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    1. *40 Hour Work Week*
    2. *Ambitious Real Estate Agent Wanted NOW*
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    4. Join Us Agents
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  • Buyer
    1. All Listings
    2. Featured Listings
    3. Sold Listings
    4. 50 Homes For 50 Fallen
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    20. Hotlist of Upscale Homes
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    25. New Homes vs Resale
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    28. Our Homes for Sale
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    31. Save Thousands
    32. Stop Paying Rent
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    34. VIP INSIDER ACCESS
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    1. Sell My Home
    2. Home Estimate
    3. 10 Questions Agents Hate
    4. 27 Seller Tips
    5. Avoid Legal Mistakes
    6. Avoid these mistakes
    7. Become a VIP Seller
    8. Buy This Home Ill Buy Yours
    9. Cash For your Home
    10. Divorce
    11. Empty Nesting
    12. Find Out What This Home Is Sold For
    13. For Sale By Owner
    14. Getting Best Price
    15. Get the Price You Want
    16. Guaranteed Offer
    17. How to Sell a Home that Didnt Sell
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    19. Kids and Moving
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    21. Pass Your Inspection
    22. Why Didnt My Home Sell
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478 Properties

478 Properties Available In Winter Park

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FL >Winter Park >
Market Insights
1792 KILLARNEY DR, Winter Park, FL 32789
1/34 34

$649,000

Open Fri 4PM-6PM

Single Family Home

4 Beds 3 Baths 2,264 SqFt

1792 KILLARNEY DR, Winter Park, FL 32789

RENOVATED and MOVE-IN READY in WINTER PARK 32789 with DEEDED LAKE ACCESS! Located on a fully fenced ¼-acre corner lot, t...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
130 KILLARNEY BAY CT #5-3, Winter Park, FL 32789
1/54 54

$479,000

Open 8/2 11AM-1PM

Condo

2 Beds 3 Baths 1,536 SqFt

130 KILLARNEY BAY CT #5-3, Winter Park, FL 32789

SUPERB LOCATION! Don't miss out on this beautifully updated 2 bedroom 2.5 bath 2-story condo in Killarney Bay. Upon en...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
2008 NOTTINGDALE LN, Winter Park, FL 32792
1/48 48

$365,000

Open Sat 10AM-2PM

Single Family Home

3 Beds 2 Baths 1,278 SqFt

2008 NOTTINGDALE LN, Winter Park, FL 32792

Nestled in the highly desirable Winter Park, Florida, 2008 Nottingdale Lane presents a meticulously updated and move-in-...

Listed by EXP REALTY LLC

Stellar MLS
1640 CYPRESS POINT LN, Winter Park, FL 32792
1/37 37

$714,900

Open Fri 5PM-6:30PM

Single Family Home

3 Beds 2 Baths 1,704 SqFt

1640 CYPRESS POINT LN, Winter Park, FL 32792

Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom h...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
5234 OHIO ST, Winter Park, FL 32792
3D

$382,500

Open Sat 11AM-1PM

Single Family Home

3 Beds 2 Baths 1,226 SqFt

5234 OHIO ST, Winter Park, FL 32792

Tropical Vibes + Total Privacy in Winter Park! A rare find, indeed!! Tucked away at the very end of a quiet cul-de-sac, ...

Listed by MARKET CONNECT REALTY LLC

Stellar MLS
618 BLAIRSHIRE CIR, Winter Park, FL 32792
1/39 39

$699,900

Open Sun 12PM-3PM

Single Family Home

3 Beds 3 Baths 1,876 SqFt

618 BLAIRSHIRE CIR, Winter Park, FL 32792

First time on the market! This one-owner, 3-bedroom, 3-bathroom single-family pool home offers the perfect blend of clas...

Listed by FANNIE HILLMAN & ASSOCIATES

Stellar MLS
1371 LYNDALE BLVD, Winter Park, FL 32789
1/50 50

$1,349,500

Open Sat 1PM-4PM

Single Family Home

4 Beds 3 Baths 2,714 SqFt

1371 LYNDALE BLVD, Winter Park, FL 32789

One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city...

Listed by ALIGN REAL ESTATE LLC

Stellar MLS
3050 AUTUMN CT, Winter Park, FL 32792
1/17 17

$2,100

Open Mon 5AM-7PM

Townhouse

3 Beds 2 Baths 1,266 SqFt

3050 AUTUMN CT, Winter Park, FL 32792

Spacious 3BR/2BA townhome in highly desirable Winter Park! This well-maintained home features a large kitchen with dine-...

Listed by MEP REALTY INVESTMENTS LLC

Stellar MLS
1330 MERRYDALE WAY, Winter Park, FL 32792
1/28 28

$479,900

Open Sat 1PM-3PM

Townhouse

3 Beds 3 Baths 2,312 SqFt

1330 MERRYDALE WAY, Winter Park, FL 32792

Welcome to Enclave at Hawks Crest! This corner-unit 3-bedroom, 2.5-bath townhome offers added privacy, extra natural lig...

Listed by SELECTA REALTY LLC

Stellar MLS
2080 WOOD THRUSH LN, Winter Park, FL 32792
1/41 41

$1,200,000

Open Sat 12AM-3PM

Single Family Home

6 Beds 4 Baths 4,277 SqFt

2080 WOOD THRUSH LN, Winter Park, FL 32792

Exceptional Living Awaits in the Heart of Winter Park <br>Nestled in the sought-after community of Waters Edge at Hawks ...

Listed by LOKATION

Stellar MLS
512 CLARENDON AVE, Winter Park, FL 32789
1/44 44

$1,100,000

Open Sat 10AM-12PM

Townhouse

4 Beds 4 Baths 2,826 SqFt

512 CLARENDON AVE, Winter Park, FL 32789

Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins Colle...

Listed by COMPASS FLORIDA LLC

Stellar MLS
1819 SHADYHILL TER, Winter Park, FL 32792
3D

$535,000

Open Sat 2PM-4PM

Single Family Home

4 Beds 3 Baths 1,811 SqFt

1819 SHADYHILL TER, Winter Park, FL 32792

Welcome to your own private retreat, perfectly situated at the end of a quiet CUL-DE-SAC on one of the most SCENIC LOTS ...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
1471 BROAD WING LN, Winter Park, FL 32792
3D

$450,000

Open Sun 1PM-3PM

Townhouse

3 Beds 3 Baths 2,010 SqFt

1471 BROAD WING LN, Winter Park, FL 32792

Step into comfort and style in this beautifully maintained townhome, built in 2020 and thoughtfully designed for modern ...

Listed by EXP REALTY LLC

Stellar MLS
1920 WOODCREST DR #15, Winter Park, FL 32792
1/20 20

$285,000

Open Sun 11AM-1PM

Condo

2 Beds 2 Baths 1,010 SqFt

1920 WOODCREST DR #15, Winter Park, FL 32792

Gorgeous, fully renovated 2-bedroom / 2-bathroom condominium nestled in the heart of Winter Park along a beautiful and q...

Listed by COLDWELL BANKER RESIDENTIAL RE

Stellar MLS
1840 BISCAYNE DR, Winter Park, FL 32789
1/47 47

$949,000

Open Sun 1PM-3PM

Single Family Home

4 Beds 3 Baths 2,646 SqFt

1840 BISCAYNE DR, Winter Park, FL 32789

Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom H...

Listed by CORCORAN PREMIER REALTY

Stellar MLS
1270 ARLINGTON PL, Winter Park, FL 32789
1/74 74

$1,750,000

Open Sun 1PM-4PM

Single Family Home

3 Beds 4 Baths 2,964 SqFt

1270 ARLINGTON PL, Winter Park, FL 32789

Modern Elegance in the Heart of Winter Park! <br> <br>Located just a half-mile from the renowned shops and dining of Par...

Listed by RE/MAX 200 REALTY

Stellar MLS
3759 KINSLEY PL, Winter Park, FL 32792
1/77 77

$689,900

Open Sat 1AM-4PM

Single Family Home

4 Beds 3 Baths 2,251 SqFt

3759 KINSLEY PL, Winter Park, FL 32792

EXPECT TO BE IMPRESSED! Tucked away in a quaint and quiet Winter Park neighborhood, this beautifully maintained two-stor...

Listed by COMPASS FLORIDA LLC

Stellar MLS
620 DARCEY DR, Winter Park, FL 32792
1/30 30

$765,000

Open Fri 2PM-5PM

Single Family Home

4 Beds 2 Baths 2,076 SqFt

620 DARCEY DR, Winter Park, FL 32792

New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heig...

Listed by PREMIER SOTHEBY'S INTL. REALTY

Stellar MLS
100 S INTERLACHEN AVE #204D, Winter Park, FL 32789
1/51 51

$840,000

Open Sat 2PM-4PM

Condo

2 Beds 2 Baths 1,143 SqFt

100 S INTERLACHEN AVE #204D, Winter Park, FL 32789

Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned bet...

Listed by COLDWELL BANKER RESIDENTIAL RE

Stellar MLS
1742 TEMPLE DR, Winter Park, FL 32789
1/58 58

$3,899,000

Open Sat 11AM-1PM

Single Family Home

4 Beds 5 Baths 3,658 SqFt

1742 TEMPLE DR, Winter Park, FL 32789

In one of Winter Park's desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 ...

Listed by PREMIER SOTHEBY'S INTL. REALTY

Stellar MLS
2211 AZALEA PL, Winter Park, FL 32789
1/99 99

$6,180,000

Open Sat 1PM-3PM

Single Family Home

5 Beds 7 Baths 7,278 SqFt

2211 AZALEA PL, Winter Park, FL 32789

Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront...

Listed by FORTUNE INTERNATIONAL REALTY

Stellar MLS
1780 MIZELL AVE., Winter Park, FL 32789
1/61 61

$1,695,000

Open Sat 12PM-2PM

Single Family Home

4 Beds 4 Baths 2,743 SqFt

1780 MIZELL AVE., Winter Park, FL 32789

Experience the height of modern luxury in this newly constructed home, masterfully designed by esteemed architect Gary H...

Listed by PREMIER SOTHEBY'S INTL. REALTY

Stellar MLS
1350 LYNDALE BLVD, Winter Park, FL 32789
1/40 40

$1,675,000

Open Sun 12PM-3PM

Single Family Home

4 Beds 5 Baths 3,478 SqFt

1350 LYNDALE BLVD, Winter Park, FL 32789

THIS HOUSE CHECKS ALL OF THE BOXES!!! <br>Situated on a quiet one-way street in Winter Park and recently renovated is th...

Listed by PALMANO GROUP RE BROKERAGE LLC

Stellar MLS
1926 NATALEN RD, Winter Park, FL 32792
1/49 49

$649,900

Open Sat 12PM-3PM

Single Family Home

3 Beds 2 Baths 1,469 SqFt

1926 NATALEN RD, Winter Park, FL 32792

*** MUST SEE WINTER PARK POOL HOME *** <br>Explore the virtual tours to fully appreciate the beauty of this completely r...

Listed by EXP REALTY LLC

Stellar MLS
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Buy With Boland

Whitney Boland

+1(727) 657-1265 whitney@buywithboland.com

2234 Lithia Center Lane, Valrico, Florida, 33596, USA
    • Home
      Seller
      1. Sell My Home
      2. Home Estimate
      3. 10 Questions Agents Hate
      4. 27 Seller Tips
      5. Avoid Legal Mistakes
      6. Avoid these mistakes
      7. Become a VIP Seller
      8. Buy This Home Ill Buy Yours
      9. Cash For your Home
      10. Divorce
      11. Empty Nesting
      12. Find Out What This Home Is Sold For
      13. For Sale By Owner
      14. Getting Best Price
      15. Get the Price You Want
      16. Guaranteed Offer
      17. How to Sell a Home that Didnt Sell
      18. How to Sell Your Home for More
      19. Kids and Moving
      20. Pets and Moving
      21. Pass Your Inspection
      22. Why Didnt My Home Sell
    • General
      1. *40 Hour Work Week*
      2. *Ambitious Real Estate Agent Wanted NOW*
      3. *Your Referrals Help The Kids
      4. Join Us Agents
      5. Local Real Estate Information
      6. Our Team
      7. Refer a Friend
      8. Save on Expenses
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      5. Blogs
    • Buyer
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. 50 Homes For 50 Fallen
      5. 10 Best Buy Hotlist
      6. 13 Extra Cost
      7. 6 Buyer Mistakes
      8. 9 Common Buyer Traps
      9. Ask a Real Estate Expert
      10. Best Financing Rate
      11. Buy With Zero Down
      12. First Time Buyer Hotlist
      13. Exclusive Fixer Upper Hotlist
      14. Fixer Uppers: Myths and Facts
      15. Foreclosures Hotlist
      16. Get New Listings
      17. Home Warranty
      18. Homes with Land Hotlist
      19. Homes with Pools Hotlist
      20. Hotlist of Upscale Homes
      21. Mortgage Pre-Approval
      22. Moving Company
      23. Moving Up
      24. Multiple Listing
      25. New Homes vs Resale
      26. No Money Down Hotlist
      27. Open House
      28. Our Homes for Sale
      29. Real Estate Lawyer
      30. Save $5000 Guaranteed
      31. Save Thousands
      32. Stop Paying Rent
      33. Sunday Tour of Homes
      34. VIP INSIDER ACCESS
      Market Snapshot

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
site logo
Buy With Boland

Whitney Boland

+1(727) 657-1265 whitney@buywithboland.com

2234 Lithia Center Lane, Valrico, Florida, 33596, USA
    • Home
      Seller
      1. Sell My Home
      2. Home Estimate
      3. 10 Questions Agents Hate
      4. 27 Seller Tips
      5. Avoid Legal Mistakes
      6. Avoid these mistakes
      7. Become a VIP Seller
      8. Buy This Home Ill Buy Yours
      9. Cash For your Home
      10. Divorce
      11. Empty Nesting
      12. Find Out What This Home Is Sold For
      13. For Sale By Owner
      14. Getting Best Price
      15. Get the Price You Want
      16. Guaranteed Offer
      17. How to Sell a Home that Didnt Sell
      18. How to Sell Your Home for More
      19. Kids and Moving
      20. Pets and Moving
      21. Pass Your Inspection
      22. Why Didnt My Home Sell
    • General
      1. *40 Hour Work Week*
      2. *Ambitious Real Estate Agent Wanted NOW*
      3. *Your Referrals Help The Kids
      4. Join Us Agents
      5. Local Real Estate Information
      6. Our Team
      7. Refer a Friend
      8. Save on Expenses
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      5. Blogs
    • Buyer
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. 50 Homes For 50 Fallen
      5. 10 Best Buy Hotlist
      6. 13 Extra Cost
      7. 6 Buyer Mistakes
      8. 9 Common Buyer Traps
      9. Ask a Real Estate Expert
      10. Best Financing Rate
      11. Buy With Zero Down
      12. First Time Buyer Hotlist
      13. Exclusive Fixer Upper Hotlist
      14. Fixer Uppers: Myths and Facts
      15. Foreclosures Hotlist
      16. Get New Listings
      17. Home Warranty
      18. Homes with Land Hotlist
      19. Homes with Pools Hotlist
      20. Hotlist of Upscale Homes
      21. Mortgage Pre-Approval
      22. Moving Company
      23. Moving Up
      24. Multiple Listing
      25. New Homes vs Resale
      26. No Money Down Hotlist
      27. Open House
      28. Our Homes for Sale
      29. Real Estate Lawyer
      30. Save $5000 Guaranteed
      31. Save Thousands
      32. Stop Paying Rent
      33. Sunday Tour of Homes
      34. VIP INSIDER ACCESS
      Market Snapshot

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.