Winter Park, FL Homes

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  $126,000

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  7326 Swallow Run Unit 7326, Winter Park, FL 32792

  **** Ground floor 2 bed 2 bath condo in a nice quiet community *** move-in ready with granite tops, upgraded plumbing, on-demand water heater, vinyl plank flooring throughout. One of the best priced units available on MLS. Well maintained community and roof replaced within past two years. Owner is Listing Agent, Broker and Realtor so an efficient sale can be expected. All offers to be on FAR/BAR

  Kevin Mernan CREATIVE HOMES OF ORLANDO

  7326 Swallow Run Unit 7326, Winter Park, FL 32792
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  /2

  $755,000 Sold Jul 18, 2025

  1000 Howell Branch Rd, Winter Park, FL 32789

  • Land
  • 0.55 Acre
  • $1,372,727 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 241 Days On Market

  Current Estimated Value $848,211

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1000 Howell Branch Rd, Winter Park, FL 32789
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  /25

  Est $250,000 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft

  5408 Peaco Place, Winter Park, FL 32792

  5408 Peaco Place, Winter Park, FL 32792
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  /64

  $680,000

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  681 Overspin Dr, Winter Park, FL 32789

  Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024), new HVAC systems (2024/2025), and

  Gail Higley RE/MAX SELECT GROUP

  681 Overspin Dr, Winter Park, FL 32789
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  /2

  $150,000 Sold Mar 18, 2025

  3358 Cedar Springs Place Unit 159, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  Last Sold Summary

  • 33% Below List Price
  • $145/SF
  • 59 Days On Market

  Current Estimated Value $156,110

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  3358 Cedar Springs Place Unit 159, Winter Park, FL 32792
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  /16

  Est $1,029,825 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  2400 Roxbury Rd, Winter Park, FL 32789

  2400 Roxbury Rd, Winter Park, FL 32789
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  /17

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,117 Sq Ft

  7426 Wynnewood Square Unit 195, Winter Park, FL 32792

  Excellent opportunity to acquire a 3-bedroom, 2-bath first-floor end-unit condo offering approximately 1,117 sq ft in a well-established community. The unit features a functional layout and a highly desirable location near UCF, Full Sail University, Valencia College, and major shopping and dining. Priced to sell, this property is ideal for investors seeking a light-to-moderate rehab with strong

  Qing Lin SPRINGHILL PROPERTIES LLC

  7426 Wynnewood Square Unit 195, Winter Park, FL 32792
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  /2

  $3,845,000 Sold May 16, 2025

  2020 Venetian Way, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $918/SF
  • 4 Days On Market

  Current Estimated Value $3,984,825

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  2020 Venetian Way, Winter Park, FL 32789
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  /19

  Est $2,596,810 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft

  350 Beloit Ave, Winter Park, FL 32789

  350 Beloit Ave, Winter Park, FL 32789
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  /89

  $1,799,999

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  Listed at APPRAISED VALUE **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
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  /2

  $130,000 Sold Nov 25, 2025

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Below List Price
  • $179/SF
  • 35 Days On Market

  Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
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  /35

  Est $292,354 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  228 Balfour Dr Unit 17, Winter Park, FL 32792
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  /65

  $2,295,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 2,714 Sq Ft

  660 Osceola Ave Unit 101, Winter Park, FL 32789

  Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  660 Osceola Ave Unit 101, Winter Park, FL 32789
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  /2

  $170,000 Sold Sep 24, 2025

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $152/SF
  • 74 Days On Market

  Current Estimated Value $172,527

  Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
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  /80

  Est $1,170,137 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,307 Sq Ft

  1999 Soaring Oak Way, Winter Park, FL 32792

  1999 Soaring Oak Way, Winter Park, FL 32792
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  /12

  $424,900

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft

  2232 Shadowland Loop, Winter Park, FL 32792

  Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and

  He Gao U S GLORY REALTY

  2232 Shadowland Loop, Winter Park, FL 32792
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  /2

  $475,000 Sold Feb 02, 2026

  1740 Anzle Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 1956

  Last Sold Summary

  • 40% Below List Price
  • $263/SF
  • 109 Days On Market

  Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  /11

  Est $428,375 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2770 Bright Bird Ln, Winter Park, FL 32792

  2770 Bright Bird Ln, Winter Park, FL 32792
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  /41

  $1,550,000

  • 4 Beds
  • 3.5 Baths
  • 2,985 Sq Ft

  507 Country Club Dr, Winter Park, FL 32789

  Designed for elevated living in the heart of Winter Park, this custom-built pool home on the largest interior lot in the community combines timeless craftsmanship, modern comfort, and an unbeatable location just steps from premier shopping and dining. Featuring 4 bedrooms, 3.5 bathrooms, a private pool, and a spacious backyard, this stunning home is thoughtfully designed for both comfortable

  Lianna D'Angelo SOTERA LIVING

  507 Country Club Dr, Winter Park, FL 32789
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  /2

  $350,000 Sold Feb 06, 2026

  1438 Tierra Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft
  • Built 1968

  Last Sold Summary

  • 8% Below List Price
  • $215/SF
  • 3 Days On Market

  Last Listing Agent Meir Tenenbaum CARDINAL REALTY GROUP, LLC.

  1438 Tierra Cir, Winter Park, FL 32792
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  /46

  Est $879,973 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft

  1913 S Lakemont Ave, Winter Park, FL 32792

  1913 S Lakemont Ave, Winter Park, FL 32792
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  /15

  $425,000

  • Land
  • 0.11 Acre
  • $3,863,636 per Acre

  786 W Canton Ave, Winter Park, FL 32789

  Incredible opportunity for the right family. This is a 49x96 Perfectly high and dry lot with a tree to shade your backyard. Nestled in the highly sought after City of Winter Park amongst million dollar homes. LOCATION LOCATION LOCATION! A perfect home site for your future custom dwelling. Bring your imagination creativity and builder to take a look. What a Winter Park sweet spot. Lots in this

  Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

  786 W Canton Ave, Winter Park, FL 32789
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  /2

  $240,000 Sold Mar 03, 2025

  200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,165 Sq Ft
  • Built 1970

  Last Sold Summary

  • 26% Below List Price
  • $206/SF
  • 217 Days On Market

  Current Estimated Value $234,932

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792
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  /11

  Not Listed For Sale

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792
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  /28

  $255,000

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  2651 Cayman Way, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and

  Kyle Clark RE/MAX TOWN & COUNTRY REALTY

  2651 Cayman Way, Winter Park, FL 32792
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  /2

  $325,000 Sold Oct 03, 2025

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 0 Days On Market

  Current Estimated Value $329,831

  Last Listing Agent Tyler Gibson LPT REALTY, LLC

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
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  /11

  Est $425,285 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2737 Bright Bird Ln, Winter Park, FL 32792

  2737 Bright Bird Ln, Winter Park, FL 32792
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  /48

  $4,950,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 6,406 Sq Ft

  1660 Palmer Ave, Winter Park, FL 32789

  New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
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  /2

  $415,000 Sold Jun 10, 2025

  3063 Ash Park Loop, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $248/SF
  • 23 Days On Market

  Current Estimated Value $421,940

  Last Listing Agent Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

  3063 Ash Park Loop, Winter Park, FL 32792
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  /21

  Est $436,725 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2861 Clever Ln, Winter Park, FL 32792

  2861 Clever Ln, Winter Park, FL 32792
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  /46

  $4,250,000 Pending

  • 4 Beds
  • 5.5 Baths
  • 3,720 Sq Ft

  702 Via Bella, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  702 Via Bella, Winter Park, FL 32789
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  /2

  $385,000 Sold Nov 12, 2025

  4421 Steed Terrace, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $215/SF
  • 209 Days On Market

  Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

  4421 Steed Terrace, Winter Park, FL 32792
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  /23

  Est $283,450 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3197 Crown Jewel Ct, Winter Park, FL 32792

  3197 Crown Jewel Ct, Winter Park, FL 32792
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  /27

  $381,000

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft

  958 Dupont Ave, Winter Park, FL 32789

  Welcome to 958 Dupont Ave, a home that exudes charm and functionality. The kitchen is a chef's dream, boasting all stainless steel appliances that add a sleek, modern touch. Step outside to a spacious, fenced-in backyard, perfect for privacy and outdoor activities. Enjoy leisurely afternoons or entertain on the covered patio, a delightful extension of the living space. A storage shed provides

  Karen Albright OPENDOOR BROKERAGE LLC

  958 Dupont Ave, Winter Park, FL 32789
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  /2

  $665,000 Sold Jun 18, 2025

  2817 Prince John Rd, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,183 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 37 Days On Market

  Current Estimated Value $653,959

  Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

  2817 Prince John Rd, Winter Park, FL 32792
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  /32

  Est $627,268 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  1178 Wildmeadow Run, Winter Park, FL 32792

  1178 Wildmeadow Run, Winter Park, FL 32792
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  /16

  $40,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  3028 George Mason Ave Unit 7, Winter Park, FL 32792

  Under contract-accepting backup offers. Two-bedroom two bath in the Winter Park School District. Convenient to shopping and bus service. Property needs rehab.

  David Rollins FLORIDA REALTY INVESTMENTS

  3028 George Mason Ave Unit 7, Winter Park, FL 32792
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  /2

  $2,835,000 Sold Nov 24, 2025

  255 Stirling Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,635 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $780/SF
  • 25 Days On Market

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  255 Stirling Ave, Winter Park, FL 32789
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  /18

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft

  1411 Miller Ave, Winter Park, FL 32789

  1411 Miller Ave, Winter Park, FL 32789
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  /31

  $349,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,242 Sq Ft

  5047 Ferncrest Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Lovingly Maintained by original owner. This is a true 4-bedroom home with 2 bathrooms and a single car garage. Located in desirable Winter Park with easy access to major roads, convenient to shopping, the post office, restaurants, higher education, and airports. This solid built home features a split plan, large living room with a wall of closet space, easy

  Wanda Perkins GLOBAL PROPERTIES SALES & MGMT

  5047 Ferncrest Dr, Winter Park, FL 32792

Showing Results 641 - 680, Page 17 of 18