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    1. *40 Hour Work Week*
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    1. All Listings
    2. Featured Listings
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400 Properties

400 Properties Available In Winter Park

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FL >Winter Park >
Market Insights
701 DENTON RD, Winter Park, FL 32792
1/32 32

$565,000

Active

Single Family Home

3 Beds 2 Baths 2,268 SqFt

701 DENTON RD, Winter Park, FL 32792

Motivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Park Estates! Nestled on a quart...

Listed by Liz Boyce CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
101 S INTERLACHEN AVE #104, Winter Park, FL 32789
1/26 26

$635,000

Active

Condo

2 Beds 2 Baths 949 SqFt

101 S INTERLACHEN AVE #104, Winter Park, FL 32789

FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN HOUSE – AVAILABLE FOR RENT OR P...

Listed by Kelly Price KELLY PRICE & COMPANY LLC

Stellar MLS
1360 FORMOSA AVE, Winter Park, FL 32789
1/26 26

$625,000

Active

Multi-Family

3 Beds 3 Baths 1,890 SqFt

1360 FORMOSA AVE, Winter Park, FL 32789

Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the highly sought-after Winter Pa...

Listed by Salvison Dickson TOP FLORIDA HOMES

Stellar MLS
1564 CAVENDISH RD, Winter Park, FL 32789
1/17 17

$450,000

Active

Single Family Home

3 Beds 1 Bath 1,140 SqFt

1564 CAVENDISH RD, Winter Park, FL 32789

Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potential. Updated with original har...

Listed by Julie Wright CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
5325 CYPRESS RESERVE PL, Winter Park, FL 32792
1/17 17

$918,000

Active

Single Family Home

5 Beds 4 Baths 3,598 SqFt

5325 CYPRESS RESERVE PL, Winter Park, FL 32792

ATTENTION BUYERS!! Price adjusted to $918,000 and $15K SELLER CONCESSION TOWARDS BUYERS CLOSING COST WITH FULL ASKING P...

Listed by Dori Estrada PLLC LPT REALTY, LLC

Stellar MLS
250 CORTLAND AVE, Winter Park, FL 32789
1/68 68

$950,000

Active

Single Family Home

3 Beds 2 Baths 2,114 SqFt

250 CORTLAND AVE, Winter Park, FL 32789

Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of th...

Listed by Alexandra Nordine EXP REALTY LLC

Stellar MLS
3071 GEORGE MASON AVE #5, Winter Park, FL 32792
1/19 19

$89,900

Active

Condo

1 Bath 549 SqFt

3071 GEORGE MASON AVE #5, Winter Park, FL 32792

NEW PRICE!!! Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat! <br>Welcome to this well-mai...

Listed by Katherine Bordelon CASTLE & COTTAGE REALTY LLC

Stellar MLS
607 DUNBLANE DR, Winter Park, FL 32792
1/44 44

$675,000

Active

Single Family Home

4 Beds 3 Baths 2,046 SqFt

607 DUNBLANE DR, Winter Park, FL 32792

Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenu...

Listed by Khozaif Merali CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
1444 PELICAN BAY TRL, Winter Park, FL 32792
1/57 57

$999,950

Active

Single Family Home

4 Beds 3 Baths 3,121 SqFt

1444 PELICAN BAY TRL, Winter Park, FL 32792

Seller Financing Available--Attractive Terms--Potentially Below Market Rate. <br> <br>A True Gem on the Lake! <br> <br>...

Listed by Jacob Hara TRANSCEND REALTY

Stellar MLS
1695 LEE RD #C202, Winter Park, FL 32789

$210,000

Active

Condo

3 Beds 2 Baths 1,149 SqFt

1695 LEE RD #C202, Winter Park, FL 32789

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rolli...

Listed by Hoover Yap PRIMESTATE REALTY, INC.

Stellar MLS
7706 COUNTRY PL #7706, Winter Park, FL 32792
1/19 19

$245,000

Active

Condo

3 Beds 2 Baths 1,230 SqFt

7706 COUNTRY PL #7706, Winter Park, FL 32792

Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas,...

Listed by Carmen Vazquez REALTY TECH INC

Stellar MLS
1400 ALABAMA DR, Winter Park, FL 32789
1/84 84

$5,895,000

Active

Single Family Home

5 Beds 9 Baths 7,916 SqFt

1400 ALABAMA DR, Winter Park, FL 32789

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one of Winter Park's mos...

Listed by Rachel Peters, LLC THE AGENCY ORLANDO

Stellar MLS
3011 GEORGE MASON AVE #3, Winter Park, FL 32792
1/21 21

$135,000

Active

Condo

2 Beds 2 Baths 1,056 SqFt

3011 GEORGE MASON AVE #3, Winter Park, FL 32792

Spacious and inviting, this 2-bedroom, 2-bathroom condo in Winter Park is a fantastic investment or personal home. The o...

Listed by Kayla Long WHEATLEY REALTY GROUP

Stellar MLS
1660 PALMER AVE, Winter Park, FL 32789
1/48 48

$4,950,000

Active

Single Family Home

5 Beds 7 Baths 6,406 SqFt

1660 PALMER AVE, Winter Park, FL 32789

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening t...

Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY

Stellar MLS
2923 ANTIQUE OAKS CIR #39, Winter Park, FL 32792
1/22 22

$200,000

Active

Condo

2 Beds 2 Baths 1,105 SqFt

2923 ANTIQUE OAKS CIR #39, Winter Park, FL 32792

Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor co...

Listed by Michell Carrasquero GLOBALWIDE REALTY LLC

Stellar MLS
726 and 720 N PENNSYLVANIA AVE, Winter Park, FL 32789
1/49 49

$1,215,000

Active

Multi-Family

6 Beds 4 Baths 2,284 SqFt

726 and 720 N PENNSYLVANIA AVE, Winter Park, FL 32789

Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibility and investment potential. W...

Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

Stellar MLS
726/720 N PENNSYLVANIA AVE, Winter Park, FL 32789
1/49 49

$1,215,000

Active

Single Family Home

6 Beds 4 Baths 2,284 SqFt

726/720 N PENNSYLVANIA AVE, Winter Park, FL 32789

Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you're looking for...

Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

Stellar MLS
726 N PENNSYLVANIA AVE, Winter Park, FL 32789
1/30 30

$695,000

Active

Single Family Home

3 Beds 2 Baths 1,167 SqFt

726 N PENNSYLVANIA AVE, Winter Park, FL 32789

Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location....

Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

Stellar MLS
720 N PENNSYLVANIA AVE, Winter Park, FL 32789
1/26 26

$550,000

Active

Single Family Home

3 Beds 2 Baths 1,115 SqFt

720 N PENNSYLVANIA AVE, Winter Park, FL 32789

Nestled in one of Winter Park's most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern el...

Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

Stellar MLS
625 BRECHIN DR, Winter Park, FL 32792
1/42 42

$765,000

Active

Single Family Home

3 Beds 2 Baths 1,827 SqFt

625 BRECHIN DR, Winter Park, FL 32792

PICTURE PERFECT HOME IN WINTER PARK'S KENILWORTH SHORES! Homes of this quality and preservation hardly come on the marke...

Listed by Kelly Price KELLY PRICE & COMPANY LLC

Stellar MLS
2500 LEE RD #202, Winter Park, FL 32789
1/39 39

$239,990

Active

Condo

2 Beds 2 Baths 956 SqFt

2500 LEE RD #202, Winter Park, FL 32789

2/2 * IMMACULATE CONDO * LOW HOA * LIVE ON LAKE KILLARNEY * ENJOY PARK AVE IN WINTER PARK * 3 MILES T...

Listed by Alison Maltby THE ANDERSON GROUP & CO PL

Stellar MLS
2033 CANNY CV, Winter Park, FL 32792
1/34 34

$432,000

Active

Townhouse

3 Beds 3 Baths 1,907 SqFt

2033 CANNY CV, Winter Park, FL 32792

Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and living area—perfect for entertai...

Listed by Monica Puche LPT REALTY, LLC

Stellar MLS
1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
1/50 50

$1,250,000

Active

Single Family Home

4 Beds 3 Baths 2,310 SqFt

1400 S PENNSYLVANIA AVE, Winter Park, FL 32789

Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. <br>You will...

Listed by John Keller JACK KELLER INC

Stellar MLS
1660 WALNUT AVE, Winter Park, FL 32789
1/11 11

$1,759,000

Active

Single Family Home

4 Beds 4 Baths 2,172 SqFt

1660 WALNUT AVE, Winter Park, FL 32789

Under Construction. Elegant and modern new construction home perfectly situated in beautiful Winter Park. Scheduled for ...

Listed by Julie Christensen COMPASS FLORIDA 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.