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Winter Park, FL Townhomes for Sale

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  • /42

    $435,000

    • 3 Beds
    • 3 Baths
    • 2,346 Sq Ft

    2224 Shadowland Loop, Winter Park, FL 32792

    **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 450-7733

    2224 Shadowland Loop, 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

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft

    7506 Cranes Creek Ct Unit 30, Winter Park, FL 32792

    Beautiful, move-in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home offers comfort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4the room on the first floor, ideal for a home office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and everyday

    Sylvia Marchese TRANSCONTINENTAL REALTY GROUP,

    7506 Cranes Creek Ct Unit 30, 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
  • /37

    $560,000

    • 3 Beds
    • 3.5 Baths
    • 1,937 Sq Ft

    1250 Formosa Ave, Winter Park, FL 32789

    Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a

    Jeanine Louis-Alcime EXP REALTY LLC

    1250 Formosa Ave, Winter Park, FL 32789
  • /52

    $318,985

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    758 Warrenton Rd, Winter Park, FL 32792

    Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas

    Nicholas Musashe SUN PROPERTIES, INC.

    758 Warrenton Rd, Winter Park, FL 32792
  • /29

    $225,000

    • 2 Beds
    • 1 Bath
    • 854 Sq Ft

    2400 Dominica Run, Winter Park, FL 32792

    CHARMING 2/1 MOVE IN READY TOWNHOME in highly sought-after Windward Square community of Winter Park! NEWER Roof 2025! Spacious floor plan with soaring ceilings! Inviting entertainment space with dining/living combo off kitchen. Ample natural light fills this home with double glass sliders and multiple skylights all in living area! Relaxing views of back park like green space! Convenient location

    Laura Toppin FLORIDA HOME TEAM REALTY LLC

    2400 Dominica Run, Winter Park, FL 32792
  • /51

    $1,395,000

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    1780 Mondrian Cir, Winter Park, FL 32789

    Luxury Lakeview Townhome in Winter Park! Experience elevated living in this newly built 3-bedroom, 3.5-bath residence with over 2,300 sq ft and breathtaking direct views of Lake Killarney. A dramatic 17-ft foyer welcomes you into a bright, open-concept great room featuring 11-ft ceilings and floor-to-ceiling windows that capture stunning water and nature views. The designer kitchen is built for

    Lisa Gould KELLER WILLIAMS WINTER PARK

    1780 Mondrian Cir, Winter Park, FL 32789
  • /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
  • /26

    $315,000

    • 3 Beds
    • 3.5 Baths
    • 1,652 Sq Ft

    1515 Winter Green Blvd, Winter Park, FL 32792

    Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the

    Jill Healey KELLER WILLIAMS WINTER PARK

    1515 Winter Green Blvd, Winter Park, FL 32792
  • /46

    $899,000

    • 3 Beds
    • 2.5 Baths
    • 1,884 Sq Ft

    1405 Miller Ave, Winter Park, FL 32789

    Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes.Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet, the home features a desirable

    Rikhil Amin FANNIE HILLMAN & ASSOCIATES

    1405 Miller Ave, Winter Park, FL 32789
  • /25

    $200,000

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    4864 Tangerine Ave Unit 4864, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. This low-maintenance Winter Park one-story condo just became even more affordable ... 4.99% INTEREST RATE OFFERED FOR QUALIFIED BUYERS! This beautifully upated home is Move-in Ready with no neighbors above or below! Enjoy corner-unit privacy, a screened patio overlooking a serene and well-manicured courtyard, and inside you will love the updated

    Allison Day RE/MAX TOWN & COUNTRY REALTY

    4864 Tangerine Ave Unit 4864, Winter Park, FL 32792
  • /39

    $265,000

    • 2 Beds
    • 2 Baths
    • 1,199 Sq Ft

    2530 Leeward Way, Winter Park, FL 32792

    Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample

    Jennifer Wemert WEMERT GROUP REALTY LLC

    2530 Leeward Way, Winter Park, FL 32792
  • /47

    $545,000

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

    1781 Indiana Ave Unit A, Winter Park, FL 32789

    Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed

    James Rouadi CARLISLE REALTY, LLC

    1781 Indiana Ave Unit A, Winter Park, FL 32789
  • /20

    $359,500

    • 3 Beds
    • 2.5 Baths
    • 1,872 Sq Ft

    7474 Aloma Pines Ct, Winter Park, FL 32792

    ***PRICE REDUCTION*** **Seller offering closing credit**Nestled on a quiet cul-de-sac in desirable Winter Park, this well-maintained home offers a thoughtful layout with bright, open living spaces designed for both comfort and everyday living. The kitchen flows seamlessly into the main living and dining areas, making it ideal for gathering and entertaining. Generously sized bedrooms provide

    Jakki Kim OAK HOLLOW PROPERTIES

    7474 Aloma Pines Ct, Winter Park, FL 32792
  • /20

    $695,000

    • 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
  • /18

    $269,000

    • 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
  • /36

    $399,000

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

    2834 Bright Bird Ln, Winter Park, FL 32792

    Priced BELOW appraised value for a quick sale! Welcome to this stunning newer-construction townhome offering modern design, spacious living, and unbeatable value in one of Orlando’s most convenient locations. Featuring 3 bedrooms, 3 bathrooms, and nearly 2,000 sq ft of living space, this home boasts an open-concept layout, contemporary finishes, and abundant natural light throughout. The kitchen

    Irene Navarro LIFESTYLE INTERNATIONAL REALTY

    2834 Bright Bird Ln, Winter Park, FL 32792
  • /30

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,178 Sq Ft

    5473 Bracken Ct, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open

    David Fraser KELLER WILLIAMS ADVANTAGE III

    5473 Bracken Ct, Winter Park, FL 32792
  • /64

    $444,900

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft

    1951 Canny Cove, Winter Park, FL 32792

    Price improvement! Discover comfortable Winter Park living in this bright 3-bedroom, 2.5-bath corner-unit townhome located in the gated Grayson Square community. Freshly painted and filled with natural light, the open-concept living and dining area opens to a covered lanai, ideal for everyday living and entertaining. The kitchen features stainless steel appliances, quartz countertops, ample

    Denise Del Castillo LPT REALTY, LLC

    1951 Canny Cove, Winter Park, FL 32792
  • /20

    $218,000

    • 2 Beds
    • 1.5 Baths
    • 1,085 Sq Ft

    200 Saint Andrews Blvd Unit 3001, Winter Park, FL 32792

    Experience the best value in Winter Park. Beautifully maintained corner-unit townhome in the desirable Four Seasons community, offering a perfect blend of comfort, privacy and style. This bright and inviting residence features modern laminated floors, new carpet in the bedroom areas, granite kitchen countertops, updated lighting, and recently painted interiors. Enjoy the convenience of a private

    Magaly Laplana Kleros Realty

    200 Saint Andrews Blvd Unit 3001, Winter Park, FL 32792
  • /33

    $320,000 Open Sun 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,719 Sq Ft

    2401 Antilles Dr, Winter Park, FL 32792

    Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a

    George Freelove KELLER WILLIAMS REALTY AT THE PARKS

    2401 Antilles Dr, 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
  • /26

    $189,000

    • 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
  • /15

    $319,900

    • 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
  • /26

    $465,000

    • 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
  • /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
  • /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
  • /31

    $749,000

    • 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

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
$605,000
Median Townhouse Sale Price
$455,000
Median 2 Bedroom Sale Price
$199,000
Median 1 Bedroom Sale Price
$153,000
Average Price Per Sq Ft
$366
Number of Homes for Sale
305
Last 12 months Home Sales
1,009
Months of Supply
3.60
Median List Price
$529,900
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
1%
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