Winter Park, FL Homes

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  /28

  $145,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

  Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
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  /35

  $1,750 - $2,750 per month

  Hannibal Square

  2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  433 W New England Ave, Winter Park, FL 32789
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  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,609,583

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
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  /30

  Est $1,562,226 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789
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  /32

  $949,000

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  1929 S Lakemont Ave, Winter Park, FL 32792

  This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compton, offering a rare mix of style, comfort, and convenience. This home feels tucked away while still keeping you close to everything you love about Winter and Baldwin Park. Inside, the layout is open and easy to live in. The kitchen features stone countertops, stainless steel appliances, and a large island

  Brandon Geers COMPASS FLORIDA LLC

  1929 S Lakemont Ave, Winter Park, FL 32792
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  /12

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • House for Rent

  148 Oak Grove Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Amazing upgraded centrally located in Winter Park home. One story 3 bedrooms and 2 bathrooms. Location is amazing near jobs and main roads of Winter Park, short drive to I4. High ceilings in living and master bedroom and bath. New laminate flooring, being installed, in all bedrooms and common areas. Enjoy with family and friends the spacious and

  Salvatore Cavalieri THE CAVALIERI PROPERTY MANAGEMENT LLC

  148 Oak Grove Rd, Winter Park, FL 32789
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  /2

  $335,000 Sold Sep 23, 2025

  5144 N Orange Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $263/SF
  • 128 Days On Market

  Current Estimated Value $340,165

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5144 N Orange Ave, Winter Park, FL 32792
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  /47

  Est $248,989 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  200 Saint Andrews Blvd Unit 1203, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1203, Winter Park, FL 32792
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  /53

  $950,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,838 Sq Ft

  210 Laurel Park Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to 210 Laurel Park Court—a thoughtfully designed, single-story residence offering 4 bedrooms, 3 bathrooms, and a dedicated home office. Nestled on a ?-acre lot with a beautiful lake view of Lake Ann, this exquisite home is part of a private, gated enclave of just eight custom-built homes, perfectly situated close to everything you love about Winter

  Alireza Partovi EXP REALTY LLC

  210 Laurel Park Ct, Winter Park, FL 32792
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  /17

  $1,300 - $1,855 per month

  La Aloma

  1 - 3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  3040 Aloma Ave, Winter Park, FL 32792
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  /45

  $322,000 Sold Mar 12, 2025

  7319 Blue Jacket Place W, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,118 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $288/SF
  • 5 Days On Market

  Current Estimated Value $320,475

  Last Listing Agent Jennah LeBruno, LLC THE WILKINS WAY LLC

  7319 Blue Jacket Place W, Winter Park, FL 32792
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  /64

  Est $668,555 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,575 Sq Ft

  1327 Fountain Hills Ct, Winter Park, FL 32792

  1327 Fountain Hills Ct, Winter Park, FL 32792
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  /20

  $220,000

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

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

  This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

  Manny Celi YOUNG REAL ESTATE

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
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  /25

  $1,975 per month

  • 2 Beds
  • 2.5 Baths
  • 1,236 Sq Ft
  • Townhouse for Rent

  5169 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to Lazy Oaks condominium. This townhome features two levels with an open floor plan that consist of 2 bedrooms, 2.5 bathrooms, and a Florida Room. Also, it can be delivered furnished as well! Over 1200 sqft of living space awaits you with a upgraded laminate flooring, baseboards, lighting, and ceiling fans. A prime location that is nestled near Full Sail, UCF, Lynx bus stop, major

  Damon Mayers MAYERS REAL ESTATE LLC

  5169 Lazy Oaks Dr, Winter Park, FL 32792
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  /2

  $397,000 Sold Jul 01, 2025

  1109 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 83 Days On Market

  Current Estimated Value $395,719

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1109 Denton Rd, Winter Park, FL 32792
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  /2

  Est $369,246 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
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  $1,185,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,710 Sq Ft

  5236 Lake Howell Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. Experience the best of Winter Park living in this stunning new custom-built pool home situated on a generous .29-acre lot just 1.9 miles from Park Avenue. Designed with a modern aesthetic and built to the highest standards, this 4-bedroom, 3-bath residence is a true showcase of craftsmanship and luxury. Step inside to discover a stunning vaulted great room

  Troy Hensley BHHS FLORIDA REALTY

  5236 Lake Howell Rd, Winter Park, FL 32792
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  /35

  $991 - $1,737 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  /2

  $3,200,000 Sold Apr 30, 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $671/SF
  • 5 Days On Market

  Current Estimated Value $2,912,426

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
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  /18

  Est $252,443 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft

  7781 Country Place Unit J-1, Winter Park, FL 32792

  7781 Country Place Unit J-1, Winter Park, FL 32792
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  /30

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft

  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. The gourmet kitchen boasts 42” black cabinets, granite countertops, a decorative backsplash, and stainless steel appliances, making it a stunning focal point of the home. The open-concept dining and living room create a spacious feel, while ceramic tile and wood floors enhance

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
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  /11

  $3,800 per month

  • 4 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • House for Rent

  1690 Dale Ave, Winter Park, FL 32789

  Located in one of the best areas of Winter Park, this home offers top- rated schools, welcoming neighborhood, and unbeatable convenience. just a mile from Park Avenue, you will enjoy easy access to shops, restaurants, and all the charm Winter Park is known for.With plenty to do nearby and a family - friendly environment, this is the perfect place to raise a family and enjoy the Winter Park

  Farzaneh Alijani ZAMIN INC

  1690 Dale Ave, Winter Park, FL 32789
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  /2

  $145,000 Sold Aug 13, 2025

  7352 Swallow Run, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 802 Sq Ft
  • Built 1983

  Last Sold Summary

  • 39% Below List Price
  • $181/SF
  • 68 Days On Market

  Current Estimated Value $144,914

  Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

  7352 Swallow Run, Winter Park, FL 32792
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  /17

  Est $192,065 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7460 Swallow Run Unit 42, Winter Park, FL 32792

  7460 Swallow Run Unit 42, Winter Park, FL 32792
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  /32

  $649,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,951 Sq Ft

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  Under contract-accepting backup offers. Back on Market- Buyer Financing fell through--Beautiful Winter Park townhome that feels like a single-family residence. Situated on a private lane with no through-traffic. Ten-minute walk to Park Avenue and Rollins, five-minute walk to Lake Virginia. This exquisite end-unit is part of a sought-after 10-unit community. Three Bedrooms and two and a half

  Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

  595 Huntington Ave Unit 4, Winter Park, FL 32789
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  /30

  $1,802 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Community

  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

  3045 Aloma Ave, Winter Park, FL 32792
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  /2

  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $234,534

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  /30

  Est $624,441 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  1086 Azalea Ln Unit 1, Winter Park, FL 32789
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  /26

  $572,500

  • 2 Beds
  • 2 Baths
  • 858 Sq Ft

  640 N Park Ave Unit 26, Winter Park, FL 32789

  A gem in the heart of the city -was completely renovated in 2024, downtown Winter Park -walk to restaurants and shopping, ample parking and private storage. Laundry on 3rd floor and basement. Can be leased. Lots of south sunlight, #26 is on the 2nd floor overlooking pool area. New appliances. Rare opportunity to own in Park Aire!

  Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

  640 N Park Ave Unit 26, Winter Park, FL 32789
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  /36

  $4,950 per month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst Ave, Winter Park, FL 32789
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  /2

  $385,000 Sold Apr 03, 2025

  1873 Poinciana Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,904 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $202/SF
  • 2 Days On Market

  Current Estimated Value $403,451

  Last Listing Agent Benondre Cerezo COLDWELL BANKER REALTY

  1873 Poinciana Rd, Winter Park, FL 32792
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  /2

  Est $1,258,062 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft

  1782 Mondrian Cir, Winter Park, FL 32789

  1782 Mondrian Cir, Winter Park, FL 32789
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  /29

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,401 Sq Ft

  1670 Clematis Ln, Winter Park, FL 32792

  This stunning home has been completely renovated and is ready for you to move in! Featuring 3 bedrooms, 2 full bathrooms, and a screened-in pool with a spacious deck, it blends modern style with everyday comfort. Inside, you’ll find brand-new waterproof laminate flooring, fresh paint throughout, and stylish modern finishes that create a light and inviting atmosphere. The open and spacious common

  Gea Gomez LPT REALTY, LLC

  1670 Clematis Ln, Winter Park, FL 32792
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  /27

  $1,360 - $2,151 per month

  Westmount at Winter Park

  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

  1701 Lee Rd, Winter Park, FL 32789
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  /2

  $399,900 Sold Oct 08, 2025

  7553 Laurel Springs Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1973

  Last Sold Summary

  • $338/SF
  • 20 Days On Market

  Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

  7553 Laurel Springs Dr, Winter Park, FL 32792
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  /2

  Est $499,407 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  1303 Merrydale Way, Winter Park, FL 32792

  1303 Merrydale Way, Winter Park, FL 32792
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  /26

  $235,000 Pending

  • 1 Bed
  • 1 Bath
  • 772 Sq Ft

  700 Melrose Ave Unit J23, Winter Park, FL 32789

  Beautiful 1-Bedroom Condo in the Heart of Winter Park Located on the second floor close to ELEVATORS. Please click on virtual tour to get an over view of this exceptional community.This is stunning one-bedroom condo featuring beautiful wood floors, an updated kitchen with wood cabinetry, solid surface counter tops, and a tankless water heater. The remodeled bathroom boasts a spacious walk-in

  Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit J23, Winter Park, FL 32789
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  /12

  $1,399 per month

  • 2 Beds
  • 1 Bath
  • 660 Sq Ft
  • Townhouse for Rent

  1502 Michigan Ave Unit B, Winter Park, FL 32789

  Tucked along tree-lined Michigan Avenue, Unit B offers a bright, easygoing retreat in a quiet Winter Park setting near parks, shops, and local favorites. Inside, you’ll find a comfortable layout with flexible living space, a practical kitchen, and thoughtful touches that make day-to-day life simple. Natural light, neutral finishes, and a relaxed flow create an inviting backdrop for your style.

  Steve Simpson 407 PROPERTIES

  1502 Michigan Ave Unit B, Winter Park, FL 32789
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  /2

  $199,900 Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  /2

  Est $1,186,000 Not Listed For Sale

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

  1830 Pineview Cir, Winter Park, FL 32792

  1830 Pineview Cir, Winter Park, FL 32792

Showing Results 241 - 280, Page 7 of 18