Recently Sold Homes in 32789

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  $799,000 Sold Apr 30, 2025

  • Land
  • 0.28 Acre
  • $2,853,571 per Acre

  • 2 Days On Market

  2320 Janice Ave, Winter Park, FL 32789

  Amazing opportunity to build your dream home in Winter Park. A tremendous location with just a short stroll to East End Market and all the shops and restaurants Corrine Drive has to offer! Zoned for the Audubon K-8 school that you can also walk to! This lot is over a 1/4 of an acre and is tucked away at the end of a dead end street for privacy. This is one you don't want to miss!

  Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2320 Janice Ave, Winter Park, FL 32789
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  /2

  $3,200,000 Sold Apr 30, 2025

  • 4,770 Sq Ft
  • $671/SF
  • 5 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a

  Christopher Christensen COMPASS FLORIDA LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
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  /2

  $520,000 Sold Apr 30, 2025

  • 1,900 Sq Ft
  • $274/SF
  • 51 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1926

  1481 Harmon Ave, Winter Park, FL 32789

  Welcome Home to Orwin Manor – Where Historic Charm Meets Modern Comfort!Nestled in the heart of Winter Park’s highly sought-after Orwin Manor, this 1926 historic gem is brimming with character and thoughtfully updated for today’s lifestyle. Priced below a recent appraisal, this four-bedroom, three-bath home showcases original hardwood floors, a brand-new roof (2024), and reinforced crawl space

  Laura Napoleon KELLER WILLIAMS WINTER PARK

  1481 Harmon Ave, Winter Park, FL 32789
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  /2

  $430,000 Sold Apr 28, 2025

  • 1,226 Sq Ft
  • $351/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  2743 Sanbina St, Winter Park, FL 32789

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the heart of charming Winter Park!From the moment you step inside, you'll be greeted by an abundance of natural light that fills the space and highlights the beautifully polished terrazzo flooring and fresh interior paint throughout. The open and airy layout creates an inviting atmosphere perfect for both relaxing and

  Logan Coon KELLER WILLIAMS WINTER PARK

  2743 Sanbina St, Winter Park, FL 32789
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  /2

  $482,500 Sold Apr 28, 2025

  • 960 Sq Ft
  • $503/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  710 W Swoope Ave, Winter Park, FL 32789

  Bungalow with metal roof approximately one block from Winter Park mall. Considered an excellent location.

  Firmin Emanuel FIRMAN A. EMANUEL

  710 W Swoope Ave, Winter Park, FL 32789
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  /2

  $375,000 Sold Apr 28, 2025

  • 1,015 Sq Ft
  • $369/SF
  • 11 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1948

  2259 Minnesota Ave, Winter Park, FL 32789

  Come build your dream home on this oversized single family corner lot (62.5 by 141.5) in Winter Park Florida with amazing views of Dubsdread Golf Course hole 6. Located just a short drive or walk away from all your favorite shops and restaurants (Agave Azul, Publix, Tap Room, Black Bean Deli) Convenient access to I-4 making it easy to get around the greater Orlando area. Less than a minute drive

  Kayla Barnes LPT REALTY, LLC

  2259 Minnesota Ave, Winter Park, FL 32789
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  /2

  $635,000 Sold Apr 28, 2025

  • 901 Sq Ft
  • $705/SF
  • 53 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1971

  100 S Interlachen Ave Unit 111, Winter Park, FL 32789

  Fresh, modern and move-in ready. This pristine, first-floor condo is located in historic downtown Winter Park at the coveted Cloisters Condominiums. Professionally designed and remodeled in 2021, this two-bedroom, two-bathroom unit includes an open floor plan with marble tile throughout and a screened patio with built-in planters and mature garden views. The large, open kitchen includes a

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  100 S Interlachen Ave Unit 111, Winter Park, FL 32789
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  /2

  $535,000 Sold Apr 25, 2025

  • 1,795 Sq Ft
  • $298/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1947

  1531 Norfolk Ave, Winter Park, FL 32789

  Welcome to your dream home nestled in the highly sought-after College Park district of Winter Park! This charming residence seamlessly blends history with modern upgrades, offering a perfect balance of comfort and convenience.Step inside to discover a beautifully updated kitchen featuring elegant granite countertops, ideal for both casual meals and entertaining guests. The home now boasts 1,795

  Erica Diaz HOMEVEST REALTY

  1531 Norfolk Ave, Winter Park, FL 32789
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  /2

  $1,516,500 Sold Apr 24, 2025

  • 2,420 Sq Ft
  • $627/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  335 Beloit Ave, Winter Park, FL 32789

  A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course.Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space.

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  335 Beloit Ave, Winter Park, FL 32789
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  /2

  $1,295,000 Sold Apr 22, 2025

  • 2,795 Sq Ft
  • $463/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2017

  1601 Chestnut Ave, Winter Park, FL 32789

  Nestled in one of the most sought-after locations, the “Tree Streets” of Winter Park. 1601 Chestnut Avenue is a stunning Modern European Cottage-style home, built in 2017, that masterfully blends classic charm with modern finishes. Offering over 2,800 square feet, this pool home includes: four bedrooms, three full baths, and an over-sized loft. Step inside to hard wood flooring, complemented by

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  1601 Chestnut Ave, Winter Park, FL 32789
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  /2

  $580,000 Sold Apr 21, 2025

  • 1,710 Sq Ft
  • $339/SF
  • 1 Day On Market

  • 4 Beds
  • 2 Baths
  • Built 1953

  3006 Northwood Blvd, Winter Park, FL 32789

  Discover the perfect blend of classic charm and modern potential in this delightful single-family home with endless possibilities, nestled in a prime Winter Park location! This inviting fully fenced home features a comfortable layout with 3 bedrooms and 1 bathroom in the main living area. An exciting attached addition has a separate entrance leading to a spacious 4th bedroom and 2nd bathroom,

  Chris Creegan CREEGAN GROUP

  3006 Northwood Blvd, Winter Park, FL 32789
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  /2

  $4,100,000 Sold Apr 18, 2025

  • 4,582 Sq Ft
  • $895/SF
  • 1 Day On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  1691 Chestnut Ave, Winter Park, FL 32789

  Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park.  Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft.

  Sue Silberbusch COMPASS FLORIDA LLC

  1691 Chestnut Ave, Winter Park, FL 32789
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  /2

  $480,000 Sold Apr 17, 2025

  • 1,920 Sq Ft
  • $250/SF
  • 29 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1981

  423 Ololu Dr, Winter Park, FL 32789

  NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter ParkWelcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations.Prime Location:5 minutes to Whole Foods

  tanya fei AAA GLOBAL VENTURES PA

  423 Ololu Dr, Winter Park, FL 32789
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  /2

  $615,000 Sold Apr 17, 2025

  • 2,242 Sq Ft
  • $274/SF
  • 82 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  735 Maryland Ave, Winter Park, FL 32789

  Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets,

  Chuck Massab FANNIE HILLMAN & ASSOCIATES

  735 Maryland Ave, Winter Park, FL 32789
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  /2

  $1,630,000 Sold Apr 17, 2025

  • 3,174 Sq Ft
  • $514/SF
  • 146 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2009

  101 S New York Ave Unit 302, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This one-of-a-kind duplex in the heart of Winter Park stands out as the best value in town. Discover an unparalleled living experience in over 3,100 square feet of sophisticated space. Every detail- from the exquisite wood craftmanship which exudes classic Americana to the meticulously finished gourmet kitchen, this home truly speaks of timeless

  Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY

  101 S New York Ave Unit 302, Winter Park, FL 32789
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  /2

  $770,000 Sold Apr 15, 2025

  • 2,265 Sq Ft
  • $340/SF
  • 1 Day On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  1816 Mondrian Cir, Winter Park, FL 32789

  Welcome to The Mondrian Winter Park, where modern elegance meets serene waterfront living! This extraordinary community features 30 sleek townhomes nestled alongside the tranquil shores of enchanting Lake Killarney. Step inside and be captivated by the exquisite finishes that define this remarkable residence—a true testament to quality and sophistication. Upon entering, you’ll find a palette of

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1816 Mondrian Cir, Winter Park, FL 32789
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  /2

  $2,100,000 Sold Apr 15, 2025

  • 2,894 Sq Ft
  • $726/SF
  • 35 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  1032 Early Ave, Winter Park, FL 32789

  Discover your own slice of paradise on this extraordinary property spanning nearly five acres, perfectly nestled between two serene lakes in Winter Park. Offering unmatched privacy and tranquility, this retreat is ideal for those who value seclusion, natural beauty, and convenience—all within city limits, yet feeling a world away. With motorized boats allowed on both lakes, you can spend

  Teresa Corbett KINCAID REALTY

  1032 Early Ave, Winter Park, FL 32789
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  /2

  $649,000 Sold Apr 14, 2025

  • 1,545 Sq Ft
  • $420/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  721 Glenridge Way, Winter Park, FL 32789

  Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  721 Glenridge Way, Winter Park, FL 32789
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  /2

  $315,000 Sold Apr 14, 2025

  • 1,148 Sq Ft
  • $274/SF
  • 35 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  690 Osceola Ave Unit 308, Winter Park, FL 32789

  Seller motivated!!! **Prime Location & Endless Potential!** Fantastic opportunity to make it your own Oasis with some updating. Transform this condo with your personal design. Situated in Winter Park's most sought-after zip code, this spacious 2-bedroom, 2-bath lakefront condo is an incredible opportunity to create your perfect retreat. Enjoy your dock—ideal for a boat or paddle board—and unwind

  Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

  690 Osceola Ave Unit 308, Winter Park, FL 32789
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  /2

  $140,000 Sold Apr 14, 2025

  • 582 Sq Ft
  • $241/SF
  • 152 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1960

  151 N Orlando Ave Unit 142, Winter Park, FL 32789

  Introducing a charming 1 bed, 1 bath condo located on the serene shores of Lake Killarney in Winter Park Florida. Enjoy the perfect balance of lakeside tranquility, urban convenience, with a stunning sunset and being just a short walk to Trader Joe's, movie theaters, restaurants, and coffee shops. This home is ideal for someone seeking a peaceful retreat with all the benefits of a vibrant

  TOM NOELKE EXP REALTY LLC

  151 N Orlando Ave Unit 142, Winter Park, FL 32789
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  /2

  $1,885,000 Sold Apr 11, 2025

  • 3,499 Sq Ft
  • $539/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2024

  2144 Sycamore Dr, Winter Park, FL 32789

  Stunning new Winter Park residence.

  Christopher Christensen COMPASS FLORIDA LLC

  2144 Sycamore Dr, Winter Park, FL 32789
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  /2

  $175,000 Sold Apr 11, 2025

  • 730 Sq Ft
  • $240/SF
  • 230 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1964

  700 Melrose Ave Unit E6, Winter Park, FL 32789

  Welcome to this charming first-floor, one-bedroom, one-bathroom condo in the highly sought-after Winter Park Gardens community, exclusive 55+. This bright and airy home features an open floor plan with a spacious living area and a versatile sunroom, perfect for an additional living space or home office. The sunroom offers stunning views of the tranquil pond and lush garden, creating a serene

  Milton James COLDWELL BANKER RESIDENTIAL RE

  700 Melrose Ave Unit E6, Winter Park, FL 32789
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  /2

  $1,100,000 Sold Apr 10, 2025

  • 2,432 Sq Ft
  • $452/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  1932 Temple Dr, Winter Park, FL 32789

  Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street is full of natural light, clean lines and crisp open spaces. Three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and beckons the green of an outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1932 Temple Dr, Winter Park, FL 32789
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  /2

  $1,250,000 Sold Apr 10, 2025

  • 2,334 Sq Ft
  • $536/SF
  • 267 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  858 Douglas Ave, Winter Park, FL 32789

  Stunning residence in Winter Park! Experience luxury and convenience in this highly sought-after location, so close to everything, you can walk to Winter Park Village (.5 miles), Hannibal Square (.3 miles) and Park Avenue (.6 miles), and less than a block to the beautiful Lake Island Park. You will be the envy of all who visit.This home features a gourmet kitchen with waterfall island

  Greta Bost SUMMER WIND REALTY CENTRAL FL

  858 Douglas Ave, Winter Park, FL 32789
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  /2

  $799,000 Sold Apr 08, 2025

  • 2,331 Sq Ft
  • $343/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  Unlisted Address

  A pristine location to build the home of your dreams in the heart of the Tree Streets of Winter Park. Elm is a quiet tree-lined street providing tranquility while providing the lifestyle Winter Park is known for. Elm is a block from Phelps Park, a short walk to YMCA, Interlachen Country Club and Winter Park Racquet Club. The lot is roughly 75 by 122 feet and among multimillion-dollar homes. Home

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  Unlisted Address
• 

  /2

  $585,000 Sold Apr 07, 2025

  • 1,132 Sq Ft
  • $517/SF
  • 38 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1949

  1424 Cavendish Rd, Winter Park, FL 32789

  Welcome to 1424 Cavendish Road. This Beautiful 1940’s Pool Home is tucked between the tree-lined streets of highly desired, Orwin Manor, offering the perfect blend of classic appeal and modern convenience.Step into this charming home and experience its warm and inviting ambiance. The living room is bathed in natural light, with a cozy wood-burning fireplace that adds timeless character and

  Lisa Grey KEYSEEKERS REAL ESTATE

  1424 Cavendish Rd, Winter Park, FL 32789
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  /2

  $410,000 Sold Apr 04, 2025

  • 1,292 Sq Ft
  • $317/SF
  • 45 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1954

  2111 Staunton Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to a delightful property that boasts a modern, neutral-colored paint scheme throughout. The kitchen is a chef's dream, equipped with all stainless steel appliances. The outdoor area is perfect for entertaining, featuring a deck and covered patio in the backyard. The property also includes a fenced-in backyard, providing privacy and security.

  GREGORY BLACKALL VERANDA REALTY GROUP

  2111 Staunton Ave, Winter Park, FL 32789
• 

  /2

  $600,000 Sold Apr 04, 2025

  • 1,751 Sq Ft
  • $343/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  631 Callahan St, Winter Park, FL 32789

  **PRICED TO SELL** Welcome to this beautifully remodeled ranch-style home, where modern elegance meets timeless charm. Located less than half a mile from the vibrant heart of Park Avenue, this home has 1,750 square feet of living space, presenting the perfect blend of contemporary functionality. Remodeled in 2022, Roof replaced in 2023. New Paver Patio and Turf. Step inside to discover

  Yousef Zeidan CORCORAN PREMIER REALTY

  631 Callahan St, Winter Park, FL 32789
• 

  /2

  $1,000,000 Sold Apr 04, 2025

  • 2,458 Sq Ft
  • $407/SF
  • 141 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1001 Tuscany Place, Winter Park, FL 32789

  Located in the Tuscany Place neighborhood in the heart of Winter Park, this home offers endless potential for those looking to create their dream residence. With its classic ranch architecture and original features, this property is a blank canvas awaiting your personal touch, or provides a great opportunity to build new on its 0.39-acre corner lot. The home includes 3 bedrooms and 2 bathrooms, a

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
• 

  /2

  $1,290,000 Sold Apr 04, 2025

  • 2,350 Sq Ft
  • $549/SF
  • 173 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  840 W Comstock Ave, Winter Park, FL 32789

  Immerse yourself in the serenity this modern boutique home offers in the heart of Winter Park, FL. Walking up you are greeted by an adorable front patio enticing you to enjoy your favorite beverage amongst the lush landscape. Once inside the arched entry door you will be transported to an open floor plan with lots of natural light adorned with oversized windows, showcasing flora at every turn,

  Elizabeth Hall CHARLES RUTENBERG REALTY ORLANDO

  840 W Comstock Ave, Winter Park, FL 32789
• 

  /2

  $850,000 Sold Apr 03, 2025

  • 2,066 Sq Ft
  • $411/SF
  • 251 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1905 S Lakemont Ave, Winter Park, FL 32792

  Special financing or closing cost credits available for qualified buyers!Introducing the 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! This exceptional, move-in ready residence is perfectly situated between the serene shores of Lake Spier and Lake Compton in the exclusive Lake Spier Crossing community of Winter Park.Discover modern luxury with 10 impeccably designed two-story townhomes,

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1905 S Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $2,495,000 Sold Apr 01, 2025

  • 4,168 Sq Ft
  • $599/SF
  • 4 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1926

  140 Cortland Ave, Winter Park, FL 32789

  Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom,

  Stephen Hachey FLAT FEE MLS REALTY

  140 Cortland Ave, Winter Park, FL 32789
• 

  /2

  $1,877,500 Sold Apr 01, 2025

  • 4,612 Sq Ft
  • $407/SF
  • 5 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1925

  1446 Berkshire Ave, Winter Park, FL 32789

  Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads

  Jimmy Hendrickson SERHANT

  1446 Berkshire Ave, Winter Park, FL 32789
• 

  /2

  $685,000 Sold Mar 31, 2025

  • 1,267 Sq Ft
  • $541/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1971

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

  Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
• 

  /2

  $5,250,000 Sold Mar 31, 2025

  • 5,264 Sq Ft
  • $997/SF
  • 125 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2024

  210 Chelton Cir, Winter Park, FL 32789

  This gorgeous, new-construction FG Schaub custom home is the epitome of stunning contemporary design by architect, Michael Weinrich. As you enter this sprawling residence, with views of both Lake Sue and Lake Chelton you'll be greeted by exquisite tile work with brass inlays, wood floors, drop down ceiling, crown molding, wainscoting and natural light that pulls the outside living in. The first

  Laura Earl CORCORAN PREMIER REALTY

  210 Chelton Cir, Winter Park, FL 32789
• 

  /2

  $1,100,000 Sold Mar 28, 2025

  • 2,651 Sq Ft
  • $415/SF
  • 42 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1912

  567 Osceola Ave, Winter Park, FL 32789

  Walk to beautiful downtown Winter Park for fabulous shopping, restaurants, SunRail/Amtrak station and just steps to Rollins College campus. Make yourself at home in this beautifully restored historic 4 bedroom 3 ½ bath home with award winning finishes. Quality features include beautiful hardwood floors, intricate crown moldings, high ceilings and an expansive wraparound front porch. The open

  Susannah Dance COLDWELL BANKER RESIDENTIAL RE

  567 Osceola Ave, Winter Park, FL 32789
• 

  /2

  $2,400,000 Sold Mar 28, 2025

  • 4,074 Sq Ft
  • $589/SF
  • 94 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2017

  1010 N Pennsylvania Ave, Winter Park, FL 32789

  New price is $150K below a November 2024 appraisal! Home has been pre-inspected; seller is willing to share the 4PT Report as well as the appraisal. Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market.

  Dana Laing BHHS FLORIDA REALTY

  1010 N Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  $2,625,000 Sold Mar 27, 2025

  • 3,792 Sq Ft
  • $692/SF
  • 0 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2018

  141 N Virginia Ave, Winter Park, FL 32789

  Step into luxury with this stunning three-story townhouse featuring an elevator and abundant natural light. A breathtaking staircase elegantly wraps around a magnificent chandelier, creating a striking focal point from the first floor to the third. The first floor boasts a chef's kitchen with high-end cabinets, top-of-the-line appliances, and premium flooring. The second floor offers four elegant

  Maria Velez Restrepo KELLY PRICE & COMPANY LLC

  141 N Virginia Ave, Winter Park, FL 32789
• 

  /2

  $411,250 Sold Mar 27, 2025

  • 1,132 Sq Ft
  • $363/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1958

  767 Baffie Ave, Winter Park, FL 32789

  Welcome to this beautifully maintained Winter Park gem, offering exceptional curb appeal and bursting with charm, character and timeless style. Located in the highly desirable Dubsdread Heights neighborhood, bordering Little Lake Fairview and the Dubsdread Golf Course, this home places you just minutes from the boutique shops, dining options and festivals of Park Avenue, with easy access to I-4.

  Jeffrey Petch GECKO REALTY, INC

  767 Baffie Ave, Winter Park, FL 32789
• 

  /2

  $3,130,000 Sold Mar 27, 2025

  • 4,188 Sq Ft
  • $747/SF
  • 6 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2025

  210 E Lake Sue Ave, Winter Park, FL 32789

  Exquisite Winter Park residence built by Davila Homes, where luxury meets functionality. This impressive home features 5 spacious bedrooms, 5.5 beautifully designed bathrooms, and a generous 4,188 square feet of meticulously crafted living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of beautiful hardwood floors and the high ceilings. The

  Christopher Christensen COMPASS FLORIDA LLC

  210 E Lake Sue Ave, Winter Park, FL 32789

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