29

Winter Park, FL Townhomes for Sale

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  • /37

    $950,000

    • 3 Beds
    • 3.5 Baths
    • 2,116 Sq Ft

    1251 Arlington Place, Winter Park, FL 32789

    STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

    Brad Barnett ANNE ROGERS REALTY GROUP INC

    1251 Arlington Place, Winter Park, FL 32789
  • /84

    $445,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    1900 Erudite Way, Winter Park, FL 32792

    Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features, including a convenient keypad entry and smart lighting throughout.Inside, an open-concept layout welcomes you with rich wood floors, designer lighting,

    Erica Diltz BALDWIN PARK REALTY LLC

    1900 Erudite Way, Winter Park, FL 32792
  • /15

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,837 Sq Ft

    2417 Passamonte Dr Unit 1E, Winter Park, FL 32792

    Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, 3 Bedroom Town Home with a Garage in the VIA LAGO GATED community?? ABSOLUTELY! Meticulously maintained and spacious town home is just waiting for its new owner! Elegant brick paver driveway and entryway greet you as you pull up. The downstairs is open, light and bright. The beautifully appointed kitchen has

    Stephen Hachey FLAT FEE MLS REALTY

    2417 Passamonte Dr Unit 1E, Winter Park, FL 32792
  • /22

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,556 Sq Ft

    1122 Washington Ave Unit 7, Winter Park, FL 32789

    Welcome to 1122 Washington Avenue – a delightful 2-bedroom, 2.5-bath townhome located in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue, Rollins College, the Winter Park Tennis Center, and the brand-new Seven Oaks Park, this home offers the perfect blend of lifestyle and location.This area is undergoing tremendous transformation, especially along the

    Raul Veitia BELMONT REALTY

    1122 Washington Ave Unit 7, Winter Park, FL 32789
  • /28

    $524,000

    • 3 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    1745 Indiana Ave Unit J, Winter Park, FL 32789

    Welcome to this beautifully updated townhome, conveniently located near everything you need. Step inside to discover a bright, open floor plan with new luxury vinyl plank flooring that flows seamlessly throughout the main level. The kitchen has been recently updated with white cabinets and features newer appliances, including a refrigerator, dishwasher, and washer/dryer—all added in the past

    Chase Morton Tate COMPASS FLORIDA LLC

    1745 Indiana Ave Unit J, Winter Park, FL 32789
  • /43

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2812 Bright Bird Ln, Winter Park, FL 32792

    Built in 2024, this move-in ready 3-bedroom, 2.5-bathroom townhome is located in the gated community of Grayson Square, just a little over 15 minutes from Park Avenue in downtown Winter Park. Designed with a sleek, neutral gray color scheme and modern finishes throughout, the home features an open-concept layout filled with natural light that enhances its bright and airy feel. The main level

    Jessica Snyder LPT REALTY, LLC

    2812 Bright Bird Ln, Winter Park, FL 32792
  • /18

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 2,076 Sq Ft

    1522 Bantam Way, Winter Park, FL 32792

    Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood. The corner townhouse has huge living room with a high ceiling when you walk into the house, screen patio with the tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy

    He Gao U S GLORY REALTY

    1522 Bantam Way, Winter Park, FL 32792
  • /34

    $452,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2033 Canny Cove, Winter Park, FL 32792

    Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and living area—perfect for entertaining. The modern kitchen is equipped with stainless steel appliances, sleek gray cabinets, and elegant quartz countertops. Upstairs, the Primary Bedroom features a spacious walk-in closet and a luxurious en-suite bathroom with a dual-sink quartz vanity and a private water

    Monica Puche LPT REALTY, LLC

    2033 Canny Cove, Winter Park, FL 32792
  • /65

    $564,900

    • 3 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    5489 Baldwin Park St, Orlando, FL 32814

    MOTIVATED SELLER OFFERING FIRST YEAR HOA FEE TO BE PAID AT CLOSING!!! Luxury & Location define this sensational two story townhome.This beautiful place features an open, designer kitchen with gorgeous granite countertops throughout, upgraded appliances, and a very convenient under sink reverse osmosis system. The breakfast bar opens to a cozy dining/family room. The large, tranquil owner's suite

    Oliver Figuereo EXECUTIVE REAL ESTATE

    5489 Baldwin Park St, Orlando, FL 32814
  • /36

    $599,900

    • 2 Beds
    • 2.5 Baths
    • 1,897 Sq Ft

    2979 Upper Park Rd, Orlando, FL 32814

    Stately Townhome in Baldwin Park! Welcome to this exquisite townhome, ideally situated adjacent to the charming Windsong community and the well-established City of Winter Park. This spacious residence offers a refined living experience with a perfect blend of comfort and elegance.Upon entry, you are greeted by a formal living and dining room, providing an open and inviting space for entertaining

    Timothy Bratcher COLDWELL BANKER RESIDENTIAL RE

    2979 Upper Park Rd, Orlando, FL 32814
  • /28

    $279,900

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft

    3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792

    Cute, updated, and quietly tucked away, this one-story townhome is full of pleasant surprises. Situated on a corner lot with no rear neighbors, it offers just the right mix of privacy and convenience. Inside, you’ll find ceramic tile and luxury vinyl flooring throughout...so no carpet in sight! The kitchen and both bathrooms have been tastefully updated, and it’s all topped off with a brand new

    Allison Day RE/MAX TOWN & COUNTRY REALTY

    3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792
  • /18

    $225,000

    • 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
  • /19

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    3015 Casselwood St, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2-bath villa nestled in the highly sought-after community of Winter Park! This spacious home boasts an open floor plan, a convenient inside laundry room, and easy-to-maintain flooring—no carpet anywhere, and Solar panels! Step outside to a generously sized screened-in patio, perfect for relaxing or entertaining. Enjoy warm Florida days at the

    Michelle Parrish PARRISH REALTY GROUP INC

    3015 Casselwood St, Winter Park, FL 32792
  • /22

    $365,000

    • 3 Beds
    • 2 Baths
    • 1,235 Sq Ft

    1117 Park Green Place, Winter Park, FL 32789

    Charming One-Story Townhome in Prime Winter Park Location!Welcome to this adorable detached 3-bedroom, 2-bath townhome with a spacious 2-car garage, tucked away in the heart of Winter Park (32789). Just minutes from Winter Park Village, Fleming’s, and the boutiques and dining of Park Avenue, this home blends low-maintenance living with unbeatable convenience.Step inside to find a

    Kelly Sue Stonebreaker RE/MAX TOWN & COUNTRY REALTY

    1117 Park Green Place, Winter Park, FL 32789
  • /36

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 1,406 Sq Ft

    3118 Crown Jewel Ct, Winter Park, FL 32792

    Come to see this beautiful townhouse blends functionality with upscale finishes, a prime location ideal for families, or professionals looking for style and convenience. This home boasts numerous upgrades for both comfort and style. PAVER DRIVEWAY is designed for two cars to park, and architectural appeal adds curb appeal. SCREENED-IN LANAIS with upgraded ceiling light fans, no rear neighbors,

    Xue Gao U KEY REALTY

    3118 Crown Jewel Ct, Winter Park, FL 32792
  • /22

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft

    Unlisted Address

    Welcome to this beautifully updated townhouse located in the heart of desirable Winter Park! Step inside to find a bright and inviting interior featuring tile and vinyl flooring throughout—offering both style and easy maintenance. The newly renovated kitchen is a true showstopper, complete with stunning white quartz countertops, sleek new cabinetry, modern appliances, and a classic farmhouse sink

    Natasha Myers MARK SPAIN REAL ESTATE

    Unlisted Address
  • /22

    $275,000

    • 2 Beds
    • 2 Baths
    • 932 Sq Ft

    2426 Windward Way, Winter Park, FL 32792

    Nestled in the heart of the highly desirable Windward Square community, this beautifully maintained home offers the perfect blend of comfort, style, and convenience. Step inside from the tranquil front patio and be welcomed by a surprisingly spacious open floor plan that instantly feels like home.The kitchen shines with newer appliances, granite countertops and beautiful upgraded cabinetry.

    Kim Coburn RE/MAX TOWN & COUNTRY REALTY

    2426 Windward Way, Winter Park, FL 32792
  • /51

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 1,939 Sq Ft

    1429 Indiana Ave, Winter Park, FL 32789

    Like new and totally turn-key! Built by award-winning Winter Park Custom Homes, coastal modern residence offers thoughtful design, high-end finishes, and an unbeatable location in Winter Park's coveted 32789 ZIP code. 3-bedroom, 2.5-bath home combines privacy with convenience. Minutes from Park Avenue, downtown Orlando and major local destinations. The home features authentic reclaimed

    Jennifer Sloan KELLY PRICE & COMPANY LLC

    1429 Indiana Ave, Winter Park, FL 32789
  • /15

    $340,000

    • 3 Beds
    • 3 Baths
    • 1,803 Sq Ft

    2487 Harbour Way, Winter Park, FL 32792

    Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life.Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more!The community offers a complete infrastructure with a swimming pool, playground,

    Marcus Freire de Araujo WRA BUSINESS & REAL ESTATE

    2487 Harbour Way, Winter Park, FL 32792
  • /31

    $270,000

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

    3310 Royal St, Winter Park, FL 32792

    Welcome to 3310 Royal Street – a beautifully maintained mid-century gem nestled in one of Winter Park’s most desirable neighborhoods. This 2-bedroom, 1 and a half bath home offers the perfect blend of timeless charm and modern updates, ideal for families, professionals, or anyone looking to enjoy the Winter Park lifestyle.Step inside to discover an open-concept layout filled with natural light,

    Kevin Schudel BUY IT INC

    3310 Royal St, Winter Park, FL 32792
  • /30

    $244,900

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

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792

    THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESTLED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGERATOR AND

    Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792
  • /41

    $348,900

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    3204 Netherwood Dr, Winter Park, FL 32792

    Discover this beautifully renovated 2-bedroom, .5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-de-sac lot with no HOA, this home has been completely upgraded to offer modern comfort and style. Step inside to luxury vinyl flooring throughout, an open-concept living space, and a sleek kitchen with stainless steel appliances. The high-end bathroom remodel adds a spa-like

    Renee Anthony WATSON REALTY CORP.

    3204 Netherwood Dr, Winter Park, FL 32792
  • /26

    $494,900

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2774 Bright Bird Ln, Winter Park, FL 32792

    Motivated seller! Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same

    Priscilla Triska FLORIDA CONNEXION PROPERTIES

    2774 Bright Bird Ln, Winter Park, FL 32792
  • /14

    $179,900

    • 3 Beds
    • 2 Baths

    7340 Daniel Webster Dr, Winter Park, FL 32792

    This is a 3 bedroom and 2 bathroom condo. This condo has had everything replaced. Don't miss out on this opportunity. Call listing agent today for more information and to schedule a showing.

    Robert Castro RE/MAX - City Centre Realty

    7340 Daniel Webster Dr, Winter Park, FL 32792
  • /25

    $284,900

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft

    2335 Inagua Way, Winter Park, FL 32792

    Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

    Marion McGrath ABSOLUTE REALTY GROUP, LLC

    2335 Inagua Way, Winter Park, FL 32792
  • /26

    $469,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2949 Clever Ln, Winter Park, FL 32792

    Welcome to this stunning former model townhome built in 2023, ideally located in the highly sought-after gated community of Grayson Square in Winter Park, Florida. This beautifully designed residence offers a blend of modern finishes and functional layout, with the first floor featuring a completely open floor plan bathed in natural light. The spacious kitchen boasts quartz countertops, upgraded

    Joseph Sipp KELLER WILLIAMS WINTER PARK

    2949 Clever Ln, Winter Park, FL 32792
  • /19

    $849,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,051 Sq Ft

    1917 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

    1917 S Lakemont Ave, Winter Park, FL 32792
  • /42

    $874,700 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,063 Sq Ft

    1907 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

    1907 S Lakemont Ave, Winter Park, FL 32792
  • /44

    $469,900 Pre-Foreclosure

    • 3 Beds
    • 2.5 Baths
    • 1,801 Sq Ft

    2037 Canny Cove, Winter Park, FL 32792

    Nestled in the coveted Grayson Square community of highly desired Winter Park, FL, 2037 Canny Cove Lane is a contemporary 3-bedroom, 2.5-bath townhome built in 2023. The open-concept layout features a stylish kitchen with stainless steel appliances, quartz countertops, and ample storage, seamlessly flowing into the spacious gathering room. The owner's suite offers a private retreat with an

    Claire Sims LLC LPT REALTY, LLC

    2037 Canny Cove, Winter Park, FL 32792

Why Live in Winter Park

Winter Park, a historic urban village, offers a blend of residential and commercial areas set among the Winter Park Chain of Lakes. The neighborhood is known for its rich arts scene and highly rated schools, including Winter Park High and Trinity Preparatory School of Florida. Park Avenue remains a central hub with high-end boutiques and dining options like The Ravenous Pig. Rollins College and The Rollins Museum of Art add to the cultural attractions. Residents enjoy outdoor activities such as boating and paddleboarding on the lakes, and green spaces like Central Park, which features walking paths and a rose garden. The Winter Park Country Club and Golf Course provides a public nine-hole course. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park foster a strong sense of community. The area has a lower crime rate compared to the national average, with a violent crime rate of 2.9 per 1,000 people. Winter Park's home styles range from petite bungalows to lakeside mansions, including New Traditional, midcentury ranch, Colonial Revival, and Contemporary homes. The neighborhood is well-connected with Interstate 4, SunRail, and Lynx bus services, and is about 10 miles from downtown Orlando and 20 miles from Orlando International Airport.

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$575,000
Median Single Family Sale Price
$750,000
Median Townhouse Sale Price
$499,000
Median 2 Bedroom Sale Price
$244,400
Median 1 Bedroom Sale Price
$159,500
Average Price Per Sq Ft
$407
Number of Homes for Sale
260
Last 12 months Home Sales
692
Months of Supply
4.50
Median List Price
$625,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-5%
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