Displaying: For Sale
Location: Winter Park
Property Type(s): Townhomes
Price: $400,000 to $499,000
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Winter Park - 5 properties found
1871 CASSELWOOD ST, WINTER PARK, FL 32792
$424,9001 Day on yellowkey MLS ID: O6404306
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 1988Monthly Fee: $39 Tax: $1,223 (2024)Community: Villas Of Casselberry Ph 2Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,223
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: Beautifully updated, move-in ready home in Winter Park with space, comfort, and a clean, modern feel throughout. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall that adds warmth and character. Just behind the wall, a renovated half bathroom is conveniently located on the first floor. The kitchen is one of the main features of the home, fully renovated with custom green cabinetry, quartz countertops, a farmhouse sink with a modern faucet, gold hardware, and a clean contemporary backsplash. The space includes abundant cabinetry plus a pantry for additional storage and comes equipped with new stainless steel appliances including refrigerator, range, and range hood. Pendant lighting and chandelier details add a designer touch. The living area includes a modern electric fireplace and sliding doors that open to a screened patio, creating a comfortable indoor-outdoor flow. The outdoor space provides a private setting with a low-maintenance yard and room to relax or personalize. Upstairs, you will find all bedrooms along with a conveniently located laundry area. The primary suite is oversized and designed as a true retreat, featuring dual pendant lighting and great natural light. The primary bathroom is fully renovated with a freestanding soaking tub, double vanity, glass-enclosed walk-in shower with rainfall shower head, and modern finishes. The suite also includes dual closets for added functionality. Secondary bedrooms are well-sized and provide flexibility for family, guests, office, or additional living space. Additional improvements include a new front door, updated lighting throughout, and thoughtful design details that make this home feel clean, cohesive, and move-in ready. Located in the Villas of Casselberry community, this property has a low HOA (buyer to verify) with access to a community pool and sidewalks. Conveniently situated near major roads, shopping, dining, Full Sail University, Rollins College, UCF, and just minutes from Downtown Orlando. Move-in ready with extensive updates and a functional layout, this is a strong opportunity in the Winter Park market.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
1951 CANNY CV, WINTER PARK, FL 32792
$444,900142 Days on yellowkey MLS ID: O6367023
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1782 Built: 2023Monthly Fee: $375 Tax: $6,889 (2025)Community: Grayson SquareTownhouse
Taxes:$6,889
Tax Year: 2025
Remarks: 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 appliances, quartz countertops, and plenty of cabinet space for storage and organization. Upstairs, the owner’s suite provides a private retreat with a walk-in closet and a spacious ensuite bath featuring dual vanities and a glass-enclosed shower. A two-car garage with epoxy flooring and an in-unit washer and dryer add everyday convenience. Residents also enjoy access to a resort-style pool with cabana, along with high-speed fiber-optic internet and streaming services included. Located just minutes from downtown Winter Park, with easy access to major roadways, shopping, dining, and everyday essentials, this home offers a great balance of comfort, convenience, and low-maintenance living.HABLO ESPANOL
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Denise Del Castillo (321-960-3110)
2224 SHADOWLAND LOOP, WINTER PARK, FL 32792
$435,000146 Days on yellowkey MLS ID: O6364889
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2346 Built: 2021Monthly Fee: $320 Tax: $5,934 (2024)Community: Enclave At Hawks CrestTownhouse
Taxes:$5,934
Remarks: **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 with high ceilings, modern finishes, and tile and carpet flooring all throughout. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating a seamless environment for entertaining or everyday living. All three bedrooms include generous walk-in closets, while the primary suite offers a peaceful retreat with its own private bathroom and serene ambiance. A versatile loft on the second floor adds valuable flex space that is ideal for a home office, media area, or playroom. Outside, the home offers a cozy enclosed rear patio perfect for relaxing, dining outdoors, or enjoying your morning coffee in privacy. A spacious two-car garage provides convenience and additional storage. The community surrounding Shadowland Loop is quiet, welcoming, and beautifully maintained, with tree-lined streets and easy access to the best of Winter Park. Residents enjoy proximity to top-rated schools, charming parks, boutique shopping, vibrant dining spots, and the area’s beloved lakes and recreation. With its thoughtful design, modern amenities, and exceptional location, this townhouse delivers the ideal Winter Park lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1537 BANTAM WAY, WINTER PARK, FL 32792
$475,00047 Days on yellowkey MLS ID: O6391664
0 Days Off yellowkey (back on 3/21/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2312 Built: 2022Monthly Fee: $330 Tax: $5,964 (2025)Community: Enclave At Hawks CrestTownhouse
Taxes:$5,964
Remarks: Under contract-accepting backup offers. There’s a certain feeling you get the moment you arrive in the secure, gated community of Enclave at Hawks Crest… a sense of calm, privacy, and understated luxury that immediately sets it apart. At 1537 Bantam Way, that feeling begins the second you pull up. The clean architectural lines, paver driveway, and polished contemporary exterior create a striking first impression… but it’s what happens inside this spacious 2,312 sq ft townhome that truly defines its beauty and charm. Step through the front door and you’re immediately welcomed into a light-filled, open-concept space where every detail feels intentional. Wood-look tile flooring stretches across the first level, adding warmth and durability, while high ceilings and natural light create an airy, expansive feel. This is a home designed not just to look beautiful, but to live effortlessly. At the center of it all is a kitchen that truly anchors the home. Featuring stainless steel appliances, a large center island with seating, and a walk-in pantry, it’s built for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, creating a connected environment that feels natural, comfortable, and refined. Sliding glass doors open to a covered rear patio… a private outdoor extension where mornings begin peacefully and evenings unwind with ease. Whether entertaining guests or enjoying a quiet night in, this space becomes a natural extension of the home’s living area, offering a balance of indoor comfort and outdoor enjoyment. Upstairs, the layout continues to impress with both comfort and flexibility. The primary suite offers generous space, a large walk-in closet, and a well-appointed en suite bath with dual vanities and a spacious walk-in shower. A central loft creates an additional living area, ideal for a media room, play space, or secondary lounge. Two additional bedrooms, a full bathroom, and an upstairs laundry room provide convenience and thoughtful separation of space. On the main level, a dedicated office adds even more flexibility for today’s lifestyle, whether working from home, creating, or simply having a quiet retreat. Beyond the home itself, the community enhances the lifestyle with exceptional amenities, including a large resort-style pool perfect for relaxing weekends or social gatherings, along with a children’s playground that adds to the neighborhood’s welcoming and family-friendly environment. The gated entry provides an added layer of privacy and security, creating a sense of exclusivity while still fostering a connected community atmosphere. Located in one of Central Florida’s most desirable areas, you’re just minutes from the charm of Park Avenue, the walkable appeal of Baldwin Park, and have quick access to SR 417 and I-4, making commuting to Downtown Orlando and surrounding areas seamless. Top-rated schools, dining, shopping, and entertainment are all within close reach, placing everything you need exactly where you want it. This is more than a townhome… it’s a refined, low-maintenance lifestyle in Winter Park, combining modern design, thoughtful functionality, and the added comfort of a gated community. Buyers may also receive up to $2,500 toward closing costs or a mortgage rate buy-down when using the seller’s preferred lender, creating additional value and flexibility for today’s buyer.
Listing is courtesy of: LIVE MVRK LLC (407-756-4563)
Listing Agent: Jared Dunn (407-493-8872)
2420 FIRSTLIGHT WAY, WINTER PARK, FL 32792
$450,000204 Days on yellowkey MLS ID: O6351808
3 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2312 Built: 2019Monthly Fee: $320 Tax: $5,397 (2024)Community: Enclave At Hawks CrestTownhouse
Taxes:$5,397
Remarks: Under contract-accepting backup offers. Welcome to this beautifully designed, move-in-ready townhome— the largest end-unit in one of Winter Park’s most sought-after gated communities! This spacious townhome is conveniently located in the gated community of Hawks Crest, offering 2,312 sq ft of low-maintenance living. With 3 bedrooms, 2.5 bathrooms, a 2-car garage, filled with natural light thanks to abundant windows and soaring ceilings. The paved driveway and lush landscaping welcome you home. Step inside to find a flex space ideal for a home office, den, or second living area. The open-concept main level boasts 9-foot ceilings and seamlessly connects the expansive living room, dining area, and chef-style kitchen complete with quartz countertops, shaker cabinetry, stainless steel appliances, and a large center island perfect for entertaining. Glass sliders lead to the covered patio perfect for your morning coffee or relaxing evenings outdoors. Upstairs, a spacious loft provides a versatile bonus area—great for a media room, playroom, or home gym. The oversized primary suite impresses with tray ceilings, a spa-like en-suite bathroom featuring dual vanities, a walk-in shower, private water closet, and a generous walk-in closet. Two additional bedrooms also offer walk-in closets and share a stylish full bathroom. A conveniently located upstairs laundry room (washer and dryer included) completes the upper level. Residents of Hawks Crest enjoy access to a suite of resort-style amenities including a community pool, playgrounds, parks, picnic areas, and more. Ideally located just steps from Park Maitland Preschool and neighborhood favorites like Foxtail Coffee, Kelly’s Homemade Ice Cream, and Donut King, with quick access to Downtown Winter Park and major highways. Don’t miss your chance to own this exceptional home in one of Winter Park’s most desirable communities!
Listing is courtesy of: ATRIUM REALTY, LLC (833-919-1190)
Listing Agent: Kristan Hayden (407-489-7411)
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