19

Winter Park, FL Townhomes for Sale

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  • /37

    $419,900

    $5K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    1871 Casselwood St, Winter Park, FL 32792

    BRAND NEW ROOF 2026 to be installed next week. Beautifully updated and move-in ready home in Winter Park featuring a BRAND NEW 2026 A/C system and water heater from 2009. This 4-bedroom, 2.5-bath home with a 2-car garage offers waterproof luxury vinyl flooring, recessed lighting, updated fixtures, fireplace, screened patio, and a bright, functional layout filled with natural light. The upgraded

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 252-6747

    1871 Casselwood St, Winter Park, FL 32792
  • /26

    $425,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    1995 Canny Cove, Winter Park, FL 32792

    Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe

    Rosemary Siegler IAD FLORIDA LLC

    1995 Canny Cove, Winter Park, FL 32792
  • /64

    $444,900

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft

    1951 Canny Cove, Winter Park, FL 32792

    Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel

    Denise Del Castillo LPT REALTY, LLC

    1951 Canny Cove, Winter Park, FL 32792
  • /29

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    1261 Indiana Ave, Winter Park, FL 32789

    Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low maintenance living in a thriving Winter Park location. The main level features a spacious living and dining room combo plus a separate family room and kitchen-perfect for entertaining. The kitchen includes a gas cooktop and range, granite counters, island, breakfast nook, and built-in

    Megan Cross FANNIE HILLMAN & ASSOCIATES

    1261 Indiana Ave, Winter Park, FL 32789
  • /20

    $695,000

    $55K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,317 Sq Ft

    432 W Swoope Ave, Winter Park, FL 32789

    A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

    Thomas Bonner COLDWELL BANKER REALTY

    432 W Swoope Ave, Winter Park, FL 32789
  • /26

    $465,000

    $115K PRICE DROP
    • 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
  • /31

    $725,000

    $59K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,407 Sq Ft

    1732 Ridgewood Ave Unit S, Maitland, FL 32751

    This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step

    Brandon Geers COMPASS FLORIDA LLC

    1732 Ridgewood Ave Unit S, Maitland, FL 32751
  • /18

    $269,000

    $16K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    3220 Netherwood Dr, Winter Park, FL 32792

    Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best of all, NO HOA! Conveniently located near

    Nimrah Ashraf THE FIRM RE

    3220 Netherwood 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

    $185,000

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft

    3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

    Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own

    Qing Lin SPRINGHILL PROPERTIES LLC

    3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
  • /82

    $4,295,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 5 Baths
    • 4,231 Sq Ft

    643 N Park Ave, Winter Park, FL 32789

    Winter Park living at its best! This custom brownstone with an exclusive Park Avenue address offers an unparalleled Winter Park lifestyle. Ideally situated in the heart of Winter Park, moments from Park Avenue’s renowned dining, boutique shopping and cultural attractions...evening strolls and friendly smiles are simply part of everyday life. An inviting front courtyard welcomes you with a brick

    Sara Cambron PREMIER SOTHEBY'S INTL. REALTY

    643 N Park Ave, Winter Park, FL 32789
  • /20

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft

    5806 Marble Ct, Winter Park, FL 32792

    Welcome to this well-maintained 2-bedroom, 2-bathroom duplex with a 1-car garage, located in the desirable Seminole County side of Winter Park. This home offers a functional layout with comfortable living spaces, natural light, and a private residential setting perfect for everyday living or investment opportunities.Enjoy a convenient location with easy access to major roads, shopping,

    Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

    5806 Marble Ct, Winter Park, FL 32792
  • /36

    $248,900

    $1K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,580 Sq Ft

    7470 Canford Ct Unit 23, Winter Park, FL 32792

    New updates, a new fence, and extra outdoor space on a desirable corner lot. Beautifully updated 3 bedroom, 2.5 bath corner unit townhome located in the heart of Winter Park, offering 1,580 square feet of bright and open living space. This home features a deluxe vinyl-fenced backyard with plenty of privacy and no rear neighbors.The property is currently tenant occupied,making it a great

    Sam Nguyen FLORIDA REALTY INVESTMENTS

    7470 Canford Ct Unit 23, 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
  • /43

    $290,000

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

    3159 Greenwood St, Winter Park, FL 32792

    Location truly matters—and this Winter Park gem delivers. This beautifully maintained 2-bedroom, 2-bath townhouse offers charm, functionality, and a rare bonus: a spacious screened-in lanai and private yard. Tucked within a well-established neighborhood, the home provides a peaceful residential setting while keeping you just minutes from everything Winter Park has to offer. Inside, you’ll find a

    Joe Pietzyk GLOBAL PROPERTIES SALES/MGMT

    3159 Greenwood St, Winter Park, FL 32792
  • /34

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,787 Sq Ft

    7485 Aloma Pines Ct, Winter Park, FL 32792

    Experience the perfect blend of luxury and convenience in the highly sought-after GATED community of Aloma Trails. This meticulously maintained 3-bedroom, 2.5-bathroom townhome, built in 2017, offers 1,787 sq. ft. of living space designed for comfort and modern style. Step inside to find an inviting open-concept first floor featuring beautiful ceramic tile flooring and high ceilings. The gourmet

    Gunel Aydamirli OLYMPUS EXECUTIVE REALTY INC

    7485 Aloma Pines Ct, Winter Park, FL 32792
  • /26

    $1,099,000

    • 3 Beds
    • 3.5 Baths
    • 2,193 Sq Ft

    1768 Mondrian Cir, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience. This ultra-private corner unit boasts one of the community’s most desirable floor plans—perfectly positioned in a peaceful enclave just steps from the vibrant heart of Winter Park Village and mere minutes from I4,

    Brandon Geers COMPASS FLORIDA LLC

    1768 Mondrian Cir, Winter Park, FL 32789
  • /2

    $1,495,000

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,756 Sq Ft

    905 Enclave Place, Winter Park, FL 32792

    Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The

    Matthew Burks CORCORAN PREMIER REALTY

    905 Enclave Place, Winter Park, FL 32792
  • /2

    $1,495,000

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,738 Sq Ft

    901 Enclave Place, Winter Park, FL 32792

    Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch

    Laura Earl CORCORAN PREMIER REALTY

    901 Enclave Place, Winter Park, FL 32792

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$624,500
Median Townhouse Sale Price
$459,000
Median 2 Bedroom Sale Price
$199,900
Median 1 Bedroom Sale Price
$152,000
Average Price Per Sq Ft
$370
Number of Homes for Sale
300
Last 12 months Home Sales
982
Months of Supply
3.70
Median List Price
$535,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
0%
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