Winter Park, FL Homes

• 

  

  

  /41

  $725,000

  • Land
  • 0.34 Acre
  • $2,132,353 per Acre

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789

  Here it is! Almost impossible to find 2 adjacent 75x100 R-3 lots for a total of 75x200 or 15,000 sq/ft in top Winter Park location! Located at northwest corner of proposed Winter Park Commons project. The vacant lot to be simultaneously purchased with adjacent parcel (TAX ID 06-22-30-1168-02-022) fronting Webster with BONUS 4/2 Bungalow. Walk to WP Village, Park Ave, WP9 Golf, Hannibal Square

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789
• 

  

  

  /9

  $702,000 per month

  • Property for Rent

  7839 University Garden Dr, Winter Park, FL 32792

  Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417,

  Shettle Huynh FLORIDA REALTY INVESTMENTS

  7839 University Garden Dr, Winter Park, FL 32792
• 

  

  /2

  $2,495,000 Sold Jul 21, 2025

  • 3,967 Sq Ft
  • $629/SF
  • 56 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2020

  1690 Palm Ave, Winter Park, FL 32789

  This Fabulous transitional 5 bedroom pool home is perfect for family living & entertaining & just minutes from downtown Winter Park's shopping, entertainment & dining on Park Avenue. Floor plan is ideal w/ 2 bedroom suites downstairs plus office/flex space. Meticulously constructed by Austin Homes, modern & traditional elements blend together w/ its open layout & clean lines. Main floor features

  Daniel Robinson HOUWZER INC

  1690 Palm Ave, Winter Park, FL 32789
• 

  

  

  /14

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,470 Sq Ft

  171 Stefanik Rd, Winter Park, FL 32792

  171 Stefanik Rd, Winter Park, FL 32792
• 

  

  

  /34

  $725,000

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Stop the car! Check out this classic 4/2 Florida ranch PLUS vacant lot ready for renovation! Newer roof, water heater. HW and tile floors, screened porch, utility/storage room. 1 car carport. OR develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave, Winter Park, FL 32789
• 

  

  /35

  $2,600 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  850 W Canton Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This beautifully maintained single-family home offers 2 bedrooms, 2 full bathrooms, a bright sunroom, and a versatile bonus room perfect for a home office, guest space, or hobby room. Easy-care tile flooring runs throughout, creating a clean and modern feel.The galley-style kitchen shines with granite countertops, stainless steel appliances,

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  850 W Canton Ave, Winter Park, FL 32789
• 

  /2

  $620,000 Sold Jul 21, 2025

  • 1,727 Sq Ft
  • $359/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  2855 Lion Heart Rd, Winter Park, FL 32792

  Welcome to 2855 Lion Heart Dr, Winter Park — a beautifully remodeled home that seamlessly combines modern comfort with an unbeatable location. This move-in ready residence features a brand-new kitchen with smart stainless steel appliances, completely updated bathrooms, new luxury flooring throughout, and an open-concept layout perfect for entertaining. Major upgrades include a new roof (2025) and

  Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
• 

  

  /17

  Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,128 Sq Ft

  110 Stefanik Rd, Winter Park, FL 32792

  110 Stefanik Rd, Winter Park, FL 32792
• 

  

  /68

  $658,900

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft

  3110 Heartleaf Place, Winter Park, FL 32792

  Beautiful pool home with an open great room plan with high vaulted ceilings and master on the first floor situated on one of the largest lots in the subdivision with over an acre of land that extends all the way to Howell Creek. You’ll love the open and airy feel from the high ceilings and master suite features a large walk in closet and garden tub. Roof is 2022. The kitchen and formal dining

  Hojin Chang RE/MAX PRIME PROPERTIES

  3110 Heartleaf Place, Winter Park, FL 32792
• 

  

  /23

  $1,650 per month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great location. Don’t miss the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
• 

  /2

  $350,000 Sold Jul 21, 2025

  • 1,682 Sq Ft
  • $208/SF
  • 70 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  1541 Florentino Ln, Winter Park, FL 32792

  MOTIVATED SELLER! Beautifully maintained Townhome in desirable gated community of Vistas at Lake Howell. This spacious 3 bedroom 2 and 1 half bath home is ready for its new owner. With new carpet, paint and appliances it's in move-in condition. Large kitchen overlooks the expansive dinning living room combination with sliding doors leading out to the screened-in patio. Upstairs you will find the

  Jeffrey Friedman FANNIE HILLMAN & ASSOCIATES

  1541 Florentino Ln, Winter Park, FL 32792
• 

  

  /3

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  100 Stefanik Rd, Winter Park, FL 32792

  100 Stefanik Rd, Winter Park, FL 32792
• 

  

  /39

  $509,000

  • 4 Beds
  • 2 Baths
  • 1,508 Sq Ft

  2844 Scarlet Rd, Winter Park, FL 32792

  Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful, contemporary updates. Nestled in the highly sought-after neighborhood of Winter Park Pines, this 4-bedroom, 2-bathroom home offers over 1,500 sq ft of stylish, functional living space—and yes, your mail is still delivered to the front door! Step through a tastefully renovated entryway into an open, airy

  Amy Turner KELLER WILLIAMS WINTER PARK

  2844 Scarlet Rd, Winter Park, FL 32792
• 

  

  /7

  $1,450 per month

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft
  • Townhouse for Rent

  1512 Indiana Ave Unit B, Winter Park, FL 32789

  Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and dining room and Kitchen complete with all appliances included and great counter space. The master bedroom is spacious and bright with a large walk-in closet that also leads into the bathroom! Bathroom with shower. Washer and dryer combo included! Just a mile away from the amazing

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1512 Indiana Ave Unit B, Winter Park, FL 32789
• 

  /2

  $2,910,000 Sold Jul 21, 2025

  • 5,097 Sq Ft
  • $571/SF
  • 82 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 2001

  1911 Stonehurst Rd, Winter Park, FL 32789

  Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle.The red brick facade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1911 Stonehurst Rd, Winter Park, FL 32789
• 

  

  /17

  Est $302,346 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,554 Sq Ft

  2644 Passamonte Dr Unit 7C, Winter Park, FL 32792

  2644 Passamonte Dr Unit 7C, Winter Park, FL 32792
• 

  

  /7

  $795,000

  • Land
  • 0.19 Acre
  • $4,184,211 per Acre

  1780 Bryan Ave, Winter Park, FL 32789

  Positioned in the heart of Winter Park, this exceptional lot presents a rare opportunity to build your dream home in one of the prestigious communities in Central Florida. Just minutes from the charm and elegance of Park Avenue, you’ll enjoy effortless access to the Winter Park chain of lakes, boutique shopping, acclaimed dining, art galleries and the vibrant cultural scene that defines the

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  1780 Bryan Ave, Winter Park, FL 32789
• 

  

  /17

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
• 

  /2

  $689,500 Sold Jul 19, 2025

  • 1,750 Sq Ft
  • $394/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1129 Golfside Dr, Winter Park, FL 32792

  Nestled on an idyllic tree-lined street, this charming 3-bedroom, 2-bathroom POOL HOME offers the Winter Park Lifestyle you've been dreaming of! Step inside to discover a beautifully appointed kitchen featuring granite countertops and NEW STAINLESS STEEL APPLIANCES. The light and bright formal dining room flows seamlessly into the spacious family room, complete with vaulted ceilings and a cozy

  Tess Muccigrosso RE/MAX 200 REALTY

  1129 Golfside Dr, Winter Park, FL 32792
• 

  

  /24

  Est $651,408 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,265 Sq Ft

  5303 Pine Lily Cir, Winter Park, FL 32792

  5303 Pine Lily Cir, Winter Park, FL 32792
• 

  

  /38

  $560,000

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  8065 Pleasant Pine Cir, Winter Park, FL 32792

  **This property qualifies for a closing cost credit up to $8,800 through the Seller’s preferred lender.**Welcome home to this beautifully maintained 4-bedroom, 2-bathroom home nestled on a serene conservation lot in the heart of Winter Park. As you step inside, you’ll find two guest bedrooms at the front of the home with a full bathroom conveniently situated between them. Down the hallway is the

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  8065 Pleasant Pine Cir, Winter Park, FL 32792
• 

  /2

  $2,475 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  2748 Bright Bird Ln, Winter Park, FL 32792

  2023 Townhome with 3 bedrooms and 2.5 bathrooms located in gated community a resort-style pool with a cabana. High-speed 1GB fiber optic internet and 75 cable channels are included in the rent. Enclosed attached 1 car garage and driveway parking. Stone countertops, SS appliances, and tile floors on level one, all bedrooms and laundry are upstairs.

  Hasan Shahab EXP REALTY LLC

  2748 Bright Bird Ln, Winter Park, FL 32792
• 

  /2

  $142,000 Sold Jul 18, 2025

  • 678 Sq Ft
  • $209/SF
  • 64 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1973

  130 Lewfield Cir Unit 130, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome Home! Step into effortless style and convenience with this beautifully updated second floor condo located in the sought after Stratford community of Winter Park. With thoughtful upgrades throughout including a modern kitchen with new appliances, and luxury vinyl and tile flooring, this home is move-in ready and full of charm. Enjoy the

  Renee Kumar LA ROSA REALTY LLC

  130 Lewfield Cir Unit 130, Winter Park, FL 32792
• 

  

  /66

  Est $730,765 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1006 Wildmeadow Run, Winter Park, FL 32792

  1006 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /59

  $339,499

  • 2 Beds
  • 2 Baths
  • 1,126 Sq Ft

  1405 Auburn Green Loop, Winter Park, FL 32792

  Searching in Winter Park Orlando? Why buy a condo with high maintenance fees when you can buy a 2/2 2 car garage CBS home in Country Lane? NEW ROOF IN PROCESS! A lovely front porch and new roof installed by closing. Pay low association fees $46.33/month ( $556/yearly). This home also features a spacious screened back porch that overlooks a beautiful fully fenced backyard, generous and bright

  Geannina Mejia-Acevedo Charles Rutenberg Realty Orlan

  1405 Auburn Green Loop, Winter Park, FL 32792
• 

  /2

  $900,000 Sold Jul 18, 2025

  • 2,286 Sq Ft
  • $394/SF
  • 63 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1971

  100 S Interlachen Ave Unit 304, Winter Park, FL 32789

  Indulge in serene lakefront living from the comfort of two private balconies, each offering views of both the pool and the lake. This expansive, combined residence boasts the most generous square footage of any single unit within The Cloisters. Thoughtfully connected by an interior passthrough, it presents an ideal layout for elegant multi-generational living.Each wing of the home features

  Greg Vazzana FANNIE HILLMAN & ASSOCIATES

  100 S Interlachen Ave Unit 304, Winter Park, FL 32789
• 

  

  /48

  Est $571,655 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  7875 Pleasant Pine Cir, Winter Park, FL 32792

  7875 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /11

  $3,950,000

  • Land
  • 8.34 Acres
  • $473,621 per Acre

  2403 Euston Rd, Winter Park, FL 32789

  Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  2403 Euston Rd, Winter Park, FL 32789
• 

  /2

  $755,000 Sold Jul 18, 2025

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

  • 241 Days On Market

  1000 Howell Branch Rd, Winter Park, FL 32789

  Welcome home to 1000 Howell Branch Road, a canal front private oasis. This recently cleared lot is located on an oversized half acre+ lot with a recently dredged fresh water canal frontage, with easy access to Lake Maitland/Winter Park Chain of lakes. Hurry, it’s currently the only vacant lot available on the Chain of lakes. The private backyard is backed up to more than 2 acres of conservation

  Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1000 Howell Branch Rd, Winter Park, FL 32789
• 

  

  /20

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  7348 Daniel Webster Dr Unit 1, Winter Park, FL 32792

  7348 Daniel Webster Dr Unit 1, Winter Park, FL 32792
• 

  

  /23

  $330,000

  • 3 Beds
  • 2 Baths
  • 987 Sq Ft

  1921 Dartmouth Ave, Winter Park, FL 32789

  $5K SELLER CONCESSION TOWARDS BUYER'S CLOSING COSTS AND PRE-PAIDS!!!Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that makes every square foot count! Nestled perfectly between Winter Park and College Park, this fully renovated gem blends modern upgrades with timeless charm. From the moment you arrive, the custom-built

  Pat Hancock THOMAS LYNNE REALTY GROUP LLC

  1921 Dartmouth Ave, Winter Park, FL 32789
• 

  /2

  $420,000 Sold Jul 17, 2025

  • 1,734 Sq Ft
  • $242/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1976

  5334 Cypress Dr, Winter Park, FL 32792

  Meticulously maintained 4-bedroom, 2-bath concrete block home in desirable Winter Park, lovingly cared for by the same owners for 37 years. Upgrades include a remodeled kitchen, updated master and guest baths, double-pane windows, and re-piping (2014). HVAC and electrical panels replaced in 2016. Roof, screen porch, and patio updated in 2022. Enjoy the beautifully landscaped backyard with St.

  Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

  5334 Cypress Dr, Winter Park, FL 32792
• 

  

  /37

  Est $175,244 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 Saint Andrews Blvd Unit 608, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 608, Winter Park, FL 32792
• 

  

  /18

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  3220 Netherwood Dr, Winter Park, FL 32792

  Incredible Investment Opportunity in a Desirable Location!This 2-bedroom, 1.5-bath home is full of potential and ready for a transformation. It's a fantastic opportunity for investors, flippers, or anyone seeking a high-potential investment. With just a little TLC, this property can be turned into a beautiful primary residence or a strong income-producing rental. Whether you're looking to

  Nimrah Ashraf THE FIRM RE

  3220 Netherwood Dr, Winter Park, FL 32792
• 

  /2

  $550,000 Sold Jul 17, 2025

  • 1,867 Sq Ft
  • $295/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  1387 Sawgrass Ct, Winter Park, FL 32792

  Tucked away on a peaceful cul-de-sac, 1387 Sawgrass Court welcomes you home. This pristine, 1867 sq ft, single-story residence stands out with its distinctive and mature landscaping, perfectly nestled within a tree-lined, golf-front community. Located on a serene pond along the 15th hole of Winter Park Pines Golf Course (WP18), it offers a retreat with no rear neighbors- ideal for quiet

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  1387 Sawgrass Ct, Winter Park, FL 32792
• 

  

  /21

  Est $296,774 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  5752 Marble Ct, Winter Park, FL 32792

  5752 Marble Ct, Winter Park, FL 32792
• 

  

  /58

  $3,799,000

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  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 automation offers a blend of luxury and function. Designed with sleek lines and open-concept living, the home showcases Italian engineered wood flooring throughout, creating an elegant yet inviting atmosphere. Expansive windows flood the interiors with natural light, seamlessly

  Nathalie Bates PREMIER SOTHEBY'S INTL. REALTY

  1742 Temple Dr, Winter Park, FL 32789
• 

  /2

  $270,000 Sold Jul 17, 2025

  • 1,043 Sq Ft
  • $259/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  463 Warrenton Rd Unit 463, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Multiple Offers Received. Please present highest and best by 3pm on June 30th. Immaculate and move-in ready, this beautifully maintained 2 bed/2 bath one-story condo in sought after Winter Park Pines offers comfort, style and convenience. Step through your front courtyard, perfect for enjoying morning coffee and into a spacious great room featuring

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  463 Warrenton Rd Unit 463, Winter Park, FL 32792
• 

  

  /37

  Est $1,192,797 Not Listed For Sale

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

  325 Park North Ct, Winter Park, FL 32789

  325 Park North Ct, Winter Park, FL 32789
• 

  

  /47

  $725,000

  • 5 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  7895 Pleasant Pine Cir, Winter Park, FL 32792

  Seller Motivated – All Offers WelcomeDiscover your dream home in the prestigious gated community of Enclave at Aloma in Winter Park. This beautifully maintained 5-bedroom, 3.5-bath residence offers the perfect blend of elegance, comfort, and privacy—set on a tranquil lot with no rear neighbors.The moment you enter, you’ll be captivated by the rich engineered hardwood floors

  Yvette Hoover ALL REAL ESTATE & INVESTMENTS

  7895 Pleasant Pine Cir, Winter Park, FL 32792

Showing Results 641 - 680, Page 17 of 18