Winter Park, FL Homes

• 

  

  

  /17

  $499,990

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
• 

  

  

  /50

  $1,094 - $1,955 per month

  Winter Park Woods Apartments

  1 - 3 Beds

  349 Scottsdale Square, Winter Park, FL 32792

  This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

  349 Scottsdale Square, Winter Park, FL 32792
• 

  

  /2

  $223,000 Sold Oct 30, 2025

  1378 Chilean Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1960

  Last Sold Summary

  • $168/SF

  Current Estimated Value $350,528

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1378 Chilean Ln, Winter Park, FL 32792
• 

  

  /2

  Not Listed For Sale

  5101 N Orange Ave, Winter Park, FL 32792

  • 6 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1956

  5101 N Orange Ave, Winter Park, FL 32792

  Last Sold Summary

  • $265/SF
  • 198 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Sonia Reyes INVESTOR'S HOME REALTY
• 

  

  

  /66

  $2,395,000

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
• 

  

  /37

  $5,900 per month

  • 4 Beds
  • 3 Baths
  • 2,741 Sq Ft
  • House for Rent

  220 W Reading Way, Winter Park, FL 32789

  Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be

  Thomas Hewitt HEWITT RESIDENTIAL, LLC

  220 W Reading Way, Winter Park, FL 32789
• 

  /2

  $1,575,000 Sold Aug 14, 2025

  1394 Grove Terrace, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,958 Sq Ft
  • Built 2002

  Last Sold Summary

  • $532/SF
  • 5 Days On Market

  Current Estimated Value $1,577,588

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
• 

  

  /31

  Est $268,311 Not Listed For Sale

  2419 Gallery View Dr Unit 10, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1985

  2419 Gallery View Dr Unit 10, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $288/SF
  • 3 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
• 

  

  /26

  $285,000 Open Sat 10AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft

  2401 Sun Valley Cir, Winter Park, FL 32792

  Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and

  Jamie Vanosdol EXP REALTY LLC

  2401 Sun Valley Cir, Winter Park, FL 32792
• 

  

  /35

  $1,312 - $2,492 per month

  Summerlin at Winter Park Apartments

  1 - 3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
• 

  /2

  $625,000 Sold Sep 29, 2025

  3759 Kinsley Place, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,251 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $278/SF
  • 50 Days On Market

  Current Estimated Value $623,389

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
• 

  

  /42

  Est $1,581,353 Not Listed For Sale

  1805 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft
  • Built 2014

  1805 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $483/SF
  • 12 Days On Market

  Last Sold Price $1,475,000

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  /54

  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with

  Brian Bauer SOUTHERN LAND & HOMES

  1367 Tierra Cir, Winter Park, FL 32792
• 

  

  /90

  $13,500 per month

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft
  • House for Rent

  1860 Via Contessa, Winter Park, FL 32789

  Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched

  Kelly Price KELLY PRICE & COMPANY LLC

  1860 Via Contessa, Winter Park, FL 32789
• 

  /2

  $285,000 Sold Sep 24, 2025

  7777 Fernbrook Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Above List Price
  • $261/SF
  • 3 Days On Market

  Current Estimated Value $278,208

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  7777 Fernbrook Way, Winter Park, FL 32792
• 

  

  /26

  Est $467,074 Not Listed For Sale

  2469 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 2019

  2469 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $200/SF
  • 58 Days On Market

  Last Sold Price $462,500

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
• 

  

  /38

  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  633 Lander Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. LOCATION, LOCATION, LOCATION! Welcome to this charming 3-bedroom, 2-bathroom home nestled in the heart of Winter Park!As you enter the home, you'll notice the living room and dining area flow seamlessly together, leading you into the kitchen featuring solid surface countertops and solid wood cabinetry. The

  Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

  633 Lander Rd, Winter Park, FL 32792
• 

  

  /39

  $910 - $1,544 per month

  San Jose Apartments

  1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  2353 Winter Woods Blvd, Winter Park, FL 32792
• 

  /2

  $675,000 Sold Mar 16, 2026

  620 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,075 Sq Ft
  • Built 1967

  Last Sold Summary

  • 9% Below List Price
  • $325/SF
  • 14 Days On Market

  Current Estimated Value $709,827

  Last Listing Agent Jason Asa LPT REALTY, LLC

  620 Darcey Dr, Winter Park, FL 32792
• 

  

  /47

  Est $1,125,358 Not Listed For Sale

  1939 Woodcrest Dr, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft
  • Built 2020

  1939 Woodcrest Dr, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $454/SF
  • 2 Days On Market

  Last Sold Price $1,170,000

  Last Listing Agent Angela McCloskey KELLER WILLIAMS REALTY AT THE PARKS
• 

  

  /45

  $499,000 Pending

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

  2809 Casa Aloma Way, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 2809 Casa Aloma — a beautifully updated 3-bedroom, 2-bath charming home located on a quiet cul-de-sac in desirable Winter Park. Originally one of the subdivision’s model homes "Monaco", this property blends French Provincial design with extensive modern upgrades. Major improvements include a 2021

  Curt Marksbury WATSON REALTY CORP., REALTORS

  2809 Casa Aloma Way, Winter Park, FL 32792
• 

  

  /7

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft
  • Condo for Rent

  7326 Swallow Run Unit 7326, Winter Park, FL 32792

  Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high

  Jiny Lee NOBSKA REAL ESTATE LLC

  7326 Swallow Run Unit 7326, Winter Park, FL 32792
• 

  /2

  $315,000 Sold Jan 01, 2026

  615 Warrenton Rd, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 50 Days On Market

  Current Estimated Value $312,189

  Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
• 

  /2

  Est $369,441 Not Listed For Sale

  7604 Aloma Pines Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2016

  7604 Aloma Pines Ct, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $194/SF
  • 326 Days On Market

  Last Sold Price $362,500

  Last Listing Agent Nakarid Melean INTERINVESTMENTS REALTY, INC.
• 

  

  /71

  $699,900

  • 4 Beds
  • 3 Baths
  • 2,702 Sq Ft

  3114 Heartleaf Place, Winter Park, FL 32792

  Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

  Nadia Kurakin CHAMPION HOMES

  3114 Heartleaf Place, Winter Park, FL 32792
• 

  

  /26

  $1,170 - $1,975 per month

  Central Place At Winter Park

  1 - 3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  7000 University Blvd, Winter Park, FL 32792
• 

  /2

  $325,000 Sold Dec 30, 2025

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 6 Days On Market

  Current Estimated Value $323,555

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
• 

  /2

  Est $436,076 Not Listed For Sale

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft
  • Built 2008

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $258/SF

  Last Sold Price $413,000

  Last Listing Agent Brock Stocksett HOMEVEST REALTY
• 

  

  /66

  $1,350,000

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft

  3711 Vinsetta Ct, Winter Park, FL 32792

  Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  3711 Vinsetta Ct, Winter Park, FL 32792
• 

  

  /14

  $5,895 per month

  • 4 Beds
  • 3 Baths
  • 2,207 Sq Ft
  • House for Rent

  1235 Via Estrella, Winter Park, FL 32789

  Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island,

  Kelly Price KELLY PRICE & COMPANY LLC

  1235 Via Estrella, Winter Park, FL 32789
• 

  /2

  $790,000 Sold Jun 05, 2025

  600 Brechin Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 12 Days On Market

  Current Estimated Value $781,081

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
• 

  /2

  Est $244,382 Not Listed For Sale

  7148 Swallow Run Unit E1, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft
  • Built 2008

  7148 Swallow Run Unit E1, Winter Park, FL 32792

  Last Sold Summary

  • 11% Below List Price
  • $175/SF
  • 21 Days On Market

  Last Sold Price $274,500

  Last Listing Agent Rich Lemon CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /23

  $250,000 Open Sat 10AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, Winter Park, FL 32792
• 

  

  /19

  $1,250 - $1,350 per month

  Eastbrook Apartments

  1 - 2 Beds

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792

  Nestled within the serene and picturesque neighborhood of Lake Howell, Eastbrook Apartments offers a peaceful lakeside living experience with all the conveniences of a big city. This charming community in the Winter Park area is ideal for those seeking a blend of tranquility and accessibility. With 29 exclusive units, Eastbrook provides an intimate living environment with spacious and

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792
• 

  /2

  $517,000 Sold Nov 07, 2025

  1628 Lawndale Cir, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $301/SF
  • 6 Days On Market

  Current Estimated Value $520,042

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  1628 Lawndale Cir, Winter Park, FL 32792
• 

  /2

  Est $269,156 Not Listed For Sale

  222 Balfour Dr Unit 14, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1985

  222 Balfour Dr Unit 14, Winter Park, FL 32792

  Last Sold Summary

  • 10% Below List Price
  • $238/SF
  • 206 Days On Market

  Last Sold Price $299,000

  Last Listing Agent Tricia Ramsby BHHS FLORIDA REALTY
• 

  

  /54

  $1,974,000

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
• 

  

  /23

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

  Cozy and well-maintained 2-bedroom, 2-bath condo, washer and dryer inside, located in the desirable Winter Park area. This spacious unit features an open and comfortable layout with abundant natural light, a functional kitchen, and a small patio perfect for relaxing. The community offers great amenities including a pool, tennis courts, shuffleboard, clubhouse and beautifully maintained grounds.

  Nohora Gomez COLDWELL BANKER REALTY

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
• 

  /2

  $690,000 Sold May 08, 2025

  1806 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $342/SF
  • 61 Days On Market

  Current Estimated Value $708,223

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1806 Mondrian Cir, Winter Park, FL 32789
• 

  /2

  Est $2,919,257 Not Listed For Sale

  1618 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 8 Baths
  • 4,807 Sq Ft
  • Built 2014

  1618 Holts Grove Cir, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $603/SF
  • 173 Days On Market

  Last Sold Price $2,900,000

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

Showing Results 121 - 160, Page 4 of 18