrew Duncan
Sold
New - 264 Hours
Open House
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #A207, CLEARWATER, FL 33761
Listing Courtesy Of: KELLER WILLIAMS REALTY- PALM H, 727-772-0772, Maria Hourdas
Sold
New - 545 Hours
Open House





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••••••
4 bd
3 ba
2510 CYPRESS BEND DRIVE E, CLEARWATER, FL 33761
Listing Courtesy Of: CAMELOT INC REALTORS, 727-791-8100, Patricia Vernon, PA
Sold
New - 1,857 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #A105, CLEARWATER, FL 33761
Listing Courtesy Of: REALTY ONE GROUP MVP, 800-896-8790, Brianna Beyer
Sold
New - 1,150 Hours
Open House





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••••••
3 bd
2 ba
2566 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: MANGROVE BAY REALTY LLC, 813-444-7440, Valarie Gerbus
Sold
New - 3,496 Hours
Open House





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••••••
3 bd
2 ba
2747 SAND HOLLOW COURT, CLEARWATER, FL 33761
Listing Courtesy Of: FUTURE HOME REALTY INC, 813-855-4982, Ena Ebanks
Sold
New - 485 Hours
Open House





View listing to see more images.
••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #F209, CLEARWATER, FL 33761
Listing Courtesy Of: CHARLES RUTENBERG REALTY INC, 866-580-6402, Elena Kapetaneas
Sold
New - 1,405 Hours
Open House





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••••••
3 bd
2 ba
2722 SAND HOLLOW COURT #2722, CLEARWATER, FL 33761
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Nancy Leslie
Sold
New - 1,732 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #C309, CLEARWATER, FL 33761
Listing Courtesy Of: RE/MAX REALTEC GROUP INC, 727-789-5555, Nancy Leslie
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Pending
Sold
New - 2,791 Hours
Open House





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••••••
2 bd
2 ba
2715 HAVERHILL COURT #2715, CLEARWATER, FL 33761
Listing Courtesy Of: FUTURE HOME REALTY INC, 813-855-4982, Penny Cooper
Sold
New - 2,858 Hours
Open House





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••••••
2 bd
2 ba
2553 FOREST RUN COURT #150A, CLEARWATER, FL 33761
Listing Courtesy Of: COLDWELL BANKER REALTY, 813-253-2444, Conner McBride
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Upcoming Open Houses
Sold
New - 28 Hours
Open House





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••••••
3 bd
2 ba
2572 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Kelly Hustedde
Sold
New - 5 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #B102, CLEARWATER, FL 33761
Listing Courtesy Of: KELLER WILLIAMS REALTY- PALM H, 727-772-0772, Vanessa Leonard
Sold
New - 57 Hours
Open House





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••••••
3 bd
2 ba
2646 BARKSDALE COURT, CLEARWATER, FL 33761
Listing Courtesy Of: IVY LEAGUE REALTY, 727-687-2088, Frank Foye, Jr.
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Recently Sold
Sold
- Mar 14, 2025
New - 5,238 Hours
Open House





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••••••
3 bd
2 ba
2605 CEDAR VIEW COURT, CLEARWATER, FL 33761
Listing Courtesy Of: CHARLES RUTENBERG REALTY INC, 866-580-6402, Steph Waite
Sold
- Mar 4, 2025
New - 2,235 Hours
Open House

•
2 bd
2 ba
2638 BARKSDALE COURT #2638, CLEARWATER, FL 33761
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Courtney Hoerig
Sold
- Feb 28, 2025
New - 1,852 Hours
Open House





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••••••
2 bd
2 ba
2559 FOREST RUN COURT, CLEARWATER, FL 33761
Listing Courtesy Of: CENTURY 21 COASTAL ALLIANCE, 727-771-8880, Lisa Ulgenalp
Sold
- Feb 14, 2025
New - 3,124 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BLVD #A307, CLEARWATER, FL 33761
Listing Courtesy Of: RE/MAX BAYSIDE REALTY LLC, 813-938-1781, Michael Shea
Sold
- Feb 5, 2025
New - 3,498 Hours
Open House





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••••••
2 bd
2 ba
2595 FOREST RUN COURT #139A, CLEARWATER, FL 33761
Listing Courtesy Of: KELLER WILLIAMS REALTY- PALM H, 727-772-0772, Cathy Seguin
Sold
- Jan 10, 2025
New - 3,048 Hours
Open House





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••••••
4 bd
2 ba
2650 PEACHTREE CIRCLE E, CLEARWATER, FL 33761
Listing Courtesy Of: REMAX EXPERTS, 863-802-5262, Pavlina Blahova
Sold
- Dec 27, 2024
New - 3,362 Hours
Open House





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••••••
2 bd
2 ba
2650 COUNTRYSIDE BOULEVARD #B205, CLEARWATER, FL 33761
Listing Courtesy Of: LPT REALTY LLC, Andrew Duncan
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Nearby Schools
Public
Private
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Grade
Student-Teacher Ratio:
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Precisely
and subject to change.
Please check the applicable school district.
Transit & Commute
Estimated commute times from Winding Woods
Car-Dependent
Walkable
Very Walkable
Nearby Neighborhoods
Countryside
8
Current Listings
Bay Towne West
1
Current Listings
Fairwood Forest
1
Current Listings
Arlington
2
Current Listings
Trails Of Countryside
2
Current Listings
Shore Drive
3
Current Listings
Amberglen
Curlew City
3
Current Listings
Virginia St and Patricia Ave
22
Current Listings
Mine
8
Current Listings
Ashland Heights
Kapok Kove
3
Current Listings
Kapok Manor/Terrace Villas
4
Current Listings
Mission Hills
29
Current Listings
Highland Woods
3
Current Listings
Covered Bridge Townhomes
Scottsdale
2
Current Listings
Bay Woods I
1
Current Listings
Solon Ave
13
Current Listings
Bridgeport
North Bay Hills
7
Current Listings
Spanish Acres
1
Current Listings
Victory Clearwater
Safety Harbor
1
Current Listings
Georgetown East
Sunset Grove
2
Current Listings
Spring Lakes Of Clearwater
3
Current Listings
Montclair Lake
4
Current Listings
Dunedin Commons
Sunfish Bay
5
Current Listings
Gull Aire Village
19
Current Listings
Sunset Point Rd
12
Current Listings
Braeside
Trails West
2
Current Listings
Bay's End
Stirling Heights
Sunset Lake Estates
Del Oro Groves
5
Current Listings
N Bayshore
3
Current Listings
Spanish Pines
Harbour Towne
4
Current Listings
Curlew Groves
10
Current Listings
Amberlea
3
Current Listings
Kapok Terrace
Old Coachman
15
Current Listings
Santi's Way
14
Current Listings
Brae Moor Estates
1
Current Listings
De Soto Estates
Ohio/Falcon/Carolina
2
Current Listings
Spanish Trails
Dunedin
8
Current Listings
Spanish Manor
Green Springs
16
Current Listings
BraeMoor South
Brigadoon of Clearwater
6
Current Listings
Scotsdale Bluffs
Greenbriar
34
Current Listings
Huntington Trace
Estancia
3
Current Listings
Cypress Trace North
4
Current Listings
Villas Of Lake Arbor
7
Current Listings
McMullen Enterprise
16
Current Listings
Chesapeake
Old Coachman Rd
2
Current Listings
Sunset Point/Chancery/Elysium
6
Current Listings
Dunedin North East
9
Current Listings
Cypress Knoll
1
Current Listings
Weatherstone
2
Current Listings
Hammock Pine
6
Current Listings
Landmark Drive
Amber Glades
Sequoia Dr
3
Current Listings
Renaissance Oaks
Sunset Pointe
7
Current Listings
McCormick West
Oak Forest Of Countryside
Summerdale Drive
Westchester Lake
9
Current Listings
On Top Of The World
134
Current Listings
Bryn Mawr
6
Current Listings
Woodgate
1
Current Listings
Northwood West
5
Current Listings
Villas at Countryside
6
Current Listings
Inverness
11
Current Listings
Huntington Trail
2
Current Listings
Coachman Ridge
3
Current Listings
Safety Harbor II
31
Current Listings
Clearwater Manor
6
Current Listings
Chevy Chase
3
Current Listings
Beacon Place
7
Current Listings
McMullen Booth
26
Current Listings
Winchester
9
Current Listings
Weathersfield Dr/Allard Dr
11
Current Listings
Virginia Grove Terrace
2
Current Listings
Ranchwood Estates
1
Current Listings
Coachman
Woodlake
7
Current Listings
Lone Pine
Turnberry Countryside
8
Current Listings
Charter Oaks
College Park
1
Current Listings
Virginia Grove
4
Current Listings
Clearwater Whoop
King Arthur's Court
4
Current Listings
Estancia 2
10
Current Listings
Heather Ridge
12
Current Listings
Huntington Lakes
OTOW Paradise
7
Current Listings
Clubhouse Estates
2
Current Listings
Brookfield
8
Current Listings
Wilshire
5
Current Listings
Countryside
15
Current Listings