Winter Park, FL Homes

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  $765,000

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  625 Brechin Dr, Winter Park, FL 32792

  PICTURE PERFECT HOME IN WINTER PARK’S KENILWORTH SHORES! Homes of this quality and preservation hardly come on the market – this immaculately kept, 3-bedroom, 2 bath home offers 1,827 SF and a stunning backyard oasis! Interior offers a spacious living room, dining room, and Florida room. The elongated galley kitchen features beautiful hardwood cabinetry, solid countertops, built-in double ovens,

  Kelly Price KELLY PRICE & COMPANY LLC

  625 Brechin Dr, Winter Park, FL 32792
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  $1,273 - $3,471 per month

  Liv at Winter Park Apartment Homes

  Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  $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

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
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  /44

  Est $850,041 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  436 W Swoope Ave, Winter Park, FL 32789

  436 W Swoope Ave, Winter Park, FL 32789
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  /23

  $259,900

  • 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
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  /14

  $1,495 per month

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

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792

  This is a 2 bedroom, 2 bathroom, second floor condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include a spacious main living area, a lovely kitchen, vaulted ceilings, spacious bedrooms, and a laundry closet. Community amenities include a pool, gym, and clubhouse. Schedule a showing or submit an application online. All Real Property Management &

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792
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  $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

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  7777 Fernbrook Way, Winter Park, FL 32792
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  /33

  Est $632,489 Not Listed For Sale

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

  5319 Pine Lily Cir, Winter Park, FL 32792

  5319 Pine Lily Cir, Winter Park, FL 32792
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  $439,000

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft

  1842 Puritan Ave, Winter Park, FL 32792

  Modern design, Open concept layout, Sleek quartz counter top, All new appliances, New luxury vinyl plank flooring, New lanai upgrade. This beautiful 4 bedrooms and 2 full bath is situated on a 8,250 square feet lot was newly fenced in 2024 which gives a sense of privacy and spaciousness as you enter into the lanai. There is two detached sheds for your storage convenience. This beautiful done was

  Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

  1842 Puritan Ave, Winter Park, FL 32792
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  $999 - $1,760 per month

  Winter Park Woods

  Studio - 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
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  $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 $776,151

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 687 Sq Ft

  700 Melrose Ave Unit G, Winter Park, FL 32789

  700 Melrose Ave Unit G, Winter Park, FL 32789
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  $4,595,000

  • 4 Beds
  • 5 Baths
  • 3,181 Sq Ft

  1336 College Point, Winter Park, FL 32789

  Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1336 College Point, Winter Park, FL 32789
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  /15

  $1,975 per month

  • 4 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  275 N Capen Ave, Winter Park, FL 32789

  This unique, old Florida style 4 ba / 2 ba 1180 sqft home features a single car garage, two baths, three smaller bedrooms and a master bedroom with walk in closet. Less than a mile away from desirable Park Avenue, and Rollins Collage. Washer/dryer included. Application Fee: $50 each adult (18+)**Full Credit/Skip/Eviction/Background check is done on all applicants.**Please have the

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  275 N Capen Ave, Winter Park, FL 32789
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  $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 $715,739

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1806 Mondrian Cir, Winter Park, FL 32789
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  /31

  Est $193,974 Not Listed For Sale

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

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792
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  /29

  $750,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  1213 Lindenwood Ln, Winter Park, FL 32792

  Discover the perfect blend of mid-century modern architecture and contemporary living in this beautifully updated 4-bedroom, 2-bath residence offering over 2,500 square feet of thoughtfully designed space. Situated on a spacious lot in a private cul-de-sac, this home features an inviting open floor plan, soaring vaulted ceilings, and abundant natural light that highlights its clean lines and

  Amy Turner KELLER WILLIAMS WINTER PARK

  1213 Lindenwood Ln, Winter Park, FL 32792
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  $1,221 - $2,975 per month

  ARIUM Winter Park

  1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
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  /2

  $360,000 Sold Apr 30, 2025

  1493 Hyde Park Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $256/SF
  • 4 Days On Market

  Current Estimated Value $361,359

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  1493 Hyde Park Dr, Winter Park, FL 32792
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  /15

  Not Listed For Sale

  • 2 Beds
  • 3,098 Sq Ft

  1858 Cornell Ave, Winter Park, FL 32789

  1858 Cornell Ave, Winter Park, FL 32789
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  $1,649,999

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

  1166 Oaks Blvd, Winter Park, FL 32789

  HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space. Relax on

  Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  /48

  $10,950 per month

  • 4 Beds
  • 3 Baths
  • 2,918 Sq Ft
  • House for Rent

  2220 Via Tuscany, Winter Park, FL 32789

  Now available fully furnished, this elegant single-story residence on Winter Park’s prestigious Via Tuscany offers an exceptional opportunity to lease in one of Central Florida’s most coveted neighborhoods. Just steps from the Winter Park Racquet Club, this thoughtfully updated home features four bedrooms, three bathrooms, and designer-appointed interiors curated for both comfort and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2220 Via Tuscany, Winter Park, FL 32789
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  $351,000 Sold Sep 09, 2025

  1041 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $209/SF
  • 147 Days On Market

  Last Listing Agent Bob Paulson COLDWELL BANKER RESIDENTIAL RE

  1041 Manchester Cir, Winter Park, FL 32792
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  Est $1,635,132 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft

  1318 Chapman Cir, Winter Park, FL 32789

  1318 Chapman Cir, Winter Park, FL 32789
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  /54

  $1,973,450

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

  2614 Parkland Dr, Winter Park, FL 32789

  One of the most competitively priced, 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 exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
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  $1,344 - $2,832 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
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  $329,900 Sold Jan 30, 2025

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1960

  Last Sold Summary

  • $684/SF
  • 3 Days On Market

  Current Estimated Value $322,715

  Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789
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  /9

  Est $282,517 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  5774 Shale Ct, Winter Park, FL 32792

  5774 Shale Ct, Winter Park, FL 32792
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  $440,000 Pending

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

  1621 Puritan Ave, Winter Park, FL 32792

  Under contract-accepting backup offers. Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated pool home located in the highly desirable Winter Park area on the Seminole County side. This property qualifies for multiple down payment assistance programs, making it an excellent opportunity for first-time buyers. Recent upgrades include a new roof (2023), resurfaced

  Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
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  /22

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Townhouse for Rent

  2552 Gold Ct, Winter Park, FL 32792

  Welcome to 2552 Gold Court – Your Perfect Winter Park Rental Home!Discover comfortable living in this beautifully renovated 3-bedroom, 2-bath duplex offering approximately 1,020 square feet of thoughtfully designed space. This move-in ready home combines modern updates with practical amenities to create the ideal rental experience.This charming residence features a bright, open floor plan

  Kelly Price KELLY PRICE & COMPANY LLC

  2552 Gold Ct, Winter Park, FL 32792
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  $550,000 Sold May 08, 2025

  2906 Rapidan Trail, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1965

  Last Sold Summary

  • $236/SF
  • 4 Days On Market

  Current Estimated Value $609,023

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2906 Rapidan Trail, Winter Park, FL 32789
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  /24

  Est $189,253 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  229 Lewfield Cir Unit 229, Winter Park, FL 32792

  229 Lewfield Cir Unit 229, Winter Park, FL 32792
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  /28

  $650,000

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

  2920 Abbey Ct, Winter Park, FL 32792

  Completely Renovated and Move-In Ready! A rare found NO HOA Winter Park POOL home with top rated schools.. This 5-bedroom, 3-bath pool home has been renovated from top to bottom—featuring: NEW ROOF 2025, NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025),FRESH INTERIOR & EXTERIOR PAINT (2025) NEW POOL DECK, FILTER (2025) UPGRADED ELECTRICAL PANEL (2025) REPLUMBED (2010) AC (2016)

  Joselyne Muszynski ORLANDO INTERNATIONAL RELOCATION REALTY

  2920 Abbey Ct, Winter Park, FL 32792
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  $903 - $1,535 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
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  $2,285,000 Sold Nov 19, 2025

  521 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,883 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $588/SF
  • 118 Days On Market

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
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  Est $1,958,617 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,954 Sq Ft

  1433 Sarazens Place, Winter Park, FL 32792

  1433 Sarazens Place, Winter Park, FL 32792
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  /37

  $824,900 Pending

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

  737 N Capen Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this stunning Mid-century style 3 bedroom, 2 bath, 1930 sq ft home with a 2 car garage, where sleek modern design meets functionality. Step into the open-concept living space and be captivated by the abundance of natural light streaming through the large windows, creating a warm and inviting atmosphere. The centerpiece of this home is the gourmet

  Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
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  /7

  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Condo for Rent

  654 Trinidad Ct Unit 654, Winter Park, FL 32792

  LOCATION, LOCATION, Beautiful and well-maintained 2-bedroom, 2-bath condo for rent in the desirable Winter Park Villas community. This spacious unit offers approximately 1,120 sq ft of comfortable living space, featuring an open living/dining layout, updated flooring, ample natural light, and generous storage including walk-in closets. The kitchen comes equipped with essential appliances, and the

  Jean Fernandez LA ROSA REALTY KISSIMMEE

  654 Trinidad Ct Unit 654, Winter Park, FL 32792
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  $430,000 Sold Jul 25, 2025

  2003 Bentwood Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,675 Sq Ft
  • Built 1981

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 16 Days On Market

  Current Estimated Value $429,589

  Last Listing Agent Heather Kolin PALMANO GROUP RE BROKERAGE LLC

  2003 Bentwood Dr, Winter Park, FL 32792
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  Est $547,478 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

Showing Results 121 - 160, Page 4 of 18