Winter Park, FL Homes

• 

  

  

  /50

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 3,020 Sq Ft

  1287 Verdant Glade Place, Winter Park, FL 32792

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 384-3331

  1287 Verdant Glade Place, Winter Park, FL 32792
• 

  

  

  /18

  Starting at $1,330 Per Month

  • Studio - 2 Beds

  311 N Knowles Ave, Winter Park, FL 32789

  Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

  Park East - Park Knowles Apartments

  (689) 207-6470

  

  311 N Knowles Ave, Winter Park, FL 32789
• 

  

  /2

  $400,000 Sold Jul 16, 2025

  3443 Arnel Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 15 Days On Market

  Current Estimated Value $400,055

  Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
• 

  

  

  /42

  Est $1,551,593 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

  • 5% Above List Price
  • $483/SF
  • 12 Days On Market

  • Last Sold Price $1,475,000
  • Dec 29, 2023

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  

  /40

  $2,200,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,195 Sq Ft

  872 Granville Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. A rare offering in the highly sought-after Park Grove neighborhood, this expertly redesigned 4-bedroom residence blends elevated design with effortless everyday living. Originally renovated by award-winning interior designer John McClain and recognized with first-place honors in 2020, the home reflects a refined balance of style and functionality.??Ideally

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 485-7250

  872 Granville Dr, Winter Park, FL 32789
• 

  

  /19

  Starting at $1,250 Per Month

  • 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

  Eastbrook Apartments

  (631) 740-8886

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

  /2

  $2,050,000 Sold Apr 30, 2026

  1205 Mayfield Ave, Winter Park, FL 32789

  • Land
  • 23,958 Sq Ft
  • $3,727,273 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 89 Days On Market

  Current Estimated Value $2,230,763

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
• 

  

  /26

  Est $470,077 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

  • 2% Above List Price
  • $200/SF
  • 58 Days On Market

  • Last Sold Price $462,500
  • Jan 05, 2024

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
• 

  

  /33

  $220,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
• 

  

  /30

  Starting at $1,917

  Total Monthly Price

  • 1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar-all with an attentive team at your

  Rosalia Winter Park 55+ Active Adult Community

  (321) 732-8673

  

  3045 Aloma Ave, Winter Park, FL 32792
• 

  /2

  $890,000 Sold Jun 12, 2025

  1762 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $393/SF
  • 114 Days On Market

  Current Estimated Value $911,313

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1762 Mondrian Cir, Winter Park, FL 32789
• 

  

  /47

  Est $1,134,045 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

  • 3% Below List Price
  • $454/SF
  • 2 Days On Market

  • Last Sold Price $1,170,000
  • Apr 01, 2024

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

  

  /25

  $489,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1280 Gladiolas Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting

  

  Ian Trumbach

  FLORIDA PRESTIGIOUS HOMES INC

  (321) 577-0373

  1280 Gladiolas Dr, Winter Park, FL 32792
• 

  

  /27

  Starting at $1,469 Per Month

  • Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  Westmount at Winter Park

  (321) 248-5471

  

  1701 Lee Rd, Winter Park, FL 32789
• 

  /2

  $440,000 Sold Jan 29, 2026

  1621 Puritan Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Below List Price
  • $249/SF
  • 342 Days On Market

  Current Estimated Value $432,350

  Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
• 

  /2

  Est $375,678 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

  • 4% Above List Price
  • $194/SF
  • 326 Days On Market

  • Last Sold Price $362,500
  • Nov 01, 2024

  Last Listing Agent Nakarid Melean INTERINVESTMENTS REALTY, INC.
• 

  

  /54

  $625,000

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

  1174 Wildmeadow Run, Winter Park, FL 32792

  Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Situated on a quiet non-thru street, this SINGLE-STORY residence offers modern construction, refined finishes, and a thoughtfully designed layout for everyday living and easy entertaining. The open-concept design feels light and inviting, featuring WOOD-LOOK TILE FLOORING, crown molding, recessed lighting, CUSTOM

  

  Kara Lushear

  COLDWELL BANKER REALTY

  (321) 280-1735

  1174 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /30

  Starting at $1,200 Per Month

  • 1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  Signal Pointe

  (689) 207-5380

  

  2500 Howell Branch Rd, Winter Park, FL 32792
• 

  /2

  $800,000 Sold Apr 30, 2026

  737 N Capen Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft
  • Built 2021

  Last Sold Summary

  • 13% Below List Price
  • $415/SF
  • 99 Days On Market

  Current Estimated Value $872,499

  Last Listing Agent Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
• 

  /2

  Est $459,831 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

  • 11% Above List Price
  • $258/SF

  • Last Sold Price $413,000
  • Jun 01, 2023

  Last Listing Agent Brock Stocksett HOMEVEST REALTY
• 

  

  /36

  $399,999

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  721 Dunbar St, Winter Park, FL 32789

  Welcome to 721 Dunbar St in Winter Park, a 2-bedroom, 2-bath home with a simple layout and plenty of potential. This property offers a comfortable starting point for everyday living and a great opportunity for buyers who want a home they can make their own over time. Inside, the home offers practical living spaces and a layout that works well for daily routines. The two-bedroom, two-bath setup

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 344-8781

  721 Dunbar St, Winter Park, FL 32789
• 

  

  /16

  $2,495 Per Month

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  6877 Jackman Blvd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2639.90. That covers your base rent, $2495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  (689) 314-6885

  6877 Jackman Blvd, Winter Park, FL 32792
• 

  /2

  $1,088,000 Sold Jan 30, 2026

  1092 Wading Waters Cir, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $356/SF
  • 60 Days On Market

  Current Estimated Value $1,076,427

  Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

  1092 Wading Waters Cir, Winter Park, FL 32792
• 

  /2

  Est $259,598 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

  • 5% Below List Price
  • $175/SF
  • 21 Days On Market

  • Last Sold Price $274,500
  • Oct 04, 2024

  Last Listing Agent Rich Lemon CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /41

  $2,495,000

  • 5 Beds
  • 3.5 Baths
  • 4,011 Sq Ft

  1130 Park North Place, Winter Park, FL 32789

  Half-acre lot just steps from Park Avenue shopping and dining, tucked on a quiet cul-de-sac in the heart of Winter Park.This traditional two-story home offers a well-designed floorplan for both everyday living and entertaining. From the moment you enter, the home feels warm and inviting. The main level features a spacious primary suite along with connected living spaces that flow easily from

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 257-9480

  1130 Park North Place, Winter Park, FL 32789
• 

  

  /27

  Starting at $1,344 Per Month

  • 1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  Village Park Senior

  (689) 220-5720

  

  550 W Denning Dr, Winter Park, FL 32789
• 

  /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 $358,859

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

  1378 Chilean Ln, Winter Park, FL 32792
• 

  /2

  Est $285,653 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

  • 4% Below List Price
  • $238/SF
  • 206 Days On Market

  • Last Sold Price $299,000
  • Jan 08, 2025

  Last Listing Agent Tricia Ramsby BHHS FLORIDA REALTY
• 

  

  /31

  $499,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  841 W Swoope Ave, Winter Park, FL 32789

  This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 468-9259

  841 W Swoope Ave, Winter Park, FL 32789
• 

  

  /24

  Starting at $1,381 Per Month

  • 1 - 2 Beds

  3935 Sutton Place Blvd, Winter Park, FL 32792

  Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

  Alvista Winter Park

  (321) 316-5068

  

  3935 Sutton Place Blvd, Winter Park, FL 32792
• 

  /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 $1,551,460

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
• 

  /2

  Est $2,861,321 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% Below List Price
  • $603/SF
  • 173 Days On Market

  • Last Sold Price $2,900,000
  • Feb 07, 2025

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY
• 

  

  /23

  $1,825,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 3,655 Sq Ft

  2305 Coldstream Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 490-4786

  2305 Coldstream Dr, Winter Park, FL 32792
• 

  

  /35

  Starting at $1,441 Per Month

  • 1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  Stonecastle Apartment Homes

  (689) 219-6082

  

  2015 New Stonecastle Terrace, 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 $637,230

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
• 

  

  /43

  Est $1,770,852 Not Listed For Sale

  1809 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft
  • Built 2014

  1809 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 14% Above List Price
  • $423/SF
  • 8 Days On Market

  • Last Sold Price $1,550,000
  • May 12, 2023

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
• 

  

  /94

  $4,195,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,665 Sq Ft

  2020 Via Tuscany, Winter Park, FL 32789

  Under contract-accepting backup offers. PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept

  

  Mauro Costa

  VISTA CAY REALTY COMPANY

  (321) 978-0954

  2020 Via Tuscany, Winter Park, FL 32789
• 

  

  /16

  Starting at $1,599 Per Month

  • 2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  *Restricted units only*App and Admin special for only $175!Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

  The Vista at Winter Park

  (321) 415-9984

  

  4704 Lucier Ct, Winter Park, FL 32792
• 

  /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 $287,378

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  7777 Fernbrook Way, Winter Park, FL 32792
• 

  /2

  Est $1,838,118 Not Listed For Sale

  1411 Border Dr, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 4,638 Sq Ft
  • Built 2019

  1411 Border Dr, Winter Park, FL 32789

  Last Sold Summary

  • 9% Above List Price
  • $364/SF
  • 195 Days On Market

  • Last Sold Price $1,690,000
  • Sep 27, 2024

  Last Listing Agent Ana Scarlato CORCORAN PREMIER REALTY

Showing Results 81 - 120, Page 3 of 18